Samplebook-Tools of Organic Chemistry

Tools of
Organic
Chemistry
For world of competitions
By
AJNISH GUPTA & BHARTI GUPTA

Professor of Organic Chemistry
(i)
Copyright 2015 by Ajnish Gupta

All rights reserved.
No part of this publication may be reproduced, stored
in a database or retrieval system, or transmitted in any
form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior
written Permission of the writter.
First Indian Reprint, 2015

This edition is ma nufa ctured in India n a nd is
authorized for sale only in India, Bangladesh, Pakistan,
Nepal, Sri Lanka & Maldeves.
Printed & Distributed by:
Udaan Classes Pvt. Ltd.
Rainbow building, Patna
&
Madhur Satyapushpa
Shubhash Nagar, Kota
9122057123
Price: Rs. 499/-
(ii)
Preface
The guiding principle in writing this book was to create
a textbook for students- a textbook that presents the
ma terial in a way tha t they le arn to solve all the
questions along with the strategy to approach the
problems.
In this book we mixed all our teaching experience of 11
yea rs a long with theora tica l a nd experimenta l
knowledge to generate a hand book for all students to
reason their way to a solution rather than memorize a
multitude of facts, hoping they dont run out of memory.
This book covers mainly 4 units with 61 sections which
are real tools of Organic chemistry, which a students
must know before dealing any chemical reactions.
Organic chemistry is very easy and conceptual subject
and need proper understa nding of the basics a nd
stretegy to solve the questions in corret manner.
This book will prepare your right mindset for learning
Organic Chemistry. This mindset is essentially the one
that focuses you on a small number of straight forward,
repeated, funda menta l concepts a nd helps you to
apply them in different ways to solve the variety of
problems you face in organic chemistry.
This book is complete as it not only covers theory in
proper sequence but also provide varieties of questions
along with 10 test papers to judge your knowledge before going to start chemical reactions.
This book a lso covers a ll the questions of AIEEE,
IIT-Mains, IIT-Advanced, AIPMT & other medical exams from 2000 to 2014.
In this book balance has to be achieved between the
number of questions and the quality of the questions,
(iii)
Organic Chemistry is easy

by
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co.in
(iv)
especially because it is relatively easy to frame a very

large number of multiple-choice questions and theory
of the subject.
The questions in this book have been selected keeping
three things in mind.
First- the questions are such that they really test the
understanding of the subject.
Second- the questions cover all concepts.
Third- the number of questions has been kept large
enough to offer meaningful practice to the students.
We would like to thank the editors and production staff
for their efforts in bringing out the book. Suggestions
from readers for the improvement of the book are welcome.
Ajnish Kumar Gupta & Bharti Gupta
Ajnish@OrganicChemistry.co.in
9122057123
(v)
Acknowledgement
We are tha nkful to all the teachers who taught us
during the concept building session of our life specially
Dr. Nizamuddin sir, senior Chandra Vijay Rao and Dr.
Vijay Pratima Mittal madam.
We have written this book to remove the fever of
organic chemistry from mind of students.
We particularly want to thank many wonderful and
talented students whom we have taught over the years
who in turn taught us how to be a good teacher and
how we can help others.
We want to make this book as user friendly as possible,
and we will appreciate any comments that will help us
to achieve this goal in future editions.
Finally, this edition has been presented before you with
efforts to make it error free. Any that remain are our
responsibility; if you find any, please let us know so they
can be corrected in future printing.
Ajnish Gupta & Bharti Gupta
Professors of Organic Chemistry
Ajnish@OrganicChemistry.co.in
09122057123
(vi)
Table of Contents
Page No.
Unit 1 : Basic understanding of organic chemistry
01
Section 01 : Introduction of organic chemistry
02
Section 02 : What is organic chemistry
06
Section 03 : Representation of organic compounds
09
Section 04 : Reason for the formation of large

number of organic compounds
15
Section 05 : Functional groups
18
Section 06 : Homologue & Homologous series
25
Section 07 : Nature of C, H & functional groups
29
Section 08 : Saturated & Unsaturated molecules

with important points
34
Section 09 : Hybridization
38
Section 10 : Classification of organic compounds
42
Section 11 : Baeyers strain theory
47
Exercise 1 : Subjective approach
51
Answer
63
: Subjective approach
Exercise 1 : Objective approach
Answer
79
Single correct questions (SCQ)
79
Multiple correct questions (MCQ)
90
Assertion/reason type questions (A/R)
95
Match the column type ques. (MTC)
97
Comprehension type questions
98
Integer type questions
99
: Objective approach
(vii)
100
Unit 2 : Nomenclature of organic compounds
101
Section 01 : Alkyl groups
102
Section 02 : Basic concept of IUPAC nomenclature
106
Section 03 : Points to write IUPAC nomenclature
111

for multiple bonds & rings
116

of compounds with functional groups
122
Section 06 : Nomenclature of Bicyclic &

Spiro compounds
131
Section 07 : Some common names commonly used

in organic chemistry
135
Section 08 : Degree of unsaturation
157
Section 09 : Chemically different hydrogen
163
168
Answer
194
214
214
228
Assertion/reason type questions (A/R) 231

233
234
238
Answer
Test 1
: Basic understanding of organic

chemistry & nomenclature
Test 2
241

Test 3
240
(viii)
250

Test- 1, 2, 3 : Answer
259
268
269
Unit 3 : Study of isomerism

Section 01 : Basic concept of isomerism
270
Section 02 : Chain isomerism
273
Section 03 : Positional isomerism
277
Section 04 : Functional isomerism
281
Section 05 : Metamerism
285
Section 06 : Basic concept of tautomerism
292
Section 07 : % enol content
298
Section 08 : Types of tautomerism
303
Section 09 : Basic concept of geometrical isomerism 305

Section 10 : Nomenclature used in geometrical
isomerism
310
Section 11 : Basic concept of optical isomerism
315
Section 12 : Nomenclature used in optical isomerism 321

Section 13 : Terms used in optical isomerism
326
Section 14 : Compound showing optical isomerism

along with calculation of number of
stereoisomers
331
Section 15 : Conformational isomerism
336
Section 16 : Conformation of cyclohexane
344
Section 17 : Interconversion of one form of

molecule into another
351
Section 18 : Finding relationship between

pair of compounds
354
Section 19 : Physical properties of organic

compounds
360
(ix)
366
Answer
384
401
401
434

441
442
445
Answer
446
Test 4
: Concept of isomerism
449
Test 5
459
Test 6
468
478
Unit 4 : Electronic effect & its application
479
Section 01 : General concept of organic reactions
480
Section 02 : Inductive effect
487
Section 03 : Basic concept of resonance
491
Section 04 : Points to draw resonating structures
495
Section 05 : points to check stability of resonating

structures
499
Section 06 : Mesomeric effect
504
Section 07 : Hyperconjugation
508
Section 08 : Electromeric effect
511
Section 09 : Organic reaction intermediates
514
Section 10 : Carbocations
517
Section 11 : Stability of carbocation
520
Section 12 : Rearrangement of carbocations
524
Section 13 : Classification of carbocation
532
Section 14 : Carbanions
535
(x)
Section 15 : Free radical
540
Section 16 : Carbenes
546
Section 17 : Nitrene
550
Section 18 : Benzyne
554
Section 19 : Ajnish rule & Its application in

organic chemistry
558
Section 20 : General concept of Acid & Base
567
Section 21 : Concept to decide relative acidic

strength
572
Section 22 : Concept to decide relative basic

strength
577
581
Answer
607
639
639
697

709
712
723
Answer
726
Test 7
: Electronic effect & its application
729
Test 8
739
Test 9
749
759
Test 10
: Tools of organic chemistry
760
Test 10
: Answer
769
(xi)
Dedication
Dedicated to all those students who
are in fever of organic chemistry.
(xii)
Basic understanding of organic chemistry
Unit
Basic understanding of
Organic Chemistry
This section is designed to lay the foundation for your organic
chemistry. Here you will learn what is organic chemistry, how
orga nic compounds are represented, what is the reason for
formation of large number of orga nic compounds, functional
groups, homologues, nature of carbon & hydrogen, saturation and
unsaturation, hybridization, cla ssification of organic compounds
and Baeyers strain theory.
Organic Chemistry is easy by

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Section
Introduction of
Organic Chemistry
Have you ever thought that when you read anything from any
book your eyes use an organic compound (retinal) to convert visible
light into nerve impulses. When you pick up this book from any
place, your muscles do chemical reactions on sugars to give you
energy. As you read the words a nd sentences of this book, gaps
between your brain cells are being bridged by simple orga nic
molecules (neurotransmitter amines) so that nerve impulse can be
passed around your brain and you can understand a ll matters
correctly a nd you did all that without consciously thinking about
it.
You do not yet understand the se processes in your mind but
you are regularly carrying them out in your brain & body.
H 3 C CH 3 CH 3
HO
CH 3H 3 C
O
11-Cis retinal H
(Absorbs light when we see)
You are not alone there.........
NH2
N
H
Serotonin
(Human neurotransmitter)
No organic chemist, is so brilliant who can understand the

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detailed chemical working of human mind or body very well.
So dont be sad and give a smile to yourself so that your
journey should be cheerful....
You do at least one thing after reading this page Think the
importance of organic chemistry and try to search at least one thing
which makes your life easy but not made of CARBON.
?
?
Are you thinking of this book, which you are reading

presently - Made up of cellulose and indeed carbon
Notice board, Black or white board of schools - Made up

of wood and indeed carbon.
Cloths which you are wearing - Polyester, tericot, silk etc.

- Polymer of organic compounds
Perfumes, which you are using for good smell - Again

organic molecule such as cis-jasmone from jasmine flower
and damascenone in smell of rose.
Medicines at the time of your sickness - Made up of organic

compounds such as paracetamol and aspirin
Sugars to make your life sweet - Made up of glucose,

sucrose and indeed carbon.
Are you thinking for opposite sex attraction- Pheromones &

hormones are responsible for it, which are again made up of
carbon.
Are you now thinking for drugs - Then they are again
organic and ma de up of carbon such as coca ine, nicotine,
etc.
Polythene which are used to carry things - made up of

ethene which indeed is made up of carbon
Blue jeans, which you are wearing - made up of indigo

dyes, made up of carbon.
Petrol or diesel- Again made up of carbon

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Candles for your birthdays and parties for light - Again

made up of carbon
Are you thinking for bigger molecules such as Vitamins,

Proteins, DNA, RNA they are again organic and made
up of carbon.
Trees, plants, flowers - They too are made up of carbon
You, I or any human being along with all animals &

plants- has some sort of carbon, in one form or another.
O
H 3C CH 3
MeOOC
N
O
H3 C
CH 3
CH 3
Damascenone-The smell of rose
Cocaine O
HO
HO
CH 3
Cis Jasmone of jasmine
HO
OH
Vitamin C
OH
O
HO
HO
OH
OH
Glucose
CH 3
H3 C CH 3
CH 3
CH3
COOH
Aspirin
CH3
CH 3
OH
Vitamin A
NH 2
N
HN N
Adenine

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O
O
N
NH
NH
HN N NH 2
Guanine
NH 2
N
N O
H
Cytocine
HN
O
Indigo dye for blue colour
O
NH
N O
H
Uracil
H3 C
NH
N O
H
Thymine
Anything more which you want to suggest....

Examples may varies from yours to ours but from these
example. We want to give a clear cut picture of importance of organic
chemistry and its applications in daily life i.e. everything around
us are organic in nature so
Love organic, feel organic and give a smile for organic....

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Section
What is Organic Chemistry
What is Organic chemistry?

Why do so many people study it?
And why should I study it?
The answer to these questions is all around you. Every living
organism is made up of organic compounds. The proteins that make
your hair, skin and muscles; the DNA that controls your genetic
heritage; the food that nourish you; the clothes that keep you warm
and the medicines that heal you, are all organic chemicals. Anyone
with a curiosity about life and living things must have a basic
understanding of organic chemistry.
The foundation of organic chemistry dates from the mid 1700s,
when chemistry was evolving from alchemists art into a modern
science. At that time unexplainable differences were noted between
substances obtained from living sources and those obtained from
mineral sources. Compounds obtained from plants a nd animals
were often difficult to isolate, purify and even difficult to work.
The Swedish chemist Torbern Bergman in 1770 was the first to
differentia te organic and inorganic substances a nd the term
organic chemistry soon came to mean the chemistry of compounds

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found in living organism.
To many chemists at that time the only explanation for the
differences in behavior of orga nic and inorganic compound was
that the organic compounds must contain a peculiar vital force
as a result of their origin in living substance. Due to this vital force
theory chemist believed that organic compounds could not be
prepared and manipulated in the laboratory, as could inorganic
compounds.
In 1816, however this vital force theory received a heavy blow
when Michel Chevreul found that soap, prepared by the reaction
of alkali with animal fatcould be separated into several pure organic
compounds,which he termed fatty acid. For the first time, one
organic substance (fat) was converted into other organic substances
(fatty acids and glycerin).
Animal fat NaOH Soap + Glycerin
H O
2
soap
H 3O
Fatty acid
In 1828, vital force theory again got a heavy blow when Friedrich
Whler prepared organic compound urea, of human urine from
inorganic compound ammonium cyanate.
Heat
NH 4 OCN
NH 2CONH 2
Ammonium Cyanate
Urea
By the mid of 1800s, the weight of evidence was clearly against

the vital force theory which led William Brande in 1848 to write
No definite line can be drawn between organic and inorganic
chemistry......... Any distinction........ Must for the present be merely
considered as matters of practical convenience calculated to further
the progress of students.
Chemistry toda y is unified. The same principles that explain
the simplest inorganic compounds also explain the most complex
organic ones. The only distinguishing characteristic of organic
chemistry is that all contains the element carbon. Nevertheless, the
division between organic and inorganic chemistry, which began

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for historical reasons, maintains its practical convenience... to further
the progress of students. So, in general
Organic chemistry is a branch of chemistry which deals with
carbon and its compounds
Atomic number
6
number of electrons
number of protons
12
Symbol
Atomic mass
From the periodic table we can easily find that it comprises of

seven periods and eighteen groups. First and second groups
elements are called as s block elements, thirteen to eighteen group
elements are called p block elements, third to twelve group elements
are d block while La to Lr which are downside are called as f block
elements.
When we carefully analyze the periodic table, it is clear that
position of carbon is in second period and fourteenth group and
carbon is a non-metal.
Carbon is the basic element for life but it forms its compounds
by combination with other elements such as H, N, O, F, Cl, Br, I, S,
P etc.
In Organic chemistry we mainly deal with
Structural determination How to find out the structures

of new compounds, even if they a re available only in
invisibly small amount.
Theoretical organic chemistry How to understand those

structures in terms of atoms and the electrons that binds
them together.
Re action me chanism How to find out how those

molecules reacts with ea ch other and to predict their
reactions.
Biological chemistry How to find out what nature does

and how the structures of biologically active molecules are
related to what they do.

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Section
Representation of Organic
Compounds
Organic chemistry is the study of compounds that contain
carbon but there are some other elements too associated with it such
as H, O, a nd N. We know that carbon is tetravalent in nature and
form covalent compounds by sharing of electrons by generally H,
F, Cl, Br, I, N, O, S and P. For sake of simplicity all halogens are
generally represented by X. In the study of molecules, you will notice
that oxygen has two covalent bonds, nitrogen has three covalent
bonds and carbon has four covalent bonds when they a re neutral.
Neutral hydrogen & halogens each have one covalent bond. If atoms
have more bonds or fewer bonds than the number required for
neutral molecule then they would have either a formal charge or an
unpaired electron. These numbers are very much important to
remember when you are first dra wing structures of organic
compounds because they provide a quick way to recognize when
you have made a mistake.
C
Cl
Br
This covalent bond may be of sigma ( )or pi ( ). Sigma bond

is formed by lateral overlapping of orbitals. It ma y be of s-s, s-p or

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p-p but pi bonds are formed by sidewise overlapping of p-p orbitals
in terms of organic chemistry.
+
s
s-s overlap
s-p overlap
yx
yx
z+
z
p orbital p orbital
p-p overlap along

the orbital axis
yy
+
Py
Py
p-p sideways overlap
As sigma bonds are strong as compared to pi bonds so generally

pi bonds are involved in chemical reaction with reagent, if present
in molecule. When we compare the bond strength of bonds formed
by s-p & p-p overlapping; p-p bond is stronger so generally s-p
bond break on treatment with suitable reagent, such as in case of
alkanes.
Organic chemistry concerns itself with the way in which these
atoms are bonded together into stable molecular structures and the
way in which these structures change during chemical reactions.
For this organic molecules are represented by several ways
1.
10
Lewis structure or dot structure Here valence electrons

in a molecule are represented as dots. When you draw
Lewis structure you must make sure that hydrogen atom
is surrounded by no more tha n two electrons, and C, O, N
and halogen (F, Cl, Br, I) atoms are surrounded by no more
than eight electrons. In other words, they must obey the
octet rule. The valence electrons not used in bonding are

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called as non-bonding electrons or lone pair of electrons.
Lewis structures are useful because they show us which
atoms are bonded together and tell us whether any atom
possess lone pair of electrons or have a formal charge.
....
H
HCH
H
2.
.... .
H
HCO H
H
Dash structure or Kekule structureIn this representation,

dash represents the bonds. Single dash represents a single
bond, double dash is used for double bond of any type such
as of C=C, C=N, C=S etc. and triple dash represent triple
bond of a ny type such as C C or C N, etc. In this
representation lone pair of electrons of hetero atoms (O, N,
S, and P etc.) may or may not be shown. This representation
gives complete structural formula of any molecule.
H H
HCCH
H H
H
H
H
C=C
HC
CH
3.
Conde nse d s tructure In condensed structura l

representation, dash structures can further abbreviated by
omitting some or all of the dashes representing covalent
bonds and by indicating the number of identical groups
attached to an atom by a subscript. The resulting expression
of the compound is now called a condensed structural
formula . For exa mple, CH3 CH 3 , CH2 =CH2 , CH CH,
CH3 OH. Similarly, CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3 can be
further condensed to CH3(CH2 )6 CH3.
4.
Bond line structure In this representation of organic

molecules, carbon and hydrogen atoms bonded to carbon
are not shown and the lines representing carbon-carbon
bonds are drawn in zigzag fashion.
Even without writing the hydrogen atoms we know that they

are there and we assume that any carbon atom that does not appear
to have its potential for four bonds satisfied is also attached to the
appropriate number of hydrogen atoms.

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11

We also rub out all the C representing carbon atoms and write
only zig-za g line assuming that every kink in the line represents
carbon atom.
Pentane
Cyclohexane
Benzene
As the functional groups are the key to the organic chemistry

so they are specifically shown if present so the only a toms
specifically written are heteroatoms such as oxygen, nitrogen,
halogens, which makes the functional groups, which we will discuss
later.
every kink in the these C atoms must also carry
chain represents 2 H atoms because only 2 bonds
a C atom
are shown for each atom
This H is shown because

it is attached to an atom
other than C
OH
O
end C have 3 H these C atoms must also carry
atoms
1 H atom because only 3 bonds all 4 bonds are shown to
are shown for each atom
this c atom so no H
atoms are implied
Organic molecules should be drawn to be realistic, economical

and clear so here are 3 guidelines, which help you make structure
more realistic.
Guideline 1- Draw the chain of atoms as zigzag.
Guideline 2 Miss out the hydrogen attach to carbon

atoms, along with the C-H bonds.
Guideline 3 Miss out the capital C representing carbon

atoms.
5. 3D structure Of course, all the structures we have drawn

give only an idea of the real structure of the molecules. For example,
the central carbon atom of CH3 CH(NH2 )COOH has tetrahedral
arrangement around it but so far we have completely ignored it.
Now we want to emphasize this fa ct, so for this 3D structure of
12

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molecules a re written using wedge-dashed projection and Fischer
projection.
COOH
H2 N
CH 3
H
A.
Wedge-dash projection or perspective formula:In this wedge-dash projection, the solid wedge (
) is
used to indicate a bond projecting above the plane of paper,
towards the observer and dashed wedge (
) is used to
depict the bond projecting below the plane of the paper
and away from the observer. The bonds lying in the plane
of the paper are depicted by using a normal line (
).
bonds are in
the plane of paper
(Normal line)
bonds are away

from the observer
(Dashed wedge)
H
H
H
bonds are towards the observer
(Solid wedge)
Sometime we could miss out the hydrogen atom and draw

something bit nea ter though slightly less realistic. Here we assume
the missing hydrogen atom is below or above the plane by looking
the 3 attachments. If two bonds a re in the plane and one is above
the plane then hydrogen must be certainly below the plane and
similarly if two bonds are in the plane and one is below the plane
then hydrogen must be above the plane.
NH2
H
COOH
CH 3
NH 2
or
CH 3
COOH
H is assumed to be below the plane

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13

NH2
H
COOH
CH 3
B.
NH 2
or
COOH
CH 3
H is assumed to be above the plane
Fischer projection:
In this projection molecule is represented by horizontal and
vertical lines. Groups on horizontal line are above the plane
(towards the observer) and groups on vertical line are
behind the plane (a way from observer) a nd point of
intersection of horizontal and vertical line is carbon.
H
H
C H
H 109.5
Perspective formula of methane
14

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Section
Reason for the formation of large

number of organic compounds
What makes the carbon so special?
What is it that sets carbon apart from all other elements in the
periodic table?
Why are there so many organic compounds?
The answer lies in carbons position in the periodic table. Carbon
is in the centre of second row elements
Li
Be
Elements of the second row of the periodic table

First think why molecules are formed from atoms? It is because
of the reason that atoms combines with same or with other atoms
to form molecule so as to complete its octet and attain lower energy
state and hence become stable. That is the reason why noble gases
are considered as inert gases, they generally do not combine with
itself or with other atoms because they have complete octet. But
what about other atoms? They have incomplete octet, so they must
combines with same or other atoms to form molecule for better
stability.

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15

Elements on the left hand side of carbon have less than 4
electrons in the valence shell (Li-1, Be-2, B-3) so they have more
tendencies to loose electron to a ttain noble gas configuration for
stability. Thats why they generally forms compounds with Li+, Be2+,
B3+ by losing 1 , 2 , 3 electrons respectively. Elements present
downside in the same group too have similar tendency as that of
Li, Be and B, hence form compounds in the following states; Na+,
K+, Rb+, Cs+, Mg2+, Ca 2+, Sr2+, Ba 2+, Al3+, Ga 3+,etc.
Elements on the right hand side of carbon have more than 4
electrons in the valence shell (N-5, O-6, F-7). To complete their octet,
valence electrons must be subtracted from 8 thats why the valency
of N is (8-5) i.e. 3, O is (8-6) i.e. 2 and that of F is (8-7) i.e. 1. It is
much easier to gain 3, 2, 1 electrons to complete their octet as
compared to loosing 5,6,7 electrons to complete their octet. So these
elements have more tendency to gain electrons and form compounds
in the following states; N3-, P3-, As3-, Sb3-, Bi3-, O2-, S2-, Se2-, Te2-, Po2-,
F-, Cl-, Br-, I- .
As elements present on the left ha nd side of carbon loose
electrons to form compounds and elements of right hand side gain
electrons to form compounds so compounds formed are ionic in
nature.
But think about carbon and the elements present down side,
which are present in the middle of each period and have equal
tendency to loose or gain electrons as they have 4 electrons in their
octet. This led carbon and other elements of this group (Si, Ge, Sn &
Pb) to share electrons with itself and other elements of periodic
table to complete octet. As these compounds are formed by sharing
of electrons so they are considered to be covalently bonded.
Carbon by sharing its electrons with other carbon a toms leads
to formation of long chain carbon compounds which may be single,
double or triple bonded, cyclic or acyclic, linear or branched. This
self-linking property of carbon is called catenation. All the atoms
of 14 th group show the property of catenation but it decreases down
the group because of weak overlapping due to large size and follows
order:
C > Si >> G e > Sn > Pb
16

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Carbon may also form multiple bonds with N, P, O, S etc.
forming large number of functional group, which we will discuss
later.
This is not the end of compound formation. Carbon forms many
abnormal compounds with elements of s, p & d blocks. So for sake
of simplicity we are constructing an organic chemists periodic table
with the most important elements emphasized.
Elements, which are in dark box, are generally involved in
making organic compounds along with deuterium (D), which is an
isotope of hydrogen (H).
1
H
Li Be
Carbon
At. mass = 12.01 At. radius = 67 pm
Valency = 4
E. Con. = [He]2s2p2
EN = 2.5
Structure = Hexagonal
Na Mg 3
18
13 14 15 16 17 He
B
9 10 11 12 Al Si
N O
F Ne
Cl Ar
K Ca Sc Ti V
Rb Sr
Cs Ba
Fr Ra
Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Rf Db Sg Bh Hs Mt Ds Rg
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
As there are large number of atoms in periodic table which have

valence electrons, atomic orbital of carbon may overlap with them
and share its electron to form large number of compounds. But for
tha t ma ny other fa ctors such a s siz e, activa tion energy,
electronegativity, electron affinity, catenation etc. are responsible
w hich all come u nder one w ord Position i.e. position of carbon
in the periodic table. This word position include everything
related with molecule formation therefore the main reason behind
large numbe r of organic compound is the position of carbon in
the periodic table.

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17
Section
Functional Groups
A functional group is an atom such as halogen (-X) or group of
atoms such as carboxylic acid (-COOH) in a molecule that gives the
molecule its characteristic chemical properties. They are the action
group or reactive site in a chemical reaction and the remaining
hydrocarbon part remains inert.Each functional group undergoes
characteristic chemical reaction so by recognizing them it is possible
to predict the reaction, which that molecule undergoes.
O
HO
CH3
Carboxylic acid
CH 3
Inert
hydrocarbon part
The concept of functional group is important for organic

chemistry due to 3 reasons:
18
Each functiona l group shows its characteristic chemical

reaction i.e. a particular functional group shows same
nature of chemical reaction when present in any compound.

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Functional group helps in nomencla ture of orga nic

compounds. Each functional group have a secondary suffix
for it such as oic acid for carboxylic acid, ol for alcohol, etc.
Functional group serves to classify organic compounds into

different classes or families i.e. Compounds with same
functional group belong to same class.
A molecule may have more than one functiona l group and are
ca lled as poly functiona l group compounds or simply poly
functional compounds and properties of each functional group may
be modified by the presence of other.
O
O
Ketone
HO
OH
Alcohol
Carboxylic acid
(Polyfunctional compound)
As carbon has 4 valencies therefore compounds with all single
bond, one double bond or with one triple bond may be formed with
any atoms, which satisfy octet rule.
Functional group with bond onlyCarbon may combine with those atoms which needs 1
electron for completing their octet (such as hydrogen or
halogen) or with some groups which require one electron
for completing octet such as alkyl group (CH3 , CH2 CH3,
etc.), hydroxyl group (OH), alkoxy group (OCH 3 ,
OCH2 CH3 ), amino group ( NH2 ), thiol group ( SH) or
thioether (SCH3) to form corresponding functional groups.
|
C H/C Alkane
|
C OH Alcohol
|
C X Alkyl halide
|
|
C SH Thiol
|

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19

C O C Ether
C S C Thioether
C N H 1 amine
C N C 2 amine
C N C 3 amine
|
Functional group with one bond-
Carbon forms 1 bond with many atoms such as O, N, S,

P and even itself leading to formation of different functional
groups.
Along C=O bond

O
H/C C H Aldehyde
H/C C X Acid halide
O
O
Carboxylic
Acid
H/C C OH acid
H/C C O C H/C anhydride
H/C C N H 1 amide
H/C C N C 2 amide
H/C C N C 3 amide
|
C C C Ketone
C
Along C=N bond
C/H
C/H
C=NH Imine
C/H
C=NR
C/H
R/H
R/H
C=NOH Oxime
R/H
20
Alkyl imine
(Schiff base)
R/H
C=NNH 2 Hydrazone

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C/H
C=NNPh Phenylhydrazone
C/H
C/H
C=NN
C/H
H NO
2
C/H
C/H
NO 2 2,4-Dimitrophenyl hydrazone
C=NNCNH 2 Semicarbazone
H
Along C=C, C=S and C=P bond

S=C=S Carbon disulphide
C=C
Alkene
Ph
C=PPh Methylene triphenylphosphene
Ph
Functional group with two bondC/H
H/C Alkynes
C/H C N Nitrile (Cyanide)

H/C
C Isonitriles (Isocyanide)
Carbon do not form 3 bonds with any atom
As the size of carbon is so small it do not form compounds

which have 3 bonds. This does not mean that no compound with
3 bonds exists. There are some d block elements, which form 3
bonds and tota l four bonds. In that case there are 1 , 2 & 1
bonds. This bond indicates the 3rd bond.
Sta ble quadruple bonds a re most common a mong the
transition metals such as rhenium, tungsten, molybdenum &
chromium. Some common examples are

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21

Chromium (II) acetateCr2 ( -O2 CMe) 4 (H2 O)2 ,
Potassium octachlorodirhenate (III), K2 [Re2 Cl8 ].2H2 O &
Potassium octachlorodimolybdate K4 [Mo2 Cl8]
Cl
Cl
2-
Cl
Cl
Re
Re
Cl
Cl Cl
Cl
Along with these functional groups there are some other

functional groups which are also encountered in organic chemistry.
So learn these too with very carefully so that your understanding
about functional group should be crystal clear. We have used R for
alkyl group, which mea ns simply the hydrocarbon part of the
molecule. It may be acyclic or cyclic but attachments are same as
given above or below. For more simplicity treat R as C so that you
should get a better observa tion in molecules. These additional
functional groups are
O
R
O
O
Carbonate ester
R
O
Carboxylate
R
Benzene
R
O
H
Hydroperoxy
O
R
S
O
O
R
Peroxy
R
H
Carbonothionyl
N
H
Imide
HO
OR
R
R
Hemiketal
22
HO
OR
R
H
Hemiacetal
RO
OR
R
R
Ketal
RO
OR
R
H
Acetal
RO
OR
R
OR
Orthoester

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RO
OR
RO
OR
Orthocarbonate ester
RN
R
3 Amine
RN
RN
H
1 Amine
H
2 Amine
R
RN
R
R
4 Ammonium salt
HN=N+ =N
Azide
R O
N
Cyanate
RN=C=O
Isocyanate
N=N
R
Azo
O
ON+
R
O
Nitrate
R N C
Isonitrile
RN
O
Nitro
S
R
S
Disulfide
O
RSR
Sulfino
O
O
Nitroso oxy
N
R
O
Nitroso
RSOH
O
Sulphonic acid
RSR
R
R
Sulfinile
O
Sulfonyl
R S
N
Thiocyanate
While identifying a functional group, look at its a ttachments

very carefully. Same group with different attachements may become
different functional group. You will be surprised to note that same

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23

group such as OH when attached to single bonded carbon is
alcohol, with benzene ring it is phenol, with C=N it is oxime and
with C=O it is called as carboxylic acid.
OH
OH
H3 C
H3 C
CH 3
Alcohol
Phenol
H3 C
N OH
H3 C
Oxime
H 3C
OH
Carboxylic acid
Similarly many other differences are observed just on the basis

of attachment such as
Cl
H3 C
Cl
H2 C
Vinyl halide
H3 C
CH 3
Alkyl halide
Cl
H2 C
Cl
Allyl halide
O
H3 C
H3 C
Cl
Acid halide
O
O
Ether
CH 3
H3 C
NH 2
CH 3 R
Amine
Acid anhydride
H3 C
Aryl halide
O
Ester
CH 3
NH 2
NH 2 R
R
R
Amide
Hydrazone
As whole organic chemistry is based on functional groups and

their interconversion so revise these functional groups regularly
for best picture of organic chemistry in mind.
24

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Section
Homologue & Homologous series

A series of compounds in which members have same functional
group but differ by one or more CH2 units (molecular weight 14
or multiple of 14) is called Homologous series (homos is Greek
word which means the same as). Members of homologous series
are called homologues. Homologues are the compounds with same
general formula and possess similar chemical properties due to
presence of same functional group (if any) i.e. all carboxylic acids
are homologues to each other starting from formic acid (HCOOH)
to any carboxylic acid with formula RCOOH where R is any acyclic
saturated a lkyl group. All alka nes starting from one carbon to
infinite carbon are homologues.
Example: 1
(a) CH 4
(b) CH3 CH3
(c) CH3 CH2 CH3
(d) CH3 CH2 CH2 CH3
Example: 2
O
(a) CH COH
3
Homologous sereis
of alkanes
(b)
CH 3 CH 2 COH

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25

O
(c)
CH 3 CH 2 CH2 COH
(d)
CH 3 CH 2 COCH 3
Here (a), (b), (c) are homologues but (d) is not homologue of (a),
(b), (c) as it has different functional group.
One point should always ke pt in mind that homologues

have same functional groups or in other word have same
type of chemi cal reactions so never i nsert CH 2 unit to any
bond which create a compound with different functional
group.
O
O
H
H
H 3C
H
O
O
Homologues
Insert CH 2 unit
O
H
CH2
H 3C
Homologues
Insert CH2 unit
Insert CH 2 unit
O
H
H 3C
O
Carboxylic acid
O
H 3C
CH 3
O
Ester
Not Homologues
As the compounds within a homologous series have

the same general molecular formula and the same
functional group (amines, alcohol, carboxyl acid, ester,
alkane, alkene, alkyne etc.), so they can be prepared
using similar methods. Such as
OH
O
Cu/Heat
CH 3
CH 3
We can prepare any methyl ketone from any alcohol having

CH3 CH(OH) (by changing the number of carbon in R) as
26

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Cu/heat is used to convert secondary alcohol into ketone,
which we will study later. Similarly we can prepare any
carboxylic acid from primary alcohol (by changing the number
of carbon in R) using KMnO4 /heat
O
OH
KMnO 4 /Heat
OH
Compounds within a homologous series show gradual

change in physical properties due to increased molecular size
and mass, caused by the longer carbon chains. For example,
ethane (CH3 CH3 ), has a higher boiling point than methane
(CH4 ). It is because of the reason that ethane molecule
experiences intermolecular attraction force than methane, as
in a large molecule, the electron cloud tends to be distorted at
random to a greater extent. Thus, the London Dispersion Forces
between ethane molecules are higher than that between
methane molecules, resulting in stronger forces of
intermolecular attraction, raising the boiling point.
By observing the relative number of carbon and hydrogen
atoms in acyclic alkanes it has general formula CnH2n+2 where
n is any integer. So if alkane has 1 carbon atom it must have 4
hydrogen atoms; if it has 2 carbon atoms then it must have 6
hydrogen atoms and so on. As we know that carbon forms
four covalent bonds and hydrogen forms only one so there is
only one possible structure for an alkane with molecular
formula CH4 (methane) and only one structure for an alkane
with formula C2 H6 (ethane). As the number of carbon increases
the number of possible structures also increases. For example
C4 H10 have two, C5 H12 have three, C6 H14 have 5, and C7 H16 have
9 possible structures. This number increases very rapidly as
the number of carbon increases such as C10 H22 have 75 and
C15 H32 have 4347 possible structures which we will call later as
constitutional isomers.
As C15 H32 have 4347 possible structures but all are having
same molecular formula so they are simply constitutional
27
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isomers which we will study later but starting from CH4 , C2 H6,
C3 H8 to C15 H32 they differ (CH2 )n unit, so they all are considered
as homologues and have same nature of chemical reactions
and method of preparation. We use only the letter R for general
alkyl group (alkane 1H) starting from 1 to infinite.
Here is a table, which helps you to understand homologue
better with general formula
Homologous
General formula
Example
series
Functional group if any
Alkane
CnH2n+2 (n=1)
CH4 , n=1
Alkene
CnH2n (n=2)
C2 H4 , n=2
Alkyne
Alcohol
CnH2n-2 (n=2)
CnH2n+1 OH (n=1)
C2 H2, n=2
CH3 OH, n=1
Carboxylic acid
CnH2n+1 COOH (n=0)
CH2 O2, n=0
Carbohydrate
Cn(H2 O)y (n=3)
C6 H12 O6 n=6
There are some direct chemica l reactions from which we can

convert one member of a homologous series to the next member
and such reactions are called as homologation reactions that we
will study in chemical reactions
O
O
O
R
SOCl 2
CH 2 N 2
R
OH
R
Cl moist Ag 2O
OH
Carboxylic acid
Next higher homologue of

carboxylic acid
28

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Section
Nature of C, H & Functional groups

When you carefully look over the organic compounds then you
will find that carbon atoms are bonded with other carbon atom or
some other atoms such as H, N, S, P, O, X etc. to form molecule.
This difference in attachment leads to difference in rate of chemical
reactions. So it is important to analyze carefully the atoms directly
attached to carbon in a ny orga nic molecule. On the ba sis of
attachment of carbon with other carbon atoms, the carbon atoms in
organic compounds are classified into four types
Primary carbon (1 0 C) Carbon attached to none or one

carbon is called as primary carbon. In case when no other
carbon is attached then such carbon is sometime called as
super primary carbon such as CH4.
Secondary carbon (20 C) Carbon attached to two carbons

is called as secondary carbon.
Tertiary carbon (3 0 C) Carbon attached to three carbon is

called as tertiary carbon.
Quaternary carbon (4 0 C) Carbon attached to four carbon

is called as quaternary carbon.
These carbon atoms may be in open chain or in ring; they may

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29

be neutral, charged or in radical form. But the important part is the
attachment with other atoms and for simplicity they are generally
written with single bonded forms. These forms may be derived from
alkane, alkyl halide, alcohol, ether, amines, thioethers, thiols, etc.
1
H3 C
CH 3
3
1 CH
CH 3
3
H3 C
CH 3
H3 C
H3 C
CH 3
CH3
2 1
CH 3 CH 3
1
Hydrogens attached a t prima ry, secondary, tertia ry

carbons are called primary, secondary & tertiary hydrogen
respectively. It is important to note that carbons are of four
types but hydrogens are only of three types, as quaternary
carbon does not have any hydrogen.
Only in case of methane primary carbon have 4 H but in all

other alkanes and cycloalkanes each 10 , 2 0 , 3 0 carbon have
3, 2, 1 H respectively. To find out tota l number of 1 0 , 2 0 ,
3 0 ,4 0 carbon and 1 0 , 2 0 , 3 0 hydrogens you have to count all
the carbons or hydrogen of similar types.
In organic compounds other than alkane or cycloalkanes

you must be more careful in reporting the number H as
individual carbon may have any number of H ranging from
3 to 0 as these hydrogen are already repla ced with some
other atoms or groups.
1
CH3
H3 C N 2
CH3 O
CH 3
1H=15
2H=5
3H=0
30
CH 3
1
O
H3 C
Cl 2
3
1
2
Cl
S Br
1H=5
2H=8
3H=0
2
H3 C
H
N
NH
1
HS 2 NO 2
1H=4
2H=2
3H=0
In organic chemistry some functional groups are formed

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just by repla cement of one hydrogen, with an atom or
groups such as alkyl halide, a lcohol, primary amine, thiol,
nitro compounds, sulphonic acid, etc.
OH
H3 CCH 3
Alkane
H
+OH
H3 CCH 3
Alkane
H
+NH 2
H3 CCH 3
Alkane
H
+SH
H3 CCH 3
Alkane
H
+NO 2
H3 CCH 3
Alkane
H
+SO 3H
H 3C
Alcohol
NH 2
H 3C
Primary amine
SH
H3 C
Thioalcohol
NO 2
H 3C
Nitro alkane
SO 3 H
H 3C
Alkane sulphonic acid
So a lkyl halide formed from replacement of prima ry H,

secondary H and tertiary H are called as primary alkyl halide,
secondary a lkyl halide and tertiary alkyl halide respectively.
CH3
Cl
Cl
H3 C
Cl
1 Alkyl halide
H3 C
CH 3
2 Alkyl halide
H3 C
CH 3
3 Alkyl halide
Simila rly alcohol formed from replacement of primary H,

secondary H and tertiary H is called as primary alcohol, secondary
alcohol and tertiary alcohol respectively.

