CHEMISTRY

TARGET IIT JEE 2014

XI (P)

NOMENCLATURE OF
ORGANIC COMPOUND

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NOMENCLATURE OF ORGANIC COMPOUNDS

Mainly three systems are adopted for naming an organic compound :
(i)
(ii)
(iii)

Common Names or Trivial System

Derived System
IUPAC system or Geneva System

COMMON OR TRIVIAL SYSTEM

On the basis of

Source

Property

Discovery

Structure

(i) On the basis of source from which they were obtained.

S.No. Organic
Compound

Trivial Name

1.

CH3OH

2.

NH2CONH2

Wood spirit or Methyl

spirit
Urea

Obtained by destructive distillation

of wood.
Obtained from urine

3.

CH4

Marsh gas (fire damp)

It was produced in marsh places.

4.

CH3COOH

Vinegar

Obtained from Acetum - i.e. Vinegar

Oxalic acid

Obtained from oxalis plant.

Formic acid

Obtained from formicus [Red ant]

Lactic acid

Obtained from lactous (milk)

6.

COOH
|
COOH
HCOOH

7.

CH 3 CH COOH

5.

Source

|
OH

8.

CH 2 COOH
|
CH(OH)COOH

Malic acid

Obtain from Apple

CH3CH2CH2COOH

Butyric acid

Obtained from butter.

10.

CH3(CH2)4COOH

Caproic acid

Obtained from goats.

11.

C2H5OH

Grain alcohol

Obtained from barley.

Nomenclature of Organic Compound

[2]

(ii) On the basis of property

1. Glucose - Sweet in test
3. Glycerol - Sweet
(Glycus - Sweet)
(iii) On the basis of discovery
1. RMgx (Grigard Reagent)

2. Glycol - Sweet poisnous

2. R2Zn (Frankland reagent)

(iv) On the basis of structure

S.No.
(i)
(ii)
(iii)
(iv)
(v)
(vi)
(vii)
(viii)
(ix)
(x)

No. of Carbon atom

1C
2C
3C
4C
5C
6C
7C
8C
9C
10C

Word Root
Meth
Eth
Prop
But
Pent
Hex
Hept
Oct
Non
Dec

Common Names for Hydrocarbon Derivetives

S.No.

Compound

Name

1.
2.
3.
4.
5.

RX
R OH
R SH
R NH2
ROR

Alkyl halide
Alkyl alcohol
Alkyl thio alcohol
Alkyl amine
Dialkyl ether

6.

Dialkyl ketone

7.
8.

RNHR

Dialkyl amine
Trialkyl amine

9.

ROR

Alkyl alkyl ether

10.
11.
12.

Alkyl alkyl ketone

RNHR

Alkyl alkyl amine

Alkyl alkyl alkyl amine

R is termed as alkyl - -)

Nomenclature of Organic Compound

[3]

GROUPS
Atom or a group of atoms which possess any free valency are called as Groups.
If their are two structure of same molecular formula then some prefix (n, iso, neo) are used two
differenciate them.
Normal group :
(a) It is represented by n.
(b) Groups having no branch (Straight chain).
(c) Free bond will come either on Ist carbon atom or on last carbon atom.
n butyl
CH3 CH2 CH2 CH2
n propyl
CH3 CH2 CH2
Iso group :
When one methyl group is attached to the second last carbon of the straight carbon chain is named
as iso group.
CH 3 C H CH 2

H3 C CH
|
CH3

e.g.

CH 3 C H CH 2 CH 2

CH 3

Isopropyl

CH 3

Isobutyl

Isopentyl

Exception :

CH 3

CH 3

CH 3 C C H CH 2

CH 3 C CH 2 C H CH 2
|

CH 3

CH 3

CH 3 CH 3

(i) Iso octyl

(ii) Iso heptyl

Neo group :
(a)
When two methyl groups on second last carbon of a straight carbon chain is attached to other four
carbon atom group is named as neo group.
(b)
It is represeted by following structure C
|
CCC
|
C

(c)

for eg.

C
|
CCC
|
C

Neo pentyl

There should be one 4 carbon and atleast three methyl group on 4 carbon.

NOTE : (Optically Active) = If all valency are attached to different atoms.

Amyl group :
H
|
CH3 CH2 C CH2
|
CH3

Active amyl

CH3 CH2 CH
|
CH2
|
CH3

Secondary amyl

CH3 CH2 CH2 CH

|
CH3

Active secondary amyl

Nomenclature of Organic Compound

CH3 CH CH
|
|
CH3 CH3

Active iso secondary amyl

[4]

Secondary group :
(a) The carbon having free valency attached to two carbon is called secondary carbon.
(b) It is represented by following structure. C C C C
|

eg. (i)

CH 3 CH CH 2 CH 3
|

(ii) CH 3 CH CH 2 CH 2 CH 3
|

(secondary butyl)

(secondary pentyl)

Tertiary group :
(a) The carbon having free valency attached to three other carbon .
C
|

(b) It is represented by following structure -

C C C
|

CH3

CH3

e.g.

