Questions Chapter 1-10 PDF

General Organic Chemistry-I
1 (GOC-I)
SECTION - I : STRAIGHT OBJECTIVE TYPE
CI
is
1.1 IUPAC name of compound Br
(A) 3-Bromo7-chloro-7ethyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-3-methylnonane
(B) 3-Bromo7-chloro-5-(1,1-dimethyethyl)-7-ethyl-3methyl-5-(2-methylpropyl)nonane
(C) 3-Bromo7-chloro-7ethyl-3-,methyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)nonane
(D) 3-Bromo-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-7-chloro-7ethyl-5--3-methylnonane
1.2 Which of the following structure\s is the correct structure of 3-ethyl-5, 5-diisopropyl-7-methlnonane
(A) (B)
(C) (D)
1.3 The correct IUPAC name of the folllowing compound is
(A) 5,6-Diethyl-8-methyl dec-6-ene (B) 5,6-Diethyl-3-methyl dec-4-ene

(C) 5,6-Diethyl-3-methyl dec-4-ene (D) 2,4,5-Triethylnon-3-ene
1.4 Correct IUPAC name of the following compound is :

HO
Br
(A) 3-(Hepta-2,4,6-trienyl)-4 bromo cyclopenta-2, 4, -dien-1-ol
(B) 7-(2-Bromo-4-hydroxy cyclopenta-1,4-dienyl)hepta-1,3,5-triene
(C) 7-(5-Bromo-3-hydroxycyclopenta-1,4-dienyl)hepta-1,3,5-triene
(D) 3-Bromo-4-(hepta-2,4,6-trienyl)cyclopenta-2,4-dien-1-oll
Br
1.5 The IUPAC name of the compound will be :
(A) Tropyluim bromide (B) 1-Bromocyclohepta-2,4,6-triene

(C) 3-Bromocyclohepta-1,4,6-triene (D) 7-Bromocyclohepta-1,3,5-triene
1.6 Correct IUPAC name of the co,pound H3C – CH2 – O – C O – C – CH2 – CH3
O O
(A) 4-(Ethyl methanolyonxy)phenylpropanoate
(B) Ethyl 4-propanoyloxybenzenecarboxylate
(C) 4-(1-Oxo-2-oxabutyl)phenylpropanoate
(D) 1-(1-Oxo-2-oxbutyl)-4-(1-oxopropoxy)benzene
O
Et
1.7 Correct IUPAC name of the compound O is
Me
O
(A) 2-Ethyl-3-methylbut-2-ene-1,4-dioic anhydride

(B) 3-Ethyl_2-methylbut-2-enedioic anhydride
(C) 2-Ethyl-3-Methyl-1,4-diketobut-2-enoic anhydride
(D) 2-Ethyl-3-methylcyclopenatanoxy-1,4-dione
COOC2H5
1.8 The IUPAC name of the following compound is
COCl
(A) 2-(Ethoxycarbonyl) benzalychloride (B) Ethyl 2-(Chloroformyl)benzoate
(C) Ethyl 2-(chloromethanoyl)benzoate (D) Ethyl2-(Chorocarbonyl)benzene carboxylate.
Cl
1.9 IUAC name of CH3
Br C2H5
(A) 4-Bromo-6-chloro-2-ethyl-1-methylcyclohex-1-ene
(B) 5-Bromo-1-chloro-3-ethyl-2-methylcyclohex-2-ene
(C) 5-Bromo-3-chloro-1-ethyl-2-methylcyclohex-1-ene
(D) 1-Bromo-5-chloro-3-ethyl-4-methylcyclohex-3-ene
1.10 A hydrocarbon (R) has six membered ring in which there is no unsaturation. Two alkyl groups
are atttached to the ring adjacent to each other. One group has 3 carbon atoms with branching
at 1st carbon atom of chain and another has 4 carbon atoms. The larger alkyl group has main
chain of three carbon atoms of which second carbon is substituted. Correct IUPAC name of
compound (R) is
(A) 1-(1-Methylethyl)-2-(1-methylpropyl)cyclohexane
(B) 1-(2-Methylethyl)-2-(1-methylpropyl)cyclohexane
(C) 1-(1-Methylethyl)-2-(2-methylpropyl)cyclohexane
(D) 1-(1-Methylethyl)-2-butylcyclohexane
1.11 Identify the structure of x,
H2/Ni
CH3
X
O O O O O O
O3
CH3 – C – CH – C – H + H – C – H + CH2 – C – C – CH2 – C – H
Zn/H2O
CH3 CH3
(A) (B) (C) (D)

H3C
1.12 In the given sequence reaction which of the following is the correct structure of compounds A.
H2 / Ni
A(C10H14)
O O
(i) O3 H
+ HCHO
(ii) Zn / H2O O
H O
H
(A) (B) (C) (D)
COOH
1.13 For the following reactions sequence HOOC O3
C7H10
H2 / Ni
C7H 12
H2O2 excess
Y X
The structure consistent with X and Y are:
'Y' 'X'
(A)
(B)
(C)
(D)
1.14 An organic hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Its
structure is
(A) (B) (C) (D)
1.15 C–O and H–C–O are

O O
(A) Position isomers (B) Chain isomers
(C) Functional isomers (D) Metamers
1.16 In which reaction a chiral reactant is giving a chiral product.
CH3
HOC H CHO (i) O3
C – C2H5 –
KMnO4 / OH / (ii) Zn / H2O
(B) H C=C H
H Reductive ozonolysis
CH3 H CH3
CH3
CH = CH2 H Cl
O3/ Zn / H2O H2 / Ni
H CH2 – CH3 (D) C=O
H Cl
CH2OH
CH3
Hint : C = O + H2 H – C – OH
1.17 Which of the following statements is true abnout the follownig conformer (X)?
COOH
CH 3 I
(X)
I CH3
COOH
(A) (X) is the most stable conformer of meso-2,3-Diiodo-2,3-dimethylbutanedioic acid
I
CH3 I
(B) The most stable conformation will be COOH

(Y)
CH3
COOH
(C) The dipole moment of (X)is not zero but that fo Y is zero.
(D) None
1.18 An unsaturated hydrocarbon on jcomplete hydrogenation gives 1-isopropyl-3 methylcyclohexane,

after ozonolysis it gives one mole of formaldehyde, one mole of acetone and one moleof2,4-
Dioxohexanedial. The possible structure\s of the hydrocarbon maybe
(A) (B) (C) (D)
1.19 How manyh assymmetric carbon atoms are present in

(i) 2-Dimethyl cyclohexane
(ii) 3-Methyl cyclopentene
(iii) 3-Methylcyclohexene
(A) 2,1,1 (B) 1,1,1 (C) 2,0.2 (D) 2,0,1
1.20 Which of the following statements is not correct?

(A) A compound whose molecule has D configuration will always be dextrorotatory
(B) A compound whose molecule has D configuration may be dextrorotatory or levorotatory
(C) A compound whose molecule has R configuration may be dexrotatory or levorotatory
(D) A compound whose molecule has L configuration may be dextrorotatory or levorotatory
1.21 Identify the pair of enantiomers amongst the given pairs:

COOH CH3 Ph CH3
(A) D OH, HOOC OH (B) HO CH3 , HO Ph
CH3 D H H
COOH OH CH3 CH3

(C) H OH3, HOOC CH3 (D) H OH, HO Ph
CH H
CH3 CH3
1.22 The stereochemical formula of deiastereomer 'Y' of optically active compound 'X' is:
X=2,3-Dihydroxbutanedioic acid.
OH COOH COOH OH
H COOH H OH HO H H COOH
(A) HOOC H (B) HOOC H (C) H OH (D) HO COOH
OH OH COOH H
SECTION-II : MULTIPLE CORRECT ANSWER TYPE

1.23 Which of the followning statements are not correct?
(A) A meso compound has chiral centres but exhibits no optical activity
(B) A racemic mixture is optically inctive becaure of two equal and opposite rotation of same
molecules in mixture.
(C) A meso compound has molecules which are superimpossable on their mirror images even
though they contain chiral centres
(D) A meso compound is optically inctive because the rotation caused by any molecule is
cancelled by and equal and opposite rotation caused by another molecules that is the mirror
image of the first
1.24 Consider following compounds

OH
OH OCH3 CH2OCH3
CH – CH3
C2H5 CH3
(I) (III) (IV)
(II)
Choose the correct statement(s)from the following
(A) I,II and III are functional isomers (B) I and II re position isomers
(C) III and IV are chain isomers (D) III and IV are metamers
1.25 Which of the following statement\s is \are true about the following compounds
O
O O
(I) (II) (III)
(A) (I)and (III)are structural isomers. (B) (I)and (II)are geometrical diastereomers
(C) (II)and (III)are strukctureal isomers (D) (I)and (II)are jidentical
1.26 Which of the following is\are a meso compoumd.

COOH
CH2OH COOH CI
H
O F Br H OH
(A) CH2OH(B) (C) (D)
CI F HO H
OH NH2 COOH
OH H NH2 Br
COOH
1.27 Which of the following pair represents the correct relationship
I II Relationship
NH2
OH CI OH
(A) Positional Isomers
NH2
CI
(B) Chain Isomer
NH – C3H7 H3C – N – C2H5
(C) Functional Isomers
(D) CH3–CH2–CH2–C–OCH3 CH3–CH2–C–OCH2–CH3 Metamer Isomers
O O
SECTION-III:REASONING TYPE
1.28 Statement-1:Restricted rotation about a bond is the necessary condition for geometrical
isomerism.
Statement-2:Two different orientations are possible due to restricted rotation about a bond if
theend groups are different.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement -2 is True.
1.29 Statement-1: Aracemic mixture of 2-Chloropropanoic acid is treated with excess of (+)-2-Butanol.
The reaction can be represented as follows:
CH3–CH–COOH + CH3–CH–CH2–CH3  CH3–CH–COO–CH–CH2–CH3+CH3–CH–CH2–CH3
CI OH OH
(+)excess CI (+)(Left unreacted)
Statement-2: The solution kjof reaction mixture at time(t = 0), will be dexterorotatory because
of (+)2-butanol
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) State,emt-1is False, Statement-2 is True.
SECTION-IV : TRUE & FALSE STATEMENT TYPE

1.30 The products(ester)of following reactiongive diastereomers
Me Me
COOH + HO H2SO4
H Et
D H
Comprehension #1
Compound X(C7H14O4)on ozonolysis gives (Y) and (Z),(Z) is the aldhyde which gives only one
oxime with NH2-OH. On treatment with I2\NaOH,(Y)gives yellow solid CHI3 alongwith compound
given below.
COONa
HO H
H OH
H OH
CH2–OH
When (X)is treated with D2\Ni, it gives two optically active compound.(V)and (W).
1.31 compound(V)and (W)are

(A) Enantiomers (B) Diastereomers (C) Identical (D) Nuclear Isomers
1.32 Compound (Y)can give........ type of oximes on treatment with NH2-OH

(A) 2 (B) 6 (C) 8 (D) 7
1.33 Which of the following statement is true

(A)'X' gives positive test with 2,4-DNP and Br2 solution
(B)Y gives positive with both 2,4-DNP and tollens reagent
(C)Compound(V)give positive test with NaHCO3
CH3 NH2
C
(D) is the isomeric amide of oxime of next higher homolog of Z.
O
Comprehension#2
Structural isomers have different covalent linkage of atoms. Stereoisomers are compounds that
have same sequence of covalent bonds but differ in the relative dispositions of their atoms in
space. Geometrical and optical isomers are the two important types of configurational isomers.
The compound with double bonds or ring structure have restricated rotation, so exist in two
geometrical forms. The double bonds in larger rings (ring size 10 carbon or large) can also
cause geometrical isomerism. The optical isomers rotate the plane of plane-polarised light. Asp3
hybridised carbon atom bearting four different types of substituents is called and asymmeric
centre or chiral centre. A chiral object or molecule cannot be superimposed on its mirror image.
Stereoisomers that are mirror images of each other are called diastereomers. Deastereomersw
have different physical properties.
A racemic mixture is optically inctive and contains equal amounts of both the enantiomers .
Resolution refers to method of separating a racemic mexture into two pure enantiomers. A
mesocompound is and opticall incactive stereoisoker, which is achiral due to the presence of
and internalk plane of syummetry or centre of symmetry within the molecule.
1.34 The pair showing identical species is
Me Br
H H H OH D Et
(A) and (B) and
Cl Cl D Br H OH
Et Me
H COOH Br Br
OH
H COOH C C
(C) and (D) H CH3 and H3C H
OH HOOC Cl Cl
HOOC H H OH
OH
1.35 Observe the following reaction
CH3
HOOC CH3
* H
+ C* (R' R) + (R' S)
(1)
separation by
NH2 recrystallisation
Cl H
(2)
(R')-1-Phenylethylamine (R+S)-2-Chloropropanoic acid
hydrolysis
(R')+ (R) (R'R)
(3)
hydrolysis
(R')+ (S) (R'S)
(3)
Which statement is not correct about the above observation.
(A)The product mixture os step-1 is optically active
(B)The products R'R and R' S have identical structural formul.
(C)R'Ris nonsuperimposable on R' S
(D)R'Rand R' S have same solubillity in water.
1.36 The number of chiral centres present in the following compound is
CH2OH
H O H
H
OH H
OH
H HO
O
HOH2C O D (+) - Sucrose
H OH
H
CH2OH
OH H
(A) 7 (B) 8 (C) 9 (D) 10
SECTION-VI:MATRIX-MATCH TYPE
1.37 Column I may match with more than one conditions of column II.
Column I Column II
(A) Ph – CH = CH – Ph (p) Ozonolysis followed by reaction with
NH2 OH leads to more than one oxime
product
(B) (CH3)2C = CH – CH = Cl
(q) Can exhibit geometrical isomers
CH3
CH2 = CH – CH = CH2 (r) Compounds with this structure formula
can be separated into different fractions
upon fractional distillation
CHO – CH – CH – CHO
(s) Is capable of showing stereoisomerism
OH OH
1.38 Column I Column II
D D
HO CH3 H3C OH
(A) (p) can be separated by fractional
D OH D OH
D D
crystallisation
CHO CH 3 CHO CHO (q) Can not be separated by

(B) C C C C
CH3 CHO CH3 CH3
fractional crystallisation
COOH OH H
H OH COOH
(C) (r) Optically resolvable
COOH
H OH H OH
COOH
Cl CH 3
H OH3 H Br
(D) (s) donot have identical boilling point
Br OH2I D CH2Cl
D I
SECTION-VII: SUBJECTIVE ANSWIR TYPE
SHORT SUBJECTIVE:
1.39 Total number of stereoisomes possible for molecule A will be
H3C CH = CH CH = CH
1.40 Cl2 / hv Fractional

A B
distillation
Number of possible fractions of B are:
1.41 The number of isomers for the compound with molecular formula C2HDFCI is :
1.42 Number of sp2-sp2 sigma bonds in viven compound A is:
1.43 Write lowest molecular weight of saturated cyclic hydrocarbon which has four substtituents.
Molecular weight=98.
General Organic Chemistry-II
2 (GOC-II)
SECTION-I: STARINGT OBJECTIVE TYPE
2.1 Choose the correct statement
(A) I effect transfers e from one carbon atom to another
(B) I effect operates in both  \p bond
(C) I effect creates not charge in moecule
(D) I effect cteates prtial cjarges and it is distance dependent
2.2 The correct stability order of following species is :
C
(x) (y) (z) (w)
(A)x>Y>w>z (B)y>x>w>z (C)x>w>z>y (D)z>x>y>w
2.3 Which of the following does not represent the resonating structure of
(A) (B) (C) – + (D) + –

–
2.4 The most stable resonating structure of CH3 – O = CH = CH2 :
+ + + +
(A) (B) H3C – O = CH – CH2 (C) H 3C – O = CH – CH 2 (D) H3C – O = CH – CH2
2.5 Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but in compound
P double bond between two rings was observed by NMR to have a rotational energy barrier of
only about 20 cal.\mol., showing that it has lot of single bond charcter.
nC3H7
nC3H7
The reason for this is

(A) Double bond having partial triple bond charcter because of resonance
(B) Doule bond undergo flipping
(C) Double bond having very high single bond charcter because of aromaticity gained in both
three and five membered rings.
(D) +I effect of nC3H7 groups makes double bond having partial single bond charcter.
2.6 Most contributing structure in nitroethene is
–
+ O + – + O – + + O + + O
(A) CH2 = CH – N (B) CH2 = CH – N (C) CH2 – CH – N (D) CH2 – CH = N
– – – –
O O O O
2.7 In which of the followig molecules all the effects namely inductive, mesomeric and hyperconjjgation
operate:?
(A) Cl (B) CH3 (C) COCH3 (D)
CH3 CH3
CH3 H
H3C + CH3 H + H
N N
2.8 Between and
(l) (ll)
(A) N(I)has more 's' charcter in N–CH3 bonds

(B) N(II)has more 's' charcter in N–H bonds
(C) N(I)has less 's' charcter in N–CH3 bonds
(D) None of these
2.9 The acid strength order is:

O OH OH
HO OH CH3 CH 3
C C
O OH O O
I II III IV
(A)I> IV> II> III (B)III> I> II> IV (C)II >III> I>IV (D)I >III >II> IV
2.10 Acid strenght of the conjugate acids of the following are-
(l) N NH (ll) N NH (lll) (lV) N

N H
(A)I> II> III >IV (B)III> II> I> IV (C) IV> III> II> I (D)None of these
2.11 The acid dissociation constants of the following acids are given as under:
Compound Ka
CICH2COOH 136 X 10–5
CH3CH2– C HCOOH 139 X 10–5
CI
CH3 C HCH2COOH 8.9 x10–5
CI
C H3CHCH2COOH 2.96 x10–5
CI
CH3CHCH2COOH 1.52 X 10–5
From this data, the following obnservations can be made. Mark the correct statements for above
mentioned compoumds.
(i) The above variation in acidities of the above acids are due to inductive effect only.
(ii) The above variation are both due to inductibve and resonance effects.
(iii) Inductive effect varies shrply with distance.
(iv) -I effect of chlorine is not much.
(A) i and ii (B) i and ii (C) ii and iii (D) iii and iv
2.12 The correct order of acidic strength is :

COOH COOH COOH COOH
OH OH OH CH3 CH3
(l) (ll) (lll) (lV)
OH
(A) III> IV> I> II (B) II> I> III> IV (C)II> III> I> IV (D)II> I> IV> III
2.13 Which one of the following reaction is not possible?