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31

OH
H3 C
OH
1 Alcohol
CH 3
OH
CH 3
H3 C
2 Alcohol
CH 3
CH 3
OH
2 Alcohol
OH
OH
1 Alcohol
H3 C
CH 3
3 Alcohol
3 Alcohol
But some functional groups are formed by chemical reactions

of two same or different functional groups such as ether, secondary
amine, tertiary amine, thioether, ester, amide, acid anhydride, etc.
H 3C
Alcohol
CH 3
O
H+H
O
H 2 O
Alcohol
O
Ether
CH3
H 3C
O
H+H
Carboxylic acid
H 2 O
Carboxylic acid
CH 3
H3 C
O
H+H
Carboxylic acid
H 2 O
H3 C
CH 3
CH3
H 3C
H+H
Carboxylic acid
O
Ester
Alcohol
O
O
H3 C
O
CH 3
Acid anhydride
32
CH 3
H 3C
NH
H 2 O
Primary amine
H3 C
NH
CH 3
Primary amide

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CH 3
H 3C
NH 2 + H NH
NH 3
Primary amine
Primary amine
CH 3
H3 C
NH 2 + H
Primary amine
CH 3
H 3C
NH
Secondary amine
CH 3
H 3C
N
NH 3
CH 3
Secondary amine
H 3C
Tertiary amine
So be careful in reporting your answer for amines or amides.

Secondary alcohol is that in which OH is attached to
secondary carbon but secondary amine is that in which
nitrogen is directly attached to two carbon a nd one
hydrogen. Tertiary amine is one in which N is directly
bonded to three carbon. So secondary or tertiary amine may
be present over primary, secondary or tertiary carbon.
NH 2
H3 C
NH 2
1 Amine
H3 C
1 Amine
CH 3
2 Amine
3 Amine
NH
NH
2 Amine
2 Amine
CH 3
3 Amine
CH 3
NH 2
H3 C
CH 3
1 Amine
NH
2 Amine
N
3 Amine
3 Amine

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33
Section
Saturated & unsaturated molecules

with important positions
In organic chemistry when we look over the molecules we will
find that some molecules are only single bonded but some molecules
are multiple bonded and that multiple bond may be of many types
such as double bonds of C=C, C=N, C=O, C=S or triple bonds of
C N or C C. To differentiate these compounds word saturated
and unsaturated is used.
To understand these terms, take a glass full of water and add a
spoon of sugar in it and stir it with spoon. You will find that whole
sugar dissolves in it. But when you continuously go on adding
spoons of sugar in it and stirring it then after some time you will
find that dissolution stop and sugar settles at the bottom of it. At
that time you will say that no more sugar is dissolving in it i.e. it is
saturated. Similarly when no further bond can be added to a
molecule at room temperature then such compounds are called as
saturated compounds and if further bonds can be added in it then
they are called as unsaturated compounds. As we know that single
bond has no te ndency to add anything at room temperature and
have only tendency to substitute some atom or group so they are
considered as sa tura ted compounds and multiple bonde d
compounds have tendency to add bond so they are considered as
unsaturated compounds.
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A B C
A C B
A B C D
A B
Substitution reaction
Addition reaction
C D
Saturated compounds may be cyclic or acyclic; may be only of

carbon and hydrogen or may ha ve some hetero atoms such as
halogens, nitrogen, oxygen or sulphur. The multiple bond may be
of any form such as C=C, C=N, C=O, C=S, C N or C C with or
without rings.
Example of saturated compounds areCl
H3 C
H3 C
CH 3
O
H3 C
OH
H3 C
CH 3
H3 C
CH 3
S
NH 2
H3 C
CH 3
CH 3
SH
CH 3
H3 C
CH 3
OH
O
NH
N
H
Example of unsaturated compounds areO
H3 C
CH 2
H3 C
H3 C
O
H3 C
CH
CH 3
H3 C
O
OH
H3 C
NH 2
O
H3 C
NH
OMe
OH
O
N
If compounds are saturated with presence of only carbon &

hydrogen then such compounds a re ca lled a s sa tura te d

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35

hydroca rbon, such as alkane and cycloalkane but if any hydrogen
in it is replaced with any other atom or group such a s Cl, OH,
NH2 , SH then they are considered as derivatives of saturated
hydrocarbons. Similarly if compounds are unsaturated and have
only ca rbon & hydrogen, they are called as unsa turate d
hydrocarbon such as alkene, alkyne, cycloalkenes & cycloalkynes
but if hydrogen in it is replaced with any atom or group then they
are considered as derivatives of unsaturated hydrocarbon.
CH3 CH 2 CH 3
Alkane
CH 3 CH 2CH2 Cl
Derivative of alkane
CH2 =CHCH3 ClCH=CHCH3

Alkene
Derivative of alkene
When you a gain carefully analyze the functional groups you

will find that some functional groups have presence of carbon within
it such as nitrile (CN), aldehyde (-CHO), ketone (-CO-), carboxylic
acid (-COOH), acid halide (-COX), acid anhydride (-COOCO-), ester
(-COOC), amide (-CONH2 ) etc but some functional groups do not
have carbons such as amine (NH2 ), alcohol (-OH), thiol (-SH), nitro
(-NO2 ), Sulphonic acid (-SO3 H), ether (-O-), thioether (-S-), etc.
In organic chemistry some common positions such as zero (0),
alpha ( ) , beta () , gamma ( ) , delta () , and epsilon ( ) have
been commonly encountered so we must have a clear cut picture of
it too.
If any functional group do not have carbon in it then the carbon
directly attach to it is given the position alpha followed by beta,
gamma, delta and epsilon to next carbons in sequence such as

H3 C
H3 C
NO 2
36
Cl
CH 3

H3 C
H3 C
OH
CH 3

H3 C
H3 C
SO 3 H

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NH 2
CH 3
O
CH 3

H3 C
CH 3
N
+
N
H3 C
CH 3
CH 3
CH 3
+
S
CH 3
CH 3
But if any functional groups have carbon in it then that carbon

is give position zero followed by alpha, beta, gamma , delta and
epsilon to next carbons in sequence such as
O
O

H3 C
H3 C
0 H
0 OH
H3 C
H3 C
0 Cl
H3 C
CH 3
0 COOCOCH3
CH 3
0 COOCH 3
0
CH 3
O
O
0
This zero (0), alpha ( ) , beta () , gamma ( ) , delta () , and

epsilon ( ) have very much importance in organic chemistry as
many named reactions such as Aldol reaction, Cannizzaro reaction,
Claisen rearrangement, HVZ reaction etc involve these terms, which
we will study later.
Aldol condensation- When aldehyde having alpha
hydrogen is treated with base, it first give beta hydroxy aldehyde
which later looses a water molecule to form alpha,beta-unsaturated
aldehyde as a product.
O
CH 3 CH
OH
Base
Aldehyde
having H
CH3 CHCH2 CH
0

-Hydroxy
aldehyde
CH 3 CH=CHCH
0
,-unsaturated
aldehyde

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37
Section
Hybridization
When we carefully look over the organic molecules we will find
that some carbon atom is single bonded while some others are
multiple bonded. These single or multiple bonds create some fixed
shape or geometry in molecule such as linear, planner, tetrahedral,
etc. Molecular geometry or molecular structure is the 3-dimensional
arrangement of the atoms that constitute a molecule. It determines
several properties of a substance including its reactivity, polarity,
phase of ma tter, color, magnetic properties, and even biological
activities. The molecular geometry can be determined by various
spectroscopic methods & diffraction methods such as Infrared (IR),
microwave & Raman spectroscopy can give information about the
molecule geometry. X-ray crystallography, Neutron diffraction and
Electron diffraction can give molecular structure for crystalline
solids based on the distance between nuclei and concentration of
electron density. Gas electron diffraction can be used for small
molecules in the ga s phase. Nuclear magnetic resonance (NMR)
& Frste r (Fluorescence) resona nce ene rgy tra nsfer (FRET)
methods ca n be used to determine complementary information
including rela tive dista nces, dihedra l a ngles, a ngles, a nd
connectivity. Molecular geometries a re best determined a t low
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temperature and can be different as a solid, in solution, and as a
gas.
As you learned earlier that these single or multiple bonds are
formed by overlapping of atomic orbitals either by axial overlapping
or by lateral overlapping, molecular geometries ca n be specified in
terms of bond lengths, bond angles and torsional angles.The bond
length is defined to be the average distance between the centers of
two atoms bonded together in any given molecule. A bond angle is
the angle formed between three a toms across at least two bonds.
For four atoms bonded together in a chain, the torsional angle is
the angle between the plane formed by the first three atoms and
the plane formed by the last three atoms.
To expla in the shape of any molecule new concept of
hybridization was proposed which is mixing of atomic orbitals of
same or nea rly same energy and redistribution of energy to form
new hybrid orbitals of equa l energy a nd sa me sha pe. So
hybridization is simply a mathematical approach to explain the
shape of any molecule i.e. if a molecule is tetrahedral then its
tetrahedral shape is explained by sp3 hybridization and similarly if
a molecule is planner then to explain it we have to use the concept
of sp2 hybridiza tion and for linear molecules sp hybridization. In
organic chemistry when we have to find out hybridiza tion of any
atom always count the number of sigma bond and lone pair of
electrons present on it (if any).
180
120
109.5
Tetrahedral shape
Planner shape
A
Linear shape
As the shape of atomic orbitals is derived from Schrodinger wave

equation so it is purely a mathematical term. Some shapes commonly
encounted in chemistry are

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39

(A) Linear shape
(B) Trigonal planner
(C) Bent shape
(D) Tetrahedral shape
(E) Trigonal pyramidal
(F) Trigonal bipyramidal
(G) Seesaw
(H) T shaped
(I)
(J)
Octahedral
Square pyramidal
(K) Square planar
(L) Pentagonal bipyramidal
(M) Pentagonal pyramidal
(N) Planner pentagonal
(O) Square antiprismatic
(P) Tricapped trigonal prismatic
As organic compounds are carbon containing compounds and

carbon has only s and p orbitals so the hybridization commonly
observed in organic chemistry a re sp, sp & sp. To ca lculate
hybridization of any atom always counts the number of sigma bonds
and lone pa ir of electrons present on it.
If the sum of number of sigma bonds and lone pair of

electrons = 2, atom have sp hybridization.
If the sum of number of sigma bonds and lone pair of

If the sum of number of sigma bond and lone pair of

There is no role of positive cha rge in ca lcula ting the

hybridization of any atom as that contains no electrons or bonds.
Negative cha rge is also considered as 2 electrons system similar to
lone pair.
H
sp 3
H
H
H
sp3
sp
H3 C OH
H2 C
sp 2
sp2
sp
sp2
H2 C C CH 2
O
sp3
sp 3
sp3
3
sp2
sp
CH 3
sp2
sp2
sp
sp
sp 2
H2 C
sp3
sp2 sp
sp2
CH 2
CH
sp
sp2
sp2
sp2
sp
sp 2
sp2
As we told you earlier that it is simply a mathematical approach
40

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to explain the shape of molecule so there may be some violation of
it. These violations are commonly of three types:
If system have A=B-C, where C have lone pair of electrons

then one of the lone pa irs present is not counted for
hybridiza tion and geometry along C is planner & its
hybridization will be either sp or sp
H2 C
..
NH
H2 C
sp 2
.SH
. sp
..
H2 C
If system have A=B-C, where C have negative charge then

ve charge is not counted for hybridization and geometry
along C is planner & its hybridization will be either sp or
sp
H2 C
.OH
. sp
..
sp 2
CH
H2 C
.O.
sp 2
H2 C
..NH
sp 2
You must remember these two structures where all atoms

are sp but molecule is not planner at all.
(Non Planner)
or
Cyclooctatetraene = COT
or
10 Annulene
Overall Tub shaped

H
(Non Planner)
Hydrogens present in the central

carbon disturbe the plane

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41
Section
10
Classification of organic compounds
Up to this point you are familiar with the common functional
groups, sa tura ted a nd unsa turated compounds with their
hybridiza tion and shape so now we can cla ssify the organic
compounds into different categories on the basis of their shape and
stability. Organic compounds are divided into two classes- Acyclic
or aliphatic & cyclic compound. Acyclic compounds or aliphatic
compounds a re those which do not have any ring. The word
aliphatic comes from aleiphar which mean fat or oil. Here carbon
atoms can be joined together in straight chains or branched chains.
They can be saturated, joined by single bonds (a lka nes), or
unsaturated, with double bonds (alkenes) or triple bonds (alkynes).
Besides hydrogen, other elements can be bound to the carbon chain,
the most common being oxygen, nitrogen, sulfur and halogen. The
simplest aliphatic compound is metha ne (CH4 ). If a liphatic
compounds are cyclic in nature then such compounds are called
as alicyclic (Aliphatic + cyclic) such as cycloalkanes, cycloalkenes,
cycloalkynes, cyclic esters, cyclic ketones etc.
42
Aromatic compounds are the most important class of

organic molecules due to their extra stability. Many natural
products such as DNA, RNA, hemoglobin, chlorophyll,
medicines, and polymers are aromatic in nature. For a

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compound to show aromatic nature it must follow these
four conditions.
(I)
Compounds should have at least one ring.
(II) Each atom of the ring should have sp or sp hybridization,

no matter it is made up of C, N, S, O or a ny other atom.
(III) The ring should be planner or nearly planner, so that
effective overlapping of pi bond is possible.
(IV) The ring should follow Huckels rule i.e. the ring must have
(4n + 2) electrons, where n is any number starting from 0
to . If the value of n=0, ring must have 2 electrons; for
n=1, 6 electrons must be present a nd so on.
If any compound violates any of the above conditions then it
will not be considered as aromatic and not get extra sta bility. For
example, Hexa-1,3,5-triene (CH2 =CHCH=CHCH=CH2 ) follows
last three conditions but violates the first one so is not an aromatic
compounds.
Aromatic compounds are further of two types one with

attachment of benzene nucleus and other with absence of
benzene nucleus. Those which contain benzene ring are
called benzenoid while those which do not ha ve benzene
ring are considered as non-benzenoid.
Cyclic system may be homocyclic (carbocyclic) where each

atom of the ring is made up of carbon or may be heterocyclic
where at least one atom of the ring is hetero atom such as
N, S or O.
Examples of 2 Pi electrons aromatic system:

+
HO
NC
CN
HO
NC
H3 C
Ph
CN
CH 3
Ph
+
+
Ph
Ph

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O
Ph
Ph
O
+
+
43

Examples of 6 pi electronsaromatic system:
CH 3
H 3C
+
N
Fe
Dimethyl fulvene Calicene
Ferrocene
+
CH 2
Tropylium ion
Group
+
CH 2
Substituted
Benzene
Examples of heterocyclic 6 pi electron aromatic system:

H
N
H
N
Pyrole
Furan
Thiphene
N
Imidazole
N
Pyridine
CH 3
N N
O
Pyrylium ion
Nicotine
NH 2
NH 2
COOH
N
N
Pyrimidine
44
N
Niacin
N
O
N
N
H
HO
Cytosine

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O
HN
O
OH
HN
N
N
H
HO
OH
CH 3
N
H
CH 3
HO
Thymine
Uracil
Examples of 10 pi electronsaromatic system:

N
Iso quinolene
N
Quinoline
Naphthalene
NH
S
Benzothiophene
Benzofuran
Indole
N
Indenyl anion
NH
N
N
Purine
N
N
NH
H2 N
NH
N
Adenine
N
N
N
NH 2
Azulene
Indole
NH
NH
H 2N
N
OH
NH
N
Guanine
Examples of 14 pi electron aromatic system:
Anthracene
Phenanthrene
Phenalenyl anion

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45

+
(14) Annulene
Anti- Aromatic compounds are very unstable compounds

at room temperature so they either dimerize or trimerise to
become alicyclic one.
Theoretica lly Antia roma tic compounds follow these 4

conditions:
Compounds should have at least one ring.
All atoms of ring should have sp or sp hybridization, no

matter it is made up of C, N, S, O or any other atom.
The ring should be planner or nearly planner, but it is

important to note that there no effective overlapping of pi
bond is observed.
Compound will not follow Huckels rule and ring must

have (4n) electrons, where n = 1 to H
Some common examples of anti aromatic compounds are:
Cycloprop-2-enide ion
Cyclobuta-1, 3-diene
+
Cyclopenta-2,4-dienylium ion
46

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Section
11
Baeyers strain theory

When we carefully look over the cyclic saturated compounds
we find that each atom is sp3 hybridized so it must have bond angle
1 09 0 2 8 but in cycloa lka nes this angle is ma thema tica lly
180-(360/n) where n is the number of atoms making ring i.e. in
Cyclopropane this angle is 600 ; in Cyclobutane it is 90 0 and so on.
This difference in desired bond angle and real bond angle causes
strain in bond which affects the reactivity as well as stability of
molecule. Greater is the deviation from the theoretical angle greater
is the strain. To calculate the distortion or strain in ring we assume
the atoms of ring in a plane, such as in cyclopropane, all the 3 carbon
atoms occupy one corner of an equilateral triangle with bond angle
60 0 . As two corners bent themselves to form bond so strain too is
divided equally. So strain in cyclopropane will be (1090 28 60 0 )
= +24 0 44.
10928'
2444'
60
2444'
Deviation of bond angle in cyclopropane

from normal tetrahedral angle

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47

Distortion or strain = (109 0 28 bond angle of ring). So angle
strains in some cycloalkanes a re listed in the ta ble below.
Compound
No. of C
Angle between
Distortion
in the ring
the Carbon atoms
or strain
Cyclopropane
600
24 0 44
Cyclobutane
900
9 044
Cyclopentane
1080
0 044
Cyclohexane
1200
-5 0 16
Cycloheptane
1280 34
-9 0 33
Cyclooctane
1350
-12 0 62
From the table it is clear tha t cyclopropane has the maximum

distortion, so it is highly strained molecule and consequently more
reactive than any of the monocyclic alkanes, which is clear from
the reaction that ring can be opened very easily to relieve strain on
reaction with Br2 , HBr or H2 /Ni at high temperature. In contrast,
cyclopentane & cyclohexane have least strain so they are found more
readily and are very stable as compared to cyclopropane.
Baeyer strain theory satisfactorily explains the typical reactivity
and stability of smaller rings (from C3 to C5 ) i.e.
Cyclopropane< Cyclobutane < Cyclopentane
(stability order)
but not valid for cyclohexane onwards because the strain again
increases with the increase in number of carbon atom but actually
large rings are more stable. So molecular orbital theory is also
considered according to which covalent bond is formed by coaxial
overlapping of atomic orbitals. The greater is the extent of overlap
the stronger is the bond formed. In case of sp3 carbon, C-C bond
will have maximum strength if the C-C-C bonds have the angle
109 0 28. If cyclopropane is an equilateral triangle then the bond angle
of each C-C-C bond would be 60 0 . Therefore it was proposed by
Couson that in cyclopropane the sp3 hybridized orbitals are not
present exactly in one straight line due to mutual repulsion of orbital
of these bonds resulting thereby loss of overlap. This loss of overlap
48

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weakens the bond and is responsible for its instability and strain in
molecule. Similarly, in case of cyclobutane, there is a lso loss of
overlap but the loss is less than in cyclopropane, so cyclobutane is
more stable than cyclopropane. Overlapping of orbitals in large ring
compound (5 or more carbon atoms) is however much better which
accounts for the greater stability of such compounds.
H
H
C
H C
H
C H
H
It is natural that when a molecule has strain within it, it will

affect the stability of molecule. The stability of molecule can be
calculated easily by measuring heat of combustion which will give
the measure of total strain and thermochemical stability which can
be calculated mathematically.
Total strain = (No of carbon atom in the ring observed heat
of combustion/CH 2 ) - obse rve d he a t of
combustion/CH 2 for n alkane.
Experimental data of total strain for different cycloalkanes
No of C
Heat of combustion
Total
atom in ring
KJ/CH 2
strain in KJ
697
120
685
112
664
35
659
12
662
35
8-11
661-665
32-88
12-onwards
657-661
0-48
From the da ta above it is clear that strain decreases from C3 to

C6 i.e. stability increases, but stability again deteriorates from C7 to
C11 ring system but interestingly increases from C12 and attain the

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49

same stability of six membered ring. According to this theory, the
carbon atoms in 5 membered and smaller rings can lie in one plane
as explained by Baeyer but Sachse suggested that in six membered
and higher rings the carbon atoms are present in different plane i.e.
the ring is puckered. In this wa y the normal valency angle 1090 28
is retained and the ring produced is completely strainless. Thus he
proposed that cyclohexane exist in two puckered forms as boat and
chair form in which chair form is more stable. These forms are
readily interconvertible through half chair and twist boat forms
simply by rotation about the single bonds which we will study later
in conformation.
Chair
Half chair
Twist boat
Boat
These forms of cyclohexane are to give a real picture of it but on

paper we commonly ma ke its planner form.
50

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Exercise
01
Subjective Approach
You cant mug-up organic chemistry because theres too
much of it. You can remember trivial things like name of compounds
but that doesnt help you to understand the principle behind the
subject. You have to understand the principle because the only
way to tackle organic chemistry is to learn to work it out. That is
why we are first providing you some questions so tha t your
understanding about the topic should be increased. These problems
will set you on your way but they are not the end of the journey, as
here you a re beginning your journey to understa nd organic
chemistry.
The problem would be of little use to you when you could
not check your answers. For the maximum benefit, you need to solve
all the problems without looking the answers. Then you should
compare your answers or suggestions with ours before going to
next chapter. If any answer is mismatch then darken those question
numbers with red pen and again have a microscopic look over it
and its theory and correct it before proceeding further. Here starts
the first set of 60 questions
01. What is organic chemistry? Write at least 4 characters which
distinguish organic compounds from inorga nic compounds.

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51

02. What is the reason behind the formation of large number of
organic compounds?
03. Which organic compound was first prepared in laboratory?
04. Which a tom is the centre of a ttraction in whole organic
chemistry?
05. What is the position of carbon in the periodic table?
06. What is Octet Rule?
07. What is electronegativity and electron affinity?
08. What is the electronegativity value of C, H, N, O and F in Pauling
scale?
09. What is the valency of C, H, N, O and F?
10. What is the symbol for the representation of all halogens?
11. Write C-F, C-Cl, C-Br and C-I bonds in decreasing order of their
bond strength.
12. Draw structures of single bonded hydrocarbons with 6 carbon
atoms having linear, branched and cyclic frameworks.
13. What is wrong in given structure? Suggest better way to
represent the molecules?
H O
H
NH
H
H H
N
OH
H3 C
H
NH 2
14. What is the carbon carbon bond length in ethane, ethene, ethyne
& benzene?
15. Which bond is weaker in C-H & C-C bond of alkane?
16. Write the decreasing order of bond strength of carbon- carbon
single, double a nd triple bond?
17. How many electrons are involved in formation of single, double
and triple bond?
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18. What are isotopes? Comment on the isotopes of carbon &
hydrogen?
19. Oxygen has atomic number 8 and have 3 isotopes with molecular
mass 16, 1 7 & 18 respectively. How many protons, electrons
and neutrons does each of these isotopes have?
20. What is Aufbau Principle?
21. What is Pauli Exclusion Principle?
22. What is Hunds Rule?
23. What is the ba sic difference between Principle and Rule?
24. Potassium has atomic number 19 and atomic mass 39, with one
unpaired electron in its valence shell. Which orbital does the
unpaired electron occupy?
25. Write electronic configuration of F (Atomic no. 9), Cl (Atomic
no. 17), Br (Atomic no. 35) & I (Atomic no. 53)?
26. What are ionic, covalent, co-ordinate & polar covalent bonds?
27. Which of the following among given compound have most and
least polar bond? NaI, LiBr, Cl2 , KCl
28. What is dipole moment?
29. What is formal charge and how it is calculated in molecules
such as H3 O+?
30. Write the Lewis structures of formic acid, formaldehyde &
methanol?
31. Determine the partial positive charge on oxygen atom in a C=O
bond if it has bond length 1.22 and bond dipole moment 2.30
D?
32. Predict the relative length of HF, HCl, HBr & HI bonds?
33. Use the symbol and to show the direction of polarity of the
bonds shown in given compounds?
CH3 -Cl, CH3 -NH2 , HO-Br, I-Cl, CH3-OH, CH3 -MgBr & NH2 -OH
34. Name at least 10 organic compounds which make your life easy?

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53

35. What is functional groups and why they are important in organic
chemistry?
36. Name the compound in which -OH group is attach to tetrahedral
carbon, C=C, aromatic ring and C=O group?
37. Convert these condensed form of molecules into bond line
structures.
(A) C6 H5 CH(OH).(CH2 )4 COC2 H5
(B) O(CH2 CH2 )2O
(C) (CH3 O) 2 CHCH=CHCH(OMe)2
38. Draw bond line structures for these compounds showing the
hydrocarbon framework clearly and showing all the bonds
present in functional groups
(A) AcO(CH2)3 NO2
(B) MeO2 .CH2 .OCOEt
(C) CH2 =CH.CO.NH(CH2 ) 2 CN

39. What are the probable formula s for the following compounds
GeCl?, AlH?, CH?Cl2 , SiF?, CH3 NH?, AlCl?, CF2 Cl?, NI? & PH?.
40. Why cant organic molecule having formula C2 H7 , C2 H7 N &
C3 H5 Br2 exist at room temperature?
41. Fill the non bonding valence electrons if present that are missing
from the following bond line structure.
O
O
H3 C
CH 3
H3 C
H3 C
CH 3
Cl
O
H3 C
H3 C
CH 3
42. Convert the following molecula r formula s into bond line

structures leaving lone pair electrons as they are assumed to be
present there
(A) C3 H8
(B) CH5 N
(D) C2 H4 O (3 possibilities)
54
(C) C2 H6 O (2 possibilities)
(E) C3 H9 N (4 possibilities)

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43. Sodium methoxide (NaOCH3 ) contains both covalent and ionic
bonds. Indicate the linkage which gives a clear cut picture of it.
44. What are homologues? Write at least 4 homologues of methane,
formaldehyde, acetone and formic acid each.
45. How are molecules with a single functional group represented?
Write a general formula of alkyl chloride, alkyl alcohol, and alkyl
carboxylic acid?
46. How do the compounds in homologous series differ in molecular
formula, physical & chemical properties?
47. Name the word used for sulphur analogs of alcohol & ether?
48. Find out the functional groups present in following compounds
SH
H 3C
SH O
CH 3
SH
Compound with worst smell
I
H 3C
CH 3
CH 3
Compound with worst smell
II
O
O
Olean sex pheromone of olive fly
(III)
N
CH 3
N CH 3
Compound from coffee
(V)
O
Compound from cakes & biscuits
(VI)
O
OH
H 3C
H 2C
Cl
Vinyl chloride
(IV)
O
Corylone
ceramel roasted protein
(VII)
OH H
N
CH 3
CH 3
Zeneca's tenormin
For treatment & prevention
of heart deasese
(VIII)

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55

MeO
OH
CHO
HO
Vanillin of vanilla
(IX)
N
Pyridine
(X)
N +2 Cl
Aniline
(XII)
H 3 C CH3
OOH
Cummene Cummene peroxide

(XV)
(XVI)
O
H H
N
O
Phenol.
(XI)
H3 C CH 3
CH 2
Diazonium salt Styrene

(XIV)
(XIII)
NH 2
CH 3
CH 3
COOH
O
Penicilin
(XVII)
CH 3
Nicotine
(XVIII)
CH 3
COOH
Aspirin
(XIX)
EtO
H
N
HO
CH 3
O
Paracetamole
(XX)
H3 C
S
N
NH
N
N
O
O
H 3C
Pfizer's sildenafil (Viagra) CH 3

(XXI)
CH 3OH
CH 3 H
H
H
O
Testosteron (Hormone)
(XXII)
56
O
H3 C N
O
O
Cocaine O
(XXIII)

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CH3

O
H2 C
OH N
O
HO
H 3C
N
Quinine
(XXIV)
NH
O
CH3
HO
Fialuridine (Anti viral compound)
(XXV)
OH
H3 C
CH 3
Cl
Chloroxylenol
(XXVI)
HN
NH
O
Indigo dye
(XXVII)
Cl O
O
NH
S NH 2
O
OH
Furosemide (Sulpha drug)
(XXVIII)
49. Give the structural formula for a 3 carbon compound containing

each of the following functional groups
(a) C=C
(b) C C
(c) Cl
(d) OH
(e) CHO
(f) C=O
(g) C N
50. Draw one possible structure for each of these molecules selecting
any group of your choice for the wild card substituents for
R1
R
A
Ar2 O
Ar1
Ar3

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57

51. Find the total number of primary, seconda ry, tertiary and
quaternary carbon in given molecule.
H3 C
H3 C
CH 3
H3 C
II
CH3
OH Cl
H2 N
H 3C
CH 3
CH 3 CH 3
H3 C
H3 C
H3 C
III
CH 3
CH 3
IV CH 3
O CH
3
V
CH3
HN
CH3
VI
OCH3
CH 3
CH 3
CH 3
Br
CH 3
N
H3 C
VII
CH 3
CH 3
OH
O
N
O
VIII
52. Find the total number of primary, seconda ry a nd tertiary

hydrogen present in given molecule.
H3 C
H3 C
H3 C
CH 3
CH 3
H3 C CH CH3
3
II
H3 C
H3 C Cl
III
CH 3
OH
CH 3
CH 3
CH3
Cl
O CH
3
IV CH 3
V
53. What are alicyclic compounds? Write at list 10 compounds with
different chemical nature.
54. Write the structure of smallest cyclic

(a) Alkane
(b) Alkene
(c) Alkyne
(d) Ether
58

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(e) sec-Amine
(f)
(g) Thioether
(h) Ester
(i)
(j)
sec-Amide
(l)
Aromatic compound
Acid anhydride
(k) t-Amide
t-Amine
(m) Anti-aromatic compound.

55. Write the structure of open chain molecule tha t meet the
following descriptions
A.
Contains 2 sp hybridized ca rbon and 2 sp hybridized C.
B.
Contains only 4 carbons, all sp hybridized.
C.
Contains 2 sp hybridized carbons and 2 sp hybridized C.
56. What bond angles do you expect for each of the following and
what kind of hybridization do you expect for the central atom
in each case?
A.
The C-O-C angle in CH3 -O-CH3
B.
C-N-C angle in CH3 -NH-CH3
C.
The C-N-H a ngle in CH3 -NH-CH3
D.
The O=C-O angle in acetic acid
57. Write the hybridization of each carbon in the given molecule?