(i) CH3 C CH3

CH3 C CH2 CH3

(Tertiary butyl)

(Tertiary pentyl)

Alkyl group :
When a hydrogen is removed from Alkane (saturated hydrocarbon) then alkyl group is formed.
A bond is vacant on alkyl group on which any functional group may come.
Alkyl alkane
H
(CnH2n+2)

(CnH2n+1)

e.g.
CH3
(i) CH4
H
Methane

Methyl
CH3CH2
(ii) CH3 CH3
H
Ethane
(iii) CH3CH2CH3
Propane

ethyl
CH3CH2CH2
n-Propyl

CH3CHCH3
iso-Propyl

(iv) CH3CH 2CH2CH3

n-Butane

CH 3CH2CH 2CH 2
n-Butyl
CH 3CHCH2CH3
Sec. Butyl

CH3CHCH2
(v) CH3CHCH3

iso-butyl
iso-butane
CH3CCH3
tertiary-butyl

Nomenclature of Organic Compound

[5]

CH3CH2CH2CH2CH2
n-pentyl
(vi) CH3CHCH2CH2CH3
n-pentane

CH3CHCH2CH2CH3
active secondary amyl
C2H5CHC2H5
secondary amyl

CH3CHCH2CH2
iso-pentyl
CH3CCH2CH3
H

(vii)

tertiary-pentyl
C2H5CHCH2

iso-pentane

active amyl
CH3CHCH
Active isosecondary amyl

CH3
(viii)

CH3
H

CH3
neo-pentane

CH3
neo-pentyl

Alkenyl group :
Alkenyl alkene
H
(CnH2n)
CH2 = CH
Vinyl

CH2= CH CH2
Allyl

(CnH2n1)
CH3 CH = CH
Propenyl(1-propenyl)

CH3 C CH2
|

Isopropenyl (1-methyl-1-ethenyl)

Nomenclature of Organic Compound

[6]

Alkynyl group
Alkynyl alkyne
H
(CnH2n2)
CH C CH2
Propargyl (2-propynyl)

CH C
Ethynyl

(CnH2n3)
CH3 C C
Propynyl (1-propynyl)

Alkylidene group
2 H

alkane from

Alkylidene same carbon

Alkylene group
2 H

alkane from

Alkylene different carbon

Position of double bond :
In an unsaturated hydrocarbon if the position of double bond is on Ist or last carbon then its prefix
will be (alpha) if it is on 2nd carbon it is termed as (Beta) & the (gamma) & (delta) and so
on.
eg. H2C = CH CH2 CH3 - butylene
H3C CH = CH CH3 - butylene
H3C CH2 CH = CH2 - butylene
H2C = CH CH3 or H3C CH = CH2
(Both are same positions, propylene)
H3 C C CH2
|
CH3

Isobutylene

CH3CH2CH=CHCH2CH3 - hexylene
CH3 CH2 CH2 CH=CHCH2 CH2 CH3
- octylene
COMMON NAMING OF DIHALIDES
(a)
(b)

When two same halogen atoms are attached to the same carbon such compounds are called
Gemdihalides.
Common names of such compounds are alkylidene halides

eg. :

Cl
Cl
Ethylidene chloride

Exception : Methylidene halide (wrong)

I
I
H3
Isobutylidene Iodide
X
X

Methylene halide (right)

Nomenclature of Organic Compound

[7]

(c) When two same halogen atoms are attached to adjacent carbon, these are called as vicinal dihalides.
Common names of such compounds are alkylene halide.

CH3 CH CH2
|
|

eg

Cl
|
H3 C C CH2 Cl
|
CH3

Propylene Iodide

Isobutylene chloride

(d) When two same halogen atoms are attached at the two ends of a carbon chain its common naming
will be polymethylene halide.
poly word indicates the number of CH2 groups.
CH2
2
3
4
5
6
Poly
di
tri
tetra penta Hexa
CH2 CH2 CH2 CH2 CH2
|
|
Br
Br

CH2 CH2 CH2

|
|

eg.

Trimethylene Iodide

Pentamethylene Bromide

Exception :
CH2 X dimethylene halide
|
CH2 X ethylene halide

(wrong)
(right)

COMMON - NAMING OF DI-HYDROXY COMPOUNDS

(a) When two OH groups are attached to adjacent carbon atoms they are termed as alkylene glycol.
CH3 CH2 CH CH2
|
|
OH OH

OH
|
CH3 CH2 C CH2 OH
|
CH3

Butylene glycol
Active amylene glycol
(b) When two OH group are attached at the two ends of a carbon chain, these compounds are named
as polymethylene glycol.
Poly Number of CH2 groups.
eg. :

CH2 CH2 CH2 CH2 CH2 CH2

|
|
OH
OH

CH2 CH2 CH2 CH2

|
|
OH
OH

Tetra methylene glycol

Hexamethylene glycol

Exception :
CH2 OH

Dimethylene glycol (wrong)

|
CH2 OH

Ethylene glycol

(right)

Nomenclature of Organic Compound

[8]

COMMON-NAMING OF THE FUNCTIONAL GROUP HAVING CARBON

(Common naming for Hydrocarbon derivatives)
S.No.