(A) CH3COONa + HCI  CH3COOH + NaCI
(B) CH3 –SO3 H + H – C = C – Na  CH3SONa + H – C = C – H
(C) R – C = C – H + PhONa  PhOH + R – C = C – Na
(D) H – C = C – H + NaH2  H – C = C – Na + NH3
O
CH 3 S
P
2.14 If H is mixed with NaOH solution. Acid base reaction occurs and HO snatches H from
R O
Q
organic molecule. Which carbon will loose H easily?
(A) P (B) Q (C) R (D) S
OH
2.15
COOH (x)
OH
(z) HOOC
HO
COOH (y)
The correct acidic strength order of acidic hydrogen x,y and z is respectively.
(A) x > z > y (B) x > y > z (C) z > y > x (D) y > z > x
2.16 H
(p)
N NH(r)
O N O
H
(q)
The correct basicity order of atoms p,q and r is :

(A) p > q > r (B) r > p > q (C) r > q > p (D) q > p > r
O
2.17
N N N
N
H H H
I IV
II III
The order of basicity is
(A) I > IV > II > III (B) I > II > IV > III
(C) III > II > IV > I (D) II > III > IV > I
2.18 The correct basic strengtyh order is:

O O O
NH CH3
C CH3 C NH2 H2N C
NH CH2 CH 3
O
I II III IV
(A) I > II > IV > III (B) IV > III > II > I
(C) III > II > IV > I (D) III > IV > II > I
2.19 The correct order of acid and basic strength for the following pair of compounds should be?
COOH COOH COOH COOH
CH3 CH3
Acid strength : and ; and
(I) (II) (III) (IV)
NH2 NH2 NH2 NH2

CH3 CH3
Basic strength : and ; and
(V) (VI) (VII) (VIII)

(A) I > II ; III > IV ; V > VI ; VII < VIII
(B) I < II ; III > IV ; V < VI ; VII > VIII
(C) I > II ; III > IV ; V > VI ; VII > VIII
(D) I < II ; III > IV ; V < VI ; VII < VIII
2.20 Observe the foolowing reaction :

– +
O Na
COOH COONa OH
+ +
NO2
NO2
OH ONa
+ NaHCO3 + H2CO3
NO2 NO2
ONa OH
+ H2CO3 + NaHCO3
Which of the following is the correct order of acid strength :
COOH OH OH COOH OH OH
(A) > > H2CO3> (B) > > > H2CO3
NO2 NO2
COOH OH OH OH COOH OH
(C) > H2CO3 > > (D) > > > H2CO3
NO2 NO2
2.21. Which of the following statement is CORRECT regarding the inductive effect?
(A) electron-donating inductive effect (+ l effect) is generally more powerfull than electron-
withdrawing inductive effect (–l effet t)
(B) it implies the shifting of s electrons from more eletronegative atom to the lesser eletronegative
atom in a molecule.
(C) it implies the shifting of r electrons from less electronegativbe atom to the more electronegative
atom in a molecule
(D) it increases with increase in distance.
2.22 Which of the following statement regarding resonance is NOT correct?

(A) the different resonating structures of a molecule have fixed arrangement of atomic nuclei.
(B) the different resonbating strcutues differ in the arrangement of electrons.
(C) the hybrid structure has equal contribution from all athe resonationg structures always.
(D) None of the individual resonating structure explains all charcteristics of the molecule.
SECTION-II: MULTIPLE CORRECT ANSWER TYPE

2.23 Which of the following statements would be incorrect about this compoud?
NO2
3
1 5
NO2 NO2
Br
(A) All three C – N bond are of same length
(B) C1 – N and C3 – N bonds are of same length but longer than C3 – N bond
(C) C1 – N and C5 – N bonds are of same length but longer than C3 – N bond
(D) C1 – N and C3 – N bonds are of different length but both are longer than C5 – N bond
2.24 Choose the incorrect statement:

(A) Salicylic acid (o–Hydroxybenzoic acid) is much stronger than its m-,p-isomers and benzoic
acid itself.
(B) Acidity of salicylic acid is due to steric inbibition of re3sonance, as – OH group forces –
COOH out of the plane of ring
(C) The orbitals which are in the same plane take part in resonance
(D) All the resonating structures have real existence
2.25 In which of the following pairs the first one is the stronger base than second.
(A) CH3CHOO, HCOO (B) HO,NH
(C) CH2=CH: , H – C = C (D) CH3NH2, CH3,OH
2.26 Which statement among the followijng are corect?
(A) Hydration effect stabilises dimethyl ammonium ion more than trimethyl ammonium ion
(B) In chlorobenzene as there is no hydration effect so, trimethyl ammonium ion gets less
stabillised than dimethyl ammonium ion
(C) RCONH2 is feebly acidic with respect to RCOOH
(D) CH3 > NH2 > OH is the basicityh order
2.27 Resonance structures of a molecule should have.

(A) Identical arrangement of atoms (B) Nearly the same energy content
(C) The same number of paired electrons (D) Identical bonding
SECTION-III : ASSERTION AND REASON TYPE

2.28 Statement-1: Ortho iodobenzoic acid is strongest acid among all ortho halobenzoic acids.
Statement-2: Iodine exerts maximum ortho effect (steric effect) so the acid weakening resonace
effect of aromatic romg os decreased/
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
Statement-1
(C) Satement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
2.29 Statement-1: Salicylic acid is much stronger than its m-, p-isomers adnsf benzoic acid itself.
Statement-2: It is due to steric inhibition of resonance, as – OH group forces – COOH out of
the plane of ringt.
Statement-1
SECTION - IV : TURE AND FALSE TYPE

2.30 Give the correct order of initials T or F following statements. Use T if statement is true and F
if it is false .
S1 : Both the C – O bond lengths in HCOOK are equals
NH2 both have same dipole moment value.
S2 : HO OH and NH2 NH2
S3: Propyl chloride shows maximum dipolemoment in anti conformer.

NH2
S4 : is stronger base then

N
N
(A) T T T T (B) T F T F (C) T T F F (D) F F T T
SECTION - V : COMPREHENSION TYPE
comprehension # 1
The concept of resonance explains various properties of compounds. The molecules with
conjugated system of p bons, are stabilized by resonace and have low heat of hydrogenation.
Hyperconjugative stabilization also decreases heat of hydrogenation. In aromatic rings a functional
group with a lone pair of electron exerts +m effect. Some functional groups like –NO, –NC,–CH
= CH2 can function both as electron releasing (+m, +R) or electron withdrawing (–m, –R)
groups. More extended conjugation provides more stabilization.
2.31 The correct heat of hydrogenation order is

(p) 1,3-Pentadiene (q) 1,3-Butadiene
(r) 2,3-Dimethyl-1, 3-butadiene (s) Propadiene
(A) p > q > r > s (B) s > q > p > r
(C) q > s > p > r (D) s > q > p > r
2.32 The most stable carbocation is
(A) (B)
(C) (D)
2.33 The most stable resonating structure of following compound is O = N N=O
(A) O – N N=O (B) O – N N–O
(C) O = N N=O (D) O – N N=O
Comprehension # 2
The key concepts of resonance are :
Resonance occurs because of the overlaping of orbitals. Double onds are made up of pi bonds,
formed from the overlap of 2p orbitals. The electrons in these pi orbitals will be spread over mor4
than two atoms, and hence are delocalized . Both paired and unshared electrons may be
delocalized , but all the electrons must be conjugated in a pi system. If the orbitals do not overlap
(such as in orthogonal orbitals) the sturctures are not true resonance structures and do not mix.
Molecles or species with resonance structures are generally considered to be more stable than
those without them. The delocalization of the electrons lower the orbital energies, imparting this
this stability. The resonhance in benzene gives rise to the property of aromaticity . The gain in
stability is called the resonance energy. All resonance structures for the same molecute must
have the same sigma framework (sigma bond form from the "head on' overlap of hybridized
orbitals). furthermore, they must be correct Lewis structures with the same number of
electrons(and consquent charge) as well as the same number of unpaired electrons.
Resonancestructures with arbitrary separation of chargfe of charge are unimportant, as are
those with fewer covalent bonds . theese unimportant resonance structures only contribute
minimum (or not at all) to the overall. From the above theory of resonance answer the followings.
2.34 The correct resonation structre of 1, 3-butakiene is -
+ – – +
(A) CH2 — CH — CH = CH2 (B) CH2 — CH — CH = CH2
– +
(C) CH2 — CH = CH — CH2 (D) None of these
2.35 The correct stable resonating structure of benzene is -
– +
+ – –
(A) + (B) (C) + + (D) None of these
– –
2.36 Which resonating sturcture is not correct
+ +
(A) CH2=CH—CH2 CH2 — CH = CH2 (B) NH2—C—NH2 NH2 — C = NH2
+
NH2 NH2
O O
(C) CH3—C—NH CH3—C=NH (D)

N N+
H H
SECTION - VI : MATRIX - MATCH TYPE

2.37 Match the following
CH3
CH3 (p)  is more

(A) N
CH3
CH3
Cl
+
(B) O2N N=O – (q)  is less
O
Cl
CH3
(C) O2N NH2 (r) Larger C– N compared to C – NO2
CH3
CH3
CH3
(s) Larger C – N bond largteer compared to aniline
(C) O2N N
CH3
CH3
2.38 Match the pKa values with the given compounds
Acid pKa
OH
NO2 NO2
(p) 4
(A)
NO2
(B) CH3COOH (q) 9
(C) NH
(r) 5
O
Phthalimide
COOH
(D) (s) 0.74
SECTION - VII : SUBJECTIVE ANSWER TYPE

SHORT SUBJECTIVE :
2.39 For the compound :
OH
Give the number 1 for presence of resonance only, 2 for presence of resonance and
hyperconjugation only, 3 for presence of resonance, hyperconjugation and inductive effect and
4 for presence of resonance hyperconjugation, inductive effect and electromaric efffect.
HOOC OH
2.40 x mole NH2

Br
CH
2 –C
–H
OHC
Br
value of X used for complition of reaction will be :
2.41 Incorrect statement among these four :

(i) I effect is prermanent polarisation of sigma bond pair of electrons in the molecule.
(ii) In resonation structures the hybridisation of atoms do not change.
(iii) In Hyperconjugative structures the hybridisation of carbon atom change.
(iv) Presence of methyl group on an anion always destabilises ith anion.
2.42 Maximum number of hyperconjugtation forms of structure :

2.43 In the following set of resonationg structures which sets have the second resonation structure
more contributing than first :
O O
I :
N N
+
OCH3 OCH3
II : +
NH2 NH2
+
O O
III :
N N
O O O O
IV : +
Cl Cl
3 Reaction Mechanism
3.1 Read the following road map carefully
CH3
Ph–CH2CHOH
1-Phenyl-2-propanol III TsCl
K I
S.R = +33.02°
CH3 CH3
Ph–CH2CHOK + gas Ph–CH2–CHOTs
II EtOTs IV C2H5OK
CH3 CH3
Ph–CH2–CH–OC2H5 Ph–CH2–CH–OC2H5
ethyl–1–phenyl–2–propylether Ethyl–1–phenyl–2–propylether
(A) Both the ethers obtained by the two routes have opposite but equal optical rotation.
(B) One of the ether is obtained as a recemic mixture.
(C) Step II & III both are SN2 reaction and both have inversion.
(D) Step II has inversion but step III has retention.
3.2 A compond A has the molecular formula C5H9CI. It does not react with bromine in crabon
tetrachloride. On treatement with strong base it produces a single compound B. B shas a
molecular formula C5H8 and reacts with bromine in carbon tetrachloride. ozonolysis of B produces
a compound cC which has a molecular formula C5H8O2. Which of the following structures is
that of A?
Cl
Cl
(A) (B)
CH3
Cl Cl
(C) CH3 (D)
Me2 SO4
3.3 PhOH 
NaOH
 P, P is
(A) Ph–O–SO2OMe (B) PhOMe (C) PhOSO2OPh (D) PhMe
3.4 COCH2COCH3
NaOH
P= Br P
D H
Which of the following statement is correct
O
COCH2COCH3
(A) P = (B) P = C –CH3
OH
H D
O
D H
O O
(C) P = CH3 (D) P =
H O H
D D
Br
3.5 NaOH
OH
OH
OH
(A) (B) (C) (D)
O
OH O OH
3.6 (i) CH3O

CH3– CH2SH Product, Product is :
(ii) ethylene oxide
(iii) H2O
(A) CH3 – CH2 – S – CH2 – CH2 – OH (B) CH3 – CH2O

CH2
(C) CH3 – CH2 – O – CH2 – CH2 – OH (D) CH3 – CH2 – S
CH2
3.7 Br
EtO
Ph + Ph – CH2 – NH2 Product, Product is
O
OEt
(A) Ph (B) Ph NH Ph
O
O
Br
(C) Ph NH Ph (D) Ph NH Ph
OH
CH 3
conc. H2SO4
3.8 In the reaction CH 3 A. The product is -
OH OH
CH3 CH3
(A) (B)
O CH 3
CH3
CH 3
CH3
(C) (D) CH3
COCH3 O
3.9 H
CH3(CH2)6
TsCl Kl, DMSO
C OH A B (Major);
C2H5
(A) R (B) S (C) R,S both (D) None of these
3.10 NO2 NO2
CH3 H+
CH3 C C A;
OH OH
NO2 NO2
(A) CH3 C C (B) NO2 C C NO
CH3
NO2 NO2
NO2
(A) CH3 C CH(OH) CH3
CH3
NO2
H3O
, is
3.11 The products of hydrolysis of
O O – C2H5
(A) HOCH2CH2CH2CH2 CHO + CH3CHO (B) HOCH2CH2CH2CH2OH + CH3CHO
(C) HOCH2CH2CH2CH2CHO + C2H5OH (D) HOCH2CH2CH2CH2CH2OH + C2H5OH
CH2– OH
H2SO4/H
3.12 A. The product A is :
CH2
CH2– HSO4 CH2 CH2
(A) (B) (C) (D)
OH
3.13 (CH3)3CCI + (CH3)3CO–K+  Product
(A) SN Product will be more (B) E2 Product will be more
(C) both will be same (D) None of these
3.14 Neopentyl iodide is treated with aq. AgNO3 solution, a yellow precipitate is formed along with
other compound which is
OH ONO2
(A) (CH3)3CCH2ONO2 (B) (CH3)2C – CH2CH3 (C) (CH 3)3CCH 2OH (D) (CH3)2C–CH2CH 3
3.15 The major end product of the following reaction is
CH2Cl
aq. AgNO3
H3C OH
CH3
CH2– OH
O O
(A) (B) (C) H3C O (D)
OH
H3C H3C CH3
3.16 The major product P of the following reaction is

NH2 CH3 CH3
CH – CH – CH NH2 CH3OH (P)
Cl
NH2 NH2 CH3 CH3

CH3 CH3
(A) C – CH2 – CH NH2 (B) CH – CH2 – C NH2
OCH3 OCH3
NH2 CH3 CH3 NH2 CH3 CH3

(C) CH – CH – CH NH2 (D) CH – CH = C NH2
OCH3
3.17 The product of following reacting is
O
14
H3O
O
Ar
OH O
(A) 14 (B) 14
+ ArOH
O
OH
Ar
OH O
(C) 14
+ ArOH (D) 14 + ArOH
O O
+
3.18 14 H /H2O
18
H2C CH2
O
Which can not be the product.
14 14
H2C CH2 CH2 CH2 CH2 CH2
(A) (B) (C) (D) A and B both
18 18 18 18
OH OH OH OH OH OH
3.19 The correct order of SN2 \ E2 ration for the % yield of product of the following halide is -
Ph
(P) CH3 – CH – C – CH3 (Q) CH3 – CH – CH – CH3(R) CH3 – CH2 – I (S) CH3 – CH – CH – CH3
I Ph I I
(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S
3.20 The poduct in the given reaction is
Me Br
H ONa + H Me P
Ph Ph
I II
Me H Me H
(A) H O Me (B) H O Ph
Ph Ph Ph Me
Ph Ph Me Ph
(C) H O Me (B) H O Me
Me H Ph H
3.21 reaction Rearranged most stable Carbocation is
Ph
(A) (B) (C) (D)
Ph Ph Ph
Ph
3.22 H Br
Ag+
Rearranged Carbocation + AgBr
Rearranged carbocation is :
CH3
(A) (B) (C) (D) +
SECTION - II : MULTIPLE CORRECT ANSWER TYPE