H
H3 C
I
Cl
H 3C
H2 C
CH 2
H2 N
II
OH
COOH
IV
CH 3
VI
CH2
CH 2
HN
XI
VIII
VII
NH 2
IX
III
S
XII
CH+2
N
XIII

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59
H3 C
H3 C
CH3
CH 3
CH 3
CH3
XIV
CH 3 H
H
H
H
CH 3
XV
58. State whether the given molecules are planner or non-planner.
H
C
III
IV
H2 C +
H2 C
II
H3 C
VI
CH 2
VII
CH 2
VIII
H2 N
H3 C
IX
CH 2
CH 2
X
CH 2
XI
H
N
XIII
XIV
N
XV
XII
59. Classify the following molecules into saturated and unsaturated

compounds?
H3 C
Cl
H3 C
CH 3
H3 C
CH 3
HO
CH 3
I
II
III
H3 C
Br
IV
H3 C
O
60
CH 3
VII
V
H3 C
O
VI
CH 3
VIII
H3 C
O

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CH 3
IX

H3 C
H3 C
CN
H
N
CN
H3 C COOH
XI
XII
Cl
XIII
XIV
XV
60. Classify the following molecules into aromatic, anti aromatic
and non aromatic compounds.
II
IV
III
VI
VIII
VII
IX
.
XIII
XII
XI
XIX
XX
XXIV
XIV
XV XVI
XVII
XXII
XXI
XVIII
XXIII
H
N
H
N
XXV
XXVI
XXVII
XXVIII XXIX
N 2Cl
XXXI
XXX
HO
OH
Squaric acid
XXXV
XXXII
N
+
Sydnone Ph
XXXVI
XXXIII
XXXIV
Tropone
XXXVII
Tropolone
XXXVIII

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OH
61
O
Pyrylium ion Phenalenyl anior
XXXIX
XL
N
H3 C
N+
XLV
XLVI
O
Ph
Ph
XLVIII
XLIX
62
Heptalene
XLII
CH 3
XLIV
XLIII
Pentalene
XLI

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XLVII
Answers
01
Subjective Approach
01. Orga nic chemistry is the chemistry of ca rbon a nd its

compounds with some exception of CO3 2 , CO, CO2 etc whose
properties resembles more with inorga nic compounds. In
general organic compounds
(A) Rea ct more slowly and required higher tempera ture for
reaction.
(B) Undergoes more complex reactions and produce side
products.
(C) Has lower melting and boiling points with low solubility
in wa ter.
(D) Are cla ssified into families of compounds such a s
alcohols, ethers, carboxylic acid etc which have sa me
reactive groups so have similar chemical reactions.
02. Position of carbon in the periodic table.
03. Urea
04. Carbon
05. 2 nd period & 1 4 th group.
06. In trying to expla in why atoms form bonds, Lewis proposed
that a n a tom is most sta ble if it has a filled outermost shell or
an outer shell of eight electrons, which is called a s Octet rule.
According to it, a n a tom will give up, accept, or share
electrons in order to achieve a filled shell or an outer shell
tha t contains 8 electrons.

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63

07. Electronegativity is a chemical property that describes the
tendency of an atom or a functiona l group to attract the bond
pa ir electrons towa rds itself. An atoms electronegativity is
affected by both its atomic number and the distance tha t its
valence electrons reside from the charged nucleus. The higher
the associated electronega tivity number, the more an element
attracts electrons towards it. There are many scales to measure
it but Pauling scale is most common a mong these.
Electron a ffinity of a n a tom or molecule is the a mount of
energy released when an electron is added to a neutra l atom
or molecule to form a negative ion.
X e
X
This property is measured for a toms a nd molecules in the

ga seous sta te only, since in the solid or liquid states their
energy levels would be changed by conta ct with other atoms
or molecules.
08. 2.5 , 2.1, 3.0, 3.5, 4 .0 respectively
09. 4, 1, 3, 2 & 1 respectively
10. X
11. C-F > C-Cl > C-Br > C-I
12. Linea r, bra nched a nd cyclic fra meworks of 6 ca rbon
hydrocarbons are
H3 C
CH 3
H3 C
CH3
CH 3
CH
CH3 3
CH3
H3 C
H 3C
CH 3
64
CH 3
H3 C
H3 C
CH3
CH 3
CH 3
CH 3
CH 3
H3 C
CH 3
H3 C
H3 C

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CH 3
CH 3
H3 C
CH 3
H3 C
CH 3
CH3
CH 3
H3 C
CH 3
CH 3
H3 C
CH 3
CH 3
13. Those structures are not a ccording to geometry and may
create confusions so better representa tions a re
H
OH
N CH 3
H3 C
NH 2
14. 1.54, 1.34, 1.20 a nd 1.39 respectively

15. C-H bond is weak
16. Bond strength follows C C > C=C > C-C
17. 2, 4 & 6 respectively
18. Isotopes are variants of a particula r element such as C or H.
All isotopes of a given element share the same number of
protons but differs in its number of neutrons. The term isotope
is formed from the Greek words isos means equal a nd
topos means pla ce , hence: the same pla ce, meaning
that different isotopes of a single element occupy the sa me
position on the periodic table. The number of protons within
the atoms nucleus uniquely identifies an element, but a given
element may in principle ha ve any number of neutrons. The
number of nucleons (protons and neutrons) in the nucleus is
the mass number, and each isotope of a given element has a
different mass number. For example, C-12 , C-13 & C-1 4 a re
three isotopes of the element carbon with mass numbers 1 2,
13 and 1 4 respectively. The atomic number of carbon is 6
which means that every carbon a tom ha s 6 protons, so that
the neutron number of these isotopes a re 6,7 & 8 respectively.

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65

H have three naturally occurring isotopes, sometimes denoted
as 1H (Hydrogen), 2 H (Deuterium, D), and 3 H(Tritium, T)
with 1 proton and 1, 2, 3 neutron respectively.
19. Each isotopes of oxygen have 8 protons & 8 electrons but have
8,9 ,10 neutrons respectively.
20. Aufba u princi ple (Ge rma n wor d, Aufb a u me a ning
building up, construction) is used to determine the
electronic configura tion of a n atom, molecule or ion. The
principle postulates a hypothetical process in which an a tom
is built up by progressively adding electrons. As they a re
added, they assume their most stable conditions (electron
orbital) with respect to the nucleus and those electrons
already there. According to the principle, electrons fill orbitals
sta rting at the lowest available (possible) energy levels before
filling higher levels (e.g. 1s before 2s). The number of electrons
tha t ca n occupy each orbital is limited by the Pauli Exclusion
Principle& Hunds rule.
21. Pa uli Ex clusion Principle is the quantum mecha nica l
principle that states that no two identical fermions (pa rticles
with half-integer spin) ma y occupy the same quantum sta te
simultaneously. A more rigorous statement is tha t the total
wave function for two identica l fermions is a nti symmetric
with respect to exchange of the particles. For example, no two
electrons in a single atom can have the same four quantum
numbers; if n,l, and ml a re the same, ms must be different
such tha t the electrons have opposite spins, and so on.
22. H unds rules refer to a set of rules which a re used to
determine the term symbol that corresponds to the ground
state of a multi electrons a tom. In chemistry, the first rule is
especially important a nd is often referred to as simply Hunds
rule.
66
For a given electronic configura tion, the term with

ma ximum multiplicity has the lowest energy. The
multiplicity is equa l to2S + 1, where S is the total spin
angula r momentum for all electrons. The term with
lowest energy is also the term with ma ximum S.

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For a given multiplicity, the term with the largest value

of the orbita l angular momentum numberL has the
lowest energy.
For a given term, in a n a tom with outermost sub shell

ha lf-filled or less, the level with the lowest value of the
total angular momentum quantum number J (for the
operator J = L + S) lies lowest in energy. If the outermost
shell is more than half-filled, the level with the highest
va lue of is lowest in energy.
These rules specify in a simple wa y how the usua l energy

interactions dicta te the ground state term. The rules a ssume
that the repulsion between the outer electrons is very much
greater tha n the spinorbit intera ction which is in turn
stronger than a ny other rema ining intera ctions. This is
referred to a s the LS coupling regime. Full shells and sub
shells do not contribute to the quantum numbers for totalS,
the total spin a ngular momentum a nd forL, the tota l orbital
angular momentum. It can be shown that for full orbitals and
sub orbitals both the residua l electrostatic term (repulsion
between electrons) and the spinorbit interaction can only
shift all the energy levels together. Thus when determining
the ordering of energy levels in general only the outer valence
electrons need to be considered.
23. Rules can be violated but Principle cant be violated and have
no exceptions at all.
24. 4S1
25. F 1s2s2p5
Br [Ar]4s3d10 4p5
Cl [Ne]3 s,3 p5
I [Kr]5 s4d10 5p5
26. Ionic bonds a re formed by either loss or gain of electrons

such as NaCl which is origina lly Na+Cl . Covalent bonds are
formed by sharing of electrons between two a toms. This
sharing may be from sa me atoms or from different atoms such
as H or O. If atoms are same then bonds are purely covalent
but if a toms a re different then such bonds are considered as
polar cova lent. Coordina te bond is a lso a type of covalent

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67

bond but here sha ring of electrons ta kes place from a single
at om such as comp oun d of N H 3 BF3 in which N sha res its
electron with B.
27. Most polar is KCl & least pola r is Cl2 .
28. The nega tive a nd positive ends of a pola r bond ma kes it a
dipole. The pola rity of the dipole is indicated by the dipole
moment ( ). The dipole mome nt of a bond is the product of
ma gnitude of the charge (e) on the atom (either the pa rtial
positive charge or the pa rtial negative cha rge beca use they
have the same magnitude) a nd the distance between the two
charges (d). Dipole moment is mea sured in a unit called
Debye (D).
= e d
29. Formal cha rge is the difference between the number of
va lence electrons a n a tom ha s when it is not bonded to a ny
atom and the number of electrons it a ctually owns when it
is bonded. An atom owns all of its nonbonding electrons
and half of its bonding electrons.
Forma l cha rge = No of valence ele ctrons (N o of non
bonding e lectrons + No of bonding e lectrons)
Oxygen has 6 valence electrons but own electrons of oxygen
in H3 O+ is 5 (2 non bonding plus 3, ha lf of six bonding). As
the number of number of own electron is 1 less tha n its
va lence electron so its forma l charge is 1.
30. Lewis structures of formic acid, formaldehyde and metha nol
are respectively
O
H
O
C
C
H
H
H
H
H
H
O
Formic acid Formaldehyde Methanol
31. If there wa s a full negative charge on the oxygen a tom, the
dipole moment would be
C
(4.80 10 -10 esu)(1.22 10 -8 cm) = 5.86 10 -18 esu.cm = 5.86 D
68

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Knowing that the dipole moment is 2.30 D, partia l positive
charge on oxygen atom will be 2 .30 /5.86 = 0 .39 . From this
we ca n conclude that oxygen has an excess of a bout 0 .4
electron and carbon atom has a deficiency of 0.4 electrons.
32. Bond length of HX follows
HI (1 60 pm) > HBr (1 41 pm) > HCl (127 pm) > HF (9 2 pm)
33. CH
, CH
HO Br , I Cl ,
3 Cl
3 NH2
, CH3 Mg Br a nd NH 2 OH
CH
3 OH
34. Ten organic compounds a re

SN
Compound Use
CH3
01
Flavoring compound from

OH
the essential oil of spearmint
H3 C CH 3
Menthol
O
CH 3
02
Perfume distilled from ja smine

CH 3
NH 2
03
Ba sis for the Dyestuffs industry

Aniline
OH
04
Antiseptic in surgery
Phenol

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69
05
CH3
CH 3 CH 3
H3 C
Major constituent of petrol
CH 3
Iso-octane
CH3
CH 3
H3 C CH 3
OH
06
For treatment ofblindness

Vitamin A
CH 3
07
08
OH
O
HO
HO
OH
Glucose
OH Energy source for living organism
CH2 OH
Ordinary sugar
H H O H HOH 2 C O H
isolated from
H HO
O
CH 2 OH sugarcane or
HO OH H
OH H
sugar beet
H OH
(Sucrose)
H2 C
HO
09
H 3C
Medicine used to trea t ma laria
N
Quinine
HS
10
70
SH
H 3C
CH3 Worst smell in the world

Propanedithiol

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35. Functional group is an a tom or group of atoms in a molecule
tha t gives the molecule its characteristic chemical properties.
The importa nce of functional groups lies in the fact that it is
the site of atta ck of reagent, makes families for orga nic
compounds and helps in nomenclature.
36. Alcohol, enol, phenol and carboxylic acid respectively
37. Bond line structures a re
O
HO
H3 CO
(A)
(B)
OCH3
(C) H3 CO
OCH3

O
+
N
(A)
(B)
O
O
O
NH
(C)
N
39. Proba ble formulas are GeCl4 , AlH3 , CH2 Cl2 , SiF4 & CH3 NH 2,
AlCl3 , CF2 Cl 2 , NI3 , PH3 .
40. Carbon ha s only four va lencies and donot ha ve any vaca nt

orbital so cannot expa nd its octet. Thats why molecules with
such structures a re not possible at room tempera ture.
41. Non bonding electrons a re
H3 C
H3 C
CH 3
H3 C
CH 3

O
H3 C
H3 C
Cl
CH 3

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71

(A)
(B) H 3 C NH 2
(C)
(D)
(E)
OH and
O
H ,
NH2 ,
and
NH 2
,
OH
H
N
and
Ionic bond
+
43. H3 C O Na
Covalent bond
44. Homologue s are the compounds with same general formula

and possess similar chemical properties due to presence of
sa me functiona l group (if any) i.e. a ll carboxylic a cids a re
homologues of each other starting from formic acid (HCOOH)
to any ca rboxylic a cid with formula RCOOH where R is a ny
acyclic sa turated a lkyl group. All a lka nes starting from 1
carbon to infinite carbon are homologues. Homologues differ
by (CH2 )n units.
Homologues of Methane are Etha ne, Propa ne, Butane &
Pentane;
Homologues of Forma ldehyde (Methanal) a re Ethana l,
Propanal, Butana l and Pentanal;
Homologues of Acetone a re Buta none, Penta none,
Hexanone & Heptanone;
Homologues of Formic a cid a re Acetic acid, Propanoic
acid, Butanoic acid and Pentanoic acid.
45. Molecules with single functional groups are considerd to be
derived from a hydroca rbon by replacing one of its H atoms
with a functional group. If the hydroca rbon is aliphatic then
72

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then the a lkyl group is represented by R, and the molecule
containing functional group may be represented as RG where
G is functional group such a s RCl for alkyl chloride, ROH for
alcohol and RCOOH for carboxylic acid.
46. Compounds in homologous series differ by (CH 2 ) n units
which increa ses the size of alkyl group, so physica l properties
changes gradually such a s genera l increase in melting point,
boiling point is observed with decrease in solubility in water.
They undergo similar chemical reactions whose ra te depends
on the siz e of a lkyl group and shape of molecule.
47. The word thio is usua lly used to indicate the presence of S.
So sulphur ana log of a lcohol is thiol & ether is thioether.
48. The functional groups present a re
(I)
Thiol
(II)
Thiol & Ketone
(III)
Acetal
(IV)
Alkene & Halide
(V)
Imine
(VI)
Ether & Ketone
(VII)
Ketone & Enol
(VIII)
Ether, Alcohol & Amine
(IX)
(X)
(XI)
(XII)
(XIII)
(XIV)
(XV)
(XVI)
(XVII)
(XVIII)
(XIX)
Ether, Phenol & Aldehyde

Imine
Phenol
Aniline
Diazo
Alkene & Benzene
Alkyl Benzene
Peroxide
Amide, Thioether & Carboxylic acid
Amine & Imine
Ca rboxylic acid & Ester

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73

(XX)
Phenol & Amide
(XI)
Amine, Amide, Ether & Sulphonamide
(XXII)
Alcohol, Alkene & Ketone
(XXIII)
Amine & Ester
(XXIV)
Amine & Alcohol
(XXV)
Alcohol, Ether & Amide
(XXVI)
Phenol & Halide
(XXVII) Amine, Ketone & Alkene
(XXVIII) Ether, Amine, Carboxylic acid & Sulphonamide
49. Structura l formula s for compound with such skeletons a re
(A)
(C)
(D)
H3 C
H3 C
H3 C
H3 C
(E)
(B)
CH 2
H 3C
Cl or
Cl
H3 C
CH
CH 3
H 3C
OH or
CH 3
HO
H3 C
(F)
CH 3
(G)
H3 C
O
O
50. There are of course ma ny possible structures. A could be
heteroatom or a structural fragment while Ar could be a ny
of a very large number of substituted benzene rings or even
other types of a romatic rings. Four membered rings could
ha ve A = O, NH, CO, SO2 or even alkene while the R1 & R2
could be sa me or different. To make such structure a lwa ys
be ca reful tha t molecule must follow octet rule.
74
COOH
NH 2
Ph
CH 3
CH 3
CH 3
HN
H2 C

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OCH 3
OCH3
Ph
OCH3
S
The three aryl groups in second exa mple, all might be

different or some might be same.
OH
COOH
CHO
OH
CHO
O
Cl
OH
O
O
51. Tota l number of primary, secondary, tertia ry and quaternary

carbons are
Com. Primary C
Secondary C Tertiary C
Quaternary C
II
III
IV
VI
VII
VIII
10

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75

52. Total number of prima ry, secondary, tertiary hydrogens a re
Compound
I
Primary H
9
Secondary H
2
Tertiary H
1
II
15
III
IV
53. Alicy clic com pounds a re simply the cyc lic a lip ha tic
compounds (Cyclic + Alipha tic), which a re commonly
cycloalkane, cycloalkene, cycloa lkyne, cyclic ether, cyclic
secondary a mines, cyclic tertia ry amine, cyclic ester, cyclic
ketones, cyclic amide, cyclic acid anhydride.
54. Structures are
(a)
(b)
(c)
O
O (i) O
(h) O
55. A. H3 C
CH 3
B. H C
2
H
N
CH 3
(d)
(e)
(f)
H
N
CH3
(j) O
(k) O
(g)
(l)
(m)
CH 2
C. H C
2
CH 2
56. A. 109 28, sp3 B. 109 2 8, sp3 C. 109 28 , sp3 D. 1 20 , sp2

sp 3
H3 C
57.
sp
CH 2
sp 2
76
sp2 sp
C
H
sp2
II

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sp3
sp 2
2
H2 N
sp sp3
H 3C
sp
OH
H2 C
sp
sp
sp 2
CH 2
sp 2
sp 2
sp3
O
sp
sp
CH 3
IV
All sp 2
VII
All sp 2
VI
sp 2
Cl
III
All sp 2
V
COOH
HN
sp3
XI
S
XII
All sp 2
IX
NH 2
All sp2
(X)
CH +2
CH 2
sp 2
All sp 2
VIII
sp 3
sp2
sp 2
sp3
N
All sp2
XIII
CH3
CH 3 H
H3 C
CH 3
H
H
CH 3
H3 C
CH3
H CH 3
3
All sp
All sp3
XIV
XIV
58. Overa ll sha pe of molecules a re
Com. Shape
Com.
Shape
Planner
II
Non-Planner
III
Non-Planner
IV
Planner
Non-Planner
VI
Non-Planner
VII
Planner
VIII
Planner
IX
Planner
Planner
XI
Planner
XII
Planner
XIII
Planner
XIV
Planner
XV
Planner

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77

59. Saturated and Unsaturated compound are
Comp. Nature
Comp. Nature
I
Saturated
II
Saturated
III
Saturated
IV
Unsaturated
V
Saturated
VI
Unsaturated
VII
Unsaturated
VIII
Unsaturated
IX
Unsaturated
X
Unsaturated
XI
Unsaturated
XII
Unsaturated
XIII
Unsaturated
XIV
Saturated
XV
Saturated
60. Classifica tion of compounds a re
Com.
Classification
Com.
Classification
I
Non-aromatic
II
Aromatic
III
Anti-aromatic
IV
Non-aromatic
V
Anti-aromatic
VI
Aromatic
VII
Anti-aromatic
VIII
Non-aromatic
IX
Non-aromatic
X
Anti-aromatic
XI
Aromatic
XII
Non-aromatic
XIII
Aromatic
XIV
Aromatic
XV
Aromatic
XVI
Non-aromatic
XVII
Aromatic
XVIII
Anti-aromatic
XIX
Non-aromatic
XX
Aromatic
XXI
Non-aromatic
XXII
Aromatic
XXIII
Aromatic
XXIV
Aromatic
XXV
Aromatic
XXVI
Aromatic
XXVII Aromatic
XXVIII Non-aromatic
XXIX
Aromatic
XXX
Aromatic
XXXI
Aromatic
XXXII Aromatic
XXXIII Aromatic
XXXIV Aromatic
XXXV Aromatic
XXXVI Aromatic
XXXVII Aromatic
XXXVIII Aromatic
XXXIX Aromatic
XL
Aromatic
XLI
Non-aromatic
XLII
Non-aromatic
XLIII
Aromatic
XLIV
Aromatic
XLV
Aromatic
XLVI
Aromatic
XLVII Non-aromatic
XLVIII Aromatic
XLIX
Aromatic
L
Aromatic
78

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Exercise
01
Objective Approach
Single Correct Questions (SCQ) :
1. First organic compound generated in 1828 by Friedrich wohler
is
+
(B) N H 4 O CN
(A) CO 2
O
(C) H 2 N - C- NH 2
(D) H 2 N - C- NH 2
2. Formation of large number of organic compound is due to

(A) size of carbon
(B) Electronegativity of carbon
(C) Catenation property of carbon
(D) Position of carbon in the periodic table
3. How many electrons are used to make a single, double & triple
bond respectively.
(A) 1,2,3
(B) 2,4,6
(C) 3,6,9
(D) 4,6,8

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79

4. Electronegativity value on Pauling scale for C, H, N, O, F are
respectively
(A) 2.1, 2.5, 3.5, 4.0
(B) 2.5, 2.1, 3.0, 3.5, 4.0
(C) 2.5, 2.1, 3.5, 3.0, 4.0
(D) 2.1, 2.5, 3.5, 3.0, 4.0
5. Tota l number of bonds in the given compound

H 2 C = C = CH - CH = C = CH 2is:
(A) 9
(B) 15
(C) 14
(D) 16
6. Molecular formula of Phenantharene

(A) C 14 H14
(B) C 14 H10
(C) C 14 H12
(D) C 12 H12
is :-
7. Number of sigma bonds in the given compound

CH3 - CH2 - CH = CH - CN is:(A) 11
(B) 15
(C) 12
(D) 13
8. Find the functional group which is absent in penicillin

O
R CN
H
O
N
COOH
Penicillin
(A) Amine
(B) Amide
(C) Thio ether
(D) Carboxylic acid
9. Homologue of CH3 COOH is

(A) CH 3 COOCH 3
(B) CH3 COCH 2 OH
(C) CH3 CH2 COOH
(D) HCOCH 2 OCH3
80

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10. Number of 1, 2, 3 & 4 carbons present in given compound
respectively is
(A) 5, 2, 1, 0
(B) 5, 1, 1, 1
(C) 5, 1, 0, 1
(D) 5, 1, 1, 0
11. Number of 1, 2, 3 Hydrogens present in given compound

respectively is
(A) 15, 2, 1
(B) 20, 2, 1
(C) 15, 4, 0
(D) 15, 4, 1
12. Number of 3 & 2 carbon atoms respectively in the following
compound
are -
(A) 5, 6
(B) 6, 6
(C) 5, 7
(D) 4, 7
OH
13. Number of 2 H atoms in the following compound

(A) 7
(B) 5
(C) 6
(D) 4
is
14. Which molecule is considered as saturated one.

(A) Alkane
(B) Alkene
(C) Alkyne
(D) Aromatic comp
15. Which molecule is considered as unsaturated one.

(A)
(C)
(B)
N
H
(D)

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81

16. Central carbon in CH 2 = C = CH 2 will ha ve which type of
hybridization.
(A) sp
(B) sp2
(C) sp3
(D) None
17. The given compound is

N CH 3
H
(A) Alicyclic heterocyclic
(B) Unsaturated homocyclic
(C) Aromatic heterocyclic
(D) Saturated heterocyclic
18. Which of the following is an alicyclic compound ?

(A)
(C)
(B)
(D)
19. The saturated heterocyclic compound is
(A)
N
H
(B)
(C)
(D)
O
20. Which of the following do not have bridge head carbon in bicyclo
compound.
(A)
(B)
(C)
(D)
82

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21. Which of the following is an unsaturated hydrocarbon.
(A) CH 3 - CH2 - C N
(B)
(C)
(D
O
CH 3 C CH 2 CH 3
22. Which molecule is not planner in shape.

(A)
(B)
(C)
(D)
23. Which molecule is heterocyclic in nature.

NH 2
(A)
(B)
OH
(C)
(D)
O
O C CH 3
COOH
24. Which molecule is anti-aromatic in nature.

+
(A)
(B)
(C)
(D)
25. Which molecule is aromatic in nature.

+
(A)
(C)
(B)
+
(D)

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83

26. Which of the following alkane do not have any 2 carbon.
(A) 2, 2-Dimethyl pentane
(B) Pentane
(C) 2-Methyl butane
(D) 2, 3-Dimethylbutane.
27. Maximum angle strain is observed in

(A) Cyclopropane
(B) Cyclobutane
(C) Cyclopentane
(D) Cyclohexane
28. In which of the following species is the underlined carbon

having sp3 hybridisation ?
[AIEEE-2002]
(A) CH3 COOH
(B) CH3 CH 2 OH
(C) CH 3 COCH 3
(D) CH 2 = CH - CH 3
29. The general formula C n H 2n O 2 could be for open chain

[AIEEE-2003]
(A) carboxylic acids
(B) diols
(C) dialdehydes
(D) diketones
30. Which one of the following does not ha ve sp2 hybridized

carbon ?
[AIEEE-2004]
(A) Acetonitrile
(B) Acetic acid
(C) Acetone
(D) Acetamide
31. Which of the following represents the given mode of
hybridisation sp 2 - sp 2 - sp - sp from left to right ?
[IIT-2003]
(A) H 2 C = CH - C N
(B) HC C - C CH
(C) H 2 C = C = C = CH 2
(D) H 2 C = CH - CH = CH 2
32. Which of the following molecules, in pure form, is (are) unstable

at room temperature ?
[IIT-2012]
(A)
(B)
O
(C)
84
(D)

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33. The number of loan pair of electrons in melamine is
[IIT-2013 (Advanced)]
(A) 4
(B) 6
(C) 6
(D) 8
34. In allene (C3H4), the type(s) of hybridization of the carbon atoms

is (are):
[IIT-2014 (mains)]
(A) sp and sp 3
(B) sp2 and sp
(C) only sp2
(D) sp2 and sp3
35. The number and type of bonds in C 2

ion in CaC2 are:
2
[IIT-2014 (mains)]
(A) One bond and one bond
(B) One bond and two bond
(C) Two bond and two bond
(D) Two bond and one bond
36. For the compounds CH3 Cl , CH 3 Br, CH 3 I and CH3 F , the correct
order of increasing C-halogen bond length is : [IIT-2014 (mains)]
(A) CH 3 F CH3 Cl CH 3 Br CH 3I
(B) CH 3 F CH3 Br CH 3 Cl CH 3I
(C) CH 3 F CH3 I CH 3 Br CH 3Cl
(D) CH 3 Cl CH 3 Br CH 3F CH 3I
37. Match the orbital overlap figures shown in List-I with the
description given in List-II and select the correct answer using
the code given below the lists.
[IIT-2014 (Advanced)]
List-I
(P)
List-II
1.
p-d antibonding

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85

(Q)
2.
d-d bonding
(R)
3.
p-d bonding
(S)
4.
d-d antibonding
Codes:
R
S
3
4
1
2
1
4
3
2
1 2 3
4
38. In the compound H2 C = C = CH CH 3 , the hybridization of 1st
(A)
(B)
(C)
(D)
P
2
4
2
4
Q
1
3
3
1
and 2 nd carbon atom is:
[BHU 2003]
(A) sp3-sp
(B) sp3-sp3
(C) sp2-sp
(D) sp2-sp2
39. Allyl cyanide contains and -bonds:
[PMT (MP) 2004]
(A) 5 , 7
(B) 9 , 3
(C) 3, 4
(D) 9, 9
40. The CH bond distance is longest in:
[UGET (Med.) 2006]
(A) C 2 H2
(B) C 2 H 4
(C) C 2 H6
(D) C 2 H 2 Br2
41. The correct order regarding the electronegativity of hybrid

orbitals of carbon is:
[AIPMT 2006]
(A) sp < sp2 > sp3
(B) sp < sp2 < sp3
(C) sp > sp2 < sp3
(D) sp > sp2 > sp3
86

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42. Number of and bon ds in C 6 H 5 COOH is:
(A) 13 , 4
(B) 14, 4
(C) 15 , 4
(D) 16, 4
[DPMT 2007]
43. What is the percentage of p-character of hybrid orbits of carbon

in methane, ethene and ethyne respectively?
[SCRA (Med.) 2007]
(A) 75, 66, 50
(B) 50, 66, 75
(C) 25, 33, 50
(D) 50, 33, 25
44. W hich one of the follow ing does not have sp 2-hybridized carbon?
[JCECE (Med.) 2008]
(A) Acetone
(B) Acetic acid
(C) Acetonitrile
(D) Acetamide
45. In the hydrocarbon H3 C CH = CH CH2 C

6 5
4
3
2
CH
1
The state of hybridization of carbons 1, 3, 5 are in the following

sequence:
[CPMT 2008]
(A) sp, sp2 , sp3
(B) sp3 , sp 2 , sp
(C) sp2 , sp, sp3
(D) sp, sp3 , sp2
46. Hybridization of nitrogen atom in pyridine
(A) sp3
(B) sp2
(C) sp
(D) sp3 d
is:
N
[BHU (Mains) 2008]
47. The number of bonds in the following compound

[DPMT 2008]
O 2 N C C NO 2 is :
(A) 2
(B) 3
(C) 4
(D) 1

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87

48. Compound where underlined carbon use sp3 hybrid orbitals for
bond formation is:
[BCECE (Med.) 2008]
(A) CH3 COOH
(B) CH3 CONH 2
(C) CH3 CH 2 OH
(D) CH 3 CH = CH 2
49. The sta te of hybridiz a tion of C 2 , C 3 , C 5 and C 6 of the

hydrocarbon,
CH 3
CH3
CH 3 C CH = CH CH C
6
5
7
4
3
2
CH 3
CH is in the following sequence

1
[AIPMT 2009]
(A) sp, sp3 , sp 2 and sp3
(B) sp, sp2 , sp2 and sp3
(C) sp, sp2 , sp3 and sp2
(D) sp 3 , sp2 , sp 2 and sp
50. Increasing order of carbon-carbn bond length for the following

is :
[CET (karnataka) 2011]
C2H 4
C 2 H2
C6H 6
C2H 6
(A)
(B)
(C)
(D)
(A) B < C < A < D
(B) C < B < A < D
(C) D < C < A < B
(D) B < A < C < D
51. Considering state of hybridization of carbon atoms, find out the

molecule among the following which is linear?
[AIPMT (Prelims) 2011]
(A) CH 3 - CH = CH - CH 3
(B) CH 3 - C C - CH 3
(C) H 2 C = CH - CH 2 - C CH (D) CH3 - CH 2 - CH 2 - CH 3

52 .Which one of the following is a non-benz enoid a romatic
compound?
[PMT (Kerala) 2011]
(A) Anthracene
(B) Tropolone
(C) Aniline
(D) Benzoic acid
88

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53. Only sp and sp2 hybrid orbitals are involved in the formation of
[PMT (Kerala) 2012]
(A) CH 3 - CH = CH2
(B) CH3 - CH3
(C) CH3 - C CH
(D) H 2 C = C = CH2
54. The CH bond and CC bond in ethane are formed by which of

the following types of overlap?
[CET (Karnataka) 2012]
(A) sp3-s and sp3-sp3
(B) sp2-s and sp2-sp2
(C) sps and spsp
(D) ps and pp
55. The radical
CH 2 is aromatic because it has [NEET 2013]
(A) 6 p orbitals & 6 unpaired electrons.

(B) 7 p orbitals & 6 unpaired electrons.
(C) 7 p orbitals & 7 unpaired electrons.
(D) 6 p orbitals & 7 unpaired electrons.
56. Which of the following compound has same hybridization as
its combusion product CO2 ?
[AIPMT 2014]
(A) Ethane
(B) Ethyne
(C) Ethene
(D) Ethanol

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89
Multiple Correct Questions (MCQ) :

57. Which statement is correct for element with single bond.
(A) Nitrogen have one lone pair of electron.
(B) Oxygen have two lone pair of electron.
(C) Fluorine have three lone pair of electron.
(D) Carbon have four lone pair of electron.
58. Which statement is correct for bond.
(A) Sigma bond is formed by axial overlapping of orbitals.
(B) Pi bond is formed by sidewise overlapping of pp orbitals.
(C) Sigma & Pi bonds are a type of ionic bond.
(D) Co-ordinate bond is a type of covalent bond.
59. Which statement is correct for functional group.
(A) Functional group shows its characteristic chemical reaction.
(B) Functional groups helps in nomencla ture of organic
compounds.
(C) Functional groups serves to classify organic compound into
different classes or families.
(D) All functional groups have same physical properites.
HO
60. Functional group is present in vitamin C
(A) Alcohol
(B) Enol
(C) Ester
(D) Ether
61. Which functional group have absence bond ?

(A) Alcohol
(B) Aldehyde
(C) Amine
(D) Alkyl halide
90

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OH
O O
HO
OH
Vitamin C
is:

62. Which functional group have bond ?
(A) Ketone
(B) Carboxylic acid
(C) 3 amine
(D) 2 amide
63. Which compound have C=N linkage ?

(A) Imine
(B) Amine
(C) Oxime
(D) Hydrazone
64. Which functiona l group is present
O
EtO
S N N CH 3
N
O
N
N
N
H (Viagra)
CH3O
(A) Amide
(B) Sulphonamide
is
Via gra
(C) Amine
(C) Ester
65. Which functiona l group is present in sulpha drug
H
O
Cl O
S NH 2
COOH
(A) Sulphonamide
(B) Carboxylic acid
(C) Amine
(D) Alcohol
66. Which compound(s) is/are homologue of Butanal ?

(A) Formaldehyde
(B) Acetaldehyde
(C) Propanal
(D) Pentanone
67. Which statement is correct for homologues ?

(A) They have same type of chemical reaction.
(B) They differ in (CH2 )n unit.
(C) They have same physical properties.
(D) They are prepared by same general method.

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91

68. Esters are formed by chemical reaction of
(A) Carboxylic acid & alcohol
(B) Acid halide & alcohol
(C) Acid anhydride & alcohol
(D) Aldehyde & alcohol
69. Which compound is unsaturated in nature ?
(A) 2,3-Dimethylbutane
(B) 2,3-Dimethylbut-2-ene
(C) 3,3-Dimethylbutyne
(D) 3,3-Dimethylbut-1-ene
70. Which compound is saturated in nature.

(A) Butan-2-ol
(B) Butan-2-amine
(C) Butan-2-one
(D) 2-Chlorobutane
71. Which molecule have correct number of 2C present.

O
(A)
(B) O O (0)
(3)
H
N
OH
(3)
OH
(C)
HO
(D)
N
H
N (3)
H
72. Which molecule have correct number of 2 H present ?

OH
NH2
(A)
(B)
(9)
(10)
(C)
(8)
(D)
(8)
Cl
73. Which molecule will have Sp 3 hybridized carbon ?

(A)
92
(B)
+ Cl

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+
(C)
(D)
74. Which molecule is/are planner in shape ?

(A)
(B)
(C)
(D)
75. Which molecules will exist at room temperature ?

O
(A)
(B)
O
(C)
(D)
76. Which molecule is/are polar in nature ?
(A)
(B)
(C)
(D)
77. Which molecule is/are aromatic in nature ?

O
(A)
(B)
NC
(C)
HO
HO
CN
(D)

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93

78. Which molecule is/are aromatic in nature ?
(A)
(B)
(C)
(D)
79. Which molecule have ( ) gamma position ?
(A) +N
(B)
(C) +N
(D) + S
+N
80. Which molecule with correct shape is mentioned ?

(A)
Tub shaped
(B)
non-planner
(C)
Planner
(D) HC CH Planner
81. The hybridizations of carbon atoms present in cumene is/are

(A) sp
(B) sp2
(C) sp3
(D) dsp2
94

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Assertion / Reason type Questions (A/R) :

Each question has 5 choice (A), (B), (C), (D) & (E) out of which
only one is correct.
(A) Statement-1 is true, Statement-2 is true and statement-2 is
a correct explanation for statement 1.
(B) Statement-1 is true, Statement-2 is true and statement-2 is
not correct explanation for statement 1.
(C) Statement-1 is true and Statement-2 is false.
(D) Statement-1 is false, Statement-2 is true
(E) Both Statement-1 and Statement-2 is false.
82. Statement-1: The concept of vital force theory was objected
by Wohler by preparing urea from ammonium
cyanate.
Statement-2: Vital force theory state that we can not prepare
organic molecule in laboratory.
83. Statement-1: Sec-butyl amine is a secondary amine.
Statement-2: In secondary amine, NH2 group attached with
secondary carbon.
84. Statement-1: tert-butyl alcohol is a tertiary alcohol.
Statement-2: In tertiary alcohol, OH group is attached with
tertiary carbon.
85. Statement-1: Oxalic acid & formic acid are homologue.
Statement-2: Homologues are those compounds which have
same nature of chemical reaction and differ in
(CH2 )n unit.
86. Statement-1:
have 1, 2, 3 & 4 carbon.
Statement-2: 1, 2, 3 & 4 carbon is that carbon which is

attached with 1,2,3 & 4 other carbon respectively.