Functional group

Suffix

(i)

O
||
C OH

-ic Acid

||

(ii)

||

-ic anhydride

O
||
C O R

(iii)

-ate

(iv)

O
||
C NH2

-amide

(v)

O
||
C X

-yl halide

(vi)

O
||
C H

-aldehyde

(vii)
(viii)

C N

-o-nitrile
-o-isonitrile

!
N C

Prefix :
1 Carbon Form-

2 Carbon Acet-

3 Carbon Propion-

4 Carbon

Normal
Butyr |
Iso

5 Carbon
Valer

eg.

3 C + (=) double bond = Acryl -

O
||
H C H

Formaldehyde
O
||
CH3 CH2 C Cl

Propionyl chloride

4 C + double bond = Croton-

O
||
CH3 C O H

Acetic Acid
O
||
CH3 CH C NH2
|
CH3

Isobutyramide

O
||
CH3 C H

Acetaldehyde

Nomenclature of Organic Compound

[9]

NOMENCLATURE OF ESTER
O
||
C O R

The group which is attached to the oxygen is written as alkyl & the remaining structure is named on
the basis of Functional Group suffix.
eg. (i)

O
||
H C O CH3

(ii)

O
||
CH3 O C H

Methyl formate
O
||
(iv) CH3 C O CH3

Methyl formate

Acetic acid
O
||
(vi) CH3 CH2 C O CH2 CH3

O
||
(v) CH3 C O CH2 CH3

Methyl acetate

(vii)

O
||
(iii) CH3 C O H

Ethyl acetate

O
||
CH2 CH C O CH2 CH3

Ethyl propionate

O
||
(viii) CH 3 CH CH C O CH 3

Ethyl acrylate

Methyl crotonate

NOMENCLATURE OF ANHYDRIDE
Rule : Add the total number of carbon atoms & divide it by 2, the substract will give you the
number of C - atom. Now name it according to suffix use for anhydride.
Total
2
4
2

= Substract
= Number of C atom
O
O
||

=2

||

6
2

||

=3

Acetic anhydride

O
||

Propionic anhydride

If R R, You need not to find out substract.

O
eg.

||

O
||

Acetic propionic anhydride (right)

Propionic Acetic anhydride (wrong)
Divide it in two parts as above & name it by suffixing ic anhydride (alphabatically)
CH3 O
O

eg.

||

||

||

O
|

||

CH3 O

Nomenclature of Organic Compound

[10]

Butyric propionic anhydride

Isobutyric Secondary valeric anhydride

O
||

Acrylic anhydride

||

DERIVED SYSTEM
According to this system name to any compound is given according to the parent name of the
homologous series. This system is reserved for the following nine homologous series.
S.No.

Name of Homologous series

Derived Name

Structure of group

1.

Alkane

Methane

2.
3.

Alkene
Alkyne

Ethylene
Acetylene

C C

4.

Alkanol

Carbinol

C OH

5.

Alkanal

Acetaldehyde

C CHO

6.

Alkanoic acid

Acetic acid

7.

Alkanoyl halide

Acetyl halide

C COX

8.

Alkanamide

Acetamide

C CONH2

Acetone

C C C

C
|

>C=C<
|
|
|
|

|
|

COOH

|
|

9.

Alkanone

|
||

Types of Ethylene: (Symmetrical & Unsymmetrical)

(a)
Symmetrical : In the given two alkyl groups one group is attached to the one carbon of ethylene
& next on the next carbon.
(b)
Unsymmetrical : When both the given groups are attached on the same carbon.
Note : Symmetrical & Unsymmetrical : Terms are used only when two alkyl groups are given.
eg.
Symmetrical dimethyl ethylene
Unsymmetrical dimethyl ethylene

Symmetrical ethyl methyl ethylene

Nomenclature of Organic Compound

[11]

Tri methyl ethylene

Tetra methyl ethylene

CH3 C C CH3

Dimethyl acetylene

IUPAC NOMENCLATUR
The name consists of three parts:
Prefix
Secondary
[Details of
substitutents]

+
Primary
[Nature of
Carbon chain
cyclic/acylic]

Word root

Suffix

[No. of carbon
atoms in the
principal chain]

Primary
[Nature of carbon
carbon bond]

Secondary
[Details of
functional
group]

Primary Prefix : It represents the nature of the principal / parent chain.

Nature of chain

Primary Prefix

Acyclic / Non-cyclic
Cyclic
Bicyclic
Tricyclic
Spiro

Cyclo
Bicyclo
Tricyclo
Spiro

Secondary prefix : It represent substituents.