3.23 The correct statement(s) about solvent effect is\are :
(A) Decreasing solvent polarty causes a large increase in therate of the SN 2 attack by ammonia
on an alkyl halide
+
RX + NH3 RNH3 + X
(B) Increasing solvent polarity causes a large decrease in the rate of the SN2 attack by hydroxide
ion on trimethyl sulphonmium ion
HO + (CH3)3S CH3OH + (CH3)3S

Trimethyl DMS
sulphonium
ion
(C) Increasing solvent polarty causes a small decrease in the rat3e of the SN2 attack by
trimethylamins on trimethylsulfonium ion.
+ +
(CH3)3N + (CH3)3S CH3N(CH3)3 + (CH3)2S
(D) all ar3e incorrect
3.24 Which of the following reaction(s) is\are posible

(A) CH3 – CH ClCH2NEt2 OH
CH3CH (NEt2)CH2 – OH
HCl
(B) Either CH3 – CH – CH2 – SEt or CH3CH(sEt)CH2OH CH3CHClCH2SEt
OH
(C) Treatment of either epoxide I or epoxide II with aqueous OH gives the same product III
O
OH
CH3 – CH – CH – CH2Br or CH3 – CH – CH – CH2 CH3 – CH – CH – CH2 – OH
O O
Br
I II III
OH –
OH OH
EtO
(D) +
EtOH
OEt OEt OEt
Cl
CH2–C–Cl
OH
3.25 NaOH O NaOH LiAlH4
1eq
P Q R 'S'
OH
O O
O
CH2 – C – Cl
(A) R = (B) Q =
O OH
O
OH
O OH
C=O
(C) Q = (D) S =
OH CH2Cl OH
3.26 CH3C6H4
Ph OH
HNO2
?
H NH2
Ph
Ph Ph
pCH3C6H5 pCH3C6H5
pCH3C6H5 O O O Ph Ph O
Ph
(A) Ph (B) pCH3C6H5 (C) (D)
Ph H Ph H
H H
3.27 Which of the following reaction will go faster if the concentration of the nucleophile is increased?
H Br
Br
(A) + CH3O (B) + CH3S
H2O Br Acetone
(CH3)3CCl KI
CH3COOH
SECTION - III : ASSERTION AND REASON TYPE
CH3
CH3 CH3 CH3
H2SO4
3.28 Statement-1 : (CH3)3C CH (CH3)3CCH=CH2+ C=C + CH2=C
CH3 CH3 CH(CH3)2
OH
40% 20% 40%
Statement-2 : It follows Hofmann's elimination by E2.
Statement-1
3.29 Statement-1 : Ethers are prepared from alcohols in acid medium through SN1 or SN2 mechanisms
depending upon nature of alcohol.
+
Statement-2 : ROH + H+ R – OH2
+ slow +
R–O R – OH2
+
R – O – R + H2O ROR + H3O
H
H
+ + slow +
or, R – OH + H R OH2 R + H2O
+ + H2O +
R +O–R R–O –R R OR + H3O
fast
H H
Statement-1
SECTION - IV : TRUE AND FALSE TYPE
OH
H2SO4
3.30 CH3 CH3 Ph (Elimination follows E1 mechanism.)
Ph Heat
Comprehension # 1
Read the following reaction
O
+
H Cl2 NaOEt / NBS NaOH
P h
Q R S T
3.31 Compound 'T' is

OH OH
OH OH
(A) (B) (C) (D)
OH HO OH
OH
3.32 Compound 'Q' is
OH
OH OH Ol
(A) (B) (C) (D)
Cl Cl Cl
3.33 When treation 'S' with strong base, product obtained is
OH
OH OH OH
Br
Comprehension # 2
A hydrocarbon (X) of the formula C6H12 does not react with bromine water but reacts with
bromine in presence of light, forming compound (Y) . Compound (Y) on treatment with A|c. KOH
gives compound [Z] which on ozonolysos gives (T) of the formula C6H10O2. compound (T
reduces Tollens reagent and gives compound (W).(W) gives iodoform t4st and produce compound
(U) which when heated with P2O5 forms a cyclic anhydride (V).
3.34 Compound V is
O O
CH3 O
(A) O (B)
O
O
O
(C) CH3 – C – CH2 – CH2 – CH = O (D) CHO – CH = CH – CHO
3.35 Compound W is
COOH
(A) COOH – (CH2)2 – COOH (B)
COOH
COCH3
(C) (D) CH3 – CH2 – CH – COOH
COOH CH = O
3.36 Compound 'X' is
(A) CH3 (B)
CH3 CH3
CH3 CH3
(C) (D)
3.37 Match the column I with column II
Column - (I) Column - (II)

Reactions Reactions
CH3 H KNH2
(X) C=C (P) -elimination
Ph Cl
CH3
SOCl2 2
(Y) H OH (Q) SN
Ph
CH3
+
N – CH3 NaOH
Ph (R) -elimination
(Z) C
CH3
O
CH2–CH2–CH3
+ NaOH
(W) CH3–N–CH2–CH3–CH3 (S) SN1
CH2–CH3
3.38 Substrate Stereochemistry of product
CH3CH2CH2
(A) C—Br + H2O (p) Retention

H3C
CH2CH3
–
(B) CH3CHDCl + OH (q) Racemisation
(C) (r) Inversion
C—Br + H2O
H3C
CH2CH3
CH3
(D) CH2=CH—C — Cl + SH / (CH3COCH3) (s) Product with -bond shift
CH3
SHORT SUBJECTIVE :
3.39 Correct statement about nucleophiles and leaving groups is/are
(i) Nucleoghiles have an unshared electron pair and can make use of theis to react with and
electron rich species.
(ii) The nucleophillicity of an element generally inhcreases on goiing left to right in periodic
table.
(iii) A nucleophile is an electron deficient species
(iv) Leaving group ability kincreased in moving from L  R and T  B in periodic table.

CH3
CH3–CH–C–CH2–Br NaOH/H2O
3.40
CH3 CH3
Which of the following stat4ements is incorrect about the given reaction
(i) The reation is SN1 reaction
(ii) The reaction intermediate is planar (sp2)
(iii) The major product will be 2-ethyl-3-methylbutan-2-ol
(iv) The major product has two stereogenic centre
3.41 which of the following will not give SN1reaction with aq. AgNO3.
Ph Br Br
CH2Br
Br Ph
(i) (ii) (iii) Br (iv)
Ph Ph
3.42 In the given reaction following products are expected.
CH2– Br CH3 CH2–OCH3 OCH3 OCH3

CH3OH
+ + + + CH3
(I) (II) (III) (IV) (V)
Which observetions seen to be incorrect
(i) Ist is the major product obtained by E1 reaction
(ii) IV is the major product obtained by SN1 reaction
(iii) formation of II or V involves a strained carbocation intermediate
(iv) In the solvolysis reactions a carbocation intermediate is formed.
3.43 Observe the following flow chart and answer the number of x,y, z, w.
Isopentane Monochlorides
Positional Total
Isomers = (X) Isomers = (Y)
KOH/DMSO
2
(SN )
Total number of 1° alcohols = (Z)
including stereoisomers
X Y Z
Grignard Reagent
4 Reduction & Alkane
4.1 2-Phenylcycloprop-2-en-1-one is allowed to react with phenylmagnesium bromide and kthe reaction
mixture is hydrolysed with prechloric acid. The product formed is
Ph Ph
Ph
Ph O
(A) Ph – C – C – CHO (B) Ph (C) (D)
OH
O OH Ph Ph
4.2 Which of the following reactions will give 2° chiral alcohol as one or more of major organic
products?
H
O
O2 H3O H3O
(A) D MgI (B) CH3MgI + H – C– OCH – C2H5
(excess) CH 3
CH3
H O
H3O
(C) MgBr + CH2 – CH2 (D) None
CH3
PhMgBr H2O Fractional distillation

CH3 – C – C – CH3 No of product (X) no. of fractios (Y)
4.3 (excess)
O O
(A) 3,2 (B)3,3 (C) 4,2 (D) 4,3
4.4 The end product of following reaction is

O O
CH3MgBr PhMgBr H
(1) (2) (3)
O
(A) ,-diketone (B) -Hydroxy acid (C)1,2-Diol (D) -Hydroxy acid
4.5 Observe the following reaction sequence

O
Br2 / hv Mg / Ether dil.H2SO4 O3/Zn/H2O

X Y Z W U O
X can be
CH3
(A) (B) (C) (D)
CH2 – C(CH3)2
4.6 SOCl2 Mg O
+ Product
pyridine, (C2H5)2O H
O CH OH
(x) 2
Product of the reaction is

CH3
(A) (B)
O CH2 – C – CH2 – CH3 O CH2– CH – C(CH3)2
OH O
CH3 CH3
(C) (D)
O CH2 – C – CH2 – OH O CH2– CH2– C – OH
CH3 CH3
4.7 Observe the following sequence of reactions.
Br2/ hv Mg/ether CH3–Br Cl2 / hv CH3OH
CH3–CH2–CH3 (X) (Y) (Z) (W) (R)
(1) (2) (3) (4) (5)
The product R is :
CH3 CH3 CH3
(A) CH3 – CH – CH2 – OCH3 (B) CH3–CH2–CH2–CH2–OH (C) CH3–C–CH3 (D) CH3 –C –CH3
OCH3 OH
4.8 (i) CH3MgBr LiAlH4

Ph – N = C = O P Q
(ii) H2O
(A) P is Ph–NH–C –CH3 and Q is Ph–NH–CH2–CH3
(B) P is Ph– NH – CH3 and Q is NH3
CH3
(C) P is PhN=C — OH and Q is Ph – NH – CH3

(D) P is Ph – NH – CH – CH3 and Q is Ph – NH – CH – CH3
OH3 CH3
4.9 Which of the following reduction methods is not suitable for preparing and alcohol?
(A) CH3COOC2H5+ NaBH4 (B) CH3COOC2H5+ Na/EtoH
(C) CH3CH2COCl+ LiAlB4 Ni

(D) CH3COOH + H2
Ph – CH H
4.10 Li / NH3 Br2 (1equivalent) C=C
C C–C C X, CH – Ph
Br H
Br
'X' is :
(A) (B) (C) both (D) none of these

O Cl
C
O
4.11 Compound on reduction with LiAIH4 produces
N O
O
CH2OH CH 2OH CH2OH CH 2OH

OH OH
(A) CH 2OH (B) (C) (D) CH2OH
N N O N O N
HO CH2OH HO CH2OH
4.12 Which one is the correct energy profile for CI reaction ?

Energy
Energy
Energy
(A) (B) (C) (D) All of these
R.coord R.coord R.coord
4.13 Which of the following is correct statement regarding relative acidic charcter of cyuclopropane
and propane ?
(A) Cyclopropane is more acidic than propane
(B) Propane is more acidic than cyclopropane
(C) Both are equclly acidic
(D) Bothe are neutral
4.14
No . of products and No. of fractions are respectively

(A) 6,5 (B) 6,4 (C) 5,4 (D) 6,3
4.15 Which of the following is correct potential energy diagram for the given chin propagatiog step.
CH3 – H+F CH3+ H– F

= –32 kcal/mol
B.E.=435kJ/mol B.E.=569kJ/mol
4.16 Consider the following reaction
CH3–CH–CH–CH3 + Br 'X' + HBr, X can be

D CH3
(A) CH3–CH–CH–CH2 (B) CH3–CH–C–CH3 (C) CH3–C–CH–CH3 (D) CH3–CH–CH–CH3

D CH3 D CH3 D CH3 CH3

4.17 Br
Mg NBS AgNO3 / H2O O3 / H2O
A B C D E+F
14 Zn
(i) CH3COCH3
(ii) H
(iii)
14 Br
14
(A) Product C is (B) E is CH2 = O & CH2 = O
14 OH O OH O 14
OH
(A) Product D is only (D) F is &
4.18 CH3
Cl2 / h
Ph – CH2 – CH – CH3 (monochlorination)
Which statements is /are correct about photochemical chlorination of theabove compound [More
than one correct]
(A) The major product wil be chiral carbon atom having optically inactive compound
(B) The intermediate free radical of the major product is resonance stabilised
(C) The intermediate free radical is tertiary
(D) THe intermediate free redical is planer , and stabilised by only hyperconjugation
4.19 Which reaction is/are correct.
C N (i) Mg / Ether
(A) tertiary alcohol
+
(ii) H3O
Cl COOH
+
Mg CO2 H3O
(B)
ether
F MgF
Mg
(C)
ether
Cl MgCl
O
HO C C – CH3
+
(D) + CH3 – C CH CH3MgBr H 3O
4.20 Point out the following incorrect Grignard synthesis.
OH
CH – Ph
Br (i) Mg, ether
(A) (ii) Ph – CH = O
N (iii) H3O N
H H
O O (i) Mg, ether O O
(B) (ii) PhCH = O
Br (iii) H3O HOCH2

O
MgBr
(C) (i) CH3 – C – CH3
OH
(ii) H3O
O HO CH2CH3
(i) CH3CH2MgBr (1eq.)
(D)
(ii) H3O
OH OH
4.21 Stetement-1 : Cyclopropane has the highest heat of combustion per methylene group.
Statement-2 : Its potential energy is raised by angle strain.
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
4.22 Statement-1 : Branched alkanes have lower boiling point than their unbranched isomers.
Statement-2 : Branched alkanes has relatively small surface area, so less London's dispersion
force act among molecules.
Statement-1
4.23 Statement-1: Alkanes float on the surface of water

Statement-2 : Density of alkanes is in the ranbe of 0.6 – 0.9 g/ml, which is lower than water.
Statement-1
4.24 Statement-1 : Grignard reagent can be prepared in all nonpolar solvent.

Statement-2 : Diethyl ether solvates the Grignard reagent.
Statement-1
4.25 Statement-1 : The preparation of G.R. occurs in solution phase.
Statement-2 : Teh reaction will be explosive in solid phase. GR. is stable only in solution phase.
Statement-1
4.26 Observe the following natural product and choose the correct statement
(x)HOOC
H
N COOCH3(w)
(y) O2N
O C6H5
(z)
O
(r)
(1) LiAIH4 will reduced x, y, z, w, r
(2) NaBH4 will reduced r
(3) Na/C2H5OH will reduced r, w
(4) (CH3)2CHOH + [(CH3)2CHO]3AI, (MPV) will reduced r
(A) TFTF (B) TTTT (C) FTFT (D) FFFT
4.27 Diethyl ether is the solvent for Griganrd reagent but not for RLi, because RLi reacts with
C2H5OC2H5 and givesw CH2 = CH2.
Comprehension # 1
Read teh following reaction
2CH2– CHO
NaOCl Mg Cl KOH NaOH (i) H2 / Pd. BaSO4
CH CH P Q R S T
Ether H2O (ii) Dil.KMnO4
4.28 'S' in the above reaction
CH2 – OH
CH2 CH2
O O CH2–OH H OH
H H
C C H OH C
(A) (B) (C) (D)
C C C
C
H
O CMgBr HO H
CH2 MgBr
CH2 – OH
4.29 'U' is
CH2 – OH CH2 – OH CH2– OH CH2– OH
H OH H OH H OH
H OH H OH HO H
(A) H OH (B) HO H (B) H (D) H OH
OH
H OH HO H H OH
CH2 – OH CH2– OH CH2– OH COOH
4.30 'Q' is
(A) CIMgC  CMgCI (B) CH  C – MgCI
(C) CI–O–C  C–MGCI (D) CI–O–C  C–OCI
Comprehension # 2
considering the following reations (I,II,III) and give your answer for following questions
O
HO C–Cl (i) CH3MgBr
(ii) H3O+
O
C–OEt
(i) CH3MgBr (excess)

(ii) H3O +
CH2 – Cl
O
(i) Ph MgBr (excess)
(a) EtO – C – OEt
+
(ii) H
O
(i) CH3 MgBr (excess)
(b) EtO – C – OEt
+
(ii) H
O
(i) Ph MgBr (excess)
(c) H – C – OEt
+
(ii) H
O
(d) H – C – OEt
+
(ii) H
(e) ClCH2COOEt
+
(ii) H
4.31 If CH3MgBr is taken in excess in reaction (I), how many moles of CH3MgBr will be consumed
in reaction (I)
(A) 2 (B) 3 (C) 4 (D) 5
4.32 The product in the reaction (II) will be

OH OH
OH
O CH3
C CH3 – C – CH3 CH3 – C – CH3
CH3 C OEt
(A) (B) (C) (D)
Cl Cl
CH2 –Cl CH2 – CH3
4.33 In which seft of the reactions in (III) the product will be 2° alcohol ?
(A) a, b, c (B) b,c,d (C) c,d (D) c,d,e
4.34 Match teh following consider the reaction of CH3MgBr with the compounds in column A and
product are written in column B.
Column A Column B
(A) CINH2 (p) CH3CN
(B) CICN (q) CH3NH2
(C) CH3COCI (r) C2H5COCH3
(D) C2H5COOC2H5 (s) CH3COCH3
4.35 Match the following :