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95

87. Statement-1: Cyclohexane is saturated while cyclohexene is
unsaturated.
Statement-2: Saturated compound is that which have only
single bond while unsaturated compound is that
which have multiple bond of any form.
88. Statement-1: Hybridization of oxygen atom in furan is sp2.
Statement-2: Hybridiz ation is a mathematical approach to
explain the shape of any atom in molecule.
89. Statement-1:
is a aromatic compound.
Statement-2: Cyclic planner molecule with (4n + 2) electrons

are called aromatic compounds.
90. Statement-1: Toluene is an alicyclic compound.
Statement-2: Alicyclic compounds a re simply the cyclic
aliphatic compounds.
91. Statement-1: Angle stra in in decrea sing order followscyclopropane > Cyclobutane > Cyclopentane >
Cyclohexane.
Statement-2: Angle stra in is the half of angle difference
between desired angle of sp3 atom and real angle
of the atom in cycloalkane.
92. Statement-1: Loss of one hydrogen from alkane leads to alkyl
group.
Statement-2: Butane have four types of alkyl groups.
96

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Match the Column type Questions (MTC) :

93 . Ma tch the compounds written in Column-I with its na ture
in Column-II :Column - I
(A)
(B)
Column - II
(P) Aliphatic compound
(Q) Aromatic compound
OCH 3
(C)
(D)
(R) Saturated compound
(S) Unsaturated compound
(T) Heterocyclic compound

94 . Ma tch the compounds written in Column-I with its na ture
Column - II
(A)
(P) Aliphatic
(B)
(Q) Aromatic
(C)
(R) Alicyclic
(D)
(S) Heterocyclic
(T) Homocyclic

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97
Comprehension type Questions :

Comprehension-01 :
Pa racetamol is widely used as analgesic (pa in reliever) &
antipyretic (fever reducer) medicine. Based on its structure, select
the correct answer among this
H
CH 3
O
Paracetamol
95. Functional group present in paracetamol is
HO
(A) Alcohol
(B) Amine
(C) Ketone
(D) 2 amide
96. Which statement is incorrect for paracetamol is

(A) Paracetamol is unsaturated compound.
(B) Paracetamol is derivative of hydrocarbon.
(C) Paracetamol is heterocyclic compound.
(D) Paracetamol is carbocyclic compound.
Comprehension-02 :
OH
OH
H 2 /Ni
O
NH 2 OH
Cu
II
Nylon-6
NOH
H
III
IV
H 2O
Polymerization
H+
N
O
V
Based on this, answer the following questions.

97. Incorrect statement about above compound is
(A) A functional group present in II is alcohol.
(B) A functional group present in III is ketone.
98

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(C) A functional group present in IV is oxime.
(D) A functional group present in V is lactone.
98. Incorrect statement about above compound is
(A) Compound I is saturated
(B) Compound II is saturated
(C) Compound III is unsaturated
(D) Compound IV is unsaturated
Integer type Questions :

99. Total number of primary carbon atoms present in
is
100. Tota l number of aromatic compounds among the given

molecule is
+
+
101. Total number of sigma bond () present in benzene
is
102. Total number of homocyclic compounds among the given

molecule is
OH
O
N
O
HO
O
OH

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99
Answers
01
Objective Approach
01.
(C) 02.
(D) 03.
(B)
04.
(B)
05.
(B)
06.
(B)
07.
(C) 08.
(A) 09.
(C) 10.
(B)
11.
(D) 12.
(A) 13.
(B)
14.
(A) 15.
(D)
16.
(A) 17.
(A) 18.
(D) 19.
(C) 20.
(C)
21.
(C) 22.
(C) 23.
(B)
24.
(B)
25.
(B)
26.
(C) 27.
(A) 28.
(B)
29.
(A) 30.
(A)
31.
(A) 32.
(B,C) 33.
(B)
34.
(B)
35.
(B)
36.
(A) 37.
(C) 38.
(C) 39.
(B)
40.
(C)
41.
(C) 42.
(C) 43.
(A) 44.
(C) 45.
(D)
46.
(B)
47.
(C) 48.
(C) 49.
(A) 50.
(D)
51.
(B)
52.
(B)
53.
(D) 54.
(A) 55.
(A)
56.
(B)
57. (A,B,C) 58. (A,B,D) 59. (A,B,C) 60. (A,B,C)
61. (A,C,D) 62. (A,B,D) 63. (A,C,D) 64. (A,B,C) 65. (A,B,C)
66. (A,B,C) 67. (A,B,D) 68. (A,B,C) 69. (B,C,D) 70. (A,B,D)
71. (A,B)
72. (A,B,D) 73. (A,B,D) 74. (A,B,D) 75. (A,C,D)
76. (B,C,D) 77. (A,B,C) 78.(A,B,C,D)79. (B,C,D) 80. (A,B,C,D)
81. (B,C)
82.
(A) 83.
(E)
84.
(A) 85.
(B)
86.
(A) 87.
(A) 88.
(B)
89.
(A) 90.
(D)
91.
(A) 92.
(B)
93. (A-P,S ; B-P,R,T ; C-P,R ; D-Q,S,T)
94. (A-Q,T ; B-P,R,T ; C-P ; D-Q,S)
95.
(D) 96.
(C)
97.
(D) 98.
(A) 99.
(4)
100. (6)
101. (12)
102. (6)
100

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Unit
Nomenclature of organic
compounds
In this section you are going to learn the basic concepts of IUPAC
nomenclature. Here you are going to learn how organic molecules
are named along with some common na mes which you will
regularly encounter in due course of organic chemistry

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101
Section
Alkyl groups
The concept of alkyl group is very much important in organic
chemistry a s it is the backbone of ca rbon skeleton of orga nic
molecule. As every organic molecule is derived from alkane, so the
alkyl group is too derived from alkane itself. If a hydrogen atom is
removed from an alkane then the partial structure that remains is
called as a lkyl group.
Alkane - H = Alkyl group
It is important to note that, as hydrogen is removed from alkane
i.e. all valency of carbon is not fulfilled, alkyl groups are not stable
compounds but they are simply a part of large compound.
Alkyl groups are named by repla cing the -ane ending of the
parent alkane with an -yl ending. For example, the removal of a
hydrogen from methane (CH4 ) generate a methyl group (-CH3 ) and
removal of hydrogen from ethane (CH3 CH3 ) generate ethyl group
(-CH2 CH3 ). Similarly removal of a hydrogen atom from the end
carbon of any n-alkane gives corresponding n- alkyl group such as
Methane - H = Methyl group (-CH3 or -Me)
Ethane - H = Ethyl group (-CH2 CH3 or -C2 H5 or -Et)
n- Propane - H = n-Propyl group (-CH2 CH2 CH3 or -Pr)
n- Butane - H = n-Butyl group (-CH2 CH2 CH2 CH3 or -Bu)
102

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Just as straight chain alkyl groups are generated by removing
hydrogen from a n end carbon, branched alkyl groups can be
generated by removing a hydrogen atom from an internal carbon.
It is possible to remove hydrogen from primary, secondary or even
tertiary carbon. So, on this basis, there are few alkyl groups which
are commonly used in organic chemistry.
n-alkyl group- If a hydrogen is removed from first carbon

of straight chain alkane then we use the word n-alkyl for
that. For example
H3 C
n-propyl
H3 C
n-butyl
iso-alkyl group- If a hydrogen is removed from first carbon

of straight chain alkane in which second last carbon have
one methyl group then we use the word iso-alkyl for that.
For example
CH3
CH 3
H3 C
Iso-butyl
H3 C
Iso-pentyl
neo-alkyl group-If a hydrogen is removed from first carbon

of straight chain alkane in which second last carbon have
two methyl groups then we use the word neo-alkyl for that.
For example
CH 3
CH 3
H3 C
H3 C
H3 C
H3 C
neo-pentyl
neo-hexyl
sec-alkyl group-If a hydrogen is removed from secondary
carbon then we use the word sec representing for
secondary. For example
H3 C
CH 3
sec-butyl

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103
tert-alkyl group- If a hydrogen is removed from tertiary

carbon then we use the word tert representing for tertiary.
For example
CH 3
CH 3
H3 C
H3 C
CH 3
CH 3
tert-butyl
tert-pentyl
It is important to note that n, iso & neo alkyl group are generally
used for removing hydrogen from primary carbon, sec for secondary
carbon and tert for tertiary carbon with an exception in iso-propyl
where hydrogen is removed from secondary carbon. It is because
of the reason that, here there is a tie between iso a nd sec and as
alphabetica lly i comes first before s, iso is considered.
H3 C
CH 3
iso-propyl
By combining these alkyl groups with different functional

groups we can generate many of the organic compounds. For
example methane can form methyl alcohol, methyl amine, methyl
chloride etc.
H 3 C OH
Methyl alcohol
H 3C NH 2
Methyl amine
H 3 C Cl
Methyl chloride
To make organic chemistry easy the symbol R is used for all

such alkyl groups. The R group ca n be methyl, ethyl, propyl, butyl
or any alkyl group of any form i.e. n, iso, neo, sec or tert. You might
take R representing the Rest of the molecule, which we are not
bothering to specify because it is not important as chemical reaction
do not occur at that part.
The term primary, secondary and tertiary are routinely used in
organic chemistry along with these common alkyl groups so they
must be crysta l clear. For example if it is said that Tertiary alkyl
halide undergoes solvolysis reaction faster than secondary and
primary alkyl halide then it must be clear to you that we are talking
104

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about those compound in which ha logen is attached with tertiary
carbon.
H3 C Cl
H3 C
CH 3
tertiary butyl chloride
Similarly, if it is said that Tertiary alcohol reacts fa ster than

secondary a nd primary alcohol with Lucas reagent then it must
be clear to you that we are talking about those compound in which
hydroxyl group is attached with tertiary carbon.
H3 C OH
H3 C
CH 3
tertiary butyl alcohol

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105
Section
Basic concept of IUPAC

Nomenclature
There are billions of organic compounds synthesized & yet
another are in lab to be synthesized. To remember their names
individually is very very difficult for chemist. So, Interna tional
Union of Pure & Applied Chemistry (IUPAC) has given a general
method to name organic compounds. This method is applied to all
the organic molecules whether it is aliphatic, alicyclic, bicyclic, spiro,
aromatic which may contain one or more functional groups.
The IUPAC na me of a ny compound may consists of 5
components which must be written in a sequence so tha t a correct
name is given to a molecule. All of these have a cha racteristic
meaning. If in any compound, any component is missing then leave
that component & move on to next one.
These components are as follow:
2 prefix + 1 prefix + word root + 1 suffix + 2 suffix
106
Secondary (2) prefix: It tells about the nature and position

of substituent if any. Substituent is any atom or group of
atoms (other than functional group for monofunctional
group containing compounds), which replaces one or more
hydrogen from the main skeleton of carbon. To find out

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the substituent in organic molecule encircle the parent
carbon chain a long with functional group. If you do not
find any cut means molecule have no substitution but if
you find a ny cut a t a ny position tha t mea ns it ha s
substitution. The number of cuts give the number of
substituent in the molecule.
CH 3
H 3C
Compound with
0 substituents
Br
F
Compound with
2 substituents
CH 3
H 3C
CH 3 Cl
Compound with 2 substituents
Br
F
Cl
H3 C
Compound with
4 substituents
Some atoms or groups are alwa ys considered as substituents

irrespective of their chemical nature. Some common substituents
are given below
Substituent
2 0 Prefix
-F
Fluoro
-Cl
Chloro
-Br
Bromo
-I
Iodo
-NO2
Nitro
-NO
Nitroso
-R
Alkyl (Example- methyl, ethyl)
-OR
Alkoxy (Example- methoxy, ethoxy)
-Ph
Phenyl
Sometimes functional groups may a lso be considered as

substituent. If compound has only one functional group then it will

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107

be treated as secondary suffix. But if compound have more than
one functional group then priority of functional group is considered.
High priority functional group is considered as main functional
group & for it secondary suffix is used while low priority
functional group is considered as substituent for which secondary
prefix is used.
Primary (1) Prefix: It is used to specify cyclic, bicyclic or

spiro nature of main chain. If main skeleton of carbon is
cyclic then primary prefix cyclo is used before the word
root; for bicyclic compounds primary prefix bicyclo is
used; for spiro cyclic compounds primary prefix spiro is
used. But if it is open chain compound then no primary
prefix is used.
CH 3
H3 C
CH 3
No 1 Prefix
H3 C
1 Prefix-cyclo
No 1 Prefix
1 Prefix-cyclo
1 Prefix-Bicyclo
1 Prefix-Spiro
1 Prefix-Bicyclo
1 Prefix-Bicyclo
CH 3
When two or more atoms are common between the two rings
then such compounds are called as bicyclic compounds but when
one atom is common between the two rings then it is called as spiro
cyclic compound. Bicyclic compound has 2 bridge head carbon
connected to each other.
Bridge head C
Bridge head C
Bridges
Spiro cyclic
compound
108
Bridge head C
Bridge head C

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Word root: It tells about the longest continuous carbon

chain which includes functional group, carbon carbon
multiple bond (double or triple bond) and substituent (if
present) at minimum position. It is called as parent chain.
For parent chain selection, the decreasing order of priority for

assigning minimum position is
Functional group > Multiple bond > Substituent
It means minimum position is given to functiona l group
(if present) followed by multiple bond (if present) then substituent
(if present). The longest chain of carbon may contain any number
of carbon starting from 1 to and for each of them specific word
root is a ssigned;
Some commonly used word roots are given belowCarbon no.
Word root
C1
Meth
C2
Eth
C3
Prop
C4
But
C5
Pent
C6
Hex
C7
Hept
C8
Oct
C9
Non
C10
Dec
For more than 10 carbons some special word such as Undec for
C11 , Dodec for C12 and so on is used which is less common.
Primary suffix: It tells about saturated or unsa turated

nature of carbon-carbon bonds in the parent carbon chain.
If in the parent chain all ca rbon carbon bonds are single
bond then 1 0 suffix ane is used, if C=C bond is present in

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109

parent chain then 1 0 suffix ene is used and for C C bond
1 0 suffix yne is used.
Secondary suffix: It tells about the main functional groups

present in the compound. As we discussed earlier that if
more than one functional group is present in any compound
then priority of functional group is taken into consideration.
High priority functiona l group is considered a s ma in
functional group and for it secondary suffix is written. The
other functional groups are then considered as substituent
and for them 2 prefix is written. For each functional group
a fixed secondary suffix is given which is tabulated below
in decreasing order of priority
Functional group
Secondary suffix
Carboxylic acid (COOH)
oic acid
Sulphonic acid (SO3 H)
Sulphonic acid
Ester (COOR)
oate
Acid halide (COX)
oyl halide
Amide (CONH2)
amide
Nitrile (CN)
nitrile
Aldehyde (CHO)
al
Ketone (CO)
one
Alcohol (OH)
ol
Amine (NH2 )
amine
So any orga nic nomencla ture is written by using these 5

components in sequential order such as
CH 3
CH 3
H3 C
CH 3 H3 C
CH 3
5
1 2 3
5
1 2 3
4
4
Pentane
3-Methylpentane
Methylcyclohexane
WR 1S
2P WR 1S
2P 1P WR 1S
110

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Section
Points to write IUPAC

Nomenclature
Now we are going to discuss the important points to write
IUPAC nomencla ture of a ny orga nic molecule. As orga nic
compounds are infinite in number so use this 5-component system
(in a sequence) to name any organic molecule so that you may write
correct name. Never forget that all IUPAC names are derived from
the basic five components only which we discussed earlier. So use
those five components in sequential order keeping the underlying
points in your mind.
First select the parent chain, which is denoted by word root.

It is the longest continuous chain of carbon containing
functional group, multiple bond & substituent at minimum
position, following the priority order: Functiona l group >
multiple bond > substituent.
4 CH 3
H 3C
1 2 3
CH 3
Incorrect
CH 3
CH 3
5
H3 C
2
1CH 3
Incorrect
4

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CH 3
111
H3 C
1 CH 3
3
2 4
CH 3
Incorrect
CH 3
CH 3
1
H 3C
2
7
CH 3
6
CH 3
Correct
If number of carbon atoms are same in more than one

longest chain then parent chain will be that, which have
more number of substituent.
2
H3 C
3
CH3
1
CH 3
4
CH 3
8
7 CH3
Incorrect
8 C in parent chain & 1 subst.
H3 C 2
4
6
8
1
3
5 7 CH 3
CH 3
correct
8 C in parent chain & 1 subst.
If numbers of substituent is also same then pa rent chain

must have substituent at lower number.
CH 3
CH3
7
5
8
8 7 6 5
CH3
4 3
CH 3
6
H3 C
H
C
1
3
4
2
H3 C
H 3C
3
1 2
CH 3
CH 3
Incorrect
Correct
In first case parent chain is of 8 carbons with 2 substituents and
first substituent is at position 3 but in second case parent chain is of
8 carbon and 2 substituent but first substituent is at position 2.
Numbering is done from that side of the parent chain so as
to give minimum number to the first substituent (lowest
set of locants). Locant is the number specifying the position
of functional group, multiple bond or substituent in parent
chain. Lowest set of locant means minimum number at first
point of difference.
112

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Cl
Cl
H3 C 2 3 4 5 6 Cl
H3 C 5 4 3 2 1 Cl
1
6
Incorrect
Correct
In first ca se the locant is 2,6 but in second case locant is 1,5.
If the position of substituents are identical from both the

ends of the parent chain, then numbering in done in
alphabetical order, i.e. substituent coming alphabetically
first must gets minimum number. For example:.
CH 3
CH 3
Ethyl (E)
CH 3
CH 3
3
3
4
8
4
8
6
2
6
H3 C 2
H
C
3
5 7
5 7
1
1
CH 3
CH 3
Methyl (M)
Incorrect
Correct
Here ethyl comes alphabetically before methyl so, ethyl must
get minimum number.
If alphabets a re also same then numbering is done from

that side of the parent chain having substituent of the
substituent at lower number
2-Chloroethyl
Cl
Cl
CH 3
CH 3
5
3
4
6
4
6
8
1
H3 C 2
5
3
7
H
C
7
3
2
1
8
H 3C
Cl
Cl
1-Chloroethyl H 3 C
Incorrect
Correct
Substituents are of two types- simple and complex. Simple
substituents a re those in which no further branching is
observed in substituents but complex substituents are those
in which further branching is observed i.e. substituents on
substituent a re observed.
Complex substituent
6
5
H3 C 7
8
Complex substituent H 3C
Cl
3
2 1 Cl
CH 3 Simple substituent
Organic
Chemistry
is easy substituents,
by
For assigning
the name
to the complex
the
113
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carbon directly attached to the main skeleton of carbon is
given number 1 & so on. First substituent of substituent is
written followed by main substituent.
1
2-Chloroethyl
Cl
5
3
H3 C 7
2 1 Cl
8
2
1 CH
1-Methylethyl H 3C
3
Here for the substituent at position-5, the main substituent is
ethyl on which another substituent Cl is present (Cl is substituent
of substituent). So it is named as 2-Chloroethyl. For substituent at
position-4, the main substituent is again ethyl on which methyl is
substituted at position 1. So it is named as 1-Methylethyl.
6
is used between number & alphabets while comma (,)

is used between two numbers, there is no gap in writing
the IUPAC name and first alphabet must be written with
capital letter.
CH 3
H3 C
CH 3
H3 C 2 3 4 5 6
1
2,2-Dimethylhexane
If a compound ha s more tha n one substituent then
substituents are written in alphabetical order irrespective
of their locant. For example
Cl
Br
H 3C
CH 3
CH 3
Br
Cl
3-Bromo-2-chloropentane 2-Bromo-3-chloropentane
Word di, tri or tetra is used for 2, 3 or 4 times presence of
same substituent.
CH3 CH3
H 3C
CH 3
H 3C 2 3 4 5 6
1
2,2,4-Trimethylhexane
H 3C
114

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In IUPAC name of simple molecules which do not have

complex substituent, d of di and t of tri is not considered
for alphabetization.
F H 3C CH 3
CH3
6
H 3C 2 3 4
5
1
2-Fluoro-4, 4-dimethylhexane
In IUPAC na me of molecules which have complex

substituent, if di or tri are the part of the name of complex
substituent then d of di and t of tri is considered for
alphabetization and the name of complex substituent is
written in bracket.
Ethyl
1
3 2
1,1-Dimethylethyl
1-(1,1-Dimethylethyl)-4-ethylcyclohexane
If same complex substituents present two, three or four

times in the main chain then word bis, tris or tetrakis
respectively is used instead of di, tri, or tetra.
1,1-Dimethylethyl
1
3 2
1,1-Dimethylethyl
1,4-Bis-(1,1-dimethylethyl)cyclohexane

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115
Section
Points to write IUPAC nomenclature

for multiple bonds & rings
Earlier we had discussed about the points to write compounds
which have single bonds and may or may not have substituents.
Now we are going to learn nomenclature of those compounds which
have multiple bonds (such as alkene or alkyne) or rings (such as
cycloalkane).
Multiple bond is given more priority a s compared to

substituents or no. of carbon. The multiple bonds may be
double (C=C) or triple (C C) in nature.
If multiple bond C=C or C C is present then parent chain

is one which includes maximum number of multiple bonds.
While selecting parent chain we may leave another chain
which have more carbon but lesser number of multiple
bond. Numbering is done from that side of the parent chain,
so that multiple bond gets minimum number (if functional
group is absent).
6
4
CH 3
7
CH 3
3
5
H3 C 2 4 5 6
3
1 2
1
Pent-1-ene
4-Methylhex-2-ene 3-Propyl hepta-1,6-diene
116

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When e of alkane, alkene or alkyne is followed by another

a, e, i, o or y of primary or secondary suffix then e of these
primary suffix is not written.
H2 C
CH
1 2 3
5
4
Pent-1-en-4-yne
When primary suffix other than ene or yne (i.e. diene, diyne,
triene, triyne etc), is used then at the end of word root an
a is added.
H3 C
1
3
2 4CH 2
Buta-1,3-diene
When double bond & triple bond are at identical position

then double bond is given high priority & compound is
named as enyne as e of ene comes first then y of yne in
alphabets.
3 4 5 6 7
CH
6
H3 C 2 4
3
5
2 1
1
Hex-2-en-4-yne
3-Ethynyl hepta-1,6-diene
When more tha n two multiple bonds are present, then
always take the lowest number for second multiple bond if
position of first multiple bond is identical.
CH 2
HC 2 3 4 5 6 7 8 9 10
1
Deca-4,9-dien-1-yne
To write the IUPAC name of cyclic compounds we use the
same process i.e. secondary prefix, primary prefix, word
root, primary suffix and secondary suffix. For example
Cyclohexane
1 Prefix
Word root
1 suffix

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117
Substituted cycloalkanes are also named by rules similar

to those used in open chain alkanes.
In case of monosubstitued cycloalkanes the carbon of the

ring to which the substituent is attached is given no. 1.
4
5
6 1
Methylcyclohexane
In case of disubstituted cycloalkane, the carbon to which

substituent coming alphabetically first is attached is given
number one and numbering continues in such direction,
so as to give minimum number to second substituent.
4
3
21
Locants:
1,5
(Incorrect)
6 1
1,3
(Correct)
In case of cycloalkanes with more than two substituent

numbering is done in such a way that lowest set of locant
is obtained.
5
4
Locants:
4
5
6 1 Br
2
3
1,3,6
3
4
2 1 Br
6
5
1,2,5
6
5
1 2 Br
43
1,2,4
(Lowest set of locant)
It there is more than one way in which identical locants are

obtained then substituent which comes alphabetically first
must get minimum number.
3
4 5 Cl
2 16
Br
1-Bromo-5-chloro-4-ethyl-2-methylcyclohexane
118

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If ring & open chain both is present then to select parent

chain priority order is :
No. of multiple bond > No. of carbon > No. of substituent

If no. of multiple bond, no. of carbon & no. of substituent, all
are same in ring and open chain then ring is parent chain.
CH 3
CH 3
3 carbons 4 carbons
1-Cyclopropylbutane
Methylcyclo
propene
H3 C
1-Cyclopropyl
propene
I
H3 C
CH 3
1-Ethyl-5-methyl
cyclopentene
1
Br
2
3-Bromo-1-iodo
Cyclohexene
cyclohexa-1,4-diene
1 CH 3
2
CH3
2
1
3-Methylcyclo
octyne
3
1
2
Cyclooctyne
3
CH 3
1,3-Dimethyl
cyclohexene
CH3
CH 3
H3 C 2 1
Cl
3
Ethylcyclohexane 1-Cyclopropylpentane 1-Chloro-2-cyclo

propylpropane
As we had told you earlier that all organic compounds are

named by same five parts of IUPAC nomencla ture i.e.
Secondary prefix, primary prefix, word root, primary suffix
and secondary suffix, no matter compound is aliphatic or
aromatic. For simplicity, we will discuss the IUPAC name
of benzene and their derivative.

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119

When you will carefully observe benzene you will find that it is
cyclic with 6 carbon & alternate single and double bond i.e. primary
prefix, word root and primary suffix is fix for benzene, so all these
three parts comes together to form the name Benzene.
1 Prefix + Word rood + 1 Suffix=Benzene

Be careful that benzene is not Cyclohexa-1,3,5-triene as it gives
the picture of alkene derivative but we know that all carbon carbon
bond length in benzene is same and it have extra stability so it is not
aliphatic but it is aromatic.
If there is any substituent present at benzene ring then it is

written as secondary prefix before the benzene, if some functional
group is present then secondary suffix for that functional group is
written at the last. For example:
COOH
COOH
CH3
CH3
Methylbenzene
Benzene
carboxylic acid
2-Methylbenzene
carboxylic acid
It is also important to know that all carbon carbon bond length

of benzene is equal and lies in between carbon carbon single and
double bond so we can theoretically think the bond length as (one
& half) which is greater than single bond but less than multiple
bond.
If aliphatic or alicyclic carbon chain without multiple bond

& functional group attached to benzene ring, then benzene
is considered as parent chain. But if aliphatic or alicyclic
carbon chain with multiple bond or functional group is
attached to benzene ring then benzene ring is considered
as substituent. When benzene is placed as a substituent then
we use the 1 prefix phenyl for it.
CH3
Benzene
120
Methylbenzene

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Cyclohexyl
benzene

CH
CH2
Phenylethene
Phenylethyne
If aliphatic or alicyclic carbon chain attached to benzene

ring (without functiona l group) has more number of
substituents, then benzene ring is consider as substituent.
3 2 Cl
1
4
CH 3
2-Chloro-1-methyl-4-phenyl
cyclohexane
CH3
1 CH
3
2
1-Ethyl-2-Methyl
benzene

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121
Section
Points to write IUPAC nomenclature

of compounds with functional groups
Functional groups are very much important in organic chemistry
as they are the site of chemical reactions. The same functional group
will undergo the same or similar chemical reaction(s) regardless of
the size of the molecule however, its relative reactivity can be
modified by nearby functiona l groups.
For naming mono functional group containing compounds we
use specific secondary suffix for each functional groups such as oic
acid for carboxylic acid.
O
Carboxylic acid
4
3
1
H3 C
OH
2
Butanoic acid
but for poly functional groups containing compounds we have

to consider the priority of functional groups. For higher priority
functional groups we use seconda ry suffix but for lower priority
functional groups we use secondary prefix. Let us take an example
where high priority carboxylic acid along with low priority alcoholic
122

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group is present. For this seconda ry suffix oic acid is used for
carboxylic acid and secondary prefix hydroxy is used for alcoholic
group.
OH O
Alcohol
Carboxylic acid
H 3 C 3 2 1 OH
4
3-Hydroxybutanoic acid
The priority of functional groups in decreasing order along with
secondary prefix and secondary suffix are given below which must
be remembered by heart without any confusion.
SN Group
Common Name 2Prefix
2Suffix
1.
COOH
Carboxylic acid Carboxy
oic acid
2.
3.
4.
5.
SO3H
Sulphonic acid Sulpho
sulphonic acid
-COOCO- Acid anhydride
oic anhydride
-COOC
Ester
Alkoxycarbonyl oate
& Alkanoyloxy
-COX
Acid halide
Halocarbonyl oyl halide
6.
7.
-CONH2
-CN
Amide
Nitrile
Carbamoyl
Cyano
amide
nitrile
8.
-CHO
Aldehyde
al
9.
-CO-
Ketone
Formyl, aldo
or Oxo
Oxo
Alcohol
Amine
Hydroxy
Amino
ol
amine
10. -OH
11. -NH2
one
Here are some example of compounds with one functional

group:
O
O
SO 3 H
H3 C
H3 C
H 3C
OH
NH 2
CH 3
Propanoic acid
Propanamide
Butane-2-sulphonic acid
O
O
H3 C
H 3C
H3 C
N
Cl
OH
Propanoyl chloride Propanoic acid Propane nitrile

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123

H3 C
O
H
NH 2
H3 C
CH 3
Butan-2-one
Propanal
H3 C
CH 3
Butan-2-amine
Some functional groups such as acid anhydride, ester and

amides are formed by chemical reaction of two similar or
different functional groups. So in those cases it is important
to know the attachments with positions. Such as
O
CH3
H 3C
O
H+H
Carboxylic acid
H3 C
O
CH 3
Acid anhydride
H 2 O
Carboxylic acid
CH 3
H3 C
O
H+H
Carboxylic acid
H 2 O
H3 C
H 3C
Alcohol
H+H
H 3C
NH
H 2 O
H3 C
Primary amine
CH 3
O
H+H
O
H 2 O
Alcohol
CH 3
NH
Amide
CH 3
CH 3
H 3C
O
Ether
H 3C
NH 2 + H NH
NH 3
Primary amine
Primary amine
124
CH 3
CH3
H 3C
Carboxylic acid
O
Ester
Alcohol
O
O
CH 3
NH
Secondary amine

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CH 3
H3 C
NH 2 + H
Primary amine
CH 3
H 3C
N
NH 3
CH 3
Secondary amine
H 3C
Tertiary amine
Acid anhydride may be symmetrical (formed by chemical

reaction of two similar carboxylic acids) or dissymmetrical
(formed by chemical reaction of two dissimilar carboxylic
acids). To name symmetrical acid anhydride we replace oic
acid of carboxylic acid (from which it is formed) by oic
anhydride and it is named as alkanoic a nhydride. But
dissymmetrical acid anhydrides are named as Alkanoic
alkanoic a nhydride, taking alphabetiz ation of carboxylic
acids.
O
O
O
O
H 3C
CH 3
H3 C
O
CH 3
O
Propanoic anhydride Ethanoic propanoic anhydride
An ester is formed from chemical reaction of two functional

groups carboxylic acid and alcohol and both have carbon.
To name an ester alcoholic part is written first as alkyl
followed by the a cidic part as alkanoate.
O
O
CH 3
H3 C
H3 C 1 O
CH 3
O H+H O
2 Ester
Carboxylic acid
Alcohol
Ethylethanoate
Secondary amides are named as N-Alkyl alkanamide and
tertiary a mide as N,N-Dialkyl alkanamide (for amide
derived from same amine) or N-Alkyl N-alkyl alkanamide
(for amide derived from two different amines).
O
O
H 3C 1 N
CH 3
H3 C 1 NH
CH 3
2
2
CH3
N-Ethylethanamide
N,N-Diethylethanamide

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125

O
H3 C
2
1 N
CH 3
CH 3
N-Ethyl-N-methylethanamide
In case of secondary or tertiary amines the alkyl group with

longest carbon chain is parent chain & the other alkyl
groups attached to nitrogen a re considered as substituent
on nitrogen. Secondary amines are na med as N-Alkyl
a lka na mine a nd tertia r y a mine a s N ,N -D ia lkyl
alkanamine, if both alkyl substituent on nitrogen are same
and N-Alkyl N-alkyl alkanamine for tertiary amines with
two different alkyl substituents on N.
H 3C 1 N
CH 3
H3 C 1 NH
2
CH 3
2
CH 3
N-Ethylethanamine
N,N-Diethylethanamine
H3 C 1 N
2
CH3
CH 3
N-Ethyl-N-methylethanamine
Ethers are always written as Alkoxyalkane as OR is always

considered as secondary prefix.
H3 C 1 O
CH 3
2
Ethoxyethane
126
Some functional groups are always present at the terminal

positions so called as chain terminating functional groups
while some functiona l groups may be present at a ny
position, hence called as non-chain terminating functional
groups. Example of chain terminating functional groups
are Carboxylic acid (-COOH), Acid halide (-COX), Amide
(CONH2 ), Nitrile (-CN), Aldehyde (-CHO) while example
of non termina ting functional groups are Sulphonic acid
(SO3 H), ketone (-CO-), alcohol (-OH), amine (-NH2)

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When chain termina ting functional group is directly

attached with ring (may be of aliphatic or aroma tic), then
special suffix is used for these functional groups.
S.N.
Functional Groups
Secondary suffix
Carboxylic acid (-COOH)
Carboxylic acid
Ester (-COOC)
Carboxylate
Acid halide (-COX)
Carbonyl halide
Amide (-CONH2)
Carboxamide
Nitrile (-CN)
Carbonitrile
Aldehyde (-CHO)
Carbaldehyde
Some common examples are

COOH
Cyclohexane
carboxylic acid
CONH 2
Cyclohexane
carbaldehyde
COCl
CN
Cyclohexane
carbonitrile
COOMe
Cyclohexane
Methylcyclohexane
carbonylchloride
carboxylate
Cyclohexane
carboxamide
COOH
Benzene
carboxylic acid
CONH 2
Benzene
carboxamide
CHO
CHO
Benzene
carbaldehyde
COCl
Benzene
carbonyl chloride
CN
Benzene
carbonitrile
COOMe
Methylbenzene
carboxylate

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127
Phenyl group is commonly written as C6 H 5 or Ph. When it

is directly attached with any functional group containing
carbon then it is considered as parent chain and word
benzene is used for it but if even one carbon is present
between phenyl a nd functional group then benzene is
considered as substituent and word phenyl is used.
COOH
2 1
COOH
2-Phenylethanoic
acid
Benzene
carboxylic acid
In writing the name of compounds with more than one

functional group the senior functional group is selected as
the principle functional group and for it secondary suffix
is considered while other functional groups are treated as
substituents and for them secondary prefix is used.
O
OH O
H 3 C 5 4 3 2 1 OH
6
3-Hydroxy-5-oxohexanoic acid
When ester is present as a substituent then two different

types of secondary prefixes are used alkoxycarbonyl
(when CO is directly attach to main chain) and alkanoyloxy
(when O is directly attached with main chain).
COOH
1 Methoxycarbonyl
2
6
O
H 3C
O 3 4 5
CH 3
O
3-Ethanoyloxy-5-methoxycarbonyl
cyclohexane carboxylic acid
Ethanoyloxy
O
128
In case of aldehydes, two different secondary prefixes are

used- Aldo or formyl & oxo. Secondary prefix formyl or

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aldo is used when -CHO is directly atta ched to main
skeleton but secondary prefix oxo is used when alkyl group
with -CHO is attached to main skeleton.
CN
formyl 2 1 6 2-Oxoethyl
CHO
OHC 3 4 5
3-Formyl-5-oxoethylcyclohexanecarbonitrile
Secondary prefix ox o is used for aldehydes as well as

ketones when CO is part of main or side skeleton and the
carbon of CO is counted in skeleton.
O
H3 C 5 4 3 2 1 OH
6
5-Oxohexanoic acid
H 5 4 3 2 1 OH
5-Oxopentanoic acid
COOH
1
2
O 6
H
5 4 3
CH 3
O
3-(1-Oxoethyl)-5-(2-oxoethyl)benzenecarboxylic acid
When ester, acid halide or amide is present as a substituent

then carbon of CO is not counted in main chain.
O
O
Cl
O
2
2
3
1 OH
3
1 OH
H3 C
O
O
3-(Methoxycarbonyl)
3-(Chlorocarbonyl)
propanoic acid
propanoic acid
H
N
O
2
3
1 OH
O
3-(N-Methylcarbamoyl)
propanoic acid
CH 3

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129
Some aromatic compounds are given a fixed name and is

retained in IUPAC nomenclature. Such as
Benzene
OH
NH 2
Phenol
Aniline
130

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Section
Nomenclature of Bicyclic &

Spiro compounds
A bicyclic molecule is a molecule that fuses two rings. These
fusion of the rings can occur in three ways:
1.
If two rings shares one carbon atoms then such compounds

are called as spirocyclic or simply spiro compound
2.
If the two rings shares two adjacent carbons then such

compounds are called as fused bicyclic compounds
3.
If the rings shares two non adjacent carbons then such

compounds are called as bridged bicyclic compounds.
or
Spiro compounds Fused bicyclic
Bridged bicyclic
As we told you that all IUPAC nomenclature consist of five

parts written in sequential order i.e.
2 0 prefix + 1 0 prefix + Word root + 10 suffix + 2 0 suffix,
IUPAC name of bicyclic compounds and spirocyclic compounds
can also be written in the same way as the other molecules, the only

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131

difference occur in primary prefix where Bicyclo or Spiro is
used so as to differentiate from acyclic and cyclic compounds.
Bicyclic compounds:
(1) Prefix Bicyclo is used followed by the name of alkane
corresponding to the total number of carbon atoms in both
ring.
(2) The number of C a toms in ea ch of the three bridges
connecting the two tertiary carbon atoms is indicated in
bracket in descending order after bicyclo.
(3) Numbering is started from one of the bridgehead carbon
and proceeds by longest possible path to the second
bridgehead carbon & continuous through next longer path
back to first bridgehead and is completed by the shortest
path.
7
2
6 1
2
or
7
3
5
5
4
3
4
Bicyclo[2,2,1]heptane
6
Here the carbon frame contains a total of 7 atoms, hence the

parent name heptane and this molecule has three bridges having 2,
2 and 1 carbon atoms, hence the name becomes Bicyclo [2, 2, 1]
heptane.
9
8
10 1 2
3
4
.
76 5
Bicyclo[4,4,0]decane
In case of writing IUPAC name of substituted compounds

or compounds with functional groups we use the concept of
secondary prefix and secondary suffix as we had used earlier.
It is also important to note that in case of bicyclo compounds
bridge head is given number 1, no matter it has substitution or
132

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functional groups, then follow the sequence in decreasing order
so that all atoms are taken in decreasing way.
7
O
6
6 1 O
or
2
7
2
5 4
5
3 F
4 3F
3-Fluorobicyclo[2,2,1]heptan-2-one
1
CH 3
7 CH
1
3
1
6
6
2
2
or
7
3
5 4
5
3
4
1-Methylbicyclo[2,2,1]heptane
H3 C 7
1
2
6
or
2
H 3C
3
5
5 4
4
3
7-Methylbicyclo[2,2,1]heptane
6
10 1 2 3 O
4
765 I
4-Iodobicyclo[4,4,0]dec-1-en-3-one
9
8
Spiro compounds:
(1) Prefix spiro is used followed by alkane corresponding to
the total number of carbon atoms in both ring.
(2) The number of carbon is both the rings, leaving the spiro
atom (a tom joining the rings) is written in bra cket in
ascending order after spiro.
(3) The numbering starts from the atom next to spiro atom in
the smaller ring & proceeds to the la rger ring via spiro
atom.