Word root : It represents the number of carbon atoms in the principal / parent chain.
No. of carbon atoms
1
2
3
4
5
6
7
8
9
10
11
12
13
20
30
40

Word root
Meth
Eth
Prop
But
Pent
Hex
Hept
Oct
Non
Dec
Undec
Dodec
Tridec
Eicos
Triacont
Tetracont

Nomenclature of Organic Compound

[12]

Primary Suffix :

It represents the nature of CC bonds in the principal/ parent chain (whether

single bond, double bond or triple bond).

Nature of bond

Primary suffix

Saturated
CC single bond

ane

Nature of bond

Primary suffix

Unsaturated
C = C bond
C C bond
2C = C bonds
2C C bonds

ene
yne
diene
diyne

C=C+CC

*
ene + yne = enyne

*
If secondary suffix starts from a vowel or y then the last e of first suffix is omitted.
Secondary suffix : is used for functional groups.
SATURATED UNBRANCHED HYDROCARBONS
IUPAC name = Word Root + Primary Suffix
e.g.
CH4

Meth + ane

Methane

CH3 CH3

Eth + ane

Ethane

CH3CH2CH3

Prop + ane

Propane

But + ane

Butane

Pent + ane

Pentane

Hex + ane

Hexane

CH3(CH2)9CH3

Undec + ane

Undecane

CH3(CH2)28CH3

Triacont + ane

Triacontane

SATURATED BRANCHED CHAIN HYDROCARBONS

Principal / parent chain
Branch / Substitutent

Nomenclature of Organic Compound

[13]

Rules for naming Branches

R H R
H

Alkane
(CnH2n+2)

Alkyl substituent
(CnH2n+1)

e.g.
Alkane

Alkyl

IUPAC names

(1)

CH4

CH3

Methyl

(2)

C 2H 6

C2H5

Ethyl

Naming of complex alkyl groups

(i)
Longest chain in a branch is selected starting from the same and where it originates from.
(ii)
Numbering is started from the originating end of a branch.
(3)

C 3H 8

CH2CH2CH3

Propyl

CH3

CH

1 Methyl ethyl

CH3
2

(4)

C4H10

C4H9

CH3CH2CH2CH2
1

Butyl

CH3CH CH2CH3

1-methyl propyl

CH3
3 2

2-methyl propyl

H3CCHCH2
2

CH3

1,1-dimethylpropyl

H3CCCH3

CH3
5

(5)

CH3CH C CH2CH2

3,3,4-trimethyl-pentyl

CH3 CH3

Nomenclature of Organic Compound

[14]

SATURATED BRANCHED CHAIN HYDROCARBONS

Rules
(1)

Longest chain rule : Select the longest possible carbon chain as the parent chain or principal
carbon chain. All other carbon chains will be considered as side chain or substituents.

CCCCC
CC
Longest chain
containing
6 carbon atoms
If there is more than one longest chain possible then select the chain which contains maximum
number of side chains
C

(2)

CCCCC

CCCCC

CC

CC

Correct

(3)

Incorrect

Lowest set of locant rule : The number given to the side chain is locant. While numbering the
parent chain, lowest set of locants rule needs to be followed. According to this rule, that set of
locants will be considered which has got a lower number at the first point of difference.
I = ( 2, 2, 3, 6, 8)

Correct

II = ( 2, 2, 4, 4, 5)

Incorrect

First point of
difference
*

First set will be considered in this case.

4

2
1

(a)

11

2
3

8
7

2,4,6-Trimethyldecane (Correct)

12

10
9

10

3,4,5-Trimethyldecane (correct)

Side chains are always written in alphabetical order.

4
2

5
3

3-Ethyl-2-methylpentane

Nomenclature of Organic Compound

[15]

(b)

Di, tri, tetra etc. are not considered in comparing alphebetical order.

(c)

3Ethyl2, 4dimethyl hexane

If lowest set of locants rule is not applicable then numbering is done according to alphabetical
order.
2

6
7

2
1

Locant3, 5 (incorrect)

Locant3, 5 (correct)

(d)

If Di, tri, tetra etc. are part of name of complex name then they considered in alphabetical
order.
6

2
1

(e)

4-(1,1-Dimethyl)-3, 5-diethylheptane

5-Ethyl-3,4-bis(1-methylethyl)-2-methylheptane

bis , tris, tetrakis are used for complex alkyl substituents

e.g.
(1)

CH3CH2CHCH2CH3

3-methylpentane

CH3
(2)

CH3CH2CHCH2CH3

3-ethylhexane

4CH
2
5CH CH
2
6 3

(3)

CH3CH2CHCH2CH3

3-ethyl-2-methylpentane

H3CCHCH3
2

Nomenclature of Organic Compound

[16]

1CH3
2 CHCH

(4)

3,3-diethyl-2,4-dimethyl-pentane

CH3CH2CHCH2CH3
3

4CHCH3
5CH
3

CH3
1

(5)

2 3

2,2,5-trimethylhexane

CH3CCH2CH2CHCH3
CH3
5

(6)