O O
Cl – C C CH = CH2
O – C – CH3
COOH
O
(i) [Al(OiPr)3] + CH3 – CH – CH3
(1) (ii) H O
2
OH
(P)
(2) NaBH4(C2H5OH + H2O)
(Q)
Na/EtOH (low temp.) (i) LiAlH4 / Et2O
(3)
(R) (S)
(4) (ii) H2O
Column - I Column - II
H OH
HOH2C C CH = CH2
(P) (X)
O – C – CH3
COOH O
O
H OH
Cl – C C CH = CH2
(Q) (Y)
O – C – CH3
COOH O
O
H OH
HOH2C C CH = CH2
(R) (Z)
O – C – CH3
COOH O
O
H OH
HOH2C C CH = CH2
(S) (W)
OH
COOH
Column A Column B
Li CH CH CI
(A) CH3CHCI 
Cul
 
3 2
? (p) (CH3)2CHCH2CH(CH3)2
Li (CH )CH Br
(B) (CH3)2CHI 
Cul
 
3 2
? (q) CH3CH2CH2CH3
Li CH CH Br
(C) CH3CH2C(CH3)2Br 
Cul
 
3 2
 (r) (CH3)3CCH2CH3
Li CH CH –Br
(D) (CH3)3CI 
Cul
 
3 2
 (s) CH3CH2C(CH3)2CH2CH3

Process Graph
Potential energy
A
B
(A) Fluorination (p)
C
Reaction CO-ordination
A B
(B) Chlorination (q)
C
B
(C) Bromination (r)
A
C
B
(D) Iodination (s) C
A
Position (A) is for CH4,X, (B) is for CH3, HX, (C) is for CH3–X,X

SHORT SUBJECTIVE :
4.38 An isomer of C5H12 gives total six isomeric products on monkochlorination. Calculate the
percentage yield of the primary monochloride which is chiral. Consider the following relative
reactivity of C–H bonds for chlorination.
Degree of C – H 1° C – H 2° C – H 3° C – H
Relative reactivity
for chlorination (RR) 1 3 5
4.39 How many molar equivalent of R-MgX is required in reaciton with formic anhydride completely?
4.40 O
C – NH2 C CH
CH3MgBr
the numbers of CH4 gas formed in this reaction
excess
HS
C – OH
O
4.41 Observe the following experiment
Mg
powder
A sweet H2O
smelling liquid (Q)
(1) (2)
(lce) (R)
An alkyl halide (P)

ethereal solution (II) (III)
(I)
(a) If the reactant 'P' is ethl chloride then the product R has the numbers of optically active
compound:
H – C – OC2H5
(b) If the loquid Q is then the product R can be (P can be any other halide)
O
CH 3 H C2H5
(1) CH3 – CH – CH3 (2) CH3– C – CH3 (3) H – C – C2H5 (4) C2H5 – C – C2H5
OH OH OH OH
CH3
(c) If R is C — CH3 then the numbers of monochlorination product are:

OH
4.42 O
1 mole CH3 – Mg – X
X
+ H2O
O
O
The numbers of stereoisomers of 'X' is :

5 Alkenes & Alkynes
NH
5.1 The major product of the following reaction would be Br2
Br
NH
N N N
(A) (B) (C) (D)
Br
Br H Br
Br H
5.2 In the following series of reactions the major products P and S are respectively.
Br2 / h tBuO , (i) HOBr/H+ (i) HOBr/H+

(P) (Q) (R) (S)
(ii) ThO2, (ii) ThO2,
(iii) alc.KOH, (iii) alc.KOH,
(A) ; (B) ;
Br Br
(C) ; (D) Br ;
Br
5.3 End product D of the following reaction will be
Cl H2O ZnCl2HCl Mg/ether D2O

A B C D
D
(A) (B) OD (C) D (D) D
OD
5.4 consider the following reactions
H5C2 C2H5
C=C
H H
R1 R H C2H5
2 C=C
H5C2 H
H5C2—C C—C2H5 R3
H5C2 C CH2 C2H5
R4
O
2CH3 CH2 COOH
The correct set of reagents for these reactions is

R1 R2 R3 R4
(A) H2 /Lindlar catalyst Na / Iiq.NH3 (i) O3, (ii) H2O H2O,H2SO4,HgSO4
(B) H2 /Lindlar catalyst Na / liq.NH3 H2O,H2SO4,HgSO4 (I) O3, (ii) H2O
(C) (i) O3, (ii) H2O H2O,H2SO4,HgSO4 Na / Iiq.NH3 H2/Lindlar catalyst
(D) H2O,H2SO4,HgSO4 H2/Lindlar catalyst (i) O3, (ii) H2O Na / Iiq.NH3
5.5 The major product of the following reaction is :

–
Na / ether Br2 / h C2H5O / C2H5OH,
Br Cl
(1) (2) (3)
(A) (B) (C) (D)
5.6 Themost ap0propriatew major product of the followning sequence of reactions would be.
O
CH3CH2 CH3
+
CH3 – C – O – O – H LiAlD4 H3O
C C
H3C H
Me Me
Et D Et DH
(A) (±) (B) (±)
H OH D H
Me CH3
Me CH3
Et OH CH3CH2 DH
(C) (±) (D)
H D H OD
Me CH3
5.7 Compound'P' of the following reaction swequence can be
+
O
O O H2O
(P) [C8H6O3] COOH
B–H
[C16H21B]
–
HOO
CrO3 / Acetone / H2O
[C8H8O] CH2 – COOH
(A) C C (B) CH2 – C CH (C) C CH (C) CH = CH2

5.8 The alkene limonene has the following structure,
Which product resutls from the reaction of limonene and 1 molar equivalent chlorine water?
OH OH CI
(A) OH (B) HO
CI (C) OH (D)
CI CI CI CI
5.9 The end product 'W' in the follownign sequence of reactions is :
CH2CH3 alc. KOH

Y
NBS Hg(OAc)2
(X) W
aq. KOH NaBH4
Z
CH3 CH3 CH3
(A) Ph – CH2 – CH2 – O – CH – Ph (B) Ph– CH – O – CH – Ph
CH = CH2
(C) Ph – CH2 – O – CH2 – CH2 – Ph (D)
Ph – CH – CH3
5.10 Which of the following corrently represents tthe rate of acid-catalysed hydration of followning
alkenes.
C = CH – CH3 CH = CH – C2H5 PhCH = CH – C2H5 CH3 – C = CH2

CH3 CH3
(l) (ll) (lll) (lV)
(A) lll > l > ll > IV (B) lV > lll > l > Il (C) l > lll> lll > IV (D) lV > lll > lll > I
+
Na/NH3 HOCl/H
5.11 Ph–C C–Ph A B ; B is
Ph Ph Ph
H OH
(A) (B) HO H (C) H OH (D) B and C both
Cl H Cl H H Cl
Ph Ph Ph
5.12 The most stable conformation of the product of followning reaction
HBr / R2O2 HBr / dark

C CH (1 eqivalent)
H Ph Ph H
Ph Br H Br H Br Br H
(A) (B) (C) (D)
H H H H H Br Ph Br
Br Br Br H
CH 3
– +
B2H6, THF H2O2, NaOH TSCl t–BuO K
5.13 In the given reaction, (Y)
(X)
The product 'Y' is
(A) A positional isomer of X (B) Identical to X
(C) Chain isomer of X (D) An oxidation product of X.
5.14 Which of the following compouinds would liberate two moles of methane when treated with
methyl magnesium bromide?
(A) CH3 – CH – CH2 – C CH (B) CH3 – C – CH2 – CH2OH
OH O
OH
CH3
(C) CH3– C – CH – C – CH3 (D)
O O
COOC2H5
5.15 The best yiest of product 'X' ca be obtained byt using which one of the foloowing sequence of
reagents and reactants
OH
X = CH3 – C C – CH – CH (CH3)2
NaNH2 (CH3)2 CHCHO H3O+

(A) CH3 – C CH
OH
NaNH2 CH3I
(B) (CH3)2CH – CH – C C–H
(C) CH3 – C C – CH – CH2 – CH3 NaNH2 CH3I
OH
OH
CH 3MgI CH3I
(D) (CH3)2CH – CH – C C–H
5.16 CH3
O
H3C – C – CH2– CH3
(i) CH3I CH3 – C – Cl
H3C – CH2 – CH2 – N X, X is
(ii) AgOH, AlCl3
H3C – C – CH3
CH3
In the above reaction the product will be–

(A) CH3 – CH – CH2 – Cl (B) CH3 – CH – CH2 – C – CH3
COCH3 Cl O
CH3
(C) CH3 – CH – C – CH2 – CH3 (B) CH3 – CH – CH2 – C – CH3
Cl O Cl O
5.17 Fastest rate of electrophilic addition will take place in
(A) HO CH = CH2 (B)ON CH = CH2
(C) CH3O CH = CH2 (D) CH = CH2
5.18 Which of the following will be the correct product (P) for the given reaction ?
Conc. H3PO4
(P)
OH
OH
(A) (B) (C) (D)
OH
HBr aq NaOH H2SO4/

5.19 CH2 X (major) Y (major) Z (major)
R2O2
Identify the correct option
X Y Z
(A) CH3 CH3 CH3

Br OH
(B)
CH3 CH3 CH3
Br OH
(C) CH3
CH3 CH2
Br
OH
(D*) CH3
CH2 CH3
Br
OH
O
(i) KMnO4 / H2O /
5.20 X + HOOC – C – CH2 – CH2 – CH2 – CH2 – COOH
(ii) H3O
X may be
COOH
COOH COOH
(A) (B) (C) (D)
O
O
5.21 D D
+
C=C (1) C6H5CO3H (2) CH3MgBr (3) H2O/H
H Product; Product is :
CH3 C
CH3
CH3
OH OH OH3OH3 OH OH3 OH3OH

(A) D C C H (B) D C C H (C) D C C H (C) D C C H
(CH3)3C D (CH3)3C D (CH3)3C D (CH3)3C D
5.22 The final product of the following reaction is

Ph
H o–COCH3
BrCl/CCl4
H Me
Ph
Ph Ph Ph Ph
H Cl H Br H Cl H Br
(A) Me Br (B) Me Cl (C) Br Me (D) Br Me
Ph Ph Ph Ph

5.23 Which statement is correct about the end product of the following reaction series,
HOCI (excess) conc. NaOH,
C CH
(1) (2)
(A) It is optically inctive hydroxy detone (B) It is a resolvable hydroxy acid
(C) It is a nonresolvable aldehyde (D) It is an optically inactive hydroxy acid
5.24 The following synthesis can not be carried out be:
I
CH = CH2 CH = CH2
CI I
CI2 ICI / CH3COOH ICI / CH3COOH Zn dust

(A) (1) (2) (3) (4)
HOCI / H CI2 / Fe ICI / ZnCI2 (excess) NaOH,

(B) (1) (2) (3) (4)
HOBr / H CI2 / Fe ICI / ZnCl2 (excess) Zn dust, CH3COOH
(C)
(1) (2) (3) (4)
Br2 / CH3COOH CI2 / Fe ICI / CH3COOH (excess) NaNH2

(B)
(1) (2) (3) (4)
LiNH2 (i) PhCHO MnO2

5.25 Bu – C CH A B C
(ii) H2O
Compound C of the above reaction can not be :
CHO CHO O
CHO
C CBu C–C CBu
(A) (B) (C) (D)
C CBu
C CBu
5.26 Acetone (CH3COCH3) is the major product in :
H3O
I CH2 = C = CH2
H2SO4 / HgSO4 / H2O
II CH3C CH
BH3- THF
III CH3C CH
H2O2 / OH
(A) I (B) II (C) III (D) none
HBr Br
5.27 Statement-1 : CH2
40°C CH2 CH2 Br
CH2 CH3 +
CH2 Major
Minor
Br
CH2
CH2 Br
CH3 + CH3
– 20°C Minor
Major
+ CH2 +
Statement-2 : CH3 CH2
Allylic CH3
+ cation
CH2 H Br
CH2 Br
Br CH2
CH3
CH2 Br
CH3 major at of high temp
major at low temp
Statement-1.
Me Me
5.28 Statement-1 : Me
NBS Me + Me
Me
Br
Br
Me
Statement-2 : Me Br. Me
–HBr Me
Me Me
Br2
Br2
Br Me
Me
Me Br
Me
Statement-1.
5.29 Statement-1 : Reduction of but-2-yne by Na/liq. NH3 given 'trans' but-2-ene.

Statement-2 : It is an example of 'anti' addition.
Statement-1.
5.30 Statement-1 : But-1-ene gives 2-Bromobutane with HBr/Preroxide

Statement-2 : The reaction involves formation of more stable free radical and in that respect the
addition is Markovnikof although the product obtained appears as anti Markovbnidof product.
Statement-1.

5.31 The addition of HBr to butadiene at –80°C to give 1, 2-adduct is kinetically controlled while that
at 40°C to give 1, 4-adduct is thermodynamically controlled.
5.32 In preparation of terminal alkynes from vicinal dihalides, at least 2 equivalents of sodium amide
must be added per mole of vicinal dihalide.
Comprehension # 1
Demercuration allows Mardownikoffs addtion of H, OH without re arangement. The net result is
the addition of H2O. Answer the following question.
5.33 CH3
i)Hg(OAc)2. THF HI (Conc.)
CH3 – C – CH = CH2 A B, Product B is :
ii)CH3OH, NaBH4NaOH
CH3
(A) (CH3)3CCH– CH3 (B) CH3I (C) CH3CH2I (D) (CH 3)3CCH– CH 3
OH
I
5.34 O
N–Br
1) Hg)OAc)2, THF
2) H2O OH
CH3CH = CH2 O
A B C.
3) NaBH4, NaOH
The product 'C' formation from B occurs throuth
(A) enol formation (B) SN1mechanism
(C) Neighbouring group particitation (D) SNAR mechanism
OH
i) Hg(OAC)2.THF
5.35 ii) NaBH4, NaOH
A,
Product 'A' is :
OH OH
OH
(A) HO (B) (C) (D)
OH
OH
Comprehension # 2
AI2O3 HI AI2O3 (i) B2H6
(A) (B) (C) (B) –
(A)
250°C (ii) AgOH 150°C (ii) H2O2,OH
In the above reaction sequence (A) and (c)are isomers. MOlecular formula of B is C5H10, which
can also be obtained from the product of the reaction with CH3CH2MgBr and (CH3) CO and
followed followed by acidification.
5.36 Identify the structure of A

(A) CH3–CH2–CH2–CH–CH3 (B) (CH3)2 CHCHOHCH3 (C) (CH3)3 C–CH2–OH (D) CH3–CH2–CH–CH2–CH3
OH OH
5.37 Identify th structure of B

CH3
CH C C=CH2
(A) (CH3)2–CH–CH=CH2 (B) 3 (C)(CH3)2CH= CHCH3 (D) CH2=CH–CH–CH3
CH3 CH3
5.38 Identify the structure of C
CH3
(A) CH3–CH2–CH2–CH–CH3 (B) CH3–CH2–C–CH3 (C) (CH3)3 C–CH2–OH (D) CH3 –CH2 –CH–CH2 –CH3
OH OH OH
SECTION - VI : MATRUX - MATCH TYPE

5.39 Match the column I with column II
Column -(I) Column -(II)
CH3
CH3
HgSO4
(A) C CD (p) OH
D2SO4, D2O *14
CH3 CH3
CH2OH
H
(B) *14 H2SO4 (q) *14
H2O
CH3
(C)
*14 B2H6/THF
(r) CD2CDO
OH /H2O2
B2D6/THF
(D) C CD (s) C – CD3
OD /H2O2
O

SHORT SUBJECTIVE :
5.40 (a) CH3 CH C C CH CH 3

(X)
OH OH
Total no. of stereoisomers of the product when above compound
(b) Total no. of stereoisomers of the product when above compound (X) is reduced by lindlar
catalyst.
(c) Total no. of stereoisomers of the product when (X) is reduced by Na/liq NH3 (Birch reduction)
(d) No. of products that we wil kjget when optically inctive form formed in part (B) reacts with
PhCOOH followed by hydrolysis.
5.41 CH3 – CH = CH – CH3 reacts with Cl2 at 500°C. Find out total no. of possible products.
CHCIBr2
5.42 m no. of products.
(CH3)3 CO–K
Et
CH3 CH3
5.43 C C + CH2N2 U m Total no. of products.
H H
CH3 Cold Dil NH2OH

HIO4
5.44 KMnO4 (excess) Total no. of isomers (including stereo) are formed in
KMnO4
the products.
6 Aromatic Compounds
SECTION-I : STRAIGHT OBJECTIVE TYPE
CH = CH – COOH
6.1 HOCI / H
The major product is :

OH
CH = CH – COOH CH = CH – COOH CH = CH – COOH CH –CH – COOH
CI
(A) (B) (C) (D) CI
CI
CI
O
+
HCI Br2 / Fe H
6.2 MeO OH CI –S Me
(1) (2) (3)
O
The major product is
Br Br Br
(A) MeO (B) MeO OH (C) MeO (D) MeO OH
Br
6.3 The product is :
OH
O
||
O product.
||
O
O
O
O O
O
(A) (B) O (C) O (D) None

OH
O O O
OH O
OH Me
Ph C C Ph AgNO3
6.4
Me I
Major product is
OH NO3 Me Me
(A) Ph C C Me (B) Ph C C Me (C) Ph C C Me (D) None of these
CH3 Ph O O Ph
Ph
CH3
6.5 Me3C–CI Ph–COCI Br2 / AICI3