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133

2
1
8 3 4
7
5
6
Spiro[2,5]octane
Here the carbon frame contains a total of 8 atoms, hence the

parent name become octane and this molecule has two bridges
having 2 and 5 carbon atoms which we have to write in increasing
order, hence the name becomes Spiro[2,5]octane.
3 2
CH3
2
1
Cl
8 3 4
5
7
6
1-MethylSpiro[2,5]octane
4 5 1
9
6
8 7
Spiro[4,4]nonane
Cl
2
1
8 3 4
5
7
6
1-Chlorospiro[2,5]oct-4-ene
1
O
8 3 4
7
5
6
Spiro[2,5]octan-4-one
134

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Section
Some common names commonly

used in organic chemistry
There are lot of organic compounds whose common names are
also important along with IUPAC name and they are frequently
encountered in organic chemistry. So remember these common
names along with a quick look of their IUPAC name
SN Com.
Common name
IUPAC name
1.
Marsh gas,
damp fire
Methane
Iso-butane
2-Methylpropane
CH4
CH 3
2.
H3 C
CH 3
CH 3
3.
H3 C
CH 3 Iso-pentane
CH 3
4.
H3 C
CH
CH3 3
Neo-pentane
2-Methylbutane
2,2-Dimethyl
propane

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135

CH 3
5.
Iso-hexane
2-Methylpentane
Neo-hexane
2,2-Dimethylbutane
7.
Benzene
Benzene
8.
Naphthalene
Naphthalene
9.
Anthracene
Anthracene
10.
Phenanthrene
Phenanthrene
Ethylene
Ethene
CH 2
Propylene
Propene
CH 2
Iso-butylene
2-Methylpropene
Allene
Propa-1,2-diene
Acetylene
Ethyne
Methylacetylene
Propyne
H3 C
CH 3
CH 3
6.
H3 C
11.
H2 C
12.
H3 C
CH 3
CH 3
CH 2
H3 C
13.
14.
H3 C
CH 2 C
CH 2
15. HC CH
16. H 3 CC CH
17.
Ethylmethyl
H3 C C C CH 2 CH 3 acetylene
Pent-2-yne
18.
H3 C Cl
Methyl chloride
Chloromethane
19. CH 2 Cl 2
Methylene chloride Dichloromethane
20. CHCl 3
Chloroform
136
Trichloromethane

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21. CCl 4
22.
H3 C
Cl
Methane
tetrachloride
Tetrachloromethane
Ethylchloride
Chloroethane
H3 C
23.
Cl
Iso-Propylchloride 2-Chloropropane
H3 C
Cl
24.
H3 C
25. Cl
26.
CH 3
CH 3
CH 3
CH 3
Cl
H3 C
CH 3
CH3
27. H C
3
28.
Cl
Sec-Butyl chloride 2-Chlorobutane
1-Chloro-2-methyl
propane
Tert-Butyl chloride
2-Chloro-2-methyl
propane
Neo-Pentyl chloride
1-Chloro-2,2-dimethyl
propane
Ethylene dichloride
1,2-Dichloroethane
Cl
CH 3
Cl
Iso-Butyl chloride
Cl
29.
H3 C
30.
H2 C
31.
H2 C
Cl
Ethyledine dichloride 1,1-Dichloroethane
Cl
Cl
Vinyl chloride
1-Chloroethene
Allyl chloride
3-Chloropropene

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137

Cl
32.
Phenylchloride
Chlorobenzene
Benzyl chloride
1-Chloro-1-phenyl
methane
Benzal chloride
1,1-Dichloro-1-phenyl
methane
Cl
33.
Cl
Cl
34.
35.
Cl
Cl
Cl
Benzo chloride
1,1,1-Trichloro-1-phenyl
methane
Cl
Cl
36. Cl
Cl
Cl Gammexane, Lindane,
Hexachlorocyclo
Benzenehexa
Cl
hexane
chloride(BHC)
OH
37.
H3 C
38.
H3 C
OH
Ethyl alcohol
(Methyl carbinol)
Ethanol
Propyl alcohol
Propan-1-ol
OH
39.
H3 C
CH 3
Iso-Propyl alcohol Propan-2-ol
OH
40.
H3 C
41. HO
138
CH 3
Sec-Butyl alcohol
Butan-2-ol
Iso-Butyl alcohol
2-Methylpropan-1-ol
CH 3
CH 3

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42.
CH 3
OH
H3 C
CH 3
CH3
43.
H3 C
44.
H2 C
OH
CH 3
OH
Tert-Butyl alcohol 2-Methylpropan-2-ol
Neo-Pentyl alcohol
2,2-Dimethyl
propan-1-ol
Allyl a lcohol
Prop-2-en-1-ol
Benzyl alcohol
1-Phenylmethanol
OH
45.
46. HC
OH
OH
47.
OH
Propargyl alcohol Prop-2-yn-1-ol

Ethylene glycol
(Glycol)
Ethane-1,2-diol
Propylene glycol
Propane-1,2-diol
OH
48.
H3 C
OH
Trimethylene
OH
glycol
49. HO
OH
OH
OH
O
50.
51.
Propane-1,3-diol
Glycerol
(Glycerine)
Propane-1,2,3-triol
Formaldehyde
Methanal
Acetaldehyde
Ethanal
Propionaldehyde
Prapanal
52.
H3 C
53.
H3 C

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139

O
54.
H3 C
n-Butyraldehyde
Butanal
55.
H3 C
Iso-Butyraldehyde 2-Methylpropanal
CH 3
O
56.
H2 C
Acrolein
Prop-2-enal
Crotonaldehyde
But-2-enal
Dimethyl ketone
(Acetone)
Propanone
Acetophenone
Phenylethanone
Benzophenone
Diphenyl
methanone
Ethyl methyl
ketone
Butanone
57.
H3 C
H
O
58.
H3 C
CH 3
59. Ph
CH 3
60.
Ph
Ph
O
61.
H3 C
CH 3
62.
H3 C
63.
H3 C
64.
H2 C
Methyl propyl
ketone
Pentan-2-one
CH 3 Diethyl ketone
Pentan-3-one
CH 3
O
O
140
CH 3
Methyl vinyl
ketone
But-3-en-2-one

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O
65.
OH
Formic acid
Methanoic acid
Acetic acid
Ethanoic acid
Propionic acid
Propanoic acid
66.
67.
68.
H3 C
OH
O
H3 C
OH
O
H3 C
OH
n-Butyric acid
Butanoic acid
69.
H3 C
OH
n-Valeric acid Pentanoic acid
70.
H3 C
OH Iso-butyric acid
CH3
2-Methylpropanoic
acid
71.
H2 C
OH
Acrylic acid
Prop-2-enoic acid
72.
H3 C
OH
Crotonic acid
But-2-enoic acid
COOH
73.
COOH
Oxalic acid
Ethane-1,2-dioic acid
Malonic acid
Propane-1,3-dioic
acid
Succinic acid
Butane-1,4-dioic acid
Glutaric acid
Pentane-1,5-dioic
acid
COOH
74.
COOH
COOH
75.
76.
COOH
COOH
COOH

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141

COOH
COOH
77.
Adipic acid
Hexane-1,6-dioic
acid
2-Hydroxy
propanoic acid
COOH
OH
CH 3
Lactic acid
H
79. H
COOH
OH
OH
COOH
Meso-Tartaric acid
78.
COOH
H
OH
d or l
80. HO
H
Tartaric acid
COOH
COOH
81.
Malic acid
HO
COOH
COOH
COOH Citric acid
COOH
82. HO
(2R,3S)2,3-Dihydroxy
butane-1,4-dioic acid
(2R,3R)2,3-Dihydroxy
Or
(2S,3S)2,3-Dihydroxy
2-Hydroxybutane
-1,4-dioic acid
2-Hydroxy
propane-1,2,3tricarboxylic acid
83.
H3 C
COOH
Pyruvic acid
2-Oxopropanoic acid
Maleic acid
Cis-But-2-ene1,4-dioic acid
COOH
84.
COOH
COOH
85.
HOOC
Fumaric acid
Trans-But-2-ene
-1,4-dioic acid
COOH
86.
142
Benzoic acid
Benzene carboxylic
acid

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87.
88.
COOH
OH
Salicylic acid
COOH
O
O
89.
90.
CH 3 Acetyl salicylic acid

(Aspirin)
COOCH 3
OH
2-Hydroxybenzene
carboxylic acid
2-(Ethanoyloxy)
benzene
carboxylic acid
Oil of winter green Methyl-2-hydroxy

(Methyl salicylate) benzenecarboxylate
COOPh
OH
Phenyl salicylate
(Salol)
Phenyl-2-hydroxy
benzenecarboxylate
Picric acid
2,4,6-Trinitrophenol
OH
O2N
NO 2
91.
NO 2
CH=CHCOOH
92.
Cinnamic acid
3-Phenyl
prop-2-enoic acid
93.
OCH 3
Methylformate
Methylmethanoate
94.
OCH2 CH3
Ethylformate
Ethylmethanoate
95.
H3 C
OCH 2 CH3
96.
Cl
Ethyl acetate
Formylchloride
(Unstable)
Ethylethanoate
Methanoyl chloride

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143

Cl
97.
Benzoyl chloride
Benzene carbonyl
chloride
Acetyl chloride
Ethanoyl chloride
98.
H3 C
Cl
99.
Acetic
H3 C
CH 3
O
anhydride
or (CH 3CO )2 O
Ethanoic
anhydride
CH 3 Propionic
O
100. H3 C
anhydride
or (CH 3CH2 CO)2 O
Propanoic
anhydride
101.
Formamide
Methanamide
Acetamide
Ethanamide
Propionamide
Propanamide
104.
Acetanilide
N-Phenyl
ethanamide
105. H 3 CON=O
Methyl nitrite
Nitrito methane
Ethyl nitrite
Nitrito ethane
Methyl amine
Methanamine
NH 2
O
102.
H3 C
NH 2
O
103. H3 C
NH 2
NHCOCH3
106. H C
3
ON=O
107. H 3 CNH 2
144

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108.
109.
110.
H3 C
NH 2
H3 CNH
CH 3
H3 C
Ethyl amine
Ethanamine
Dimethyl amine
N-Methyl
methanamine
CH 3
NH
Diethyl amine
CH 3
111. H3 CN
CH 3
H3 C
N
112.
Trimethyl amine
N-Ethyl ethanamine
N,N-Dimethyl
methanamine
CH 3
Triethyl amine
H 3C
N,N-Diethyl
ethanamine
113. H 2 NSO 3H
Sulphamic acid
114. H 3 CSO 3 H
Methylsulphonic
acid
Amino sulphonic
acid
Methanesulphonic
acid
115.
Phenyl sulphonic
acid
Benzene sulphonic
acid
116. H 3 CCN
Methyl cyanide
or Acetonitrile
Ethane nitrile
Phenyl cyanide
or Benzonitrile
Benzene carbonitrile
SO 3H
CN
117.
118. H 3 CNC
119.
H3 C
Methyl iso-cyanide or
Methylcarbyl amine
Ethyl iso-cyanide or
NC Ethyl carbylamine
Methane iso-nitrile
Ethane iso-nitrile

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145

NC
Phenyl iso-cyanide or
Phenylcarbyl amine
120.
121.
122.
123.
O
O
epoxide
Oxirane
Trimethylene
oxide
Oxetane
Tetrahydrofuran
(THF)
Oxolane
Dioxane
1,4-Dioxacyclo
hexane
Trioxane
1,3,5-Trioxacyclo
hexane
Toluene
Methylbenzene
Ethylbenzene
Ethylbenzene
124.
125.
O
O O
Benzene iso-nitrile
CH 3
126.
CH 3
127.
H3 C
CH 3
128.
H 3C
129. H3 C
Iso-propylbenzene (1-Methylethyl)
(Cumene)
Benzene
CH 3
Tert-Butyl
benzene
(1,1-dimethylethyl)
benzene
Styrene
Phenylethene
CH=CH 2
130.
146

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CH3
CH 3
131.
o-Xylene
1,2-Dimethyl
benzene
m-Xylene
1,3-Dimethyl
benzene
p-Xylene
1,4-Dimethyl
benzene
Mesitylene
1,3,5-Trimethyl
benzene
Carbolic acid
Phenol
Catechol
Benzene-1,2-diol
Resorcinol
Benzene-1,3-diol
Hydroquinone
Benzene-1,4-diol
CH3
132.
CH 3
CH 3
133.
CH 3
CH3
134.
H3 C
CH 3
OH
135.
OH
OH
136.
OH
137.
OH
OH
138.
OH

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147

OH
139.
OH
140.
- Naphthol
1- Naphthol
- Naphthol
2-Naphthol
Benzaldehyde
Benzene
carbaldehyde
Salicyldehyde
2-Hydroxybenzene
carbaldehyde
Oil of mirbane
Nitrobenzene
Anisole
Methoxybenzene
Aniline
Aniline
o-Toluidine
2-Methylaniline
m-Toluidine
3-Methylaniline
CHO
141.
142.
CHO
OH
NO 2
143.
OCH3
144.
NH 2
145.
146.
NH2
CH 3
NH 2
147.
CH 3
148

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NH 2
148.
p-Toluidine
4-Methylaniline
o-Cresol
2-Methylphenol
m-Cresol
3-Methylphenol
p-Cresol
4-Methylphenol
Iso-octane
2,2,4-Trimethyl
pentane
Mustard gas
Bis-(2-Chloroethyl)
sulphide
Westron
1,1,2,2-Tetra
chloroethane
155. ClCH CH 2
Westrosol
1,1,2-Trichloro
ethene
156. Cl 3C NO 2
Chloropicrin
tear gas
1,1,1-Trichloro-1nitromethane
Chloretone
1,1,1-Trichloro-2methylpropan-2-ol
CH3
OH
CH 3
149.
OH
150.
CH 3
OH
151.
CH 3
152.
153.
154.
CH 2 Cl
CH 2 Cl
CH2 S CH2
CHCl 2
CHCl 2
CCl 3
157. CH 3 CCH 3
OH

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149

CH 3
158.
CH 3 C
CHCH 3
Triptane
2,2,3-Trimethyl
butane
Isoprene
2-Methyl
buta-1,3-diene
Chloroprene
2-Chloro
buta-1,3-diene
Lewisite
2-chloroethenyl
arsonousdichloride
Pinacol
2,3-Dimethyl
butane-2,3-diol
Pinacolone
3,3-Dimethyl
butan-2-one
CH 3 CH 3
159.
CH 3
H2 C=CCH=CH 2
Cl
160. CH C=CHCH
2
2
ClCH
161.
HCAsCl 2
CH 3 CH 3
162. CH 3 C CCH 3
OH OH
O
163.
CH 3 C
CH3
CCH 3
CH 3
164.
CHO
COOH
Glyoxalic acid
2-oxoethanoic acid
Pivaldehyde
2,2-Dimethyl
propanal
CH 3
165.
CH 3 C CHO
CH 3
O O
166. CH CCCH Dimethylglyoxal
3
3
O O
167.
150
PhCCPh
Benzil
Butan-2,3-dione
1,2-Diphenyl
ethane-1,2-dione

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CHO
H
OH
168.
CH2 OH
169.
CHO
CHO
Glyceraldehyde
2,3-Dihydroxy
propanal
Glyoxal
Ethanedial
CHO
Methylglycol
(Pyruvic aldehyde)
170. CCH3
O
H3 C
171.
C=CHCCH=C
H3 C
H3 C
172. H C
3
CH 3
CH 3
C=CHCCH 3
Phorone
Mesityloxide
173. H 2 C=C=O
2-oxopropanal
2,5-Dimethyl-4en-3-one
4-Methylpent
-3-en-2-one
Ketene
Ethenone
Carbonic acid
Carbonic acid
174.
HOCOH
O
175. CH CCOOH Pyruvic acid
3
OH
176.
PhCHCOOH
Mendalic acid
177. H 2 NCHCOOH Glycine

178.
CH 3
H2 NCHCOOH
179. H 2 N COOH
Alanine
Carbamic acid
2-oxopropanoic acid
2-Hydroxy-2-Phenyl
ethanoic acid
Aminoethanoic acid
2-Amino
propanoic acid
Carbamic acid

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151

OH
180.
181.
COOH
OO
ClCCCl
182. H NCONH
2
4
O
Glycolic acid
2-Hydroxy
ethanoic acid
Oxalyl chloride
Ethanedioyl
dichloride
Ammonium
carbonate
Ammonium
carbonate
183. CH CCH COEt

3
2
Acetoacetic
ester
Ethyl-3-oxo
butanoate
184.
Phosgene
Carbonyldichloride
Urea
Carbamide
Indole
Indole
Pyridine
Pyridine
188. N
H
Pyrrole
Pyrrole
189.
Thiophene
Thiophene
Furan
Furan
Azulene
Bicyclo[5,3,0]
decapendaene
Cl C Cl
185. H NCNH
2
2
N
H
186.
187.
190.
S
O
191.
192. H2 N
152
SO 3H
Sulphanilic
acid
4-Aminobenzene
sulphonic acid

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O
193.
O
194.
OH
Tropone
Cyclohepta-2,
4,6-trienone
Tropolone
2-Hydroxycyclo
hepta-2,4,6-trienone
OH
HO
O
195.
Phenol
phthalin
O
H Cl
Cl
Cl
Cl
196.
Cl
197.
N N
DPT
Hydrazo
benzene
3,3-Bis-(4-Hydroxy
phenyl) Isobenzo
furan-1-one
1,1,1-Trichloro-2,
2-Bis-(4-chloro
phenyl)ethane
1,2-Diphenyl
hydrazine
H H
OH
O2N
NO 2
198.
O
Picric acid
2,4,6-Trinitrophenol
mcpba
3-chloroperbenzene
carboxylic acid
O-toluic acid
2-Methylbenzene
carboxylic acid
m-toluic acid
3-Methylbenzene
carboxylic acid
NO 2
COOH
199.
Cl
200.
COOH
CH 3
COOH
201.
CH 3

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153

COOH
p-toluic acid
4-Methylbenzene
carboxylic acid
Phthalic acid
Benzene-1,2-di
carboxylic acid
Isophthalic acid
Benzene-1,3-di
carboxylic acid
Terephthalic acid
Benzene-1,4-di
carboxylic acid
Anthranilic acid
2-Aminobenzene
carboxylic acid
207. N
H
Pyrrolidine
Pyrrolidine
208. N
H
Piperidine
Piperidine
Morpholine
Morpholine
Aziridine
Aziridine
202.
CH 3
COOH
203.
COOH
COOH
204.
COOH
COOH
205.
COOH
COOH
NH 2
206.
209. N
H
210.
N
H
154

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211. PhCH=CHPh Stibene
N
1,2-Diphenylethene
Urotropine
1,3,5,7-Tetraaza
tricyclo [3,3,1,1]
decane
Guanidine
Guanidine
Amidine
Acetamidine
Phthalic
anhydride
Benzene-1,2dicarboxylic
anhydride
Phthalimide
Isoindole-1,3-dione
217.
Cinnamaldehyde
3-Phenylprop-2-enal
218. CH3 SCH 3
Dimethylsulphide
Dimethysulphide
(DMS)
212. N N
N
NH
213. H NCNH
2
2
NH
214. CH CNH
3
2
O
O
215.
O
O
NH
216.
O
CH=CHCHO
219. CH SCH
3
3
O
220.
HCNCH 3
CH 3
Dimethyl
sulphoxide
(DMSO)
Dimethyl
sulphoxide
Dimethyl
formamide
(DMF)
N,N-Dimethyl
methanamide

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155

H
221.
O
N
Barbituric acid
O
OH
222.
O O
HO
HO
Ascorbic a cid
OH
O OH
222.
PhCCHPh
Benzoin
Pyrimidine
-2,4,6-trione
(1,2-Dihydroxyethyl)
-3,4-dihydroxy
furan-2-one
2-Hydroxy-1,2diphenylethanone
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Section
08
Degree of unsaturation
Degree of unsatura tion (DU) is very importa nt in orga nic
chemistry as it helps to predict different structures for any molecular
formula. It is also called Double bond equivalent (DBE) or Index
of hydrogen deficiency (IHD). Degree of unsaturation is simply
the hydrogen deficiency index from a ny acyclic sa tura ted
hydrocarbon.
We know that formation of a bond occur by loss of two hydrogen
atoms from adjacent position, for the formation of a triple bond
four hydrogen atoms are removed from adjacent position, loss of
two hydrogen atoms also lead to the formation of a cyclic system if
they are not removed from adjacent position. So one bond or one
ring is equal to 1 DU. So DU is equal to sum of bonds a nd rings
in the structures. Such as
Structure
DU
Structure
DU

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157

7
OH OH
HO
OH
As the bond or ring is formed by loss of hydrogen from acyclic

saturated hydrocarbon (i.e. alkane having general formula (CnH2n+2 ),
mathematically it can be calculated from known molecular formula.
DU =
(2C + 2) H X + N
2
Where C is the total number of carbon atoms, H is the total number

of hydrogen atoms, X is the total number of halogen atoms and N is
the total number of nitrogen atoms.
It is important to note that there is no role of oxygen atom or
any atom of 16 th group such as S in calculation of DU.
If the value of DU comes to be zero, it means that molecule

is acyclic and saturated with no double or triple bond and
also without any ring.
If DU is equal to one then molecule must have a bond or

a ring. The bond may be between carbon atoms or
between carbon and others atoms (like N, O etc) if these
atoms are present in the molecular formula. Similarly, the
ring may conta in only carbon or ring with hetero atoms
may be formed.
If the value of DU comes to be two that means molecule

must have a triple bond, two double bonds, one double
bond and a ring or two rings.
Example 1: Write all the possible structures with molecular formula

C5H12
To solve such questions first ca lculate DU. It will give a clear
cut picture to think about acyclic saturated molecule as DU comes
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to be zero. Then draw all possible structures starting from maximum
carbon in main chain and then go on decreasing one carbon in main
chain and placing the remaining carbon in the form of side chain at
possible positions. So the possible structures are:
CH 3
H
C
CH 3
3
H3 C
CH 3
CH 3
H3 C
CH 3
CH 3
Pentane
2-Methylbutane 2,2-Dimethylpropane
C6 H14.
Use the same process i.e. first calculate DU and then write the
structures in same way. The possible structures are :
H3 C
H 3C
CH 3
Hexane
CH 3
H3 C
CH 3
2-Methylpentane
H3 C
CH 3
CH 3
3-Methylpentane
CH 3
CH
CH 3 3
CH 3
2,2-Dimethylbutane
H 3C
CH 3
CH 3
2,3-Dimethylbutane

C5 H10 .
Here the value of DU comes to be one so write all the structures
containing one double bond or one ring. To write structures with
one bond first draw all possible skeleton of carbon then find
chemically different positions (positions which leads to different
IUPAC name) where bonds can be placed. To write structures
with one ring first draw ring with maximum number of carbon and
then go on reducing the number of carbon in the ring and place the
remaining ca rbon in the form of substituents at possible positions.
In this way, all possible structures with molecular formula C5 H10
are:

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159

H 2C
H2 C
CH 3 H2 C
Pent-1-ene
1
H 3C
CH 3
CH 3
2-Methylbut-2-ene
4
CH 3
CH 3
Pent-2-ene
2
CH 3
CH 3
2-Methylbut-1-ene
3
H 3C
CH 2
CH 3
3-Methylbut-1-ene
5
CH 3
H 3C
CH 3
Cyclo
pentane
6
CH 3
CH 3
Ethylcyclo 1,1-Dimethyl
1,2-Dimethyl
cyclopropane cyclopropane
propane
9
8
10
C4H6.
Methylcyclo
butane
7
Here value of DU comes to be two so write all the structures

containing one triple bond, two double bonds, one double bond
and one ring or compounds with two rings. To write such structures
follow the same concept as discussed above i.e. first draw the
skeleton and then find the chemically different positions and finally
write the structures. So all possible structures of compounds with
molecular formula C4 H6 are :
C5H10 O.
When some hetero atom is present in molecular formula then
structures must contain functional group with that hetero atom.
Here, DU is z ero so alcohol and ether functional groups a re
considered. The possible structures are:
CH 3
CH 3
HO
OH
H3 C
OH
CH
3
CH3
CH 3
HO
CH 3 H C
3
2-Methyl
2-Methyl
Butan-1-ol
Butan-2-ol
propan-1-ol propane-2-ol
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CH 3
O
CH 3 H C
CH 3 H C
O
CH 3
3
3
O
2-Methoxy
Ethoxyethane
1-Methoxypropane
propane
H3 C

C3 H6 O.
Here DU is one which can be in the form of one bond (C=C,
C=O) or one ring (homocyclic or heterocyclic) along with the
functional groups. In this way nine compounds with molecular
formula C3 H6 O are possible with different IUPAC names .
CH 3
HO
Prop-1-en-1-ol
1
CH3
H 2C
OH
Prop-1-en-2-ol
2
H2 C
OH
Prop-2-en-1-ol
3
OH
CH 3
H
Propanal
4
H3 C
CH 3
Propanone
5
CH 3
2-methyloxirane
7
Oxetane
8
Cyclopropan-1-ol
6
H3 C
O
CH 2
Methoxyethene
9
Limitations of DU:
Calculation of DU is very much important to draw structure of
any compound with known molecular formula but it has some
limitations such as
It is used to draw all possible structures of a molecular

formula but we cannot reach the final structure only by
DU calculation .

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161
It does not tell a bout the position of double bond in

compound with known molecular formula.
It does not tell anything about the nature of loss of hydrogen

i.e. it does not tell whether DU is in the form of ring or
bond.
It is generally applicable to those organic molecules in which

ring or bond is with carbon. S=O, S=S, N=O bonds also have
unsaturation but it can not be found by DU calculation. For example,
Methanesulphonic acid (CH3 SO3 H) have two S=O bonds but by
calculation DU comes to be zero.
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Section
09
Chemically different hydrogen

Ea rlier we have discussed about the types of carbon a nd
hydrogen (i.e. carbon are of four types 10 , 2 0 , 3 0 , 4 0 and hydrogen are
of three types 1 0 , 2 0 , 3 0 ) on the basis of number of carbon to which a
carbon is directly bonded.
1
CH 3
4
CH 3
3
1
H3 C 2
CH 3
1
1
H3 C
H3 C
2
2
CH 3
1
Example 1:
In pentane there are two types of ca rbon (two 1 0 and three 2 0
carbon). But when we carefully analyze this molecule we find that
replacement of one H by any atom or group such as Cl from the
carbon skeleton leads to three different products.
Cl
CH 3 H
CH 3
H3 C
+Cl Cl
H 3C
CH 3
Pentane
1-Chloropentane 2-Chloropentane
Cl
H 3C
CH3
3-Chloropentane

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163

On the basis of chemical reaction it is seen that replacement of
secondary H from 2 nd and 3 rd positions leads to different products,
it means that they are of different chemical nature so are considered
as chemically different. Therefore by definition chemically different
hydrogens a re those hydrogens which give different products on
chemical reactions. These types of H atoms are also known as nonidentical H, non-equivalent H.As we have not discussed about the
chemical rea ctions so far, the best way to find the chemically
different H is to see the attachments (atoms or groups) on carbon. If
attachments (atoms or groups) are different on carbon then
such carbons are chemically different and hydrogens attached to
such carbons are chemically different hydrogen. For example, in
case of Pentane 1 st carbon and last carbon is attached with three H
and one butyl group, so they are of same chemical nature; 2nd carbon
and 2 nd last carbon a re attached with two H, one methyl and one
propyl groups so they are of same chemical nature but 3 rd carbon is
attached with two H and two ethyl groups. So H at 1st, 2 nd and 3 rd
carbon are of different chemical nature.
Alterna tively, to find chemically different hydrogen, write the
IUPAC name of products by replacing H with any atom or group
such as Cl. The hydrogen which on replacement with any atom or
group gives product with different IUPAC name is chemically
different.
CH3 or
Cl
CH 3 H
H3 C
Cl
H 3C
+Cl
Pentane
1-Chloropentane
Cl
Cl
H 3C
CH 3 or H 3 C
2-Chloropentane
CH 3
Cl
CH 3
H3 C
3-Chloropentane
The knowledge of chemically differe nt hydrogen is of much

importance in organic chemistry as it gives idea about a ll possible
structures which can be obtained on replacement of hydrogen with
any atom or group.In case of saturated hydrocarbons such as alkane,
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cycloalkanes, bicyclic alkanes we can finds chemically different
hydrogen by replacing H with Cl or Br by monohalogenation which
is carried out in presence of light.
Example 2:
Write the total number of che mically different hydrogen in
2-Methylbutane.
CH3
CH3
CH 3
H 3C
Cl 2 /light
H3 C
CH3
Cl
CH3
CH3 +
Cl
2-Methylbutane
1-Chloro-3-methyl
2-Chloro-3-methyl
butane
butane
CH 3
CH 3
Cl
H 3C
+
CH3
Cl
2-Chloro-2-methyl 1-Chloro-2-methyl
butane
butane
H3 C
Here, four different products are obtained on monochlorination

so four types of chemically different hydrogens are present.
Example 3:
Methylcyclopropane.
CH 3
CH3
Br
CH 3 Br
Br2
+
+
light
Br
Methyl
cyclopropane
Bromomethyl 1-Bromo-1-methyl 1-Bromo-2-methyl

cyclopropane
cyclopropane
cyclopropane
Here, three different products are obtained on monobromination

so three types of chemically different hydrogens are present.
Example 4:
Bicyclo[1.1.0] butane.
Here, two different products are obtained on monobromination
so two types of chemically different hydrogens are present.