CH3
2

3-Ethyl-4-methylhexane

CH3CH2CHCHCH2CH3
CH3 CH2
CH3
H 3C

CH3
CH

(7)

CH3CHCH2CCH2CH2CH3
CH3
H 3C

2-methyl-4-bis(1-methylethyl)heptane

CH
CH3

CH2CH3
6

CH3CH2CH2CHCHCH2CH3

(8)

4-(1,1-dimethylethyl)-3-ethylheptane

H3CCCH3
CH3

UNBRANCHED UNSATURATED HYDROCARBON

Numbering of carbon chain
Rule-1 : If unsaturated bond is present in the molecule at the terminal carbon, then numbering done from the side
of unsaturated carbon.
1

eg. CH2 = CH CH2 CH3

3

eg. CH C CH2 CH3

But1ene

But1yne

Rule-2 : If unsaturated bonds like double bond and triple bond is present at terminal carbon, then numbering
always done from double bonded terminal carbon.
(Double bond preferred over triple bond when both bonds are at same position)
1

eg. CH2 = CH C CH

But1en3yne

Nomenclature of Organic Compound

[17]

Rule-3 : If unsaturated bonds like double bond or triple bond is present at terminal carbon, then numbering is
done from either way.
1
2
3
4
eg. CH
2 = CH CH = CH 2

But1, 3diene

1
2 3 4
eg. CH
2 C C CH

But1, 3diyne

Rule-4 : If triple bond is present at terminal carbon and double bond is located at any carbon except other
terminal carbon. Then numbering is done from triple bond.
1
2 3
4
5
CH C CH CH CH3

Pent 3 en 1 yne

Rule-5 : If double bond is present at terminal carbon and triple bond is present at any other position except
other terminal carbon, then numbering is done from double bonded terminal carbon.
1

eg. CH2 = CH C C CH3

Pent 1 en 3 yne

BRANCHED UNSATURATED HYDROCARBON

Longest chain :
Rule-1 : If unsaturated bonds like double bond or triple bond is present in the molecule, then that parent chain
is considered which is containing unsaturated bonds like double bond or triple bond.
7

eg. CH3 CH2 CH2 CH2 CH CH = CH2

|
CH2 CH2 CH3

eg.

Parent chain

5
6
4
3
2
1
CH3 CH = CH CH CH = CH2
|
CH2 CH2 CH3

Rule-2 : A primary suffix is added to the word root to indicate presence at double or triple bond in the parent
chain.
For one double bond = Word root + locant + ene
For one triple bond = Word root + locant + yne
In case the parent chain contains two or more double bonds, the prefixes di, tri, tetra, etc. are used
before primary suffix.
For two double bonds = Word root + locant + diene
For two triple bonds = Word root + locant + diyne
Numbering of carbon chain :
Rule-1 : In branched alkene, select that parent chain which is containing maximum unsaturated double bond or
triple bond and follow properly of lowest locant rule.
2
1
CH = CH2

eg.

eg.
Cyclohexyl eth -1-ene

CH3 CH3
|5
1
2
4
7
6
3
CH3 CH = C CH CH CH2 CH3
4, 6-dimethyl hept-2-ene

Nomenclature of Organic Compound

[18]

3
1
2
CH2 CH = CH2
6
4 5
eg. CH3 CH2 CH2 CH2 C = CH CH3

1 2
C CH

eg.
Cyclohexyl eth -1-yne

4Butylhexa-1-4-diene

Rule-2 : In branched alkene, if unsaturated double bond or triple bond is present in the cyclic ring, then
numbering is done from double bonded carbon of the cyclic ring and follow lowest locant rule properly.
6

eg.

5
4

1 CH2 CH3

2
3
1-ethyl cyclohex-1-ene

IUPAC NAMING OF ORGANIC COMPOUND CONTAINING FUNCTIONAL GROUPS

In IUPAC nomenclature functional groups are catagorized into two type.
TypeI : Groups of this type are not considered as functional groups in IUPAC nomenclature. They are considered
as substituents & therefore represented by prefix. type I functional group & their prefix are shown
below:
Groups
F
Cl
Br
I
NO2
NO
OR
CC

Prefix
fluoro
chloro
bromo
iodo
nitro
nitroso
alkoxy
epoxy

Rules for their nomenclature :

Rule I : If two substituents are present on same position from different ends, then priority is decided on the basis
of alphabetical order.
5

CH2 CH2 CH2 CH2 CH2

|
|
Cl
Br

Rule II : If multiple bond and type I functional group both are present, the priority is given to multiple bond.
1

H3C CH = CH CH CH2 Cl

Rule III : These groups are written is alphabatical order in IUPAC name.
eg.