AICI3 AICI3 Product is
Me O Me O Me O Me O
C –Ph Br C –Ph C –Ph C –Ph
(A) (B) (C) (D)
Br
C(Me)3 Br C(Me)3
6.6 Why does the reaction produce stable salt?
HCI + OH –
O CI
A
Because
(A) In 'A' the ring is aromatic
(B) 6 p electrons are present
(C) Ring in a is stabilised by closed loop conjugation
(D) All of these
6.7 The major product of reaction

O
C O
HNO3 + H2SO4
OMe
O O O O
C O C O C O C O
NO2
(A) (B) (C) (D)
NO2 NO2
OMe NO2 OMe OMe OMe
6.8 The end product of the folloowing reaction sequence is:
OCH3
|| O
Dry. AICI3 Zn – Hg / HCI SOCI2 / Pyridine
+ O
OH (tautomerises) Dry. AICI3

H2O
OCH3OH OCH3 OH
OH CH3O OH CH3O
(A) (B) (C) (D)
6.9 The end product of following reaction is
CH3COCI / AICI3 C2H5COCI / AICI3 CIO

(1) (2) (3)
COO
(A) O = C (B) OOC C – C2H5
C2H5
O
(C) COO (D) OOC COO
C
||
O C2H5
6.10 The product of the followiing reactions is
O
O ||
|| CH3 – C – CI
C CH3
AICI3
O O
|| ||
(A) C – CH3 (B) C – CH3
C=O C – CH3
CH3 O
O O O
|| ||
(C) C – CH3 (D) H3C – C C – CH3
H3C – C
O
6.11 Which of the following is best sequence of reagents for the conversion of
CH3
Br
Br2 / Fe conc. H2SO4 CH3CI / AICI3 H3O
(A)
CH3CI / AICI3 conc. H2SO4 Br2 / Fe H3O

(B)
CH3CI / AICI3 3CI2/ h Br2 / Fe Zn / HCI
(C)
HNO3 + conc. H2SO4 CH3CI / AICI3 Sn / HCI NaNO2 / HCI CuBr
(D)
6.12 The intermediate product 'X' of following synthesis is identified as :

CI2/FeCI3 conc. H 2SO 4 Fuming HNO 3 NH3/Cu2O/ dil.H 2So 4,
'X' 2, 6-Dinitroaniline
120°C 100°C
CI CI
CI O2N SO3H HO3S NO2
(A) (B) (C) (D)
HO3S NO2 CI O2N NO2
NO2 SO3H SO3H
6.13 The major product of the following reaction sequence will be
PhCOCI / Pyridine CH3COCI/AICI3 Zn – Hg / HCI / Br2/Fe
OH
(1) (2) (3) (4)
(A) CH3CH2 O C (B) H3C–CH2 O C

O O
Br Br
CH2 – CH3
(C) Br O C (D) CH3 – CH2 O – CH2
O Br
6.14 In the following reactions X, Y and Z are respectively :
NH2
(x) H2/Ni Br2/KOH,

(Z)
OMe
NaNH2/NH3(l)
(Y)
X Y Z
CH = NOH CONH2
CI
(A) , ,
OMe
OMe OMe
NO2 CI CONH2
(B) , ,
OMe OMe OMe

CONH2 CN NO2
(C) , ,
MeO MeO MeO

–
CN COO NH4 CI
(D) , ,
OMe
OMe OMe
NH2
+
6.15 CH3COCI Br2 + H2O H3O
A B C
C (major product) is
NH2 NH2 NH2

Br
(A) (B) (B) (D) none of these
Br
Br
6.16 Which of the following is regenerated at the end of the reaction
(C2H5)2SO4 / NaOH Sn / HCI NaNO2 / HCI C6H5OH

p – Nitro phenol (Y)
(X) (1) (2) (3) (4)
HI NaNO2 NaNO2/ HCI Sn / HCI NaOH / C2H5Br

(?) (W) (Z)
(9) CuNO2 (7) (6) (5)
(8)
(A) X (B) Y (C) Z (D) W
6.17 Consider the following reaction sequence
HNO3+H2SO4 Sn+HCI NaNO2+HCI Cu2(CN)2+HCN H2O

Product
(6H)
Product is:-
CH2OH CN COOH NH2

CN
(A) (B) (C) (D)
OH
6.18 The products R and S are respectively
NO2 KMnO4/ OH / Br2 / Fe

(X) (W) (R)
Sn/HCI
KMnO4/ OH / Br2 / Fe
(Y) (Z) (S)
NH2
HOOC Br HOOC HOOC Br
(A) and (B) : R and S are same products
HOOC HOOC HOOC
Br
NO2 NO2 NO2
HOOC HOOC Br HOOC HOOC
(C) and (D) and
HOOC Br HOOC HOOC Br HOOC
Br
6.19 The end product 'Z' of the reaction sequence is
CI
AICI3 Zn/Hg Se/
CI O X Y Z
Conc. HCI
(A) (B)
(C) (D) Both A and B
6.20 NO2
+
H3O NaOH+CaO
KCN/C2H5OH A C. Product 'C' is
distilation
Br
COONa NO2
COONa
(A) (B) (C) (D) None of these
Br Br
NH2
HNO2
A B, Product 'B' is
6.21
NH2
+ –
N2 CI N
(A) (B) N
N
N H
(C) N (D) All of these

N
H
(1) Sn/HCI
NO2 'x'
(2) KMnO4
B A
6.22
KMnO4
'y'
[O]
'x' and 'y' are respectively :
NO2 NH2
COOH COOH COOH COOH
(A) B and A (B) A and B
COOH COOH COOH COOH
NH2 NO2
COOH COOH COOH COOH
(C) A and A (D) B and B
COOH COOH COOH COOH
6.23 Which of the following electophilic substitution reaction represent correct product.
NO2 NO2
(A) Br2/FeBr3 Br
OCH3 OCH3
Br
(B) Br2/FeBr3
O O O O
COOCH3 COOCH3
Br2/FeBr3
(C) OCH3 OCH3
Br
(D) C–CH3 Br2/FeBr3 C–CH3

O O
Br
6.24 Which of the followning reactions give alkylation product:
OH
(A) + H (B) + H
AICI3 AICI3
(C) + CH3COCI (D) + Me3C – COCI
6.25 The following conversion reafction can be carried out by using reaction sequence/s.
O O COOH
OH
+
Zn / Hg / HCI, Br2 / h KCN H3O,
(A)
NaBH4 AI2O3, O3 / H2O (oxidative)
(B)
+
Heat I2/NaOH, H
(C)
(D) KMnO4 / OH / heat

6.26 Which of the following ion will be aromatic in nature?
CI N
(A) (B) H (C) (D)
H +
N N
| H H
H
6.27 Statement-1 : Benzene and ethene both give reactions with electrophilic reagents.
Statement-2 : Benzene and ethene both have loosely bound  electrons, which can be donated
to vacant orbital of the electrophile.
Statement-1.
6.28 Statement-1 :
H H
C is less Acidic than C

(Fluordane)
(Triphenylmethane)
Statement-2 : coplanar arrangement of three rings in fluordane, allows more extensive
delocalisation in conjugate anion.
Statement-1.
6.29 Statement-1 : Polycylation in benzene does not occur during friedel Craft's acylation.
Statement-2 : As the product ketone is much more reactive than starting material.
Statement-1.
AIBr3
6.30 Statement-1 : Ar C(CH3 )3 Br2   ArBr   CH3 2 C  CH2

but AIBr
ArCH2 CH3 Br2  3
 o,p – BrC6H4CH2CH3

Statement-2 : In the first case ipso substitution takes place in which Br displaces (CH3)3C+, a
stable cation but removel of CH3CH2 cause large amount of energy.
Statement-1.
6.31 Statement-1 : 1, 3, 5 trihydroxybenzene reacts with NH2OH togive oximino derivative where as
1, 3 dihydraxy benzene do not
O NOH OH
||
Statement-2: Former exist in which gives NOH where at later exists in
|| O
O NOH OH
no substantial keto form is present which can give oximino derivative

Statement-1.
6.32 The product of reaction of with conc. H2SO4 is

CH2 – OH
4
3
6.33 The best position for ArSE in pyridine 2 is 4
N
1

Comprehension # 1
COOH
SOCI2 Solid N2O5 (CH3)2 CuLi Fe / H (i) NaNO2 / H

Q R S T (U)
(ii) PhOH / OH
6.34 The product U is
CH3 O
||
(A) C (B) H3C – C N=N OH
H N=N OH
N=N OH
(C) (D) N=N OH
H3C – C
O CH2CH3
6.35 S on reaction with CI2/ NaOH or on reaction with CI2/ NaOH followed by acidification will not give
which of the followong
NO2 NO2 NO2
(A) (B) (C) CHCI3 (D)

COONa CH2COONa COOH
6.36 T on reaction with NaNO2/HCI followed by reaction with H3PO2 will give.
CH2COCH3 COCH3 COCH3 COCH3
(A) (B) (C) (D)

OH
CH3
Comprehension # 2
The compound C8H9CI (A) on treatments with KCN followed ny hydrolysis gives C9H10O2 (B).
Ammonium salt of B on dry distillation yields C. Which reacts with alkaline solution of bromine
to gives C8H11N. (D) Another compound E (C8H10O) is obtained by the action of nitrous acid on
D. or by the action of aquous potash A. E on oxidation gives F (C8H6O) Which gives the inner
anhydride G on heating.
6.37 The compound A is
CH2 – CI CH2 – CI
CH2 – CI
CH2 – CH2 – CI
(A) (B) (C) (D)
CH3 CH3
CH3
6.38 The compound D is reacts with CHCI3 + NaOH gives a compound H. The structrure of H.
CH2 – CH2 – NC CH2 – NC
(A) (B)
CH3 CH3
CH2 – CN
CH2 – NH – CH3
CH3
(C) (D)
CH3
6.39 The compound A on reaction with AgCN gives.
(A) co,pound H. (B) Compound B (C) compound G. (D) compound D
Comprehension # 3
CH2 – CO
AICI3 Zn(Hg) HCI/ SOCI2
O C10H10O3 (C10H12O2)
(1) (2) (3)
CH2 – CO (X) (Y)
(Z) (C10H11OCI)
Pt, heat H2SO4 / H2 / Pt AICI3

(C10H8) + H2 (C10H10) (C10H12O) (C10H10O)
(7) (6) (5) (4)
(T) (S) (R) (W)
6.40 What product will be obtained if 'W' is treated with C6H5MgBr followed by D3O and then by
heating?
(A) (B)
Ph
OD OD
(C) (D)
Ph Ph
6.41 What product is obvtained when (X) is heated with conc. H2SO4
O O O O
O
(A) (B) (C) (D)
O O O
6.42 What product is obtained when W is heated with KMnO4 / OH.
COOH
COOH
(A) (B)
COOH
COOH
O
(C) O (D) O

6.43 Match the following
:e
(A) (p) Anti aromatic

e:
(Non-Planar)
(B) (q) Aromatic
:e
(C) (r) Non aromatic
(Planar)
(D)
(s) G.F = CnHn
(Planar)
6.44
NO2
(1)Sn/HCI
(2) (CH3CO)2O HNO3 Dil.
A B C
H2SO4 H2SO4
Br2
(1) CuBr
H3PO2 (2)Sn/HCI NaNO2
G F (3) NaNO2, HSO4 E D
H2SO4
HBF4,
H
Write the correct combinations
Column-I Column-II
Br
(p) Br Br
(A) A
Br
(q) Br Br
(B) B
NHCOCH3
(C) G
(r)
NO2
NHCOCH3
(s)
(D) H
6.45 Match the correct properties of compounds of column I with column II.
(I) (II)
O–CH=CH2
(A)
(p) Gives Benzoic acid with hot alkaline KMnO4
CH=CH2
(B) (q) o/p directing and activating for E
CH–CH3
(C) (r) Gives fastest reaction with an electrophile
OH
O
C
(D) CH3 (s) Gives an ester on reductive ozonolysis

SHORT SUBJECTIVE:
NO2
(C2H5)2SO4 Zn/HCI/ NaNO2, HCI Phenol Br2/H2O

6.46 (I)
(2)
(II) (III) (IV) (V)
OH (1) 5°C (3) NaOH (4) (5)
OH
The steps involved in the above reaction can be arranged as.
Electrophilic substitution = step (w)
Nucleophilic substitution=step (x)
Reduction reaction = step (y)
Diazocoupling reaction = step (z)
Assign the correct numbers to the type of reactions as follows w x y z
6.47 Observe the following reaction sequence
(1)
NaOH (1 eq) HCN, HCI/AICI3 NH2–NHPh
Phenol (X) (Y) (Z)
Me (3) (4)
(2) D I
H
Answer the following questions in the given format :
P Q R S
P = Number of organic products formed in step-1
Q = Number of organic products formed in step-2 (singnificant products)
R = Number of organic products formed in step-3 (singnificant products)
S = In which step aromatic electrophilic substitutiion has taken place
6.48 CH3CI/AICI3 Br2/h (1 eq.) Na/ether
(1) (2) (3)
(4) Br2/h (1 eq.)
(monobromination)
(5) alc.KOH
(i) O3
(P)
(2 moles) (ii) Zn/CH3COOH
Find the structure formula and molecular weight 'P'.
6.49 Indicate the most probable sites for ArSE reactions.
(A) C O (B) NO2
1 2 1 2
NO2
(C) CH2
(D)
1 1 2 3
2
NHCOCH3
NH
(E)
NH O
O
||
C AICI3/ Na/C2 H5OH
CI A B C
6.50 + (CH2)2 C CI
|| Se/
O
Find the molecular weingt of the compound C and D.
6.51 In the following sequence of reaction how many nucleophilic substitution taking place.
OH O
SOCI2 alc.KOH CI –C – CI CH3MgBr HBr
AICI3
H
7 Carbonyl Compounds
SECTION-I : STRIGHT OBJECTIOVE TYPE
7.1 OH– OH– H

PhCOCHBr2  A  B 
C
The compound'C' is
(A) PhCH(OH)CHO (B) PhCH(OH)COOH (C) PhCOCBr2 (D) Ph–C–CH2–OH
H O
7.2 The product/s of the following reaction is
O
Ph ||
C – C – Me PhCO3H
Me
H
O Ph
Ph ||
(A) C – C – O – Me (A) C– O – C – Me
Me
Me H
H O
Ph ||
Ph
(B) C – O – C – O – Me (D) C = O + HO – C – Me
Me Me
H
7.3 Which step is not feasible in the following loop?
+
Br
EtOH, H
CH2(Br)CH2CHO a CH2 –– CH2CH(OEt)2
d alc. KOH b alc. KOH
+
H2O, H
CH2=CHCHO CH2 =CHCH(OEt)2
c
(A) step - a (B) step - b (C) step - c (D) step - d
+
7.4 OH H3O
CH3 COCHO P Q
H2SO4
2Q R The product R is :
O
||
C O
(A) CH3 CH(OH)COOH (B) CH3 CH CH CH3
O C
||
O
O
(C) CH3 CH = CH – COOH (D) CH3 CH C CH3
O OH
7.5 CH3 – C – (CH2)4 – C – CH3
|| || OH/ A Ph–MgBr B Zn–Hg C
O O + Conc.HCI
H
The product 'C' is
Ph O Ph Ph
Ph ||
(A) (B) (C) (D)
CH3COONa HBr
7.6 PhCHO + (CH3CO)2O A B
The product B is
(A) PhCH = CHCH2Br
(B) PhCH – CH2 – COOH
Br
(C) PhCH2 CH(Br) COOH (D) PhCH= CH – COBr
7.7 The number of stereoisomeric products formed in the following reaction is

Ph Ph
H D + H MgBr Ether H2O
CHO CH3
(Optical pure) Optical pure
(A) 1 (B) 8 (C) 4 (D) 2

7.8 The end products of following reaction would be,
CHO
HCHO (excess),
NaOH (aqueous)
C
O CH3
CH2OH CH2OH
(A) + HCOONa (B) + HCOONa
C C
O CH3 O C(CH2OH)3
CHO COONa
(C) (D) + CH3OH
C C
O C(CH2OH)3 O C(CH2OH)3
7.9 In which of the following compounds O18 exchange can be observed on keeping it in H2O18
O
||
COOH SO3H OH
CH3
(A) (B) (C) (D)
7.10 What will be the product of the following reaction

O O
NH2 || || +
H/
H3C – C – (CH2)2 – C – CH3
CH3
Ph H3C CH3
(A) (B) (C) (D)
H3C N
N
|
CH3 N CH3 CH3 N CH3 |
Ph
Ph
Ph
7.11 The possible number of stereoisomers of the product of following reaction would be :
Ph – CH = CH – CH – CHO
NH2OH
CH3
(A) 2 (B) 4 (C) 6 (D) 8
7.12 Which of the following ketone recemises in aqueous solution containing some acidic or basic
impurities.
CH3CH – CH – C – CH3 C2H5 – CH – C – CH3

(A) (B)
Ph Ph O CH3 O
CH3 O
Ph
Me
C6H5– C – C – C2H5
(C) (D) Me
O Ph
7.13 The final product (X) of the following reactions would be
NH2OH.HCI PCI5 Br2/Fe