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165

To find chemically different hydrogen in aromatic compounds
we generally use nitration reaction in which aromatic compound is
treated with nitrating mixture (conc. H2 SO4 /HNO3 ) in which H of
aromatic ring is replaced with NO2 group.
NO 2
Conc.H 2SO 4 /HNO 3
Benzene
Nitrobenzene
Cl
Cl
Conc. H 2 SO 4
Cl
NO 2
Cl
+
NO 2
Chloro
1-Chloro-2-nitro
NO 2
1-Chloro-3-nitro
benzene
benzene
1-Chloro-4-nitro
benzene
benzene
Benzene on nitration gives only one product so all hydrogens
in benzene are identical whereas chlorobenzene on nitration gives
three different products so three types of chemically different
hydrogens are present in chlorobenzene.
HNO 3
In ca se of a romatic compounds having alkyl substituents

chemically different hydrogen depends on the nature of reaction.
For example, hydrogen of alkyl part is replaced with chlorine in
presence of light but that of aromatic part is replaced with nitro
group in presence of conc.H2 SO4 /HNO3 .
CH3
CH 3
Conc.H 2SO 4
NO 2
HNO 3
CH3
CH 3
CH 3
+
NO 2
CH 2 Cl
NO 2
Cl 2 /Light
Chemically different position is used to decide position of

multiple bond ( C=C or C C) in the skeleton of carbon. For example,
to know the total number of alkene possible in skeleton of n-butane
place double bond in that carbon skeleton at different positions and
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write their IUPAC name. If IUPAC name are different then positions
are also different.
Example 5:
Write the total number of chemically different positions of
double bond in skeleton of n-Hexane.
To solve such questions first draw the skeleton of carbon and
place double bond at different positions and write their IUPAC
names. It can be seen that double bond between 1-2 a nd 6-5 give
same name a s Hex-1-ene so they are chemically same positions;
similarly double bond between 2 -3 and 5-4 give same compound,
Hex-2-ene so are also same but double bond between 3-4 bond give
product Hex-3-ene, so skeleton of n-Hexane have three chemically
different positions which are a=e, b=d and c
6
2
1 a b c4 d eCH 3
H3 C
3
5
Example 6:
Write the total number of chemically different positions for

ketones in skeleton of n-pentane.
As in above question, first dra w the skeleton and then try to
place =O group in the carbon skeleton. Both terminal positions are
same and leads to aldehyde. Position 2, 3 and 4 forms ketone of
which ketone at position 2 and 4 are identical and are different from
ketone at position 3. So total ketones possible in skeleton of
n-pentane are two.
CH 3
H3 C
&
are same
O
O
H3 C
CH 3
H 3C
CH 3
&
CH 3
H 3C
are different

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167
Exercise
02
Subjective Approach
01. What are the five basic components which are alwa ys used to
write the IUPAC nomenclature of any organic molecules and
a lso write the role which they pla y in na ming orga nic
compounds?
02. Name the prefix which is used for following substituents- F, Cl,
Br, I, OCH3 , OC2 H5 OR, NO, NO2 , C6 H5 , CH3 , C2 H5
03. Name the suffix which is used for following functional groupscarboxylic acid, sulphonic acid, ester, acid halide, amide, nitrile,
aldehyde, ketone, alcohol, amine.
04. What is difference between phenyl and benzene? When should
we use phenyl and when should we use benzene in writing the
nomenclature?
05. What is correct IUPAC nomenclature given for n propyl, iso
propyl, n butyl, iso butyl, sec butyl, tert-butyl and neo-pentyl
group?
06. Write the IUPAC nomenclature of these common compoundsn butane, iso buta ne, neo-pentane, a cetone, iso butene,
formaldehyde, acetic acid.
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07. Name the functional groups for which we use some other
secondary suffix such as addition of the word carb when directly
attached to aliphatic or aromatic rings?
08. Write the structure of following compounds
A.
1,1-Dibromo-3-ethyl-4-flourohexane
B.
4-Ethyl-2-methyl-1-propylcyclohexane
C.
6-Chloro-4-ethyl-5-methylhept-5-en-1-yne
D.
3-Methylcyclohex-1-ene
E.
2-Methylpentane-2,4-diol
09. Select the main chain which is used as a principal chain or word
root for naming compounds?
CH 3
CH 3
H 3C
H3 C
H3 C
H3 C
CH 3
CH 3
CH 3
CH 3
II
CH 3
10. How many substituents are present on the ma in cha in

CH 3
CH 3
H 3C
H3 C
H3 C
H3 C
CH 3
CH 3
CH 3
CH 3
II
CH 3
11. Na me the substituents present over the ma in cha in

CH 3
Br
CH 3
H3 C
H3 C
NO 2
I
MeO
CH 3
H3 C
Cl
CH 3
II

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169

12. Write the position of substituent over the ma in cha in
CH3
H3 C
H3 C
Br
CH 3
II
MeO
H3 C
ON
Br
CH 3
Cl
CH 3
IV
CH3
Cl
O2N
CH 3
III
CH 3
Cl
CH 3
CH3
Br
Br
Cl
NO 2
V
Br
CH 3
Cl
NO 2
VI
CH 3
13. Write the IUPAC nomenclature of following compounds

CH3
Br
H3 C
NO 2
I
CH 3
H3 C
CH 3
IV
H3 C
H3 C
Pr
VI
CH 3
Et Et
Pr
VII
CH 3
Me
CH 3
H3 C
CH 3
H3 C
H 5C 2 Br
III
170
Cl
II
CH 3
CH 3 O
H3 C
CH 3
CH 3O
H3 C
CH 3
Et Et
CH 3
Me
Bu
Pr
VIII

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14. Write the name of complex substituents
H3 C
H3 C III
H3 C
H 3C
IV
CH 3
H3 C
II
H 3C
CH 3
CH 3
CH 3
CH3
CH 3
VI CH 3
CH 3
15. Write the IUPAC name of following compounds?

H3 C
CH3
CH 2
H3 C
CH CH 3 CH 3
CH 3 3
I
CH 3
III
II
H3 C
CH
CH 2
CH 3
CH 3
CH 3
IV
16. What is the general priority of functional groups in decreasing

order in IUPAC nomenclature?
17. When the prefix formyl and oxo is used for aldehyde?
18. Why two different prefixes - a lkoxycarbonyl and a lkanoyloxy
is used for ester. How they are different. Explain with the help
of an example?
19. Which multiple bond is given priority when double and triple
bond is attached in same molecules in different positions.
20. What are the two functional groups which on chemical reaction
losses a water molecule to form ester as a product. Which alkyl
group is written first in IUPAC nomenclature followed by alkyl
group of another?
21. When the word bis is used in IUPAC nomenclature. Explain
with the help of an example.

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171

22. What are the two functional groups which on chemical reaction
losses a water molecule to form acid anhydride as a product.
Write the IUPAC name of smallest anhydride and its next higher
homologues?
23. When will we use the prefix methylene, ethylidene?
24. What are the structures of vinyl, allyl, benzyl halides.
25. Write the structure of benzene, benzyne, benzil and also give
the structure of benzyl, benzoyl, benzal & benzo groups?
26. Write the IUPAC names and also the more logical common
names which sounds more easy to be pronounced.
CH 3
CH3
CH 3
CH 3
H 3C
H 3C
CH3
H 3C
CH 3
CH 3
CH 3
I
II
27. Write the IUPAC name of following compounds.
Cl
HC
CH 3
OH
H3 C
O
H3 C
O
OH
II
CH3
III
CH 2
NH 2
CH 2 CH 3 CH 3 CH 3
V
IV

CH3
O
H3 C
CH 3
H3 C
172
III
CH 3
H3 C
CH 3
II
CH 3
O
O
CH 3
CH 3 O
CH 3
O
H3 C
O
CH3 IV

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CH 3
Cl

O
H3 C
H3 C
CH 3
O
I
CH 3 O
H3 C
III
O
CH3 II
O
O
CH 3
O
CH 3
H3 C
O
O
IV
CH 3

Cl
CH 3
H3 C
CH3
H3 C
Cl Cl
Cl
CH 3
CH 3
CH 3
Cl
Cl
II
Cl
Cl Cl
CH 3
III
31. Name the following halides according to IUPAC system and
classify them as alkyl, allyl, benzyl (primary, secondary, tertiary),
vinyl or aryl halides:
(A) (CH 3 )2 CHCH(Cl)CH3

(B) CH3 CH 2 CH(CH 3 )CH(C 2 H 5 )Cl
(C) CH 3 CH 2 C(CH 3 )2 CH 2 I
(D) (CH 3 )3 CCH 2 CH(Br)C 6H 5
(E) CH3 CH(CH 3 )CH(Br)CH 3
(F) CH3 C(C 2 H 5 )2 CH 2 Br
(G) CH3 C(Cl)(C 2H 5 )CH 2 CH 3

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173

(H) CH3 CH = C(Cl)CH 2 CH(CH 3 )2
(I)
CH3 CH = CHC(Br)(CH 3 )2
(J)
p - ClC 6H 4 CH 2 CH(CH 3 )2
(K) m - ClCH 2 C 6 H 4 CH 2C(CH3 )3

(L) o - Br - C 6 H 4 CH(CH3 )CH2 CH3
(M) CH 3 CH 2CHCH3
Cl
(N) CH 3CHCH 2 CH2 CH 2CH2 Cl
CH3
Br
(O)
(P)
CH 3 CHCH 3
F
(Q) CH3 CH 2 CH2 CH2 CH2 Cl

CH 3
(R)
Cl
(S)
(T)
CH3
CH 3CCH 2CH 2CH2 Cl
OH
CH 3CHCH 2 CHCH 2 CH 3
CH3
Cl
(U) CH 3CHCH 2 CHCH2 CHCH 2 CH 3

Cl
CH 3
CH 3
174

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Br
Cl
(V)
CH 3 CH 2
OH
NO 2
(W)
Br
(X)
(Y)
CHO
NO 2
COOH
(Z)
F
32. Give the IUPAC names of the following compounds:

(A) CH 3 CH(Cl)CH(Br)CH 3
(B) CHF2 CBrClF
(C) CICH 2 C CCH 2 Br
(D) (CCl 3 )3 CCl
(E) CH 3 C(p - ClC 6 H 4 )2 CH(Br)CH 3
(F) (CH 3 )3 CCH = C(Cl)C 6 H 4 I - p
(G). CH3 OCH2 CH3
(H) CH3 CH 2 OCH2 CH3
(I)
CH 3CH 2CH2 CH 2CHCH 2 CH 2 CH 3

OCH3
(J)
CH3 CH 2 CH 2 OCH 2CH 2CH 2CH 3

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175

CH 3
(K) CH 3CHOCHCH 2 CH 2 CH 3
CH3
(L)
CH 3CHOCH2 CH2 CHCH 3

CH 3
CH 3
(M)
(N)
OH
(O)
OH
(P)
(Q)
Cl
HO
(R)
(S)
(T)
CH 3CH2 CHCH2 CH 2CHCH 3

CH 3
NHCH 3
CH2 CH 3
CH 3
(U) CH 3CH2 CHCH2 CHCH 2 CH 3
CH2 CH 3
CH3
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CH 2 CH 3
(V) CH 3CHCHCH 2 CH2 CH2 Cl
Cl
(W) CH 3CH 2CH2 CH2 CHCH 2 CH 2 CH 2 CH 3

CH 3 CCH 2 CH 3
CH 3
CH2 CH3
(X) CH 3CH2 CH2 CH2 CH2 CHCH 2 CHCH 2 CH 3
CH 2
CH 3 CCH 3
CH 2 CH3
(Y) H2 C
OH
Br
(Z) H3 C
OH
Cl
33. Write IUPAC names of the following compounds:
CH 3
(A) CH 3 CH CH C CH 3
CH 3 OH CH 3
(B)
H3 C CH CH 2 CH CH CH 2 CH 3
OH
OH C 2 H 5
(C) CH 3 CH CH CH 3
OH OH
(D) HO CH 2 CH CH 2 OH
OH
(E)
CH 3
OH
CH 3
(F)
OH

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177

CH 3
(G)
OH
CH 3
OH
(H)
CH3
(I)
CH 3
CH 3 O CH2 CH CH 3
CH3
(J) C 6 H 5 O C 2H 5
(K) C 6 H 5 O C 7 H 15 (n-)
(L)
CH 3 CH2 O CH CH 2 CH 3
CH 3
CH 3
CH 3
(M) CH 3CH2 CHCH 2 CCH 3
CH 3
(N) CH3 CH 2 C(CH 3 )3

CH3
(O) CH 3CHCH 2 CH 2 CHCH 3
CH2 CH 3
(P) CH3 CH 2 C(CH 2 CH 3 )2 CH2 CH2 CH3

(Q) CH3 CH 2 C(CH 2 CH 3 )2 CH(CH 3 )CH(CH 2 CH 2 CH 3 )2
(R) CH 3CH 2CH 2 CHCH 2 CH 2 CH 3
CH 3 CHCH 2 CH 3
(S)
178
CH 3 CH 2 CH 2 CH 3
CH 3C CHCH 2 CH 3
CH2 CH2 CH 3

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(T)
CH 3CH 2CH2 CH 2CHCH 2 CH 2 CH 3

CH(CH 3 )2
(U)
CH 2 CH 3
CH 3
CH 2 CH 3
(V)
H 3C
(W)
(Y)
H3 C
(X)
CH 2 CH 3
CH 3CHCH2 CH2 CH3
CH2 CH 3
(Z)
CH 2 CHCH3
CH 3
34. Name the following compounds according to IUPAC system of

nomenclature:
(A) CH3 CH(CH 3 )CH 2 CH 2 CHO
(B) CH3 CH 2 COCH(C 2 H 5 )CH 2 CH 2Cl
(C) CH3 CH = CHCHO
(D) CH3 COCH 2 COCH3
(E) CH3 CH(CH3 )CH 2 C(CH3 )2 COCH3
(F) (CH3 )3 CCH 2 COOH
(G) OHCC 6 H 4CHO - p
Br
CH 3CHCH 2 CH 2 CHCH 2 CH 2 CH 3
(H)
CH 3
(I)
(CH 3 )3 CCH 2 CH 2 CH2 CH(CH 3 )2

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179

(J)
(L)
CH 3
CH 3 CHCH 2 CHCHCH 3
CH 3
CH 3
(K) (CH 3CH2 )4 C
CH 3CHCH 2 CHCH 2 CH 3
CH 3
OH
(M) CH 3CH2 CHOCH 2 CH 3

CH 2 CH 2 CH 2 CH 3
CH 3
(N)
(O)
CH3
NCH 3
Br
CH 2 CH 3
(P)
(Q) CH3 OCH 2CH 2CH 2 OCH 3
OH
(R) CH3 CH 2 CH 2 OCH2 CH3
(S)
(T)
(U) CH 3 CH 2CHCH3
Cl
CH 3 CH 2CHCH3
NH2
(V) CH 3 CHCH 2 CH 2 CH3

CH 3
(X)
OH
CH 3CHCH 2 CH 2 CH 2 OH
CH 3
CH 3
(W) CH3 CBr
CH 2 CH 3
(Y)
Br
(Z) CH 3CHNH 2
CH 3
35. Write IUPAC names of the following compounds and classify
them into primary, secondary and tertiary amines.
(A) (CH3 )2 CHNH 2
(B) CH3 (CH2 )2 NH 2
(C) CH3 NHCH(CH 3 )2
(D) (CH3 )3 CNH2
180

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(E) C 6 H 5NHCH3
(F) (CH3 CH 2 )2 NCH3
(G) m - BrC 6 H 4 NH2

(H) CH 3 CH 2 CH 2 CH 2 CH 2 CH 2NH2
(I)
CH3 CH 2 CH 2 NHCH 2 CH 2 CH 2 CH 3
(J)
CH 3CHCH 2 NHCHCH 2 CH3

CH 3
CH 3
(K) CH 3CH 2CH2 NCH2 CH3

CH 2 CH 3
(L)
NH 2
(M) CH 3CHCH 2 CH 2 CH 2 CH 2 CH 2 NH2

CH 3
(N) CH 3CH 2CH2 NHCH 2 CH 2 CHCH3
CH 3
CH 3
(O) (CH3 CH2 )3 N
(P)
NH 2
H3 C
COOH
COOH
(Q)
NH 2
(R)
COOH
(S)
COOH
(T)
NH 2

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181

NH 2
NH 2
(U)
(V)
CN
COOH
NH 2
(W)
NH 2
(X)
CHO
Cl
NH 2
NH 2
(Y)
(Z)
OH
36. Write the structures of the following organic compounds.

(A) 2-Chloro-3-methylpentane
(B) p-Bromochlorobenzene
(C) 1-Chloro-4-ethylcyclohexane
(D) 2-(2-Chlorophenyl)-1-iodooctane
(E) 2-Bromobutane
(F) 4-tert-Butyl-3-iodoheptane
(G) 1-Bromo-4-sec-butyl-2-methylbenzene
(H) 1,4-Dibromobut-2-ene
(I)
2,3-Dimethylhexane
(J)
4-isopropyl-2,4,5-trimethylheptane
(K) 4,4-Diethyldecane
(L) 2,2-Dimethyl-4-propyloctane
(M) 4-isobutyl-2,5-dimethyloctane
(N) 4-(1,1-dimethylethyl)octane
(O) 2-Methylbutan-2-ol
(P) 1-Phenylpropan-2-ol
182

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(Q) 3,5-Dimethylhexane-1,3,5-triol
(R) 2,3-Diethylphenol
(S) 1-Ethoxypropane
(T) 2-Ethoxy-3-methylpentane
(U) Cyclohexylmethanol
(V) 3-Cyclohexylpentan-3-ol
(W) Cyclopent-3-en-1-ol
(X) para-toluidine
(Y) meta-cresol
(Z) para-xylene
37. Draw the structures of the following compounds.
(A) 3-Methylbutanal
(B) p-Nitropropiophenone
(C) p-Methylbenzaldehyde
(D) 4-Methylpent-3-en-2-one
(E) 4-Chloropentan-2-one
(F) 3-Bromo-4-phenylpentanoic acid
(G) p,p-Dihydroxybenzophenone
(H) Hex-2-en-4-ynoic acid
(I)
2-Methyl-2-bromo-1-propanamine
(J)
N-Ethylethanamine
(K) 5-Methylhexan-1-amine
(L) Methyldipropylamine
(M) N,N-dimethylpentan-3-amine
(N) Cyclohexylethylmethylamine
(O) 5-Ethyl-2-methyloctane
(P) 1,3-Dimethylcyclohexane
(Q) 2,3,3,4-Tetramethylheptane

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183

(R) Propylcyclopentane
(S) 2-Methyl-4-(1-methylethyl)octane
(T) 2,6-Dimethyl-4-(2-methylpropyl) decane
(U) 3,3-Dimethylcyclopentene
(V) Ethyl vinyl ether
(W) 6-Bromo-2,3-dimethyl-2-hexene
(X) Allyl alcohol
(Y) Cyclooctyne
(Z) isopropylacetylene
38. Write a structure for each of the following compounds:
(A) isopropyl alcohol
(B) isopentyl fluoride
(C) sec-butyl iodide
(D) neopentyl chloride
(E) tert-butylamine
(F) isooctyl bromide
(G) 2-Hexyne
(H) 1-Bromo-1-pentyne
(I)
(J)
5-Ethyl-3-octyne
Propargyl bromide
(K) Methylacetylene
(L) Diethylacetylene
(M) Vinylacetylene
(N) di-tert-butylacetylene
(O) Methoxyethyne
(P) Cyclopentylacetylene
(Q) sec-butyl-tert-butylacetylene (R) 5,6-Dimethyl-2-heptyne

(S) m-Ethylphenol
(T) 2-Chloroanthracene
(U) p-Nitrobenzenesulfonic acid(V) m-Chlorostyrene

(W) (E)-2-Phenyl-2-pentene
(X) o-Nitroanisole
(Y) o-Bromoaniline
(Z) 2,4-Dichlorotoluene
39. Write a structural formula for each of the following compounds.

(A) sec-butyl tert-butyl ether
(B) isoheptyl alcohol
(C) sec-butylamine
(D) neopentyl bromide
(E) 1,1-Dimethylcyclohexane (F) 4,5-Diisopropylnonane

(G) Triethylamine
184
(H) Cyclopentylcyclohexane

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(I)
4-tert-butylheptane
(J) 5,5-Dibromo-2-methyloctane
(K) 1-Methylcyclopentanol
(L) 3-Ethoxy-2-methylhexane
(M) 5-(1,2-Dimethylpropy)nonane (N) 3,4-Dimethyloctane

(O) m-Dichlorobenzene
(P) 3-Benzylpentane
(Q) p-Bromophenol
(R) m-Chlorotoluene
(S) o-Nitroaniline
(T) 2,5-Dinitrobenzaldehyde
(U) 2-Bromo-4-iodo-1-nitrobenzene
(V) o-xylene
(W) 2-phenylhexane
(X) 2-Ethanoyloxybenzoic acid

(Y) 2-Methoxycarbonylbenzoic acid
(Z) 2-Oxocyclohexane carboxylic acid
40. Give the systematic name for each of the following compounds.
(A) CH 3CHCH = CHCH3
CH 3
(B)
BrCH 2 CH 2 CH = CCH3
CH 2 CH 3
CH 3
(C) CH 3CH2 C = CCHCH 3
(D) H C
CH 3
3
CH 3 CH3
Br
(E)
(F) CH3 CH = CHOCH 2 CH 2 CH 2 CH 3
(G) CH 3CH2 CHCH = CHCH2 CH2 CHCH 3

Br
H 3C
(H)
C=C
CH 3CH2
CH2 CH 3
CH2 CH 2 CHCH3
CH 3
CH3
(I)
Br
CH 3

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185

H3 C
(J)
H3 C
C=C
CH 2 CH 3
CH 2 CH 2 CHCH3
(K) BrCH 2 CH 2 C CCH3

(M)
(N)
(O)
(P)
(L) CH3 OCH 2C CCH 2 CH 3
CH 3CH2 CHC CCH 2CHCH 3

Br
CH 3CH2 CHC
Cl
CH
CH 2 CH 2 CH 3
CH 3C CCH 2 CHCH 3
Br
CH 3C CCH 2 CHCH3
CH 2 CH 2 CH 3
CH 3
(Q)
CH 3C CCH 2 CCH 3
CH3
(R)
CH 3CHCH 2 C CCHCH 3
Cl
CH 3
(S)
(T)
CH 3
CH 3
(U) CH 2 = CHCH 2 C CCH 2 CH 3

(V) HOCH 2 CH 2 C CH
186

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CH3
(W)
CH 3CH = CCH 2 CH = CH2
(X) CH3 CH = CHCH = CHCH = CH 2

CH3 CH 3
(Y) CH 3CH = CCH 2 CHCH2 CH3
(Z)
CH 3CH2 CH = CCH 2 CH 2 C CH
CH = CH 2
41. Give the systematic name for each of the following compounds:
(A) CH3 C CCH 2 CH 2 CH 2 CH = CH 2
HOCH 2 CH 2
(B)
H
C=C
CH 2 CH 3
H
(C) CH3 CH 2 C CCH2 CH2 C CH

CH 2 Br
Cl
(D)
CH 3
(E)
CHBr2
CH 3
(H) H3 C
CH 3
Br
COOH
OH
(G)
(J)
(F)
(I)
Br
OCH 3
(K)
SO 3 H
(L)
CH 2 CH 3
Cl

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Cl
187

CH = CH 2
CH 2 CH 3
(M)
(N)
Cl
Br
(O
Br
NO 2
Br
CN
(P)
(Q)
CH3
Cl
(R) CH3 CH 2 CH 2 C N
CH 3
O O
(S) CH 3CH 2CH2 COCH2 CHCH 3
(T)
CH 3CH2 COCCH3
(U) CH 3CH 2CH2 CH2 CH 2CN(CH 3 )2 (V) CH 3CH2 CH2 COCH3

O
(W)
NH2
(X) CH 3CH2 CH 2 CH 2 CCl

COOH
COOH
(Y)
(Z)
O
CHO
42. Name the following compounds:

CH 2 CH3
(A) CH 3CH2 CHCH 2 CH 2 CH 2COH (B) CH 3CH2 CH 2 CH 2 CCl

O
O O
(C) CH 3CH2 COCH 2 CH 2 CH 3 (D)
COCCH 3
O
(E) CH 3 CH 2 CH 2 CH 2 C N
188
(F)
CH 2 = CHCH2 CNHCH 3

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CH2 CH3
O O
(G) CH 3CH 2COCCH2 CH3
(H) CH 3
CH 2C N
(I)
C H
CH2 COOH
CH 3 CH 2CH 2 CN(CH 3 )2
(J)
CH 3
H
CH 2 CH 2 CH 3
(K) CH 3CH2 CHCH 2CH
(L)
CH 2 CH 2 CH 2 CH
CH 3
(M) CH 3CH 2CH2 CCH 2 CH 2 CH 3

CH 2 CH 3
(N) CH 3CH2 CHCH 2 CH 2CH

O
(O) CH 3CHCH 2 CCH 2 CH 2 CH 3

CH 3
(P)
CH 2 = CHCCH 2 CH 2 CH 2 CH 3
O
(Q) CH 3CHCH 2 CH 2 CCH 2 CH 3
(R)
OH
C N
OH
(S)
CH 3CH 2CHCH 2 CNH2
(T) Br
Cl
HC=O

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189

Cl
OH
H2 C
(U)
(V) Br
Cl
OH
OH
OH Br
CH
(W)
CH
Br
CH 3
(X) H3 C
H3 C
Cl
CH 2
H3 C
(Y) Cl
OH
OH
CH 2
(Z)
43. Write the IUPAC names of following compounds

CH
CH 2
(A) H3 C
(B)
H3 C
CH2
(C) H3 C
CH 2
(D)
CH
(E)
H3 C
H 2C
O
(G)
H2 C
(I)
190
Cl
O
CH 2 (F)
H2 C
CH 2 CH 2
Br O
CH 2
(H) H C
3
Br O
N
H
Br
(J)
Cl
N
H
Br O

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CH 3
I
N
H
Cl

Br O
Cl
(K)
CH 3 (L) O
CH 3
CH 3
(M)
Cl
CH 3
(N)
H3 C
OH
CH 3
CH CH
O
(O)
H3 C
OH (P)
H
N
CH3 O
CH CH
Cl
CH 2
OH
(Q) HC
CH 3
(R)
SO 3H
CH
(S)
(T)
OH
(U)
CH 2
(V)
CN
O
O
H3 C
CHO
COOH
COOH
NH 2
(W)
OH
Br
OH
(X)
O

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191

Br
CH 3
OH
(Y)
(Z)
H3 C
O O
44. Write the IUPAC names of following compounds
(A)
(B)
H3 C
NH 2
H3 C
Cl
Cl
OH
(D) HC
(C)
H3 C
(E) HC
O
CH3
H3 C
CH 3
CH 3
OH
H3 C
CH 3
H3 C
CH3
(F)
CH 3
CH 3
Cl
Cl
Cl
Cl
(G)
(H)
H3 C
CH3
CH3
Cl
Cl
Cl
H3 C
(I)
CH 3
CH3 Cl Br
O O
(J)
H3 C
CH 3 Cl
192

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CH 3

O O
O O
(K)
OH
(L)
NH 2
O O
(M)
O
H
(M)
(O)
(Q)
(S)
(P)
CH 2 CH 3
O
(R) HCNH
2
O
HCCl
(W)
O
(Y)
O
NH 2
(T)
HCH
(U)
HCNCH3
OH
(V)
OH
O
(X)
OH
O
(Z) HCO

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193
Answers
02
Subjective Approach
01. Five basic components are mainly- Secondary prefix, Primary

prefix, Word root, Primary suffix and Secondary suffix. Their
role are
Secondary prefix-It tells a bout the nature and position

of substituent if any.
Primary prefix-It is used to specify acyclic, cyclic, bicyclic

or spiro nature of ma in chain.
Word root-It tells about the longest continuous carbon

chain which includes functiona l group, carbon carbon
multiple bond (double or triple bond) a nd substituent at
minimum position.
Primary suffix-It tells about sa turated or unsaturated

na ture of carbon-carbon bonds in the parent carbon
chain.
Secondary suffix-It tells a bout the ma in functional

groups present in the compound
02. Prefix used for them are tabulated below

Substituent
Prefix
Substituent
Prefix
Fluoro
OR
Alkoxy
Cl
Chloro
NO
Nitroso
Br
Bromo
NO 2
Nitro
194

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I
Iodo
C6 H5
Phenyl
OCH3
Methoxy
CH3
Methyl
OC2 H5
Ethoxy
C2 H5
Ethyl
03. Suffix used for following functiona l groups are

Functional group
Secondary suffix
Carboxylic acid (COOH)
oic acid
Sulphonic acid (SO3 H)
Sulphonic acid
Ester (COOR)
oate
Acid halide (COX )
oyl halide
Amide (CONH2)
amide
Nitrile (CN)
nitrile
Aldehyde (CHO)
al
Ketone (CO)
one
Alcohol (OH)
ol
Amine (NH2 )
amine
04. Benzene is the correct IUPAC name of Cyclohexa-1,3,5-triene.

As aromatic compounds are different from alkenes and polyene
in chemica l reactions so 1 Prefix, Word root and 1 Suffix
combines to give a name Benzene. If one hydrogen is removed
from benzene ring then the skeleton that remains is called as
phenyl group. In IUPAC nomenclature, if benzene ring is parent
chain then benzene is used but if in any compound benzene
ring is present as substituent then phenyl is used.
05. Correct IUPAC of common groups are
Groups
IUPAC name
n propyl
Propyl
iso propyl
1-Methylethyl
n butyl
butyl
iso butyl
2-Methylpropyl
sec butyl
1-Methylpropyl

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195

tert butyl
1,1-Dimethylethyl
neo pentyl
2,2-Dimethylpropyl
06. The correct IUPAC name of given common compounds are

Common compounds
IUPAC name
n butane
Butane
iso butane
2-Methylpropane
neo pentane
2,2-Dimethylpropane
acetone
Propanone
iso butene
2-Methylpropene
formaldehyde
Methanal
acetic acid
Ethanoic acid
07. These functional groups are commonly Carboxylic acid, Ester,

Acid halide, Amide, Nitrile and Aldehyde
08. Structure of given compounds are
F
Br
(A)
Br
CH 3
(B)
CH 3
CH 3
(C)
HC
H3 C
09. Main chain is
H3 C
(D)
Cl
CH 3 OH
(E)
CH3
H3 C OH
CH3
CH 3
H 3C
H3 C
H 3C
CH 3
196
CH 3
CH 3
CH 3
I
10. 2, 4 respectively
CH 3
CH3
H3 C
CH 3
II

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CH 3
CH 3

11. Substituents in I are- Bromo, Nitro & Propyl and substituents
in II are Chloro, methyl & 1-Methoxyethyl
12. Position of substituents are
I- 1,2,4;
II- 1,1,3,4,5;
III- 1,2,3,5;
IV- 1,2,3,4,5 ;
V- 1,1,2,3,3,4,5,6;
VI- 1,1,2,5,5
13 I- 3-Bromo-5-ethyl-4-nitrooctane
II- 2-Chloro-6-(1-methoxyethyl)-3-methylnonane
III- 5-Bromo-6-(1-methoxyethyl)-3-methylnonane
IV- 1,4-Dimethylcyclohexane
V- 1,2,4-Trimethylcyclohexane
VI- 3-Ethyl-2-methylhexane
VII- 3,5-Dimethyl-4-propylheptane
VIII- 5-Ethyl-3-methyl-4-propylnonane
14. I- 1-Methylethyl;
II- 2-Methylpropyl;
III- 1-Methylpropyl;
IV-2,2-Dimethylpropyl;
V- 3-Methylbutyl;
VI- 1,1-Dimethylethyl
15. I- 7 -Ethyl-2,4,5 ,6-tetramethyldeca- 1,8-diene

II- 3-Ethynylhepta-1,5-diene
III- Prop-1-enylcyclobutene
IV- 1,3 -Diethylcyclobutene
V- 1-Ethyl-2-methylcyclohexa-1 ,4-diene
16. Carboxylic acid > Sulphonic acid > Ester > Acid halide >
Amide > Nitrile > Aldehyde > Ketone > Alcohol > Amine
17. When CHO is directly attached as a substitution then word
formyl is used but if one or more carbon is present between
main chain and CHO then oxo is used.
18. Two different prefixes are used for ester on the ba sis of
attachment with main chain. 2 Prefix alkoxycarbonyl is used

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197

when ester group is directly attached to main chain by CO group
while alka noyloxy is used when directly attached atom is O.
For example:
COOH
Ethanoyloxy
Methoxycarbonyl
O
O
H3 C
O
CH 3
O
19. Both multiple bonds denotes unsaturation in carbon carbon
bonds. So position of minima for unsaturation will decide the
lowest position for ene or yne. For ex.
CH 3
4
H2 C 2 3 5 6
1
Hex-1-en-4-yne
CH 3
HC 2 3 4 5 6
1
Hex-4-en-1-yne
20. Carboxylic acid and alcohol combines together and looses a

water molecule to form ester as a product. In nomenclature of
ester, alkyl part of alcohol is written first followed by alkyl part
of carboxylic acid as alkylalkanoate
21. When two sa me complex substituents is presents in a ny
molecule then to indicate its repeatition two times, word bis is
used. For example
CH 3
CH 3
H 3C
CH 3
CH 3
CH 3
1,4-Bis-(1,1-Dimethylethyl) cyclohexane
22. When two same or different carboxylic acid combines together

and loose a water molecule then acid anhydride is formed as a
product. IUPAC name of smallest anhydride and its next higher
homologues are Methanoic anhydride and Ethanoic methanoic
anhydride respectively.
23. Word methylene is used to a carbon bounded with 2 hydrogen
atoms. In case of substituent, word methylene is used for =CH2
group and ethylidene for =CHCH3
198

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24. The structure are
H 2C
Cl
Vinyl chloride
25. Structures are
H 2C
Cl
Allyl chloride
O
Ph
Ph
Benzene
Cl
Benzyl chloride
O
Benzil
Benzyne
Benzyl
Benzoyl
26. I)
Benzal
Benzo
1-(1,1-Dimethyl ethyl)-4-(1-methyl ethyl) cyclohexane or

1-Iso propyl-4-tert butyl cyclohexane
II)
1,4-Bis- (1,1-Dimethyl ethyl) cyclohexane or

1,4-Bis( tert. Butyl) cyclohexane
27 I)
II)
Pent-4-yn-1-ol
3-Chloro-5-methylcyclohexanol
III) 2-Methylcyclopent-2-enone
IV) 3-Methylcyclobut-2-enamine
V) 4,5,6,8-Tetramethylnona-1,8-dien-3-one
28. I)
II)
1-Methylethylethanoate
1-Methylethyl-2-methylpropanoate
III) 1-Methylethyl-3-methylbut-2-enoate
IV) 2-Methyl 3-oxo-butyl-4-chloropentanoate
29. I)
II)
Ethanoic anhydride
Ethanoic-2-methylpropanoic anhydride
III) Ethanoic-3-methylbut-2-enoic anhydride

IV) Butanoic-3-oxobutanoic anhydride

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199

30. I)
II)
1,4-Bis-(1,1-dimethylethyl)cyclohexene
1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)ethane
III) 3,7-Bis-(dichloromethyl)nona-2,7-diene
31.
IUPAC Name
Nature of halide
A.
2-chloro-3-methylbutane
2 Alkyl halide
B.
3-chloro-4-methylhexane
2 Alkyl halide
C.
1-Iodo-2,2-dimethylbutane
1 Alkyl halide
D.
1-Bromo-3,3-dimethyl-1-phenylbutane 2 benzyl halide
E.
2-Bromo-3-methylbutane
2 Alkyl halide
F.
1-Bromo-2-ethyl-2-methylbutane
1 Alkyl halide
G.
3-chloro-3-methylpentane
3 Alkyl halide
H. 3-chloro-5-methylhex-2-ene
vinyl halide
I.
4-Bromo-4-methylpent-2-ene
3 Allylic halide
J.
1-chloro-4-(2-methylpropyl)benzene
Aryl halide
K.
1-chloromethyl-2-(2,2-dimethyl
propyl) benzene
1 benzyl halide
L.
1-Bromo-2-(1-methylpropyl)benzene
Aryl halide
M. 2-Chlorobutane
2 alkyl halide
N. 1-chloro-5-methylhexane
2 Alkyl halide
O.
Bromocyclohexane
2 Alkyl halide
P.
2-Fluoropropane
2 Alkyl halide
Q.
1-chloropentane
1 Alkyl halide
R.
1-chloro-4-methylcyclohexane
2 Alkyl halide
S.
1-chloro-4-methylpentan-4-ol
1 Alkyl halide
T.
4-chloro-2-methylhexane
2 Alkyl halide
U.
4-chloro-2,6-dimethylhexane
2 Alkyl halide
V.
4-chloro-3-ethylcyclohexanol
2 Alkyl halide
W. 1-Bromo-2-nitrobenzene
200

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Aryl halide

X.
1-(1-Brmoethyl)-4-nitrobenzene
1 benzyl halide
Y.
3-Fluorobenzene carbaldehyde
Aryl halide
Z.
3-(1-Fluoroethyl)benzene
carboxylic acid
2 Alkyl halide
32. A.
2-Bromo-3-chlorobutane
B.
1-Bromo-1-chloro-1,2,2-trifluoroethane
C.
1-Bromo-4-chlorobut-2-yne
D.
1,1,1,2,3,3,3-Heptochloro-2-trichloromethylpropane
E.
3-Bromo-2,2-bis-(4-chlorophenyl)butane
F.
1-Chloro-1-(4-iodophenyl)-3,3-dimethylbut-1-ene
G.
Methoxyethane
H. Ethoxyethane
I.
4-Methoxyoctane
J.
1-Propoxybutane
K.
2-(1-methylethoxy)pentane
L.
3-Methyl-1-(1-methylethoxy)butane
M. 1-Methoxypropane
N. Propan-1-ol
O.
4-Propylnonan-1-ol
P.
4-Methyl-5-(1-methylethyl)octane
Q.
6-chloro-4-ethyl-3-methyloctane
R.
5-Methyl-3-propylhexan-1-ol
S.
2,3-Dimethyl-6-(2-methylpropyl)decane
T.
N-Methyl-6-methylheptan-3-amine
U.
3-Ethyl-2,3,6-trimethyloctane
V.
1,4-Dichloro-5-methylheptane
W. 5-(1,1-Dimethylpropyl)nonane
X.
5-(2-Ethylbutyl)-3,3-dimethyldecane

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201

Y.
Pent-4-en-1-ol
Z.
2-Bromo-3-chlorohept-5-en-1-ol
33. A. 2,2,4-Trimethylpentan-3-ol B.
5-Ethylheptan-2,4-diol
C.
Butane-2,3-diol
D.
Propane-1,2,3-triol
E.
2-Methylphenol
F.
4-Methylphenol
G.
2,5-Dimethylphenol
H. 2,6-Dimethylphenol
I.
1-Methoxy-2-methylpropane J.
K.
1-Phenoxyheptane
L.
Ethoxybenzene
2-Ethoxybutane
M. 2,2,4-Trimethylhexane
N. 2,2-Dimethylbutane
O.
2,5-Dimethylheptane
P.
Q.
3,3-Diethyl-4-methyl-5-propyloctane
R.
3-Methyl-4-propylheptane
S.
5-Ethyl-4,4-dimethyloctane
T.
4-(1-methylethyl)octane
U.
1-Ethyl-2-methylcyclopentane
V.
Ethylcyclobutane
3,3-Diethylhexane
W. 4-Ethyl-1,2-dimethylcyclohexane
X.
3,6-Dimethyldecane
Y.
2-Cyclopropylpentane
Z.
1-Ethyl-3-(2-methylpropyl)cyclohexane
34. A.
4-Methylpentanal
B.
6-chloro-4-ethylhexan-3-one
C.
But-2-enal
D.
Pentan-2,4-dione
E.
3,3,5-Trimethylhexan-2-one
F.
3,3-Dimethylbutanoic acid
G.
Benzene-1,4-dicarbaldehyde
H. 5-Bromo-2-methyloctane
202

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I.
2,2,6-Trimethylheptane
J.
2,3,5-Trimethylhexane
K.
3,3-Diethylpentane
L.
5-Methylhexan-3-ol
M. 3-Ethoxyheptane
N. 1-Bromo-4-methylcyclohexane
O.
N,N-Dimethylcyclohexanamine
P.
3-Ethylcyclohexanol
Q.
1,3-Dimethoxypropane
R.
1-Ethoxypropane
S.
4-Methylpentan-1-ol
T.
Butan-2-amine
U.
2-chlorobutane
V.
2-methylpentane
W. 2-Bromo-2-methylbutane
X.
Cyclohexanol
Y.
Z.
Propan-2-amine
35. A.
Propan-2-amine
1 amine
B.
Propan-1-amine
1 amine
C.
N-Methylpropan-2-amine
2 amine
D.
2-Methylpropan-2-amine
1 amine
E.
N-Methylaniline
2 amine
F.
N-Ethyl-N-methylethanamine
3 amine
G.
3-Bromoaniline
1 amine
H. Hexan-1-amine
1 amine
I.
N-propylbutan-1-amine
2 amine
J.
N-(2-methylpropyl)butan-2-amine
2 amine
K.
N,N-Diethylpropan-1-amine
3 amine
L.
Cyclohexanamine
1 amine
Bromocyclopentane
M. 6-Methylheptan-1-amine
1 amine
N. N-Propyl-3-methylbutan-1-amine
2 amine
O.
N,N-Diethylethanamine
3 amine
P.
2,5-Dimethylcyclohexanamine
1 amine
Q.
3-Aminomethylbenzenecarboxylic acid
1 amine

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203

R.
3-(Methylamino)benzenecarboxylic acid
2 amine
S.
3-(N-Ethyl-N-methylamino)
benzenecarboxylic acid
3 amine
T.
3-Aminobenzene carboxylic acid
1 amine
U.
3-Amino-2-ethylbutanoic acid
1 amine
V.
3-Amino-2-ethylbutane nitrile
1 amine
W. 3-Amino-2-ethylbutanal
1 amine
X.
3-Chloropentan-2-amine
1 amine
Y.
2-Aminopentan-3-ol
1 amine
Z.
Methyl-3-amino-2-ethylbutanoate
2 amine
Cl
Cl
36. A.
B.
Br
Cl
C.
E.
D.
Br
Cl
F.
I
Br
G.
H.
I.
J.
K.
L.
204
Br

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Br
M.
N.
O.
P.
Q.
OH
OH OH
OH
OH
Ph
OH
R.
OEt
OEt
S.
CH2 OH
U.
T.
V.
OH
NH 2
OH
W.
X.
CH 3
CH 3
OH
Y.
Z.
CH 3
CH 3
O
O
37. A.
B.
O2N
CHO
C.
D.
CH 3

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205

Ph
E.
Cl
OH
F.
Br O
O
G.
H.
HO
I.
NH 2
J.
Br
K.
M.
NH 2
N.
P.
Q.
R.
S.
T.
U.
V.
Y.
206
Br
N
H
L.
O.
W.
OH
OH
X.
OH
Z.