(i)

CH3 CH2 CH2 CH CH3

|
F

2-fluoropentane

Nomenclature of Organic Compound

[19]

(ii)

(iii)

F
|
H3C CH CH2 CH2 CH Cl
|
CH2
|
CH3
F
|
H3C CH2 CH CH2 CH Cl
|
CH2
|
CH3

5-chloro-2-fluoroheptane

3-chloro-5-fluoroheptane

(iv)

H3C CH CH CH CH3
|
|
|
CH2 NO2 CH2
|
|
CH3
CH3

3, 5-dimethyl-4-nitro heptane

(v)

CH2 CH2 CH CH2 C CH2 CH3

|
|
||
NO
I
CH2

2-ethyl-4-iodo-6-nitroso hex-1-ene

(vi)

HC = CH C CH2 CH2 Cl
||
|
Cl
CH2

1-chloro-3-chloroethylbuta-1, 3-diene

(vii)

H 3C CH2 O CH2 CH3

ethoxy ethane

(viii)

H3C CH2 O CH2 CH2 CH3

1-ethoxy propane

(ix)

H3C CH2 CH O CH2 CH2 CH3

|
CH3

2-propoxy butane

(x)

H3C CH2 CH O CH CH3

|
|
CH3
CH3

Epoxides :
(1)

CH3 CH CH2

2-(methyl ethoxy) butane or 2-isopropoxy butane

1, 2-epoxy propane

(2)

3, 4-epoxy heptane

Nomenclature of Organic Compound

[20]

Cl

(3)

2-chloro-5, 6-epoxy octane

O

(4)

1, 3-epoxy propane
O

(5)

2, 4-epoxy-3-methyl pentane

Type-II : Groups of this type are treated as functional groups and represented by suffix in IUPAC nomenclature.
Priority table for functional group.

S.No.
(1)
(2)
(3)

Functional group
O
||
C OH
SO3H
COC
||
||
O
O

Name

Suffix

Prefix

Carboxylic acid

oic acid

Carboxy

Sulphonic acid

sulphonic acid

Sulpho

Acid anhydride

oic anhydride

(4)

C OR
||
O

Ester

(5)

C Cl
||
O

Acid chloride

oyl chloride

Chlorocarbonyl

(6)

C NH 2
||
O

Amide

amide

Carbamoyl

(7)

CN

Cyanide

nitrile

Cyano

(8)

NC

Isocyanide

isonitrile

Isocyano

(9)

CHO

Aldehyde

al

oxo / formyl

(10)

C
||
O

Ketone

one

Oxo/Keto

(11)

OH

Alcohol

ol

Hydroxy

oate (alkyl+w.r.+oate) Alkoxy carbonyl

Nomenclature of Organic Compound

[21]

(12)

SH

Thio-alcohol

thiol

Mercapto

(13)

NH2

Amine

amine

Amino

(14)

(=)

ene

(15)

()

yne

Note : Double bond & triple bond are not true functional groups.
w.r. Word Root
Rule for their nomenclature :
(1)
Selection of parent 'C' chain : longest possible 'C' chain with functional group and having maximum
number of multiple bonds is selected as parent 'C' chain.

CH3 CH2 CH CH2 CH2 CH3

|
C OOH
CH2 = CH C H CH2 CH2 CH3
|
C OOH
(2)
(a)
(b)

CH3 CH2 C CH2 CH CH3

|
||
OH
C H2

Numbering :
Numbering starts from the side of functional group for numbering priority order is given below :
Functional group > Multiple bonds > Substituents
If chain ending 'C' containing functional group is present then numbering starts from the 'C' of functional
group these functional groups are known as DON category functional groups functional groups of this
catagoly are shown below :
COOH
CN
COC
||
||
O
O

CHO

COOR
CONH2

COCl

Rule 3 : 'e' of primary suffix is dropped if secondary suffix starts from a vowel.
Example of compounds having don catagory functional groups :
(i)
CH3 CH2 CH2 COOH
Butanoic acid
(ii)

(iii)

CH 3 CH CH 2 CH 3
|
COOH
O
||
CH 3 CH 2 C CH 2 CH 2 C Cl
||
CH 2
O
||
C

(iv)
H

2-methyl butanoic acid

4-ethyl pent-4-en-1-oylchloride

methanamide
NH2

Nomenclature of Organic Compound

[22]

(v)

CHO
|
CHO

ethandial

(vi)

NC CH2 CH2 CH3

butane nitrile

(vii)

(viii)

O
||
H2N C CH2 CH CH2 CH = CH2
|
CH
||
CH2

O
||
CH2 = CH CH C Cl
|
Cl H2C H2C CH2

3-ethenyl hex-5-en-1-amide

2-(3-chloropropyl) but-3-en-1-oyl chloride

O
||
RCOR

Ester :

alkanoate
alkyl alkanoate

alkyl

e.g.
(i)

(ii)

(iii)

O
||
CH3 C O CH3
O
||
H C O CH3 CH3

O
||
CH3 CH CH2 C O CH3
|
CH2 Cl

Methyl ethanoate

ethyl methanoate

methyl-4-chloro-3-methyl butanoate

(iv)

O
||
Cl CH2 O C CH3

chloromethylethanoate

(v)

H3COOCCH3

methyl ethanoate

Nomenclature of Organic Compound

[23]

O
||

C H 2 C O CH 3
(vi)

methyl-2-ethyl butane-1, 4-dioate.