C6H5 – C – C6H5 (X)
(1) (2) (3)
||
O
(A) Br C CI (B) C NH
|| ||
N O
OH Br
(C) C NH Br (D) C NH2

|| ||
O O
Br
7.14 CH3COCH3
CH3C CNa
X
H2O
Y
H2,Pd+CaCO3
Z
AI2O3
W, W is :
(A) CH2=CH––CH=CH2 (B) CH3 – CH = CH –– CH = CH2
CH3
CH = CH––C = CH2
(C) (D) CH3–CH=CH–CH=CH–CH3
CH3
CH3
7.15 LiAIH4 HBr(excess)/ AICI3 Alc.KOH Pd,
X Y Z W
–H2
CH3
Identify X, Y, Z and W
X Y Z W
Br CH3
CH3
C6H5 – C = CH – (CH2)2 OH
(A) C6H5 – C – (CH2)3 – OH
CH3
CH3 OH
Br
CH3 CH3
C6H5 – C = CH – (CH2)2 OH Br
(B) C6H5 – C – (CH2)3 – OH
CH3
CH3
Br CH3
CH3
(C) C6H5 – C = CH – (CH2)2 OH Br
C6H5 – C – (CH2)3 – OH
CH3
CH3
Br CH3 CH3
Br
(D) C6H5 – C = CH – (CH2)2 OH C6H5 – C – (CH2)3 – OH
CH3 CH3
O +
7.16 || (1) HCI (i) LiAIH4/Et2O H3O
O C – OC2H5 X Y Z, Identify X, Y and Z
(2) CH2OH (ii) H2O
CH2OH
X Y Z
O O
|| || HO CH2OH
(A) O
C–OC2H5 O COC2H5
O
O
|| O
O COOH HO CH2OH
(B) C–OC2H5
O
O
O
|| O O CH2OH
(C) O CH2OH
C–OC2H5
O O
O HO CH2OH HO COOH
(D) CH2OH
O
7.17 C4H9Li R'X C4H9Li R''X HgCI2, H
P Q S T U
S S H2O
The final product U is
O
S S ||
(A) S S (B) S S (C) (D) C
H R' R' R'' Li R' R''
H
O
O3 OH
CH=CH–C–
7.18 X Y+Z
Zn,H2O
Compound X in the above reaction is
C=CH–CH3 CH3
(A) (B) C=CH
CH–CH=CH2
(C) CH2–CH=CH (D)
7.19 COOH
1.PCI5 NH2OH.HCI H2SO4

H Ar 2.CH3MgBr
X Y Z
Et
X, Y, Z are –
CH3 OH
COCH3 C=N
(A) H Ar (B) H Ar
Et Et
NHCOCH3 NHCOCH3
(C) H Ar (D) H Et
Et Ar
7.20 Which of the following products is/are correctly mentioned in the following reactions.
(A) HCOH 

NaOD
 HCOONa + CH3OD (B) HCDO 
NaOH
 DCOONa + CH2DOH
(C) HCDO  DCOOEt + DCH2ONa
NaOEt (D) D2CO  DCOONa + CD3OD
NaOD
7.21 The correct statement/s about the following reaction sequence is / are
CI2 / FeCI3 HNO3 + H2SO4 HNO3 + H2SO4 NH2NH2,
(P)
(1) (2) (3) (4)
O2N
(R)
CH = N – NH NO2 (Q)
(5)
(A) 'R' gives an aldol condensation reaction kon heating with NaOH solution
(B) The rate of deukteration in presence of heavy water the rate of acid cataly sed halogenation
are same
(C) Base catalysed haloform reaction involves formation of carbanion
(D) Acid catalysed halogenation of CH3COCH3 inovolves enol formation
7.22 Which statement is / are correct ?

(A) The rates of acid catalyed chlorination, bromination of acetone are same
(B) The rate of deuteration in presence of heavy water the rate of acid catalysed halogenction
are same
(C) Base catalysed haloform reactyion involves formation of carbanion
(D) Acid catalysed halogenation of CH3COCH3 inovolves enol formation
7.23 Which one can be the product of the following reaction ?

1. NaOH,
HOOC CHO +
2. H3O
(A) A diacid (B) A monoacid (C) A diol (D) An alcohol
7.24 Which of these carbony compounds on reduction winth Zn – Hg / HCI will give th3e same
compound as product
O O
|| ||
H–C CH2CH(CH3)2 H3C C – CH(CH3)2
(A) (B)
H–C=O O
||
(C) H3C CH2 – C – CH3 (D) H3C C – C(CH3)2
H
7.25 whic one of the followning compound will not show enolisation ?
O OH
O
Me O O
(A) (B) (C) (D) O OH
Ph O O O
OH
Me Ph
7.26 Statement-1 : When chloral is heated with concentrated potassium hydroxide, it yields
[CCI3 – COO - & CCI3 CH2OH]
Statement-2 : In the cannizaro reaction hydride transfer is the slowest step.
Statement-1.
KOH
7.27 Statement-1 : CH3O CHO + HCHO Expected major product from the above
reaction is
– +
CH3O CH2OH and HCOO K
Statement-2 : With increase in electrophilicity on>C = O group, rate of attack of nuecleophile

increases.
Statement-1.
7.28 Statement-1 : PhCOCOCOPh forms atable hydrate.

Statement-2 : The compound in the hydrate form has intramolecular H-bonding.
Statement-1.
7.29 Statement-1 : When PhCHO is made to react in OD / D2O no D is incorporated in to the CH2
of PhCH2OH, PhLCOO- mixture during Cannizaro's reaction.
Statement-2 : Intermolecular H transfir takes place in the rate determining step, with out getting
free in solution.
Statement-1.
7.30 Statement-1 : When 1 mole of benzaldehyde and 1 mole of cyclohexanone is treated with 1 mol
of semi carbazide, cyclohexanone semicarbazone precipotates first and finally precipitate of
semicarbazone of benzaldehyde is formed
Statement-2 : Initial one is Kinetically controlled product and tltere one is thermodynamically
controlled product.
Statement-1.
SECTIO - IV : TRUE AND FALSE TYPE

7.31 If these statements are true of false mark T and F.
(I) Base catalysed halogenations of Acetaldehyide follows the reactivityy ordeer for halogens as
CI2 = Br2 = I2
(II) High Alcohol and low water concentration shifts the aldehyde-hemiacetal and hemiacetal-
acetal equilibria towards acetal.
OH
(III) Conc. KOH changes Ph–C–C–Ph to Ph–C–COO

O O Ph
O CH3 OLi
(IV) (CH3)2 CuLi changes to

CH3 CH3
SECTIO - V : COMPREHENSION TYPE

Comprehension # 1
Aldehydes and Ketones reacts with NH2OH to form Aldoximes and Ketoximes respectively.
Configuration of these can be determined bu Beckmined by Beckmann rearrangement as that
group migartes which is anti w.r.t – OH.
R + R
R'– C = N – R H2O R'–C = N – R R'–C – NH– R
C N H C N +
R' OH R' OH2
OH O
It is interisting to note that the migration of group is completely Retentive and no loss of optical
activity is seen.
7.32 Me OH
O2 N C=N +
H
Br
O O
NH – C – Me C – NH – Me
(A) Br (B) Br
O2N O2N
O
O
C – NH – CH3
NH – C – Me
Br
(C) NO2 (D)
Br NO2
+
7.33 H Br2 /KOH
CH3CHO + NH2OH P Q R (CH3NH2) (as only product)
Following is correct
(A) Oxime P is syn form of geometrical isomer
(B) Oxime P is anti form
(C) Q is more basic than R
(D) Q is H – C – NH – CH 3
O
7.34 CH3 OH
C=N dil. H2SO4
H
C
H3C
Ph
(+) dextrorotatory
Following is true about product
(A) It is also (+) laevorotatory
(B) Both (+) (–) forms are obtained in equal amount
(C) It is having 'S' configuration for chiral carbon
(D) It is having R configuration for chiral carbon.
Comprehension # 2
Intramoloecular aldol comdensation :
The aldol condensation also offer a congenient way to synthesize molecules with five and six
membered rintg. This can be dine by and intramilecular aldol condensation using a dialdehyde,
a keto aldehyde or a diketone as the substrate. The major product is formed byu the atack of
the enolate from the ketone side of the molecule that adds to the aldehyde group . The reason
the aldehyde group undergoes addition preferentially may arise from the greater reactivity of
aldehyde towards nunleophilic addition generally. In reaction of this type five membered rings
form far more readily than seven membered rings and six membered rings are more favorable
than four or einght membered rings when possible.
7.35 1–Ehtylcyclopent–1–ene on reductive ozonolysis followed by aq. HaOH/  gives

O
CH3
H
(A) (B) (C) (D)
O O
O CH3
7.36 Which of the following compound on reaction with O3/Zn, H2O followed by aq. HaOH/  will form
(A) (B) (C) (D)
O O
CH3–C–CH2–CH2–CH2–CH2–C–H
7.37 The true statement about the major product of in reaction with aq. NaOH
followed by heating is.
(A) It gives yellow ppt with (B) It gives silver mirror with Tollen's reagent
(C) It shows stereoisomerism (D) It does not give yellow ppt with 2,4 DNP
Comprehension # 3
Observe the following reactions and its mechanistic steps and intermediate products.
Reaction -1
O O 1 O O O 2
H
O OAc O Ph
(l) (ll)
O O
O 3 O O O O
=
O O Ph
Ph O Ph
O O
(lV) (lII)
O O
H C
4 5
O OH + ACO
H –H+
Ph O O Ph
(V) (Vl)
Reaction -2
O O O
+ + ACO
Ph O Ph
7.38 The intermediate product similar to (IV) following in the reation-(2) :

Ph O Ph
Ph O Ph
Ph
O O O O
(A) (B) Ph (C) (D) Ph
O O
O O O Ph O O O O O
7.39 The leaving group of step (V) in reaction-2 :

(D) Ph – CH = CH – COOH
7.40 If Ph – CH = O18 is used then O18 is traced in reaction-2 :
(A) Ph – C –O18 – H (B) CH3 – C –O18 – H
O O
18
(C) Ph – CH= CH – C – O – H (D) H – O – C – O18 – H
O O
Comprehension # 4
In presence of excess base and excess halogen a methyl ketone is converted first into a trihalo
substituted ketone and then into a carboxylic acid. After the trihgalo substituted ketone is formed
hydroxide ion attacks the carboxyl carbon because the trihalo methyl ion is the group more easily
expelled from kthe teranhedral intermediate. The conversion of a methyl ketone to a carboxylic
acid is called a haloform reactioon beacause one of the product is haloform (CCHLI3) or CHI3
or CcHBr3.
O O
OH (excess) OH
R – C – CH3 R – C – CI3 R – C – CI3 R – C – OH + CI3 R – C – O + CHI3
I2 (excess)
O OH O O
7.41 Whichof the following compound show haloform reaction and recemisation in OD- / D2O.
O Me
O C
Me Me
(A) CH3CH2OH (B) Et (C) (D) CH3 – C – CH – Ph
Ph
O Et
7.42 Et
Ph – C – C – C – CH3 (1) I2 /OH +
product is
(2) H+
O Me O (3)
O
Ph
O (1) NaIO
7.43 product is
(2) H ,

7.44 Column-I Coulmn-II
O
(p) 1, 4-addition
Ph–CH2–C–CH=CH2
(q) Tautomerism
OHC
CH3–CH=CH–CH=CH2 (r) AgNO3/NH4OH
CH 3–C–CH 2–C–H
(s) 2,4 DNP test
O O
O
(A) NaCN + H2SO4 (A) LiAlH4

(p) Formation of six fmember ring take place
HNO2
(B) Product
O
NH2OH (q) Final product is ketone
(B) (A) H (B) LiAlH4 Product
OH Product
(C) CH3–C–CH2–CH2–CH2–C–H
(r) Final product formed will give positive tollen's test
O O
Ph
H
(D) Product (s) Final product will react with 2, 4 DNP
CH3
OH OH

(A) Ph–C–H alkaline KCN Product
(p) Final product formed give positive tollen test
O
O (1) OH
(B) Product (q) Final product give test with 2, 4 DNP
O
(1) C2H5ONa
(C) CH3–C–OEt Product
(r) Final product react with NaOCO3 and
O
liberated CO2 gas
(1) KOH
(D) Ph–CH=O Product (s) Final product react with Na and liberated H2 gas
(2) H

SHORT SUBJECTIVE :
7.47 A compound (A) of molecular formula C14H10O12 is formed formed from C14H14O2 by oxidation
Cr2O7–2. (A) upon treatment with OH–gives (B) on treatment with conc. H2SO4 and heat gives
compound (C) of molecular formula C28H20O4(B) reaponds to NaHCO3 test and effervescence
comes out. What should be the moleculat wt. of B ?
7.48 C8H6O2 on reation with conc. NaOH undergoes a redox reaction to yield (A) which on treatment
with KMnO4/H followed by HaOH/CaO gives an aromatic compound (X). Calculate the mol.
mass of aromatic compound (X).
7.49 Methyl cyclohexene on reductive ozonolysis followed by reaction with dil. HaOH gives [X] number
of products. A mixture of HCHO + PhCHO on treatment with conc. NaOH gives Y nunber of
products. 1, 2-Dimethyl cyclohexene on reaction with metachloroperbenzoic acid gives [Z] number
of products.
7.50 NH3 reacts with a gas fu\mes produced when methanol is passed through Cutube at 573K. The
compound obtained is polycyclic. How many rings does it contain = [X]. The number of Nitrigen
atoms it has = [Y] ?
CH3—CH=O + PhCH2—CH=O mixture of aldols

7.51
(z) total number of aldols including stereoisomers
8 Carboxylic Acid/Acid Derivatives
SECTION - I : STRAIGHT ONJECTIVE TYPE

8.1 PhCOOH, PhMe can be separated by
(A) KMnO4 (B) aq. NaHCO3 + n-hexane
(C) H2O (D) All of these
8.2 Reactivity order towards a nucleophile is

(A) RCOCI > RCOOEt > (RCO)2O > RCONH2
(B) RCOCI > (RCO)2O > RCOOEt > RCONH2
(C) (RCO)2 > RCOCI > RCOOEt > RCONH2
(D) (RCO)2O > RCOOEt > RCOCI > RCONH2
8.3 When phenyl glyoxal is kept in a solution of aq. NaOH it is converted to

H H
(A) Ph C C–H (B) Ph C C – ONa
ONaO O–HO
(C) Ph C C ONa (D) Ph C CH2ONa
O O O
8.4 In the given reaction, the number of isomeric products formed is-
+
H
CH3CHClCOOH + CH3 – CHDOH ester
(Racemic mixture) (optically pure d-isomer)
(A) 1 (B) 2 (C) 3 (D) 4
8.5 (CH3CO)2O, Pyridine (i) LiAlH4

NH2 (II) (III) ;
(ii) H2O
(I)
The basicity order of I, II and III is
(A) III > I > II (B) I > II > III (C) III > II > I (D) II > III > I
8.6 O
O C
H3O+
CH3CH CHCH3
O
(A) CH3CH(OH)2, CH3CH(OH)COOH
(B) CH3CHO, CH3CH(OH)COOH
(C) CH3CH2COOH, CH3CH2OH
(D) CH3CH(OH)COOH, CH3CH2OH
8.7 What will be the kmost probable product when compound 'X' is treated with two equivalents of
NaOH,
COOH
HO
X= C CH
HO NO2
O COOH O COO
(A) C CH (B) C CH
O NO2 HO NO2
HO COO HO COO
(A) C C (B) C CH
HO NO2 O NO2
8.8 Which pair of compounds on heating give isomeric products

O
(A) CH3 – CH – CH2 – C – OH and CH3 – CH – CH2 – O – H

O–H CO2H
(B) CH3 – CH2 –CH – CO2H and (CH3)2 C(OH)CO2H
O–H
(C) CH2 – CH2 –CH2 – CO2H and CH3 –CH – CH3 – CH2– OH
HO CO2H
(D) All the above
8.9 Which pair of compounds on heating give isomeric products

(D) All the above
8.9 The correct sequence of reagents for the following conversion is
O O
C–O–H CH2 – C – OH
NO2 NO2
SOCl2 Ag CH2N2 SOCl2 CH2N2 Ag

(A) H2O
(B) H2O
CH2N2 SOCl2 Ag Ag SOCl2 CH2N2

(C) H2O
(D) H2O
8.10 O
+ 18
H /H2O
X+Y
O
X, Y are
O 18 O
O–H 18
O–H
(A) 18
O–H, (B)
O–H
,
O
O–H
(C) 18 , (D) All of these
OH
8.11 O
O R
AlCl3
X+Y
X, Y both responds to FeCl3 test and 2, 4 DNP test. One is thermodynamically controlled
product (TCP) and another is kinetically controlled product (KCP). KCP is
OH OH OH
COR
(A) (B) (C) (D) All of these
COR
COR
+
8.12 PCl5 H2O H3O
X Y Z
N
OH
The product(s) Z is.
(A) , CH3NH2 (B) , CH3OH

N O NH2
CH3 CH3
(C) NH2– (CH2)5– CH – COOH, CH3NH2 (D) NH2 – (CH2)5– CH – COOH only
8.13 O
NaN3
Cl X – Product
(2) OH
Product is/are
(A) NH2 only (B) NH2, HCOOH
O
CONH2 +
(C) (D) C – OH + NH4
O
8.14 O
O Zn/Hg SOCl2 AlCl3

X Y Z W , Product 'W' is :–
AlCl3 HCl
O
O O
(A) (B) (C) (D)
8.15 O
C—Cl
NaOEt
CH2(COOEt)2 + Final product is
(1 eq.)
C
O OEt
O O O O
COOEt CH2 COOH CH COOH CH3
C CH C C C
COOEt COOH
(A) (B) (C) (D)
C COOH COOH COOH

O OEt
8.16 Which of the following undergoes decarboxylation most readily on being heated ?
O
(A) (B)
OH
O
HO OO
O
(C) HO (D) O
OH
O OH
HO O
8.17 CN
+
CN H3O
A ; product (A) of the reaction is
CN
CN
O O
COOH
C COOH C
(A) O (B) (C) O (D) CN
CN
C COOH C
COOH
O O
8.18 Which statement is correct about the following reaction
COCl
NaOH (1 eq.)
H Br
CH3
(A) There is inversion of configuration at asymmetric C* atom
(B) There is No change of configuration at asymmetric C* atom
(C) There is 100% racemisation at C* atom
(D) % inversion > % retention at C* atom
8.19 Identify C in the following sequence of reactions :
CO3H
SOCl2 NH3 P4O10
A B C
heat
CH3
OH CN CN CN
(A) (B) (C) (D) ]
CH3 CH3 CH3 CH3
8.20 MeO OMe

EtOOC CO2Et H3O
(A), Product (A) obtained is :
O O O O
O CO2Et CO2H
(A) (B) (C) (D)
8.21 Which of the following acid remains unaffected on heating ?