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38. A.
C.
OH
B.
Cl
D.
E.
NH 2
F.
G.
H.
I.
J.
K.
L.
M.
N.
O.
Q.
Br
Br
Br
P.
R.
OH
S.
Cl
T.
SO 3H
U.
V.
Cl
NO 2
W. Ph
Y.
NH 2
Br
X.
OCH 3
NO 2
CH3
Cl
Z.
Cl

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207

39. A.
B.
C.
NH 2
D.
E.
OH
Br
F.
N
G.
I.
H.
J.
Br
Br
OH
K.
L.
M.
N.
Cl
O.
P.
Cl
OH
CH 3
Q.
R.
Cl
Br
NH2
S.
CHO
NO 2
NO 2
T.
NO 2
208

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NO 2
Br
CH 3
U.
V.
CH 3
W.
Ph
COOH
Y.
40. A.
X.
O
COCH 3
Z.
O
COOH
OCCH 3
COOH
O
4-Methylpent-2-ene
B.
1-Bromo-4-methylhex-3-ene
C.
2,3,4-Trimethylhex-3-ene
D.
1,5-Dimethylcyclohexene
E.
Bromocyclopentane
F.
1-Butoxypropene
G.
3,8-Dibromonon-4-ene
H. 4-Ethyl-3,7-dimethyloct-3-ene
I.
1,5-Dimethylcyclopentene
J.
3-Ethyl-2-methylhept-2-ene
K.
5-Bromopent-2-yne
L.
1-Methoxypent-2-yne
M. 6-Bromo-2-chlorooct-4-yne
N. 3-Ethylhex-1-yne
O.
5-Bromohex-2-yne
P.
5-Methyloct-2-yne
Q.
5,5-Dimethylhex-2-yne
R.
6-Chloro-2-methylhept-3-yne
S.
Cycloocta-1,5-diene

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209

T.
1,6-Dimethylcyclohexa-1,3-diene
U.
Hept-1-en-4-yne
V.
But-3-yne-1-ol
W. 4-Methylhexa-1,4-diene
X.
Hepta-1,3,5-triene
Y.
3,5-Dimethylhept-2-ene
Z.
5-Ethenyloct-5-en-1-yne
41. A.
Oct-1-en-6-yne
B.
Hex-3-en-1-ol
C.
Oct-1,5-diyne
D.
Chlorocyclohexane
E.
1-Methylcyclohepta-1,3,5-triene
F.
1-Bromo-1-phenylmethane
G.
1,1-Dibromo-1-phenylmethane
H. 2,6-Dimethylphenol
I.
3-Bromobenzene carboxylic acid
J.
1-Bromo-2-methylbenzene
K.
1-Ethyl-3-methoxybenzene
L.
3,5-Dichlorobenzene sulphonic acid
M. 2-Chloro-4-ethyl-1-phenylbenzene
N. 4-Nitrophenylethene
O.
1,2,4-Tribromobenzene
P.
1-Cyclohexyl-4-methylbenzene
Q.
3-Chlorobenzenecarbonitrile
R.
Butanenitrile
S.
2-Methylpropylbutanoate
T.
Ethanoic propanoic anhydride
U.
N,N-Dimethylhexanamide
V.
Methylbutanoate
210

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W. 2-Aminocyclopentanone
X.
Pentanoyl chloride
Y.
Cyclopentane carboxylic acid
Z.
3-Formyl-5-oxocyclohexane carboxylic acid
42. A.
5-Ethylheptanoic acid
B.
Pentanoyl chloride
C.
Propylpropanoate
D.
Benzene carboxylic ethanoic anhydride
E.
Pentane nitrile
F.
N-Methylbut-3-enamide
G.
Propanoic anhydride
H. 3-Methylpentanoic acid
I.
N,N-Dimethylbutanamide
J.
3-Methylhexanenitrile
K.
3-Methylhexanal
L.
4-Phenylbutanal
M. Heptan-4-one
N. 4-Ethylhexanal
O.
2-Methylheptan-4-one
P.
Hept-1-en-3-one
Q.
6-Hydroxyheptan-3-one
R.
2-oxocyclohexanecarbonitrile
S.
3-Formylpentanamide
T.
4-Bromo-2-chloro-3-cyclopropylcyclohexanol
U.
3-Bromo-2-chloro-5-methylenecyclohexane-1,4-diol
V.
2-Bromo-4-chloro-5-ethynylcyclohexanol
W. 4-Ethynyl-1-methylcyclohexene
X.
3-Bromo-4-chlorooct-3-en-6-yne-2,5-diol

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211

Y.
4-Chloro-5-(1-methylethenyl)cyclopenta-1,3-diene-1-ol
Z.
5-Prop-2-enylcyclopenta-1,3-diene
43. A.
Octa-1,3,7-triene
B.
Hept-5-en-1-yne
C.
4-Ethenyl-3-ethylhept-6-en-1-yne
D.
Cyclobutylmethylcyclopropanecarboxylate
E.
Prop-2-enyl-3-ethylpent-4-enoate
F.
4-Methylenehexa-1,5-dien-3-one
G.
2-Ethenylbut-3-enal
H. N-Methyl-3-bromobutanamide
I.
N-bromo-3-bromo-4-chlorobut-2-enamide
J.
N-2-Chloro-1-iodoethyl-3-bromo-4-chlorobut-2-enamide
K.
N-Ethyl-N-methyl-3-bromo-4-chloro-2-iodobutanamide
L.
2-Oxobutanal
M. 2-(1-Oxo ethyl)pent-3-enal
N. 5-Chloro-6-cyclopropylhept-3-enoic acid
O.
3,4,5-Triethynyl-6-methyloct-7-ynoic acid
P.
2-Bromo-4-(N-formylamino)-3-methylbutanoic acid
Q. 3-Chloro-4- cyclopropyl-2-methylhept-6-ynoic acid

R. Phenylethene
S.
Phenylethyne
T.
2- Formyl-4- sulphobenzenecarboxylic acid
U. 2- Amino- 5- hydroxybenzenecarbonitrile
V.
3- Ethenyl-4-formylbenzenecarboxylic acid
W. 4- Methoxycarbonylbenzenecarboxylic acid
X. Phenylbenzene
Y. 4- (2-Bromophenyl)phenol
Z.
212
Methyl-4- (1- oxo ethyl)benzenecarboxylate

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44. A.
Methyl-4-formylbenzenecarboxylate
B.
Methyl-4-chlorocarbonylbenzenecarboxylate
C.
Methyl-4-carbamoylbenzenecarboxylate
D.
3-Chloro-4-(1-oxo ethyl)-2-methylhept-6-ynoic acid
E.
4-Formyl-2-methyl-3-oxohept-6-ynoic acid
F.
1,4-Bis-(1-methylethyl)benzene
G.
1,4-Bis-(1,1-dimethylethyl)benzene
H. 1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)ethane
I.
3 -B ro m o- 2 , 2 -d i c h l or o- 1 , 1 - bi s- ( 4 - c h l or o -3 methylethylphenyl)benzene
J.
Methyl-2-oxocyclohexanecarboxylate
K.
6-Oxocyclohex-2-enecarboxylic acid
L.
6-Oxocyclohex-3-enecarboxamide
M. 5,6-Dioxocyclohex-2-enecarbaldehyde
N. Cyclohexylbenzenecarboxylate
O.
Phenylcyclohexanecarboxylate
P.
N-Ethyl-N-methylmethanamide
Q.
Methanoyl chloride
R.
Methanamide
S.
Methanal
T.
2-Methylaminocyclohexanone
U.
2-Aminomethylcyclohexanone
V.
2-Hydroxymethylcyclohexanone
W. 2-Hydroxycyclohexanone
X.
6-Hydroxy-2,2-dimethylcyclohexanone
Y.
O,O-Dimethylcyclohex-2-enone
Z.
Phenylmethanoate

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213
Exercise
02
Objective Approach
01. The correct IUPAC name of the alkane
is :-
(A) 2-Ethyl-4-methyl hexane (B) 3, 5-Dimethyl heptane

(C) 5-Ethyl-3-methyl hexane (D) 3, 5-Dimethyl hexane
02. Which of the following is the correct priority order of functional
groups?
(A) SO 3H > COR > CHO > OH
(B) COOH > SO 3 H > CN > CONH2
(C) CN > CHO > COR > OH
(D) COOR > COX > CHO > CN
03. The correct IUPAC na me of the following compound
Et
Cl C C C H is
NO 2 Br F
214

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(A) 2-Bromo-1-chloro-1-ethyl-3-fluoro-3-iodo-1-nitro propane
(B) 2-Bromo-3-chloro-1-fluoro -l-iodo-3-nitro pentane
(C) 2-Bromo-3-chloro-3-ethyl-1-fluoro-1-iodo-3-nitro propane
(D) 4-Bromo-3-chloro-5-fluoro -5-iodo-3-nitro pentane
04. The correct structure of 6-Ethyl-2,3,5-trimethyl nonane.
(A)
(B)
(C)
(D)
05. The correct IUPAC name of incorrectly named 2,3-Diethyl butane

is
(A) 3,4-Dimethyl hexane
(B) 2,3-Dimethyl hexane
(C) 2-Ethyl-3-methyl pentane (D) 2-Ethyl butane.

06 The common & IUPAC names for the following alkyl group
respectively is
(CH 3 )2 CH CH 2 CH2
(A) Iso pentyl & 3-Methyl butyl

(B) Iso pentyl & 2-Methyl butyl
(C) Sec-pentyl & 1,1-Dimethyl propyl
(D) Neo-pentyl & 3-Methyl butyl
07. Select the structure with correct numbering in the chain.
5 4
3
2
(A) H2 C = CH CH 2 C
(B)
1
CH
1
2
3
4
5
CH 3 CH = CH CH 2 C
6
CH
7
6
5
4
3
2
1
(C) CH 2 = CH CH = CH CH 2 CH = CH 2
1
2
3
4
5
6 7
(D) CH 2 = CH CH = CH CH 2 C CH

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215

08. The
correct
IUPAC
C 2 H5
na me
of
the
compound
H2 C = CH CH 2 CH CH 3 is:
(A) 4-Methyl hex -1-ene
(B) 4-Ethyl pent-1-ene
(C) 2-Ethyl pent -4-ene
(D) 3-Methyl hex-1-ene
09. The correct structure for 2-Ethyl-3-methyl hexa-1,4-diene is

(A)
(B)
(C)
(D)
10. In which of the following compounds the carbon atom chain

has been correctly numbered ?
7
6
5
4
3
2
1
(A) CH 3 CH 2 CH CH CH 2 CH 2 CH 3
C2 H5 CH3
1
2
3
(B) CH 3 CH 2 C = CH CH 3
4
5
CH3 CH2
5
4
3
2 1
(C) CH 3 CH 2 CH C CH
CH3
CH 2 CH2 CH 3
(D) CH 3 C CH = CH CHO
4
5
3
2
1
CH 3
11. The correct IUPAC na me of the following compound
Cl
I
F
is
Br
(A) 1-Chloro-1-iodo-2-fluoro methyl -4-bromo but-1-ene.
(B) 1-Bromo -4-chloro -3-fluoro methyl -4-iodo but -1-ene.
(C) 4-Bromo -1-fluoro -2-chloro iodo methyl butene
(D) 4-Bromo -1-chloro -2-fluoro methyl -1-iodo but -1-ene.
216

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12. In which of the following, acyclic chain is main chain.
(A)
(B)
(C)
(D)
13. In which of the following compound IUPAC numbering is

correct
(A)
6
5
(C) 4
(B)
6 1
3
2
1
(D)
6 5
1 2
5 4 3
14. The correct IUPAC name of the following compound

is
(A) 2-Cyclohexyl butane
(B) Iso-butyl cyclohexane
(C) (1-Methyl propyl) cyclohexane
(D) 1-cyclohexyl-1-methyl propane
15. In which of the following, ring is the main chain.
(A)
(B)
(C)
(D)
16. The correct IUPAC name of the compound
is-
(A) 1-Ethenylcyclopenta-2,4-diene
(B) 5-Ethenylcyclopenta-1,3-diene
(C) Cyclopenta-2,4-dienylethene
(D) Cyclopenta-1,3-dienylethene

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217

Cl
17. The correct IUPAC name of CH 3CHCH 2 CH2 CH 2 C CH 3

OH
is:
Cl
(A) 6,6-Dichloroheptan-2-ol
(B) 2,2-Dichloroheptan-6-ol
(C) 6,6-Dichloroheptan-2-al
(D) 6,6-Dichloroheptan-2-one.
18. The correct IUPAC name of compound
SO 3H
(A) 6-Propyl-1-methyl-4-oxohept-6-ene-1-sulphonic acid.

(B) 5-Oxo-7-propyloct-7-ene-2-sulphonic acid.
(C) 2-Propyl-7-sulphooct-1-ene-4-one.
(D) 7-Methylene-5-oxodecane-2-sulphonic acid.
19. The correct IUPAC name of the compound NH
2
NH 2
is
(A) 4-Ethyl-3-methylnonane-2,8-diamine
(B) 6-Ethyl-7-methylnonane-2,8-diamine
(C) 5-Ethyl-1,6,7-trimethylheptane-1,7-diamine
(D) 4-Ethyl-2-methylnonane-2,7-diamine
20. The correct structure of 6-Chloro-4-hydroxycyclohex-2-ene-1sulphonic acid is
(A)
SO 3 H
Cl
SO 3H
(B)
HO
OH
SO 3 H
(C)
Cl
OH
218
Cl
SO 3H
Cl
(D)
HO

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21. The correct IUPAC name of following compound
Br
COOH
is
(A) 3-Bromobut-2-enoic acid (B) 3-Bromobut-3-enoic acid
(C) 2-Bromobut-1-en-4-oic acid (D) 3-bromo-3-carboxypropene
22. The IUPAC name of the following compound
CH 3 CH = CH CH 2 CH2 CH COOH is
NH 2
(A) 2-Aminohept-5-enoic acid
(B) 6-Aminohex-2-enecarboxylic acid

(C) 2-Aminohept-4-enoic acid
COOH
(D) 6-Aminohept-2-enoic acid.

23. The correct IUPAC name of following compound
is
Br
NH 2
(A) 4-Aminomethyl-3-bromocyclohex-5-ene-1-carboxylic acid
(B) 2-Aminomethyl-5-carboxycyclohex-3-en-1-bromine
(C) 4-Aminomethyl-5-bromocyclohex-2-ene-1-carboxylic acid
(D) 3-Bromo-4-aminomethylcyclohex-5-en-1-oic acid

O
O
24. The IUPAC name of the compound
is
O
(A) Butanoic anhydride
(B) Dibutanoic anhydride
(C) Butanoyl oxybutanoate
(D) 1-oxopropyl butanoate

O

(A) Butanedicarboxylic anhydride
O is
O
(B) Cyclobutanedioic anhydride

(C) Cyclobutanedicarboxylic anhydride
(D) Butanedioic anhydride

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219

26. The IUPAC name of compound
is
(A) Bicyclo [2,2,1] hexane
(B) Bicyclo [2,2,1] heptane
(C) Spiro [2,2,1] hexane
(D) Spiro [2,2,1] heptane
27. Aspirin is
O
(A)
(C)
O C CH 3
COOH
OH O
C OCH 3
(B)
(D)
O
O C CH 3
COOH
O
O C CH 3
OH
28. Which of the following compounds has wrong IUPAC name ?

[AIEEE 02]
(A) CH3 CH 2 CH2 COOCH 2 CH 3 Ethyl butanoate
(B) CH3 CH CH2 CHO
CH 3
(C) CH3 CH CH CH3
3-Methyl-butanal
2-Methyl-3-butanol
OH CH3
O
(D) CH3 CH C CH2CH3
2-Methylpentan-3-one
CH3
29. The IUPAC name of the compound is
HO
(A) 3, 3-Dimethyl cyclohexanol

(B) 1, 1-Dimethyl-3-hydroxy cyclohexane
(C) 3, 3-Dimethyl-1-hydroxy cyclohexane
(D) 1, 1-Dimethyl-3-cyclohexanol
220

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[AIEEE 04]

30. The IUPAC name of the compound shown below is :
Cl
[AIEEE 06]
Br
(A) 3-Bromo-1-chlorocyclohexene
(B) 1-Bromo-3-chlorocyclohexene
(C) 2-Bromo-6-chlorocyclohex-1-ene
(D) 6-Bromo-2-chlorocyclohexene
31. The IUPAC name of
is
[AIEEE 07]
(A) 3-Ethyl-4,4-dimethylheptane
(B) 1, 1-Diethyl-2, 2-dimethylpentane
(C) 4, 4-Dimethyl-5, 5-diethylpentane
(D) 5, 5-Diethyl-4, 4-dimethylpentane
32. The correct decreasing order of priority for the functional
groups of organic compounds in the IUPAC system of nomenclature is
[AIEEE 08]
(A) -COOH.- SO 3 H,-CONH 2 - CHO
(B) -SO 3 H, -COOH,-CONH 2 , -CHO
(C) -CHO,-COOH,-SO 3H,-CONH2
(D) -CONH 2 - CHO,-SO 3 H,-COOH
33. The IUPAC name of neopentane is :
[AIEEE 09]
(A) 2, 2-Dimethylpropane
(B) 2-Methylpropane
(C) 2,2-Dimethylbutane
(D) 2-Methylbutane
34. The IUPAC name of C 6 H 5 COCl is
[IIT 06]
(A) Benzene chloro ketone
(B) Benzoyl chloride
(C) Chloro phenyl ketone
(D) Benzene carbonyl chloride

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221

OH
CN
is
Br
[IIT 09]
(A) 4-Bromo-3-cyanophenol
(B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene
(D) 6-Bromo-3-hydroxybenzonitrile
36. The IUPAC name of CH 3 CH = C CH2 CH3 is:
CH 2 CH 2 CH 3
(A) 3-Propylhex-2-ene
(C) 4-Ethylhex-4-ene
[CPMT 02]
(B) 3-Propylhex-3-ene
(D) 3-Ethylhex-2-ene
CH 3
is :
(A) 3-Methyl cyclohexene

(C) 6-Methyl cyclohexene
[AIIMS 03]
(B) 1-Methyl cyclohex-2-ene
(D) 1-Methyl cyclohex-5-ene
38. The IUPAC name of the compound CH 3 CH2 CH CH 2 OH

OCH 3
is:
(A) 2-Methoxy-1-butanol
[BHU 04]
(B) 3-Methoxy-1-butanol
(C) 1-Methoxy-1-butanol
(D) 1,2-Methoxy butanol
39. The compound which contains all the four 1, 2, 3 and 4 carbon
atom is:
[CET (J & K) 05]
(A) 2,3-Dimethylpentane
(B) 3-Ethyl-2,3-dimethylpentane
(C) 2,3,4-Trimethylpentane
(D) 3,3-Dimethylpentane
222

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40. Which of the following compounds has isopropyl group?
[BHU 05]
(A) 2,2,3,3-Tetramethylpentane(B) 2,2-Dimethylpentane
(C) 2,2,3-Trimethylpentane
(D) 2-Methylpentane
41. The IUPAC name of (CH 3 )3 C CH = CH 2 is: [AMU (Med.) 05]

(A) Hex-1-ene
(B) 2,2-Dimethyl but-3-ene
(C) 2,2-Dimethyl pent-4-ene
(D) 3,3-Dimethyl but-1-ene
42. The compound Buta-1,2-diene has:
[UGET (Med.) 06]
(A) only sp hybridized carbon atom

(B) only sp2 hybridized carbon atom
(C) both sp and sp2 hybridized carbn atoms
(D) sp, sp2 and sp3 hybridized carbn atoms
Cl
is :
O
(A) 2-Ethyl-3-methyl butanoyl chloride
[AIPMT 06]
(B) 2,3-Dimethyl pentanoyl chloride

(C) 3,4-Dimethyl pentanoyl chloride
(D) 1-Chloro-1-oxo-2,3-dimethyl pentane
44. The IUPAC name of Cl CH 2 CH = C CH2 OH is: [DPMT 06]

CH2 CH 3
(A) 1-Chloro-2-ethyl-4-hydroxybut-2-ene
(B) 4-Hydroxy-1-chloro-2-ethylbut-2-ene
(C) 4-Chloro-2-ethylbut-2-en-1-ol
(D) 2-Ethyl-4-chlorobut-2-en-1-ol
is :
[UGET (Med.) 07]

(A) Bicyclo [2,2,0] octane
(B) Bicyclo [0,2,2] hexane
(C) Bicyclo [2,1,1] hexane
(D) Bicyclo [2,2,0] hexane

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223

CH3 O
46. The IUPAC name of CH 3 CH C CH 2 CH2 OH is [AIIMS 07]
(A) 1-Hydroxy-4-methylpentan-3-one
(B) 5-Hydroxy-2-methylpentan-3-one
(C) 4-Methyl-3-oxopentan-1-ol
(D) Hexan-1-ol-3-one
47. The correct IUPAC name of the compound
CHO
NO 2
OCH 3
is :
[AFMC 07]
(A) 2-Formyl-5-methoxynitrobenzene
(B) 4-Formyl-3-nitroanisole
(C) 4-Methoxy-2-nitrobenzaldehyde
(D) 4-Methoxy-6-nitrobenzaldehyde
H2 C = CH CH CH CH CH3 is:
CH3 C 2 H5 OH
[DPMT 07]
(A) 3-Ethyl-4-methylhex-5-en-2-ol
(B) 3-Methyl-4-ethylhex-1-en-5-ol
(C) 3-Ethyl-2-hydroxy-4-methylhex-5-ene
(D) None of the above
49. How many sigma and pi bonds are there in tetracyano ethylene
molecule?
[BHU (Mains) 08]
(A) 9 and 9
(B) 9 and 7
(C) 5 and 9
(D) 5 and 7
50. The IUPAC name of (CH 3 )2 CHCH 3 is:
[BHU (S) 08]
(A) Isopropyl methane
(B) 2-Methyl propane
(C) Trimethyl methane
(D) Dimethyl ethane
224

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51. The IUPAC name of CH 3 CH 2 CH C = CH 2 is :
CH 2 CH3
CH 3
[Punjab PMET (Med.) 2008; CPMT 08]
(A) 2-Methyl-3-ethyl-1-pentene
(B) 3-Ethyl-4-methyl-4-pentene
(C) 3-Ethyl-2-methyl-1-pentene
(D) 3-Methyl-2-ethyl-1-pentene
52. The IUPAC name of tertiary butyl iodide is:
[CET 08]
(A) 1-Iodo-3-methyl propane (B) 2-Iodo-2-methyl propane

(C) 4-Iodobutane
(D) 2-Iodobutane
53. The correct structure of 4-Bromo-3-methyl but-1-ene is:

(A) BrCH = C(CH3 )2
[AIIMS 08]
(B) H 2 C = C(CH3 )CH2 CH 2 Br

(C) H 2 C = CH - CH(CH 3 ) - CH 2 Br
(D) CH 3 - C(CH3 ) = CHCH 2 Br
O
CN
CH 3
is :
CH 3
[JIPMER (Med.) 08]
(A) Cyclopropionamide
(B) N-Methyl cyclopropanamide.
(C) N,N-Dimethyl cyclopropane carboxamide
(D) None of these
55. The correct IUPAC name of H 2 C = CH - C CH is :[AIPMT 09]
(A) But-3-en-1-yne
(B) But-1-en-3-yne
(C) But-1-yn-3-ene
(D) But-3-yn-1-ene

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225

56. The IUPAC na me of
CH 3 - CH = CH - C CH is:
the
following
compound
[AIPMT 10]
(A) Pent-4-yn-2-ene
(B) Pent-2-en-4-yne
(C) Pent-3-en-1-yne
(D) Pent-1-yn-3-ene
57. The IUPAC nomenclature of (CH 3 )3 C - CH = C(CH 3 )2 is:

[AFMC 10]
(A) 2,4,4-Trimethyl pent-3-ene (B) 2,4,4-Trimethyl pent-2-ene
(C) 2,2,4-Trimethyl pent-3-ene (D) 2,2,4-Trimethyl pent-2-ene
58. Which of the following is a correct name according to IUPAC
rules?
[CET (J & K) 11]
(A) 2,3-Diethyl hexane
(B) 3-Ethyl-2-methyl pentane
(C) 3,4-Dimethyl pentane
(D) 2-Ethyl-2-methyl pentane

O
OH is
(A) Prop-2-enoic acid
(B) But-1-enoic acid
(C) But-3-enoic acid
(D) Pent-4-enoic acid
60. The correct IUPAC name for the compound
is :

(A) 3-(1-Ethylpropyl) hex-1-ene (B) 3-Ethyl-4-ethenyl heptane
(C) 3-Ethyl-4-propyl hex-5-ene (D) 4-Ethyl-3-propyl hex-1-ene
Cl
H3 C
C=C
CH 2 CH 3
I
is: [AIPMT 11]
(A) 2-Chloro-3-iodopent-2-ene(B) 2-Chloro-3-iodopent-2-ene

(C) 3-Iodo-4-chloropent-3-ene (D) 3-Iodo-4-chloropent-3-ene
226

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OH O
is :
(A) 2-Hydroxy-4-pentanone
(B) 4-Hydroxy-2-pentanone
(C) 2-Oxo-4-pentanol
(D) 4-keto-2-pentanol

H3 C CH2 CH CH 2 CH CH 2 CH 3 is: [PMT (Kerala) 12]
CH 2 CH 3
CH 3
(A) 3-Ethyl-5-methyl heptane

(B) 5-Ethyl-3-methyl heptane
(C) 3,5-Diethylhexane
(D) 1,1-Diethyl-3-methylpentane
64. Which nomenclature is not according to IUPAC system?
(A) Br CH 2 CH = CH2
1-Bromoprop-2-ene
CH3
(B) CH 3 CH 2 C CH 2 CH CH3
Br
CH 3
4-Bromo-2,4-dimethylhexane
(C) CH 3 CH CH CH 2 CH 3
CH3
2-Methyl-3-phenylpentane
(D) CH 3 C CH 2 CH2 CH 2 COOH

O 5-Oxo hexanoic acid
65. The structure of isobutyl group in compound is:
(A) CH3 - CH2 - CH 2 - CH2 (C)
CH 3
CH 3
CH CH 2
(B)
[NEET 13]
CH 3 CH CH2 CH 3
CH 3
(D) CH 3 C
CH 3

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227

66. Correct IUPAC names as per rules are
(A) 1,1,1-Trichloro-2,2-diphenylethane
(B) 3-Cyclopentylbut-1-ene
(C) Cyclopentane-2,4-diene
(D) 1-Bromo-2,3-dichlorocyclopropane
67. In which of the given molecules cyclic part is/are parent chain:
Br
(A)
(B)
Br
Br
(C)
(D)
68. Which of the following is/are incorrect IUPAC name:

(A)
(B)
CH 3 CCHCH 3
O CH 3
HC CCHCH=CH 2
HC=CH 2
2-Methylbutan-3-one
3-Ethenylpent-1-en-4-yne
OH
CH3
(C)
CH2 CH2 NH2
(D)
228
CH 3 CHCCHOH
CH 3 O CH 3
3-(2-Aminoethyl)-2-methyl
cyclohexan-1-ol
4-Methyl-3-oxopentan-2-ol

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69. Which is/are the correct IUPAC name of the corresponding
structures
OH
CH3
(A)
NHCH 2 CH 3
(B)
CH 3 CHCHCHO
Br Cl
3-(N-Ethylamino)-2methylcyclohexan-1-ol
3-Bromo-2-chlorobutanal
CN
(C)
CH 2 CHCH 2 COCl
COOCH 3
(D)
CHO
Methyl 4-chlorocarbonyl
-3-cyanobutanoate
Cyclohexanal
70. Which of the following IUPAC name are correct.

O
CNH2
(A)
COCl
(B)
2-Methylcyclo
pentanecarboxamide
Cyclohexanoyl chloride
C N
(C)
2-Methylcyclo
butanecarbonitrite
CH3
Br
(D)
COOCH 3
Methyl 2-bromocyclo
hexanecarboxylate
71. Which indicated alkyl group is/are correct.

(A)
Iso-propyl
(B)
(C)
Iso-butyl
(D)
Sec-butyl
neo-pentyl

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229

72. Which of the following is/are correct IUPAC name.
Cl O
(A)
NH 2 2-Chlorocyclohexanecarboxamide
CH 3O
(B)
OCH3 Methyl-2-methylcyclohexane carboxylate
Cl O
(C)
Cl 2-chloro cyclohexanecarbonyl chloride
O O
(D)
H 2-Oxocyclohexane carbaldehyde
73. The correct combination of names for isomeric alcohols with

molecular formula C 4 H10 O is/are
[IIT Advanced-2014]
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1,1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) isobutyl alcohol and 2-methylpropan-1-ol
74. Which of the following compounds are named correctly ?
(A) (CH 3 )2 CHCH2 CH 2 CH 2 CHO (5-methyl-1-hexanal)
(B) (CH 3 )2 CHCH2 C CCOOH (5-methyl-2-hexynoic acid)
(C) CH3 CH 2 CH2 CH2 CH(CH 3 )COOH (2-methylhexanoic acid)
(D) CH3 CH 2 CH=CHCOCH 3 (3-hexen-5-one)
230

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Each question has 5 choice (A), (B), (C), (D) & (E) out of which
only one is correct.
(D) Statement-1 is false, Statement-2 is true
75. Statement-1:The locant (2,6,7) is preferred over the locant (3,4,8).
Statement-2:The first term, i.e. 2 in the first set is lower than the
first term, i.e. 3 in the second set.
76. Statement-1:The IUPAC name of CH 3 CH=CHC CH is pent2-en-4-yne and not pent-3-en-1-yne.
Statement-2:While deciding the locants for double bond and
triple bonds, lowest locant rule for multiple bonds
is followed.
77. Statement-1:The correct IUPAC na me of the compound,
CH
CH 3
CH 3
is (1-methylethyl) cyclopentane.
Statement-2:It is named as a derivative of cyclopentane because

the number of carbon atoms in the ring is more than
in the side chain.
78. Statement-1:
H
CN
is called cyclohexane nitrile.
Statement-2:It contains six carbon atoms in the ring and CN as

the functional group.

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231

79. Statement-1:The
IUPAC
na me
C 2 H 5 CCH2 OH
CH 2
for
the
compound
is 2-ethyl prop-2-en-1-ol.
Statement-2:Etlhyl (C2H5-) rather than methylene (=CH2) is

considered as the substituent group because e of
ethyl comes first in alphabetical order than m of
methylene.
80. Statement-1:The IUPAC name of citric acid is 2 -hydroxy
propane 1,2,3,-tricarboxylic acid
COOH
HOOC
COOH
OH
Statement-2:When an unbranched carbon chain is directly
linked to more then two like functional groups, then
it is named as derivative of parent alkane which
does not include the C-atoms of the functional
groups.
81. Statement-1:The IUPAC na me of the compound,
OHCCH2 CH 2 COOH is butane-3-formyl-1-oic
acid.
Statement-2:COOH is considered as substituent group while
CHO is considered as the principal functional
group.
82. Statement-1:The IUPAC na me for the compound
C 6 H 5 COOCH 2 CH 2 COOH i s 3 - b e n z o y l o x y
propanoic acid.
Statement-2: C 6 H 5 CH 2 O is called benzoyloxy group.