H 3C H 2 C CH C O CH 3
||

O
Anhydride : Nomenclature of anhydride is done on the basis of the carboxylic acid from which it is obtained.

O
||
CH3COH + CH3 C OH
||
O

H2O

H2 O
O

H3CCH2 C
||
O
ethanoic propanoic anhydride
O
||
CH2 C
|
CH2 C
||
O

CH3 C
||
O
ethanoic anhydride

ethanoic acid
O
||
CH3 C

O
||
CH3 C

O
||
CH3COH + CH3 CH2 C OH
||
O

butanedioic anhydride

O
C

Benzene carboxylic
propanoic anhydride

O
C
O

O
C
O

Benzene carboxylic-3-phenyl
propanoic anhydride

C
O

Nomenclature of Organic Compound

[24]

O
C

Benzene carboxylic anhydride

O

C
O

O
C
Benzene carboxylic cyclohexane
carbocyclic anhydride

O
C
O

Example of compounds having functional group other than DON category :

OH
|

1.

H 3C CH 2 CH 2 C H C H CH 3

(3propylheptan2ol)

H 3C CH 2 CH 2 CH 2

2.

3.

4.

5.

OH
|
CH2= CHCH2CHCHCH3
|
H3CH2CH2CCH2

SH
|
H3CC C CH2 CH3
||
CH2
Me
|
CH2 CH SO3H
|
CH2 CH SO3H
|
Et

3butyl hex5en2ol

2methylpentlene3thiol

heptane2, 5disulphonic acid

O
||
CH3CH = CH C CH2 C CH2CH3
||
CH2

5methylene oct6-en3one

Nomenclature of Organic Compound

[25]

6.

3(1methyl butyl) pent3-ene1sulphonic acid

SO3H
7.

3ethylhexan2amine
NH2

8.

CH3 CH2 CH CH2 CH3

|
NHCH2CH3

NChloromethylNmethyl pentan2amine

9.

Nethyl pentan3amine

Cl
POLYFUNCTIONAL COMPOUNDS
Rule-I : If more than one functional groups are present then one is selected as principal functional group and
represented by suffix. Other functional groups are treated as substituents & representated by prefix.
Selection of principal functional group is done according to priority table
O
||

1.

HS CH 2 C H C OH (3mercapto2methylpropanoic acid)
|

CH 3

O
||

chloromethanoylchloride

2.

Cl

Cl
O
||

amino methanomide (Urea)

3.
H2 N
CN

NH2
CN
2ethenyl2isocyano propane1,3dinitrite

4.
CN

Nomenclature of Organic Compound

[26]

O
3oxo pentanal

5.

O
O
6.

2-hydroxy-3-oxo pentanoic acid

HO

OH
O

O
7.

NH2
NH2

2amino ethanomide

Rule-II : When principal group is selected then there is no use of priority table.

8.

COOH
|
H C OH
|
H C NH2
|
COOH

3amino2hydroxy butane 1, 4dioic acid

(Incorrect)

2 amino 3 hydroxybutane 1, 4dioic acid (Correct)

Rule-III : If any DON functional group is present as sec. functional group then its 'c' is not included in principal
'c' chain except CHO group.

9.

10.

O
||
NC H2C H2C C OH

O
||
CH2 C OH
|
CH2 C Cl
||
O
H2 N
O

3-Chloro carbonylpropanoic acid

11.

Carbamoyl methanoyl chloride

O

Cl

12.

3cyanopropanoic acid

H2N

3-Ethylpent-4-yn-1-amide

||
O

Rule-IV : As secondary functional group, if 'C' of CHO group is included in parcent 'c' chain then oxo is used
as prefix, otherwise we use formyl group as prefix.
13.

||

||

H C CH 2 CH 2 C OH

4oxobutanoic acid

Nomenclature of Organic Compound

[27]

14.

15.

O
||
H C CH2 CONH2
|
CH2 CONH2

2formyl butane1, 4diamide

O
O
O
||
||
||
Cl C CH2 C CH2 C H

3, 5dioxopentanoyl chloride

IUPAC nomenclature if DON category functional group is present as principal functional group
& its 'c' is not included in parent 'c' chain
COOH
COC
||
||
O
O
COOR
COCl
CONH2
CN
CHO

Carboxylic acid
Carboxylic anhydride
Carboxylate
Carbonyl chloride
Carboxamide
Carbonitrile
Carbaldehyde

e.g.

COOH
1.

Cyclohexane carboxylic acid

COOH

2.

3.

4.

Benzene carboxylic acid

CH2 CHO
|
CH2 CHO
|
CH2 CHO

Propane1, 2, 3tricarbadehyde

CH2 COOH
|
CH CH2 COOH
|
CH2 COOH

3Carboxymethyl pentane1, 5dioic acid

O
||
C

5.