(A) malonic acid (B) maleic acid (C) Fumaric acid (D) Succinic acid

+
8.22 LAH HBr NaCN H3O ,CaO, CaO,
C4H6O4(X) Y hexanedioic acid
O
(A) X is (B) Y is O (C) X is CH2 – COOH (D) Y is O

O O
CH2 – COOH
8.23 O
+
AlCl3 Na2Cr2O7, H heat heat
Ph(CH2)5 – C– Cl (X) (Y) (Z)
CH2 COOH
(A) X is (CH2)4 (B) Y is
C COOH
O
CO CHO
(C) z is O (D) Y is
CO COOH
8.24 trans-2-methylcyclohexanol + acetyl chloride  X


X + NaOH (aq)  Y + sodium acetate.
(A) X is CH3 H (B) X is H H
H O – C – CH3 CH3 O – C – CH3
O O
(C) Y is H H (D) Y is CH3 H
CH3 OH H OH
8.25 In which of the following reactions cprrect ,akpr [rpdict os ,emtopmed ?

O O O
+
(A) H
+ CH3OH HO OCH3
O
OH O–C–CH3
H2SO4
(B) + CH3–C–O–C–CH3 + CH3COOH
COOH fast
O O COOH
(asprin)
CH2–CH3
CH2–CH3
(C) CH3–C–O–C
1. OH CH3–C–OH + HO–C
2. H H
O H O CH3
CH3
H H
(D) CH3–C–CH3 + Ph–C–OH H2SO4
CH3–C–CH3
OH O O–C–Ph
18 18
O

8.26 Statement-1 : Electron releasion group at para position of a migration aryl group enhances, the
rate of reaction in Hofmann's preparation of primary amine from amides.
Statement-2 : R +
C—N—Br Br + R—N—C=O R—N=C=O
O
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-
1.
Statement-1.
8.27 Statement-1 : The base catalysed hydrolysis of ester order is

(1) CH3–COOCH3>CH3–COOC2H5>CH3–COOCH(CH3)2.
COOC2H5 COOC2H5 COOC2H5 COOC2H5
(2) > > >
NO2 Cl CH3 OCH3

Statement-2 : SN2 Th is sterically as well as electronically controlled reaction.
Statement-1.
8.28 Statement-1 : C–O bond length is shorter in an ester as compared with an anhydride.
Statement-1 : A dregree of cross conjugation exist in the anhydride which decreases the
delocalisation to each carbonyl oxygen.
Statement-1.
8.29 Statement-1 : Acid catalysed hydrolysis of eater is reversible while base catalysed hydrolysis
is irriversible.
Statement-2 : IN acid catalysed ester hydrolysis carboxylic acid is formed on which nucleophilic
attack of alochol is possible but in base catalysed ester hydrolysis carboxylate anion is formed
on which nucleophilic attack is not possible.
Statement-1.
SECTION - IV : TRUE AND FALLSE TYPE

8.30 If these statements are true or truke or false mark T and F.
(A) CH3COCI > (CH3CO)2O > CH3COOEt > CH3CONH2 (Rate of hydrolysis)
(B) CH3
CH3–CH2–COOH > CH3–CH–COOH > CH3 COOH (Rate of esterification)

CH3 CH3
(C) OH OH OH
> > (Rate of esterification)
ON2
(D) O O
CH3–C–COOH > CH3–C–CH2–COOH > Ph–CH2–COOH (Rate of decarboxylation)

Comprehension # 1
Observe the esterfication mechanisms for primary and tertiary alcohols.
Type.1 O
CH3–COOH + CH3–CH2–CH2–OH Conc. H2SO4 CH3–C–O–CH2–CH2–CH3
Propyl = Pr
Mechanism
O OH OH O
H
OH O
Pr H Step 3
CH3–C CH3–C CH3–C CH3–C–OH CH3–C–O–CH2–CH2–CH3
Step 1. Step 2 –H
OH OH OH –H2O
O
Pr H
OH CH3
CH3
Type. 2
CH3–C + CH3–C–OH Conc. H2SO4 CH3–C–O–C–CH3
OH CH3
CH3 O
O–H
CH3 CH3 CH3–C CH3
H O
Mechanism CH3–C–OH CH3–C + H2O CH3–C–O–C–CH3
Step 1.
CH3 CH3 CH3 O
8.31 Conc.H2SO 4
CH3 – COOH + C2H518OH   (P)
CH3 – COOH + (CH3)3C – Conc.H2SO 4

OH 18
 (Q)
In the above reaction (P) and (Q) are respectively :
O O CH3 O O CH3
18 18
(A) CH3–C–O–C2H5, CH3–C–O–C–CH3 (B) CH3–C–O–C2H5, CH3–C–O–C–C2H3
CH3 CH3
O O CH3 O O CH3
18 18 18
(C) C2H5–C–O–CH3, CH3–C–O–C–CH3 (D) CH3–C–O–C2H5, CH3–C–O–C–CH3
CH3 CH3
8.32 H
Conc.H2SO4
CH3COOH + D OH (X)
CH3
CH3
Conc.H2SO4
CH3–COOH + Ph–C–OH (X)
C2H5
(A) (X) is optically active while (Y) is optically inactive

(B) Both (X) and (Y) are optically active
(C) (X) is optically inctive while (Y) is optically active.
(D) (X) is optically inactive while (Y) is optically active.
8.33 (+) Octan-2-ol esterifies with Acetic acid to give optically inctive racemised product. It must have
gone by
(A) Type I mechanism (B) Type II mechanism
(C) Mix type I and type II mechanism (D) More by type I lessw by type II mechanism
Comprehension # 2
Observe the following sequence of reaction and answer the questions based on it
CH3MgBr i) CO2 H2O/H2SO4
Phenylacetylene x y z w
– CH4 HgSO4
8.34 Compound z is
O
COOH
(A) Ph – CH2 – C – COOH (B) Ph – CH
COOH
O
(C) Ph – C – CH2–COOH (D) Ph – CH2– COOH
8.35 Which of the following statement is not correct

(A) y decolooureses Br2/H2O solution
(B) onb heationg z CO2 is liberated
(C) w on reaction with NaOI gives yellow ppt
(D) x liberates H2 gas with Na metal
8.36 Which of the following compound give benzoic acid on KMnO4 oxidation
(A) w (B) y (C) z (D) all.
Comprehension # 3
HOFMANN REARRANGEMENT
In the Hofmann rearrangement an unsubstituted amide is treated with sodium hydroxide and
bromine to give a primary amine that has one carbon lesser than starting amide.
General reaction.
O
hydrolysis
R – C – NH2 + NaOH + Br2 R–N=C=O R – NH2
isocyanate
Mech :
O O O
O
OH Br – Br R – C – NH – Br OH R – C – N – Br
R – C – NH2 R – C – NH
O OH
OH
CO2 +R–NH O – C – NH – R O–C=N–R O =C = N– R
H2O
R – NH2
If the migrating group is chiral then its cofiguration is retained. Electron releasing effects in the
migrating group increases reactivity of Hofmann rearrangement,
8.37 Which of the following compound (s) cannot gibve Hofmann rearrangement :
CH3 O
(A) C C NH2 (B) CH3–CH2–C–NH–Ph
CH3O
O O
(C) NO 2 C NH2 (D) Ph–C–NH2
8.38 Arrange the following amides according to their relative reactivity when react with Br2 in excess
of strong base
O O
C NH2 H3C C NH2
I II
O O
C2N C NH2 Cl C NH2
IV IV
(A) IV > I > II > III (B) II > I > III > I (C) II > IV > III > I (D) II > I > IV > III
8.39 O D O
15 Br2/KOH
H3C–H2C–CH–C–NH2+ CH3–CH2–C–C–NH2 Products
CH3 CH3
(R) (S)
D D
15 15
(A) H3C–H2C–CH–NH2 & H3C–H2C–CH–NH2 (B) H3C–H2C–C–NH2 & H3C–H2C–CH–NH2
CH3 CH3 CH3 CH3

(S) (R) (S) (R)
D
15
(C) H3C–H2C–CH–NH2 & H3C–H2C–CH–NH2 (D) B & C both are correct
CH3 CH3
(R) (S)

8.40 Column-I Column-II
O
C2H5O (p) Hydrolysis
(A) C 2H 5–C–OH
O
(B) C 2H 5–C–OH
C2H5OH/H (q) Esterification
O
H 3O (r) Saponification
(C) C2H5–C–OC2H5
O
OH (s) Acid base reaction
(D) C2H5–C–O C2H5
8.41 Match the column I with column II.
Column-I Column-II
CH3
HOOC COOH
(A) (p) Diastereomer
H D
Ph
COOH
D H
1. AgOH /
(B) H C
H 2. Br2 / CCl4
(q) Racemic mixture
3
Ph
CH3
(C) HOOC COOH

(r) Optically active
Et
(D) Ph–C–CD–C–OH
(s) CO2 gas will evolve
O CH3 O
SECTION-VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE :
8.42 Two stereoisomers (cis and trans) of 3, 4-Dibromocyclopentane-1, 1-dicarboxylic acid undergo
decarboxylation, find out the total number of product formed.
Et O O Et
H2O
O S O S O (Products)
8.43 warm
Me O O Me
The total number of products obtained in above reaction is.
8.44 Cl CH2—COOH
–
C2H5OH (i) C2H5ONa (i) OH + H+
A (ii) CH3–l
B + C D
(ii)H
NO2
The reaction are
If aliphatic nucleophilic substitution reaction then assign = 3.
If aromatic nucleophilic substitution reaction then assign = 4.
If esterification reaction then assign = 1.
If dehydration reaction then assign = 2.
The formation of products ABCD are the corresponding reaction, of mark the numbers.
A B C D
8.45 If formic acid,m acetic acid, propanoic acid and benzoic acid is mixed with Phosphorus and
Bromine then how many product are formed.
Ph CH3
H C NH2, CH3 C NH2,and H C NH2,

8.46 When is mixed and reacted with Br2/KOH
D O O D O
then how many products are obtained.
Biomolecules
9 (Carbohydrates, Amino acids & Polymers)

9.1 CHO
H OH HO H
H OH H OH
H OH
O HO H H O
HO H HO
H OH H OH
H OH
H OH H
H
CH2OH CH2OH
CH2OH
The above process in which  and  form remain in equilibrium with acyclic form and a change
in optical rotation is observed which is called as-
(A) Mutarotation (B) Epimerisation (C) Condensation (D) Inversion
9.2 How many moles of HIO4 is required to brak down the following molecule?
CHOCH3
H OH O
H OH
H
CH2OH
(A) 1 (B) 2 (C) 3 (D) 4
9.3 Glycoside linkage is :

(A) an acetal linkage (B) an ether linkage (C) an ester linkage (D) an amide linkage
9.4 Observbe the following laboratory tests for -D (+) glucose and mention +ve or –ve from the
code given below.
2, 4 DNP
(l)
NH2OH/H
(ll)
– D (+) glucose
Tollen's reagent
(lll)
NaHSO3
(lV)
(A) + + + + (B) – + + (C) + – + – (D) + + – –
9.5 Nitrous acid (HNO2) converts amino acids into hydroxy acids with retention of configuration.
Estimation of nitrogen gas evolved in the reaction is the basis of Van slyke estimation of amino
acids.
NH2 OH
HNO2
R – CH – COOH R – CH – COOH + N2 + H2O
Which of the following amino acids cannot be analysed by Van slyke method?
NH2
I – HS – CH2 – CH – COOH (cysteine)
II – (Proline)
N COOH
NH2
CH2 – CH – COOH
III – H – N N (Histidine)
NH2
CH3 – CH – CH – COOH
IV – (Valine)
CH3
Codes :
(A) only I (B) only II (C) IandIII (D) I, III, IV
9.6 HOOC – CH2 CH2 – Ph
H2N – CH – CO – NH – CH – COOCH3
(Aspartame)
Aspartame is 160 times as sweet as sucrose and is used as a sugar substitute.

the correct statement (s) about aspartame is (are)
I – It is an eswter derivative3 of dipeptide
II – It can be named as aspartyl phenylalanine methyl ester
III – It is a tripeptide
IV – It is having four functional groups.
(A) I, II (B) I, II, IV (C) II, III, IV (D) only II
9.7 Polymer which has amide linkage is

(A) Nylon-66 (B) Terylene (C) Teflon (D) Bakelite
9.8 Which of the following is condensation polymer

(A) Polystyrene (B) PVC (C) Polyester (D) Teflon
9.9 Which of the following aldohexoses give the same osazone derivative ?
CHO CHO CHO CHO
H OH HO H HO H HO H
HO H H OH HO H HO H
H OH HO H H OH HO H
H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH
1 ll lll lV
(A) I and IV (B) I and III (C) II and III (D) III and IV
9.10 Which of the following is a non-reducing sugar ?
H
OH CH2OH
HO OH CH2OH O O O
CH2OH O O HO H
(A) O (B) HO OH H OH
CH2OH HO
HO OH H
HO H OH
CH2OH O H CH2OH O O
CH2
HO
(C) HOHO OH O O CH2OH (D) HO OH H
HO
O
OH
HO OH HO
OH
OH H
9.11 Basic solution of fructose contains :

(A) Only fructose (B) Only glucose
(C) Fructose and glucose (D) Glucose, fructose and mannose
9.12 Which of the following is a nonreducing sugar ?

CH2OH CH2OH
O O
H H H H
(B) H
(A) OHCH2 – C – (CHOH)3 – CH2OH H
OH H OH H
OH OH
O
O
H OH H OH
CH2OH
O
H H
CH2OH CH2OH CH2OH
H
OH H
O O O OH
H H H OH H O
H H H
(C) (D) H OH
OH H H OH OH H
OH O H OH H
H OH OH H H OH
9.13 Which one of the following is non-reducing sugar ?

(A) Glucose (B) Mannose (C) Fructose (D) Sucrose
9.14 Glucose and mannose are :

(A) Anomers (B) Positional isomers (C) Functional isomers (D) Epimers
9.15 Basic solution of fructose contains :
(A) Only fructose (B) Only glucose (C) Fructose and glucose (D) Glucose,
fructose and mannose
9.16 How many moles of acetic anhydride (Ac2O) is needed to react completely with tataric acid,
ribose and glucose respectively.
Tataric acid Ribose Glucose
CH2OH
COOH CHO
OH H O HO
H
H OH H
H OH OH H
H OH HO H HO H
COOH CH2OH H OH
(A) 2,4, 5 (B) 2, 3, 4 (C) 4, 5, 6 (D) 4, 5, 5
9.17 Which of the following amino acid is most basic :
(A) H2N–C–NH–CH2CH2CH2–CH–COOH (B) H2N – CH – C – NH – CH2 – COOH

NH NH2 CH3
CO2H
(C) HOOC – CH2 – CH – COOH (D) HS
NH2
NH2
9.18 Glucose on reduction with Na/Hg and water gives ?