83. Statement-1:
is commonly called as acetone.
Statement-2:Common name is derived from 5 components i.e.

Secondary prefix + Primary prefix + Word root +
Primary Suffix + Secondary Suffix.
232

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84. Match the compounds written in Column-I with their name in
Column-II :Column - I
(A)
Column - II
COOH
CHO
(P) 2-(2-Oxoethyl) cyclohexane

carboxylic acid
COOH
(B)
CHO
(Q) 2-Aminomethyl cyclohexane

carboxylic acid
COOH
(C)
(D)
(R) 2-N-Methylaminocyclohexane
carboxylic acid
NH 2
COOH H
N
CH 3
(S) 2-Formyl cyclohexane

carboxylic acid
85. Structural formula of carboxylic acid IUPAC name

Column - I
Column - II
Br
(A) Cl
COOH (P) 2 aminbenzoic acid
Ph
(B)
CH 3 CHCOOH
COOH
(C)
NH2
(Q)
2 Methyl - 2- phenyl- 3buten- 1- oic acid
2,2,3-trifluoro
(R) propanoic acid
2-Bromo-4-chlorocy
(D) CH2 F - CF2 - COOH (S) clohexanecarboxylic acid

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233

Comprehension 01 :A saturated hydrocarbon (A) has five membered ring. Three
alkyl groups attached to the ring adjacent to each other with
following observations.
(A) First group has only two carbon atoms.
(B) Second group has four carbon atom with all hydrogens are
chemically same
(C) Third group has total five carbon atoms and its main chain
contains three carbon atoms with ethyl as a substituents.
86. The IUPAC name of compound (A) is
(A) 2 - ( 1 , 1 - D i m e t h y l e t h y l ) - 1 - ( 1 - e t h y l p r o p y l ) - 3 ethylcyclopentane
(B) 2 - (1 ,1 -Di me th yl eth yl )- 1 -e th yl -3 - (1 -e th ylp ro py l)
cyclopentane
(C) 1 -(1 ,1 -Dimet hylethyl )-3 -ethy l-2 -(1 -m ethylpro pyl)
cyclopentane
(D) 1-(1,1-Dimethylethyl)-2-(1-methylethyl)-3-(1-methylpropyl)
cyclopentane
87. How many 1 hydrogens are present in compound (A).
(A) 15
(B) 18
(C) 12
(D) 9
88. How many 3 carbons are present in compound (A).

(A) 3
(B) 2
(C) 4
(D) 5
Comprehension 02 :During nomenclature of unsaturated hydrocarbon, lowest locant

is given to multiple bond rather than any substituent, as the
priority of multiple bond is more than substituent. When the
locant for multiple bond is same from either side than double
bond, then double bond is given priority over triple bond. For
234

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selection of main chain if the size of main chain & number of
multiple bonds are equal then the priority is given to lowest set
of locants for multiple bond.
89. IUPAC name of following compound is
(A) 4-Ethenylhepta-1,3-dien-6-yne
(B) 4-(prop-2-ynyl) hexa-1,3,5-triene
(C) 3-(prop-2-ynly) hexa-1,3,5-triene
(D) 4-Ethenylhexa-4,6-dien-1-yne.
90. IUPAC name of following compound
(A) 3-Ethenylpenta-1-en-4-yne(B) 3-Ethynylpenta-1,4-diene

(C) 2,2-Diethenylpropyne
(D) 1,1-Diethenylpropyne
Comprehension 03 :The priorities for citing principal groups in a carboxylic acid
derivative are as follows :
Carboxylic acid > Sulphonic acid > ester > acid halide >
amide > cyanide
All of these groups have citation priority over aldehydes and
ketons as well as the other functional groups.
When these functional groups act as a substituent then following
2 prefix is used for them.
Group
2 prefix
COOH
carboxy
O
C OC 2 H5
ethoxy carbonyl
O C CH 3
ethanoyl oxy

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235

O
C NH 2
carbamoyl
C OCH 3
methoxy carbonyl
CH 2 C OH
C Cl
carboxy methyl
chlorocarbonyl
91. Which of the following structure has correct loctans?

O 5 COOH
6
ClC
CO 2 CH3
(A)
4
1
CN 3 2
O 6 CO 2 H
1
ClC
(B)
5
2 CO 2 CH3
CN 4 3
O 2 CO 2 H
1
ClC
(C)
3
6 CO 2 CH3
CN 4 5
O 6 CO 2 H
5
ClC
(D)
1
4 CO 2 CH3
CN 2 3
92. Which of the following is the Correct IUPAC name of given

compound is compound?
O
Cl
CNHCH 3
(A) p-acetamido chlorocyclohexane

(B) 4-chloro-N-methylcyclohexane carboxamide
(C) N-methyl amido chlorocyclohexane
(D) N-Methyl-4-chlorocyclohexane carboxamide
236

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93. For the given compound which statements is correct about the
above compound ?
O
CH 3 CNH
CO 2 H
(A) CH 3 CNH group is principal group

O
(B)
CH 3 CNH will be considered as substituent group
(C) Locant number 1 will be assigned to COOH

(D) p-acetamidobenzoic acid is its IUPAC name
Comprehension 4 :In the IUPAC nomenclature, when a substituent is complex ,
then prefixes like di, tri, tetra etc are replaced by bis, tris, tetrakis
- etc. Bused on this information answer the following questions :
94. The structural formula of 1,3 Bis (bromo methyl) benzene
CHBr2
CHBr2
(A)
(B)
CH 3
CH 3
BrCH 2
(C)
CH 2 Br
(D)
CH 3
95. The IUPAC name of C CH 2 OH 4 is
CH 2 Br
(A) 1,2,3,4 Tetra hydroxy butane

(B) tris (hydroxy ethyl) ethane
(C) tetrakis (hydroxy methyl) methane
(D) 1,1,1,1 Tetrahydroxy methyl alcohol

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237

96. Structural formula of tris (2chloroethyl) amine is
Cl
(a)
N CH 2 - CH 2 - Cl 3
(b)
(c)
CH3 - CH 2 - N - Cl 2
(d) None of these
N(CHCH 3 )3

97. How many of the functional groups have high priority than
aldehyde in seniority order when naming polyfunctional compounds.
Carboxylic acid
(I)
Amide
(V)
Nitrile
(VI)
Sulphonic acid
(II)
Ketone
(VII)
Ester
(III)
Alcohol
(VIII)
Acid halide
(IV)
Amine
(IX)
98. How many them are incorrectly named according to IUPAC

name.
OH
COOH
Et
1,1-Dimethyl
Acetone 2-Ethylbutane Pentan-2-oic acid
ethanol
(IV)
II
III
I
CN
CHO
Pentan-2-carbonitrile Pentan-2-al
(V)
(VI)
NC
CN
CN
Propane-1,2,3tricarbonitrile
(VIII)
238
1,6-Dimethyl
cyclohexene
(VII)
HO
OH
OH
Propan-1,2,3-triol
(IX)

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99. How many of them have correct common name.
COOH
COOH
Maleic acid
(II)
Iso-octane
(I)
OH
COOH
COOH
Succinic acid
(III)
COOH
OCOCH 3
Carbolic acid
(IV)
Aspirin
(V)
CH=CHCOOH
Syrene
(VI)
OH
COOH
Cumene
(VII)
Cinnamic acid
(VIII)
Salicylic acid
(IX)
100. How many groups among the following are correctly named.
n-butyl Sec-butyl
(I)
(II)
Iso-butyl tert-butyl Phenyl n-propyl

(VI)
(IV)
(III)
(V)
Iso-propyl neo-pentyl Iso-hexyl

(VII)
(IX)
(VIII)

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239
Answers
02
Objective Approach
01.
(B)
02.
(C) 03.
(B)
04.
(B)
05.
(A)
06.
(A) 07.
(D) 08.
(A) 09.
(C) 10.
(D)
11.
(A) 12.
(C) 13.
(B)
14.
(C) 15.
(A)
16.
(B)
17.
(A) 18.
(B)
19.
(A) 20.
(B)
21.
(B)
22.
(A) 23.
(C) 24.
(A) 25.
(D)
26.
(B)
27.
(B)
28.
(C) 29.
(A) 30.
(A)
31.
(A) 32.
(A) 33.
(A) 34.
(D) 35.
(B)
36.
(D) 37.
(A) 38.
(A) 39.
(B)
40.
(D)
41.
(D) 42.
(D) 43.
(B)
44.
(C) 45.
(D)
46.
(B)
47.
(C) 48.
(A) 49.
(A) 50.
(B)
51.
(C) 52.
(B)
53.
(C) 54.
(C) 55.
(B)
56.
(C) 57.
(B)
58.
(B)
59.
(C) 60.
(D)
61.
(A) 62.
(B)
63.
(A) 64.
(A) 65.
(C)
66. (A,B,D) 67. (A,B,D) 68. (A,B,D) 69. (A,B,C,D) 70. (A,C,D)
71.(A,B,C,D) 72.(A,B,C,D)73. (A,C,D) 74. (A,B,C) 75.
(A)
76.
(D) 77.
(A) 78.
(D) 79.
(C) 80.
(A)
81.
(E)
82.
(B)
83.
(C) 84.
(AS ; BP ; CQ ;
DR)
85.
(AS ; BQ ; CP ; DR) 86.
(B)
87.
(B)
88.
(C) 89.
(A) 90.
(B)
91.
(A)
92.
(B)
93.
(B)
94.
(D) 95.
(C) 96.
(A)
97.
(6)
98.
(A) 99.
(4)
100. (6)
101. (12)
102. (6)
240

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Test
01
Basic understanding of organic

SECTION-I
1. Functiona l
group
which
is
a bsent
in
Penicillin
O
RCN
H
O
S
N
is
COOH
Penicillin
(A) 2 amide
(B) 3 amine
(C) Carboxylic acid
(D) 3 amide
2. Which of the following is not the homolog of CH 3 CH 2 COOH.

(A) CH3 COOH
(B)
CH 3 CH COOH
CH 3
(C) CH 3 COOCH 2 CH 3
(D) HCOOH

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241

3. Open chain molecule with lowest molecular mass that contains
2 sp2 hybridized carbon and 2 sp3 hybridized carbon have total
carbon
(A) 2
(B) 3
(C) 4
(D) 5
4. Total number of primary, secondary, tertiary & quaternary

carbon in given molecule respectively is
(A) 6, 0, 3, 1
(B) 7, 0, 3, 1
(C) 7, 1, 3, 2
(D) 7, 1, 3, 1
5. Total number of primary, secondary & tertiary hydrogens

respectively present in given compound is
(A) 9, 6, 1
(B) 9, 4, 1
(C) 11, 4, 1
(D) 11, 6, 1
6. Molecular formula of anthracene
is
(A) C 14 H14
(B) C 14 H10
(C) C 14 H12
(D) C 12 H12
7. Total number of sp2sp2 bond present in given molecule

(A) 2
(B) 3
(C) 4
(D) 5
8. In which of the following compound IUPAC numbering is

correct
(A)
242
6
5
1
4
2
3
(B)
2
1
6 5

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5
(C) 4
6 1
3
(D)
1 2
5 4 3
SO 3H
(A) 6-Propyl-1-methyl-4-oxohept-6-ene-1-sulphonic acid.

(B) 5-Oxo-7-propyloct-7-ene-2-sulphonic acid.
(C) 2-Propyl-7-sulphooct-1-ene-4-one.
(D) 7-Methylene-5-oxodecane-2-sulphonic acid.
10. The correct structure of 6-Chloro-4-hydroxycyclohex-2-ene-1sulphonic acid is
(A)
SO 3 H
Cl
SO 3H
(B)
HO
OH
SO 3 H
(C)
Cl
OH
Cl
SO 3H
Cl
(D)
HO
SECTION-II
HO
11. Functional group is present in vitamin C
(A) Alcohol
(B) Enol
(C) Ester
(D) Ether
OH
O
OH
HO
Vitamin C

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is:
243

12. Which molecules will exist at room temperature ?
O
O
(A)
(B)
O
(C)
(D)
13. Which molecule have ( ) gamma position ?

(A) +N
(B) +N
(C) +N
(D) + S
14. The pair of compounds having the same general formula.

H
(A)
and
(B)
(C)
and HC CC CH
(D)
and
H
C=C=C
and
15. The correct structure/s of 2,3,4-Trimethylhexane is/are

(A)
(B)
(C)
(D)
16. Which of the following pair/s have same IUPAC naming

Br
COOCH3
(A) Br
COOH
244
COOH
&
OCOCH3

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I
Br
Br
(B) I
Cl
&
Cl
F
&
(C)
F
(D)
NH2
OH
Cl
&
H2 N
Cl
OH
17. Which of the following IUPAC names are incorrect

(A) 3-Ethyl-5-methylhepta-1,6diene
(B) 3-Methyl-5-ethylhepta-1,6-diene
(C) 3,4-Dimethylpentane
(D) 1-Bromo-3-chloro-4-fluorobut-2-ene
SECTION-III
This section has 5 questions. Each question has 5 choice (A),
(B), (C), (D) & (E) out of which ONLY ONE is correct.
(D) Statement-1 is false, Statement-2 is true.
18. Statement-1: Sec-butyl amine is a secondary amine.
Statement-2: In secondary amine, NH2 group attached with
secondary carbon.

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245

19. Statement-1: Oxalic acid & formic acid are homologue.
Statement-2: Homologues are those compounds which have
same nature of chemical reaction and differ in
(CH 2 ) n unit.
20. Statement-1: Loss of one hydrogen from alkane leads to alkyl
group.
Statement-2: Butane have four types of alkyl groups.
21. Statement-1:
is commonly called as acetone.
Statement-2: Common name is derived from 5 components i.e.

Secondary prefix + Primary prefix + Word root +
Primary Suffix + Secondary Suffix.
22. Statement-1: Cyclohexane is saturated while cyclohexene is
unsaturated.
Statement-2: Saturated compound is that which have only
single bond while unsaturated compound is that
which have multiple bond of any form.
SECTION-IV
(A)
COOH
CHO
Column - II
(P) 2-(2-Oxoethyl) cyclohexane
carboxylic acid
COOH
(B)
CHO
(Q) 2-Aminomethyl cyclohexane

carboxylic acid
COOH
(C)
246
NH 2
(R) 2-N-Methylaminocyclohexane
carboxylic acid

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COOH H
N
(S) 2-Formyl cyclohexane

carboxylic acid
24. Match the compounds written in Column-I with its nature in
Column-II :(D)
CH 3
Column - I
Column - II
(A)
(P) Aliphatic
(B)
(Q) Aromatic
(C)
(R) Alicyclic
(D)
(S) Heterocyclic
(T) Homocyclic
SECTION-V
Paragraph for Question Nos. 25-26
A saturated hydrocarbon
(A) has five membered ring. Three alkyl groups attached to the
ring adjacent to each other with following observations.
(A) First group has only two carbon atoms.
(B) Second group has four carbon atom with all hydrogens are
chemically same
(C) Third group has total five carbon atoms and its main chain
contains three carbon atoms with ethyl as a substituents.
25. The IUPAC name of compound (A) is
(A) 2 - ( 1 , 1 - D i m e t h y l e t h y l ) - 1 - ( 1 - e t h y l p r o p y l ) - 3 ethylcyclopentane
(B) 2 - (1 ,1 -Di me th yl eth yl )- 1 -e th yl -3 - (1 -e th ylp ro py l)
cyclopentane

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247

(C) 1 -(1 ,1 -Dimet hylethyl )-3 -ethy l-2 -(1 -m ethylpro pyl)
cyclopentane
(D) 1-(1,1-Dimethylethyl)-2-(1-methylethyl)-3-(1-methylpropyl)
cyclopentane
26. How many 1 hydrogens are present in compound (A).
(A) 15
(B) 18
(C) 12
(D) 9

During nomenclature of unsaturated hydrocarbon, lowest locant
is given to multiple bond rather than any substituent, as the
priority of multiple bond is more than substituent. When the
locant for multiple bond is same from either side than double
bond, then double bond is given priority over triple bond. For
selection of main chain if the size of main chain & number of
multiple bonds are equal then the priority is given to lowest set
of locants for multiple bond.
27. IUPAC name of following compound is
(A) 4-Ethenylhepta-1,3-dien-6-yne
(B) 4-(prop-2-ynyl) hexa-1,3,5-triene
(C) 3-(prop-2-ynly) hexa-1,3,5-triene
(D) 4-Ethenylhexa-4,6-dien-1-yne.
28. IUPAC name of following compound
(A) 3-Ethenylpenta-1-en-4-yne(B) 3-Ethynylpenta-1,4-diene

(C) 2,2-Diethenylpropyne
248
(D) 1,1-Diethenylpropyne

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SECTION-VI
29. Total number of homocyclic compounds among the given
molecule is
O
O
O
OH
HO
30. Total number of secondary hydrogens present in
O
OH
is

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249
Test
02

SECTION-I
01. Functional group absent in Heroin is
CH 3
N
O
O
H3 CCO
OCCH 3
O
(Heroin)
(A) Ester
(B) Ether
(C) Tertiary amine

(D) Tertiary amide
02. The number of sp sp sigma bonds in Capillin is
O
CH 3 C CC CC
(Capillin)
(A) 1
(B) 2
(C) 3
(D) 4
250

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O
03. The total number of lone pair of electrons in Dioxane is

(A) 1
(B) 2
(C) 3
(D) 4
04. Which of the following lactum have highest angle strain.

O
(A)
(B)
NH
-Lactum
-Lactum
O
NH
(C)
NH
NH
(D)
-Lactum
-Lactum
05. Total number of secondary carbon present in Decalin is
(Decalin)
(A) 6
(B) 8
(C) 10
(D) 4
06. Tota l number of tertiary hydrogen present in Steroid
R
is
(A) 7
(B) 6
(C) 5
(C) 4

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251

07. Which among the following is heterocyclic compound.
OH
(A)
(B)
Menthol
OH
H
Indole
OH
CH 3
(C)
(D)
Phenol
O-Cresol
08. Which among the following is aromatic in nature.
(A)
(B)
(C)
(D)
09. Which among the following is secondary alcohol.

(A)
OH
OH
(C)
(B)
(D)
OH
OH
10. Which among the following will not exist at room temperature.
(A)
(B)
(C)
(D)
SECTION-II
11. Which of the following is/are the homologue of Ethanoic acid
(CH3COOH) .
O
(A)
252
HCOH
(Formic acid)
COOH
(B)
(Butanoic acid)

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COOH
(C)
COOH
COOH
(Succinic acid)
(D)
(Propanoic acid)
12. Which among the following compound have atleast one sp 2

carbon present.
O
H
OH
N
HO
CH 3
(A)
(B)
HO
HO
Adrenaline
Estrone
(C)
(D)
Cubane
Cumene
13. Which among the following have structure & molecular formula
correctly matched.
(C 6 H 6 )
(A)
(C)
(C 14 H10 )
(C 10 H8 )
(B)
(C 14 H10 )
(D)
14. Which among the following have correct number of substituents present(s).
OH
(A)
OH
Cl O
(3)
(B)
COOH
(C)
Cl
(2)
O
Cl
(D)
(3)
(2)

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253

15. Which among the following structure & IUPAC name are correctly matched.
(A)
Et
2-Ethylbutane
OH O
(B)
OH
3- Hydroxybutanoic acid
(C)
6 - Methylcyclohex-2-enone
O
CCl
(D)
Benzene carbonyl chloride
16. Which among the following structure & their common name
are correctly matched.
OH
O2N
NO 2
O
(A)
(Acetone)
(B)
CH3
NO 2
(Picric acid)
(C)
(D)
HCH
(Formaldehyde)
(Toluene)
17. Which among the following alkyl groups & their name are correctly matched.
(A)
CH 3 CH 2 CH2 CH 2
(n-butyl)
CH 3 CHCH 2 CH 3
(B)
CH 3
(C) CH 3 CHCH 2
(iso-butyl)
254
(sec-butyl)
CH 3
CH3 C
(D)
CH 3
(tert-butyl)

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SECTION-III
OH
18. Statement 1 : Hydroquinone
is alicyclic compound.
OH
Statement 2 : Alicyclic compounds are simply the aliphatic
cyclic compounds.
19. Statement 1 : Azulene,
is aromatic in nature.
Statement 2 : Aromatic compounds are cyclic compounds

with each carbon sp or sp2 hybridiz ed, molecule a s a whole pla nner with tota l
electrons are 4n + 2 in number.
20. Statement 1 : General formula of
&
a re
same.
Statement 2 : General formula of any molecule is derived by
removing hydrogen from alkane which have
general formula Cn H 2n 2 .
21. Statement 1:
Tert-butyl amine is tertiary amine.
Statement 2 : Tertiary amine is that amine in which NH 2

group is attached to tertiary carbon.

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255

22. State ment 1 : Organic molecule with molecular formula
C2 H7 will not exist at room temperature.
Statement 2 : Carbon have valency four, so compound with 2
carbon can maximum accumulate 6 hydrogens
in it.
SECTION-IV
23. Match the compound given in Column I with their IUPAC
name in Column II.
Column I
O
A.
NH 2
C.
D.
P.
2-N-Methylamino
cyclohexanone
Q.
2-Aminomethyl
cyclohexanone
R.
2-Oxocyclohexane
carboxylic acid
S.
2- Formylcyclohexane
carboxylic acid
H
N
B.
Column II
CH 3
COOH
CHO
COOH
O
24. Match the compound given in Column I with their characteristics in column II.
Column I
A.
B.
C.
256
Column II
P.
Aromatic
Q.
Alicyclic
R.
Anti-aromatic

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D.
S.
Homocyclic
T.
Heterocyclic
SECTION-V
Formaldehyde CH 2 O is known to all biologists because of its
usefulness as a tissue preservative. When pure, formaldehyde
trimerises to give trioxane, C 3 H 6 O 3 , which surprisingly enough,
has no aldehydic or ketonic group. On monobromination reaction trioxane give only one monobromo derivative C 3 H 5 BrO 3 .
25. The structure of formaldehyde is
(A) HOH
H
C=O
(C)
H
(B)
O
HCH
(D) HCOH
26. The structure of Trioxane is

O
O
(A) CH CH CH
3
2
O
(C) O O
(B)
CH 3 CCH 3
(D) O O
O
Testosterone is one of the most important male steroid hormones.

When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown.
OH
H 2O / H
O
Testosterone

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257

27. The degree of unsaturation (DU) present in Testosterone is
(A) 5
(B) 6
(C) 7
(D) 8
28. Functiona l group present in product of dehydration of

Testoterone is
Acid
(A) Ester
(B) Ketone
(C) Ether (D) anhydride
SECTION-VI
29. Total number of aromatic compounds present in given molecule
are
I
II
III
IV
O
V
VI
VII
VIII
IX
30. Total number of heterocyclic compounds present in given molecules are
N
H
II
O
I
N
III
OH
IV
NH 2
N
HO
258
VI
OCCH 3
COOH
VII
N
H
N
V
O
VIII

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S
IX
Test
03

SECTION-I
1. Incorrect statement for given structures is
I
III
II
(A) I, II & III have same empirical formula
(B) I, II & III have same general formula
(C) I, II & III have same molecule formula
(D) I, II & III are homologue
2. Which statement among these is incorrect.
(A) CH2=CH2 has sp2 hybridization for each carbon with bond
angle 120.
(B) HC CH has sp hybridization for each carbon with bond
angle 180.
(C) H2C=C=CH2 has central carbon sp hybridized with bond
angle 180.
(D) HC CC CH has sp hybridization for only two carbons
with bond angle 180.

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259

3. All the members of a homologus series have same
(A) Functional groups
(B) Molecular mass
(C) Weight
(D) Physical properties
4. Number of types of carbon & hydrogen atoms present in given

compound is
(A) 1, 2
(B) 2, 2
(C) 2, 1
(D) 1, 1
5. Which among the following is not alicyclic compound.

(A)
(B)
(C)
(D)
6. Which of the following alkane have all the four types of C

present.
(A) (CH 3 )3 CH
(B) (C 2 H 5 )3 CH
(C) (CH 3 )3 CCH2 CH(CH 3 )2
(D) (CH 3 )4 C
7. IUPAC name of sec-butyl group is

(A) 2-Methylethyl
(B) 1,1-Dimethylethyl
(C) 2-Methylpropyl
(D) 1-Methylpropyl
Cl
8. IUPAC name of compound
Br
is
(A) 3 -Bromo-7 -chloro-7 -ethyl-5 -(1 ,1-dimethyethyl)-5 -(2 methylpropyl)-3-methylnonane

(B) 3-Bromo-7-chloro-5-(1,1-dimethylethyl)-7-ethyl-3-methyl-5(2-methylpropyl)nonane
260

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(C) 3-Bromo-7-chloro-7-ethyl-3-methyl-5-(1,1-dimethylethyl)-5(2-methylpropyl)nonane
(D) 3-Bromo-5-(1,1-dimethylethyl)-5-(2-methylethyl)-7-chloro7-ethyl-3-methylnonane
9. IUPAC name of the given structure is
(A) 3-Ethynyl-4-ethenyl-7-(2-methylbutyl)-8-methylnona-1,7diene
(B) 4-Ethenyl-3-ethynyl-5,8-dimethyl-7-propylnona-1,7-diene
(C) 3,4-Diethenyl-5,8-dimethyl-7-propylnona-7-ene-1-yne
(D) 4-Ethenyl-3-ethynyl-7-(2-methylbutyl)-8-methylnona-1,7diene
O
CH3
10. The IUPAC name of the compound HCN
is
CH 2 CH 3
(A) N-Ethyl-N-methylmethanamide
(B) N-Methyl-N-ethylmethanamide
(C) N-Ethyl-N-methylformamide
(D) N-Ethylmethylmethanamide
SECTION-II
11. Neohexane contains
(A) Four 1 carbon atoms and two 2 hydrogen
(B) Twelve 1 hydrogen but no 3 carbon
(C) Two 2 carbon & one 4 carbon
(D) One 4 carbon and two 3 hydrogen
12. The pair of compounds having the same general formula.
H
H
and
and
C C C
(A)
(B)
H
H
(C)
and HC
C C CH (D)
and

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261

13. The correct structure/s of 2,3,4-Trimethylhexane is/are
(A)
(B)
(C)
(D)
14. Correct structure of 5-Ethynyl-1,3,6-heptatriene

(A)
H2 C
CH 2
(B)
CH 2
(D)
CH
(C) H2 C
H2 C
CH 2
CH 2
H3 C
CH
CH 2
CH
15. Structure of 2-Ethenyl-3-methylcyclohexa-1,3-diene is/are
(A)
(B)
(C)
(D)
16. Which of the following is correct IUPAC name:

(A) H2 NCCH 2 CNH 2 Propanediamide
O
(B)
CNHCH 3 N-Methyl cyclohexanecarboxamide

O
(C) H3 COCCH 2 CH 2 OCCH 3

O
(D)
COCH 3 Methyl 5-bromocyclohex-2-enecarboxylate

Br
262
Methyl 3-ethanoyloxy
propanoate

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17. Which of the following is correct structure of 4 -(4 Methoxyphenyl)-4-oxo-butanoic acid.
OMe
(A) HO
OMe
(B)
HO
OMe
OMe
O
(C)
COOH
(D)
HO
O
SECTION-III
18. Statement-1: Neohydrocarbons contain a tertiary carbon atom.
Statement-2: Whenever a carbon atom is bonded to three carbon
atoms it is tertiary.
O
Cl CH 3
C
19. Statement-1:
NH 2 3 - B r o m o - 2 - c h l o r o - 3 Br
methylpentanamide is incorrect IUPAC name.
Statement-2: In case of chain terminating senior most functional
group numbering start from itself.

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263

20. Statement-1: Esters are formed by reaction of carboxylic acid &
alcohol.
Statement-2: Amides are formed by reaction of carboxylic acid
& amines.
21. Statement-1: OH group attached to carbon leads to formation
of many types of function group such as alcohol,
phenol, oxime, enol & carboxylic acid.
Statement-2: X group attached to carbon leads to formation of
many types of functional group such as alkyl
halide, vinyl halide, Allyl halide, Aryl halide &
acid halide.
22. Statement-1: Each carbon atom of cyclooctatetraene (COT) is
sp2 hybridized but molecule is non-planner.
Statement-2: Cyclooctatetraene (COT) is tub-shaped.
SECTION-IV
23. Match the compound written in Column-I with its nature written
MeOOC
N
O
H
C
3
(A)
Cocaine O
O
CH 3
(P) Carbocyclic
(B)
(Q) Heterocyclic
CH 3
O
(C)
CH3
COOH
Column - II
(R) Aromatic
Aspirin
264

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NH 2
N
(D)
(S) Saturated
HN N
Adenine
(T) Unsaturated
Column - II
O
COCHCH3
(A)
CH3
Methyl
(P) cyclopentylethanoate
OH
CH 2 COOCH 3
(B)
Isopropyl 3-hydroxy
(Q) cyclohexaneocarboxylate
O
COOH
(C)
OHC
HOOC
3-Carbamoylcyclobutane
carboxylic acid
(S)
4-Formyl-2-oxocyclohexane
carboxylic acid
O
NH 2
(D)
(R)
SECTION-V
Have you ever thought that when you read anything from any
book your eyes use an organic compound (retinal) to convert
visible light into nerve impulses. When you pick up this book
from any place, your muscles do chemical reactions on sugars
to give you energy. As you read the words and sentences of this
book, gaps between your brain cells are being bridged by simple
orga nic molecules (neurotransmitter amines) so that nerve
impulse ca n be pa ssed a round your bra in a nd you ca n

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265

understand all matters correctly and you did all that without
consciously thinking about it.
H C CH CH 3
3
CH 3H 3 C
O
11-Cis retinal H
(Absorbs light when we see)
25. Deegree of unsaturation (DU) present in 11-cis-retinal is

(A) 6
(B) 7
(C) 8
(D) 5
26. Which statement is incorrect for cis-retinal

(A) cis-retinal is an unsaturated compound.
(B) cis-retinal is a homocyclic compound.
(C) cis-retinal have aldehydic group.
(D) cis-retinal is isolated polyenes.
A hydrocarbon (A) has six membered ring in which there is no
unsaturation. Two alkyl groups are attached to the ring adjacent
to each other. One group has 2 carbon atoms and another has 4
carbon atoms. The larger alkyl group has main chain of three
carbon atom of which second carbon is substituted.
27. How many primary secondary & tertiary carbons are present in
this compound respectively.
(A) 2, 4, 6
(B) 3, 5, 4
(C) 3, 6, 3
(D) 4, 6, 2
28. What is the correct IUPAC name of this compound.

(A) 1-(2-Methylpropyl)-2-ethylcyclohexane
(B) 1-Ethyl-2-butylcyclohexane
(C) 1-Ethyl-2-(2-methylpropyl)cyclohexane
(D) 2-Ethyl-1-isobutylcyclohexane
266

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SECTION-VI
29. How many of the compounds among these are unsaturated in
nature.
SH O
SH
O
H3 C
O
H 3C
CH 3
CH3
CH3
SH
Olean sex pheromone
Compound with
Compound with
of olive fly
worst smell
worst smell
(III)
II
I
O
H
CH 3
N
N
CH 3
N
O
O
HO
Compound from
Paracetamole
Nicotine
cakes & biscuits
(V)
(VI)
(IV)
O
HN
H H
CH 3
S
R
N
NH
O
CH
N
O
3
Indigo dye
COOH
O
(VIII)
Penicilin
Cl O
(VII) O
NH
S NH 2
O
OH
Furosemide (Sulpha drug)
(IX)
30. How many of the compound among these have all atoms sp2
hybridized which form the ring.
N
(I)
N
H
(II)
O
(III)
N
H
H
H
(V) (VI) (VII) (VIII)
(IX)
S
(IV)

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267
Answers
Test 01
1.
6.
11.
16.
21.
24.
27.
(B)
2. (C)
3. (C)
4. (B)
5. (C)
(B)
7. (C)
8. (B)
9. (B)
10. (B)
(A,B,C,) 12. (A,C,D) 13. (B,C,D) 14. (C,D) 15.(A,B,C,D)
(C,D)
17. (B,C,D) 18. (E)
19. (D)
20. (B)
(C)
22. (A)
23. (A-S ; B-P ; C-Q ; D-R)
(AQ,T ; BP,R,T ; CP ; DQ,S)
25. (B)
26. (B)
(A)
28. (B)
29. (6)
30. (4)
Test 02
1.
6.
11.
16.
21.
24.
27.
(D)
2. (C)
3. (D)
4. (A)
5.
(C)
7. (B)
8. (C)
9. (B)
10.
(A,B,D) 12. (A,B,D) 13. (A,B,C,D) 14. (A,B,C,D) 15.
(A,B,C,D) 17. ()
18. (D)
19. (A)
20.
(E)
22. (A)
23. (AQ ; BP ; CS ; DR)
(AP,S ; BP,T ; CR,S ; DQ,S)
25. (B)
26.
(B)
28. (B)
29. (5)
30. (6)
(B)
(A)
(B,C,D)
(A)
(C)
Test 03
1. (C)
2.
6. (C)
7.
11. (A,B)
12.
16. (A,B,C,D) 17.
21. (B)
22.
DQ,R,T)
24.
27. (C)
28.
(D)
3. (A)
4. (C)
5. (D)
(D)
8. (B)
9. (C)
10. (A)
(C,D)
13. (A,B,C,D) 14. (A,B)
15. (B,D)
(A,C)
18. (D)
19. (D)
20. (B)
(B)
23. (AQ,R,T ; BP,T ; CP,R,T ;
(AQ ; BP ; CS ; DR) 25. (B)
26. (D)
(C)
29. (7)
30. (7)
268

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AJNISH GUPTA & BHARTI GUPTA

Copyright 2015 by Ajnish Gupta

First Indian Reprint, 2015

Organic Chemistry is easy

especially because it is relatively easy to frame a very

Section 01 : Introduction of organic chemistry

Section 02 : What is organic chemistry

Section 03 : Representation of organic compounds

Section 04 : Reason for the formation of large

Section 05 : Functional groups

Section 06 : Homologue & Homologous series

Section 07 : Nature of C, H & functional groups

Section 08 : Saturated & Unsaturated molecules

Section 10 : Classification of organic compounds

Section 11 : Baeyers strain theory

Exercise 1 : Subjective approach

Exercise 1 : Objective approach

Single correct questions (SCQ)

Multiple correct questions (MCQ)

Assertion/reason type questions (A/R)

Match the column type ques. (MTC)

Comprehension type questions

Integer type questions

Unit 2 : Nomenclature of organic compounds

Section 01 : Alkyl groups

Section 02 : Basic concept of IUPAC nomenclature

Section 03 : Points to write IUPAC nomenclature

Section 04 : Points to write IUPAC nomenclature

Section 05 : Points to write IUPAC nomenclature

Section 06 : Nomenclature of Bicyclic &

Section 07 : Some common names commonly used

Section 08 : Degree of unsaturation

Section 09 : Chemically different hydrogen

Exercise 2 : Subjective approach

Exercise 2 : Objective approach

Single correct questions (SCQ)

Multiple correct questions (MCQ)

Assertion/reason type questions (A/R) 231

Comprehension type questions

Integer type questions

: Basic understanding of organic

: Basic understanding of organic

: Basic understanding of organic

chemistry & nomenclature

Unit 3 : Study of isomerism

Section 02 : Chain isomerism

Section 03 : Positional isomerism

Section 04 : Functional isomerism

Section 06 : Basic concept of tautomerism

Section 07 : % enol content

Section 08 : Types of tautomerism

Section 09 : Basic concept of geometrical isomerism 305

Section 11 : Basic concept of optical isomerism

Section 12 : Nomenclature used in optical isomerism 321

Section 14 : Compound showing optical isomerism

Section 15 : Conformational isomerism

Section 16 : Conformation of cyclohexane

Section 17 : Interconversion of one form of

Section 18 : Finding relationship between

Section 19 : Physical properties of organic

Exercise 3 : Subjective approach

Exercise 3 : Objective approach