O
C
||
O

Cyclohexane-1, 2dicarboxylic anhydride

Nomenclature of Organic Compound

[28]

NOMENCLATURE OF ALICYCLIC COMPOUNDS

(A)

Unsubstituted cyclo compounds :

Example :

(B)

Prefix + word root + suffix

Cyclo + no. of C + ane / ene

Cyclobutane

Cyclopropane

Cyclohexene

Substituted cyclic compound (closed + open chain saturated)

Rule :
(i)
If number of carbons in closed chain no. of carbons in open staurated chain, then closed chain
will be selected as parent chain.
2

Example :
3

1-methyl cyclo propane

1

(Carbon of closed
chain)

Propyl cyclo pentane

1-(2-methyl propyl) cyclohexane

(ii)

If number of carbons in open chain > closed chain Open chain is parent chain
3

5
6

2-cyclopentyl-4-methyl hexane
2

5
4

1-ethyl-2-methyl cyclobutane

3-ethyl-1,1-dimethyl cyclopentane

Rule :
Cyclic compounds with functional group is considered as parent chain :

(i)

Nomenclature of Organic Compound

[29]

2 1
CH2COOH
Cyclohexyl ethanoic acid

If FG (COOH) present on both cylcic and non-cyclic then number of carbon atoms is considered.

cyclopentyl cyclohexane

If unsaturation (Multiple bond) present

Rule :
Chain containing multiple bond is selected as parent chain
1

1
3

2
3-butyl cyclopropene

1
2

1-cyclopentyl eth-1-ene

3-cyclopentyl but1ene

If ring and non-cyclic side chain both containing double bond then check the nunbmer of C atoms and
given parent chain.
4

1'

3'

2'

3-(prop-2-enyl) cyclo pent-1-ene

Number of duble bond is considered while selecting parent chain

5'
1'

4'

1
2

3'

2'

1-(cyclopent-2-enyl) buta-1,3-diene
In case of more than one multiple bond use suffix a after word root.
3
2
1

4
5

6
5-propyl cyclohexa-1, 3-diene

Nomenclature of Organic Compound

[30]

OC
O
(Parent chain)

Cyclobutyl cyclohexane carboxylate

O
O C CH2CH3

Cyclohexyl ethane carboxylate

Carboxamide

C NH2
O

eg.

C NH2

eg.

NHC CH3

Cyclohexane carboxamide

NCyclohexyl ethanamide

5
3Cyclohexyl cyclopentanol

1
2

OH

Methylene cyclohexane

NOMENCLATURE OF BICYCLO COMPOUNDS

Bicyclo compounds : If two rings are fused at two common carbon atoms then compound are known as
bicyclic compound.
Bridge head
Bridge
Bridge
*

Bridge
*

*
Bridge head
Two common carbon

(i)

*
Bridge should be present

Unsubstituted bicyclo compounds

Prefix
Bicyclo

Numbering of
carbon atoms in
each bridge in
decreasing order

Nomenclature of Organic Compound

Suffix

[31]

Biyclo (4.4.0) decane

(Bridge head C not considered)

Bicyclo [2.2.0] Hexane

eg.

Bicyclo [2.1.1] Hexane

Bicyclo [3.2.0] Heptane

eg.
(ii)

eg.

Substituted bicyclo (Bicyclo with subtitution or functional group)

In substituted bicyclic compounds numbering starts from a bridge head carbon atom and proceeds
towards longest bridge then smaller bridge & then smallest bridge.
1

2 Cl

6
7
5

2Chloro bicylo [2.2.1] heptane

eg. 3

OC
HO

bicylo [2.2.1] heptane7carboxylic acid

eg. 5

Bicyclo [2.1.1] hexane

3
4
1
2
3

5
HOOC

Bicyclo [2.1.1] hexane5carboxylic acid

4
5
HOOC

4
3

2 8

F.G. is preffered over double bond.

Bicyclo [3.2.2] dec9encarboxylic acid

1
Bicyclo [3.2.2] non8ene6carboxylic acid

Nomenclature of Organic Compound

[32]

NOMENCLATURE OF SPIRO COMPOUNDS

Spiro comp. - Two cyclic rings are fused at one common carbon (only one bridge head)
*
*

*
*

Spiro

spiro carbon
(1)

(2)

eg.

Name : Prefix + no. of carbon in bridges in increasing order + suffix

Spiro [2. 4] heptane

Spiro [2.3] hexane

eg
Spiro [4. 5] decane

Spiro

Rule for numbering : - In spiro compounds numbering starts from carbon of smaller ring which is next to spiro
carbon proceeds towards other carbon atoms of smaller ring then towards larger ring via spiro carbon
atom.
4

COOH

eg. 5

Spiro [2.3] hexane4carboxylic acid

6
9

1
OH
1

10
5

eg. 8

2
Spiro [4.5] dec7en1ol

6
4

COOH

eg.

5
6amino spiro [2, 4] heptane4carboxylic acid

3
6
2

NH2

Nomenclature of Organic Compound

[33]