(A) Sorbitol (B) Fructose (C) Saccharic acid (D) Gluconic acid
9.19 What will be product when glycine, is heated-

H
O O O
N O
Me Me
(A) H – N N–H (B) H H (C) (D)
N N–H N–H
O N–H
O
H
9.20 Salicin (structure given below) is a glycoside, found in the bark of willow tree, used in relieving
pain. Observe the following reaction of salicin.
CH2OH CH2OH
O O
H
H
dil. HCl P +Q
OH H
HO Carbohydrate
H OH
Salicin
The correct statement (s) is (are)
(A) P is D- glucose
(B) Q is 2-hydroxybenzylalcohol
(C) Q can be converted to a modern anlgesic (pain killer), aspirin
(D) The above reaction occurs through a carbocation
9.21 F H H
O2N O
+ H2N C NH COOH
2. dil. NaOH
CH3 CH2
NO2
Ph
The products can be
H
NO2
O2N NO2
H NH COO
(V) CH3
NH COO
O2N
CH2Ph
NHAC H
NO2
(D) NH2 COOH
CH2–Ph
NO2
9.22 Glucosazone is osazone derivative very similar to that formed from

(A) Fructose (B) Galactose (C) mannose (D) glucose
9.23 The correct statements about peptides are

(A) A dipeptide has one peptide link between two amino acids.
(B) By convention N-Terminus is kept at left and C-terminus at right in the structure of a peptide
(C) If only one amino group and one carboxylic acid, group are available for reaction, then only
one dipeptide can forms.
(D) A polypeptide with more than hunderd amino acid recidues (mol. mass > 10,000) is called
a protein
9.24 The correct statements about anomers are

(A) Anomers have different stereochemistry at anomeric carbon atom
(B) a-D-glucopyranose and b-D-glucopyranose are anomers
(C) a-D-glucopyranose and b-D-glucopyranose are diastereomer
(D) When pure a-D-glucopyranose is dissolved in water its optical rotation slowly changes
9.25 Observe the following reaction and mark the correct statements (s) given below-
H MeO H
CHO OMe
C C
H OH H OH
H OH
HO H MeOH HO H O
HO H O
H OH +
dry HCl H OH H OH
H OH
H H
CH2OH CH2OH CH2OH
D-glucose
(A) Methyl glucosides do not react with Fehling's or Tollen's reagent.
(B) The reaction passes through a carbocation
(C) The two forms of glucosides are enantiomers
(D) The non-reducing charcter of glucoside indicates the absence of free-CHO group in it.
9.26 Statement -1 : Gly-Ala is a structukral isomer of Ala-Gly.
statement -2 : In Ala-Gly, Alanine is the N - terminal amino acid.
Statement-1.
9.27 Statement-1 : Glucose and Fructoswe give the same osazone on reaction with excess of
phenyl hydrazine.
Statement-2 : Osazone formation involves C1 and C2 carbon but doesn't affect the other
stereocenter and glulcose and fructose have same configuration at C3, C4 and C5 carbon atom.
Statement-1.
9.28 Statement-1 : Hydrolysis of sucrose brings a change in sign of rotation towards plane polarised
light.
Statement-2 : Fructose has specific rotation – 92.4 and glucose has +52.5°
Statement-1.
9.29 Statement-1 : Pentacentate of glucose does not form oxime on treatment with H2N–OH
Statement-2 : Glucose on reaction with acetic anhydride forms pentacetate under suitable
conditions.
Statement-1.
9.30 Statement-1 : Methy -D-fructofuranoside (I) undergoes acid catalysed hydrolysis at faster rate
than that of methyl -D-glucofuranoside (II).
CH2OH
HO H
HOH2C O CH2OH
O H
H HO
H OCH3 OH H
H OCH3
HO H H OH
(I) (II)
Staftement-2 : The intermediate carbocation in case of I is more stable than in case of II.
Statement-1.

9.31 Mention true (T) and false (F) out of the following
S1 : Sucrose gives negative tests with benedict's and Tollen's solutions.
S2 : Sucrose does not form and osazone
S3 : Sucrose does not undergo mutatotation
S4 : Octamethyl derivative of sucrose, on hydrolysis, gives 2, 3, 4, 6-tetra-O-methyl-D-glucose
and 1, 3, 4, 6-tetra-O- methyl D-fructose
S5 : One mole of sucrose on acid hydrolysis yields one mole of D-glucose and one mole of D-
fructose codes :
(A) T T T T T (B) F T F T F (C) F F F T T (D) T F F F T
9.32 The true/false statements about the following compounds are :
CH2OH CH2OH CH2OH
H H H
O O O
O H H H
OH H O OH H O OH H O
H H H
H OH H OH H OH
S1 : This carbohydrate polymer is composed of -D(+) glucose.

S2 : It has a-(1, 4) glycosidic linkage
S3 : It is a non-reducing carbohydrate
(A) T T T (B) T F T (C) T F F (D) F F T
Comprehension # 1
An amino acid is charcterized by two pKa values the one corresponding to the more acidic site
is designated as pKa1 and the other corresponding to the less acidic site is designated as pKa2
The isoelectric point also called isoionic point (pI) is the pH at which concentration of zwitter ion
is maximum. pI is the average of pKa1 and pKa2. Generally the value of pI is slightly less than 7.
Some amino acids have side chain with acidic or basic groups. These amino acids have pKa3.
value also for the side chain. Acidic amino acid have acidic side chains amino acids have basic
side chains. pI for acidic amino acid is average of pKa1 and pKa3. pI for basic amino acid is the
average of pka2 and pKa3.
S.No. Amino acid P Ka1 P Ka2 P Ka3 (side chain)

l Aspartic acid 1.88 9.6 3.65
ll Glutamic acid 2.19 9.67 4.25
lll Lysine 2.18 8.95 10.53
lV Arginine 2.17 9.04 12.48
9.33 In the table given above the acidic amino acids are
(A) I, II (B) I, III (C) II, III (D) I, II, IV
9.34 The isoelectric point (pI) of Aspartic acid will be

(A) 6.62 (B) 5.74 (C) 2.77 (D) 9.74
9.35 The isoelectric point of lysinge will be
(A) 6.35 (B) 9.74 (C) 2.77 (D) 10.76
Comprihension # 2
CH2OH CH2OH CH2OH CH2OH
H O H O H H O H H O H
H
H H Dimerisation H H
OH H + OH H OH H OH H
(–H2 O) O
OH OH OH OH OH OH
H OH H OH H OH H OH
(I) (II)
Polymerisation
  Starch (polymer) (III)
9.36 What is true abouit compound (I)

(A) It has an acetal strukctukre (B) It has tertiary hydroxy group
(C) It has a hemiacetal structure (D) It's degree of unsatkuration is two
9.37 Compound (II) is/has

(A) A polysaccharede (B) Oligosacharide
(C) Monosaccharide (D) Hydrogen deficiency index is three
9.38 Assuming that polymerisation of (I) takes place in the manner similar to its dimerisation, then
the structurr os polymer (III) can be correctly represented as
CH2OH CH2OH
H O H O
O O
H H
H H (B)
(A) O O OH H
H H
OH OH OH OH
n n
CH2OH CH2OH
O H H O H
H H
(C) OH H (D) OH H
O O
H
H OH H OH
n n

9.39 Match the following column-I with column-II :
Column-I Column-II
(A) starch (p) Natural polymer

(B) Nylon-6 (q) Synthetic polymer
(C) Peptide Bond (r) Amide linkage
(D) Maltose (s) Glycoside Iinkage
(t) Oligosaccharide
9.40 Match the Column-I with Column-II.
Column-I Column-II
(A) Natural rubber (p) Thermosetting polymer

(B) Nylon-66 (q) Homopoluymer
(C) Bakelite (r) Butadiene & styrne
(D) Buna-S (s) Polyamide
(t) Copolymer
9.41 Match the Column-I with Column-II.
Column-I Column-II
(A) Fructose (p) Protein

(B) Zwitterion (q) Inversion
(C) Peptide linkage (r) -Amino acid
(D) Hydrolysis of cane sugar (s) Carbohydroate
(t) Ketose

SHORT SUBJECTIVE :
9.42 Lysine has 2 amino groups having pka1 = 2.2, pka2 = 8.5 and pka3 = 10.5 :
+
NH3 (2)
(1) H3+NCH2CH2CH2CH2CHCO2H (3)
(A) At pH = 4 the hydrogen atom (H+) is lost from -
(B) At pH = 9.5 the hydrogenatom (H+) is lost from -
(C) At pH = 13 the hydrogen atom (H+) is lost from -
HS––CH2––CH––COOH
9.43 The pka1, pka2 and pka3 values for the amino acid cysteine are
NH2
respectively 1.8, 8.3, 10.8. What is isoelectric point of cysteine amino acid ?
9.44 Give the amino acid sequence of the following polypeptides using the data given by partial
hydrolysis.
2 4 3 1 + A B C D
(a) (Ser, Hyp, Pro, Thr) H3O Ser, Thr + Thr, Hyp + Pro, Ser
9.45 The number of dipeptides that can be made from alanine and glycine are.
9.46 Observe the following reaction and find out that how many number of reactant stereoisomers
cand be reduced to optically inactive meso products.
CHO CH2OH
CHOH CHOH
CHOH NaBH4 CHOH
CHOH CHOH
CHOH CHOH
CH2OH CH2OH
10 Practical Organic Chemistry
SECTION - I : STRIGHT OBJECTIVE TYPE

10.1 Which one of the following will not give white precipitate with ammonical silver nitrate solution
(A) CH3 – C C – CH3 (B) CH3 – CH– C C – CH3
CH3
(C) CH3 – CH2– CH = CH2 (D) All of these
(i) Na metal
No H2 gas evolved
(ii) Cl2/h 3-monochloro
Compound C4H10O
10.2 products
(iii) Lucas reagent
–Ve test
Compound is
O
(A) (B) (C) O (D)
O O
10.3 An aromatic compound A (C8H10O) gives following tests with the given reagents.
Na metal
Positive
FeCl3 (neutral)
A(C8H10O) Negative
Lucas reagent
Positive
Anhydrous ZnCl2/HCl
Identify 'A'
OCH3 OH OH
CH2 – CH2 – OH
CH3 CH2–CH3
(A) (B) (C) (D)
CH3
CH3
10.4 Br2/H2O
Bayer's reagent
C4H6
(X) Na metal
(A) H3C – C C – CH3 (B) CH2 = CH – CH = CH2

C CH
(C) CH3 –CH2 – C CH (D)
10.5 The following two compounds I and II can be distinguished by using reagent
OH HO
COOH COOH
(1) aq. NaHCO3 (2) Neutral FeCI3 (aq.) (FfeCI3 + NH4OH + H2O)
(3) Blue litmus solution (4) Na metal (5) HCI (ZnCI2 anhydrous)
(A) 1 or 3 (B) 2 or 5 (C) 4 or 5 (D) 3 or 4
10.6 Tollen's regent (AgNO3 + NH4OH) can be distinguished between
O O O
O
(A) H–C–H and Ph–C–H (B) H and H H
O O
D O Me
C C=O
(C) and (D) Ph–C–Ph and Me–C–Me

O O
C=O
Me
10.7 Observe the4 following compound and select +Ve & –Ve tests respectively
(i) Na metal
HO C CH (ii) NaHCO3
(iii) 2,4-DNP
OHC COOH
(iv) Lucas reagent
(A) + + + – (B) + + + + (C) + – + – (D) + – – +
10.8 Consider following compounds and decide as to which of the following statements are true ?
CH3 CH3 CH3
CH2 = CH – C – COOH CH3 – C – OCH3 CH3O–C C–H CH3 – C – CH2OCH3

H CH3 OH
(I) (II) (III) (IV)
(A) (II) gives no reaction with Na metal, however, 1 mole of (IV) on reaction with Na metal
willliberate 22.4 litres of H2 gas at STP
(B) (I) will give brisk effervescence on addeition of NaHCO3 but will not bring any change in the
colour of Br2 water
(C) (III) Iiberates H2 gas with Na metal, gives white precipitate with Tollen's reagent but does not
respond towards lucas reagent or 2, 4-DNP test.
(D) (IV) gives turbidity with anhydrous ZnCI2
10.9 An aromatic compound 'X' (C9H8O3) turns blue litmus to red.It gives yellow precipitate with I2/
NaOH and forms Y (C8H6O4).Y forms three mononitro isomeric products. Identify X.
COCH3 COCH3 COCH3
COOH
(A) (B) (C) (D) none of these
COOH
COOH
10.10 Which will not give iodoform reaction with I2/OH–?
(A) CH3COCH2CH3 (B) CH3CONH2 (C) C6H5COCH3 (D) CH3CHO
10.11 Compound Y1C7H8O is insoluble in water, dil HCI and aqueous NaHCO3.It dissolves in dilute
NaOH. When Y is treated with bromine water it is converted rapidly into a compound of formula
C7H5OBr3.Identfy the structure of Y
OH OH O–H O – CH3
CH3
(A) (B) (C) (D)
CH3
CH3
10.12 Compounds I and II can be distinguished by using reagent
(I) (II)
4-Amino-2-methlbut-3-en-2-ol 4–Amino–2, 2-dimethylbut-3-yn-1-ol.
(A) NaNO2/HCI (B) Br2/H2O
(C) HCI/ZnCI2 (anhydrous) (D) Cu2CI2 + NH4OH
10.13 Compound P(C6H10) does not have any geometrical isomer. ON ozonolysis, two products
R(C3H4O) and Q(C3H6O) are formed. R gives negative iodoform test while Q responds positively
towards I2/NaOH solution. S, another isomer of P is an unsyumetrical alkene and on ozonolysis
produces T(C6H10O2) which also gives a yellow precipitate with I2/NaOH solution and also gives
positive test with Tollen's reagent. Which of the following does not represent any of the molecules
amongst P,Q,R,S&T.
H OO H H OO H
(A) O (B) (C) (D)
10.14 A set of reagents (1 to 8) are successively reacted with the followit compound
O
OH
OH
1. NaHCO3 2.2, 4, DNP 3.Na metal 4. AgNO3 +OH

5. Fehling's solution 6.Cu2CI2 + NH4OH 7. Br2/H2O 8. NaNO2 + HCI
The reagents which give positive test with the given compound are :
(A) 1, 2, 3, 4, 5 (B) 3, 4, 5, 6, 8 (C) 1, 2, 3, 4, 8 (D) All reagents except 1
and 8
10.15 Compounds (C8H8O) X will give following laboratory tests.
Isomers FeCl3 AgNO3 / NH4OH Na metal

X Coloured solution Negative 1/2 H2
X can be :
H3C O
OCH3 CH2OH OH
O
(A) (B) (C) (D)
CH = O CHO CH = CH2
OH
10.16 Which of the following alcohol will show positive iodoform test ?
OH OH
(A) CH3 – CH – CH2 – NO2 (B) CH3 – CH– CH2 – COOH
OH
(C) ICH2 – CH – CH2 – CH3 (D) none of these
10.17 The compound A gives following reactions.

Na metal
H2 gas
2, 4-DNP
A(C6H8O2) yellow orange ppt
O3
B(C6H8O4)
Its structure can be

(A) CH2=CH–(CH2)2–C– CH2OH (B) OHC–(H2C)2–HC = HC – COOH
O
OH OH
(C) (D)
O CHO
10.18 In compound A (C30H60O) following tests are observed negatively, A can be :
Br2 / H2O
-Ve
2, 4 DNP
C30H60O -Ve
(A) Na metal
-Ve
(A) an unsaturated ether(B) an epoxide (C) a cyclic ketone (D) a cycloalkanol
10.19 A mixture of two orgnaic compound gives red coloured precipitate with cuprous chloride
(ammonical) and silver mirror on heating with Zn dust and NH4CI followed by AgNO3 + NH4OH
solution. The mixture contains
O COOH COOH
NH2
(A) CH3–(CH2)8–CHO and (B) and
NO2 NH2
CHO CHO CHO
(C) and (D) and
NO2
10.20 2D, 3D, 4D, 5D, 6-Pentahydroxy hexanal can give.
(A) Tollen's Test (B) Lucas Test (C) 2, 4-DNP Test (D) FeCI3 Test
10.21 Compound X and Y both have the same molecular formula (C4H8O). They give following observation
in some lab test.
Test X Y
Br2–water positive negative

Na–metal positive negative
Lucas reagent turbidity after some time negative
lodoform test negative negative
The compound X and Y are
(A) OH (B) OH (C) OH (D) O
10.22 Compound 'P' (C10H12O) evolves H2 gas with Na metal. It reacts with Br2/CCI4 to give 'Q'
(C10H12Br2O). With I2/NaOH it forms iodoform and an acid 'R' (C9H8O2). 'P' has geometrical and
optical isomers. The structure of 'P and R' should be
COOH
(A) (B) PH – CH = CH – COOH
CH=CH2
OH
CH = CH – CH – CH3 CH = CH – CH3
(C) (D)
OH
10.23 compound (X) C9H10O is inert to Br2/CCI4.Vigorous oxidation with hot alkaline KMnO4/OH yields
C6H5COOH. (X) gives precipitate with 2,4-dinitrophenyl hydrazine. How can these isomers be
distinguished by the usual chemical tests?
Following are possible isomkers of X :
(l) C6H5 – CH2 – CH2 – CHO (l) C6H5 – CH – CHO
CH3
O O
(lll) C6H5 – CH2 – C – CH3 (lv) C6H5 – C– CH2 – CH3
(I) C6H5 – CH2 – CH2– CHO

(A) I gives red ppt. with Fehling solution and II & III cand be distinguished by iodoform test
(B) I & II can be distinguished by simple chemical method
(C) I & II give red ppt. with Fehling solution and III & IV can be distinguished by iodoform test
(D) II give red ppt. with Fehling solution and I & IV can be distinguished by iodoform test.
10.24 Which is/are the correct method for separating a mixture of benzoic acid, p-methylaniline &
phenol.
aq.NaHCO3
(A)  aq.NaOH aq.HCI
(B)  aq.NaHCO3
     
aq.NaOH
(C)  aq.NaHCO3 aq.NaOH
(D)  aq.HCI
     
10.25 Statement -1 : Only one Aldehyde 'X' responds positively with all the tests of carbonyl compounds
like Tollen's test, Fehling test, 2, 4-DNP test, as well as iodoform test.
Statement-2 : All aldehydes respond all the four tests given in assertion.
Statement-1.
10.26 Statement-1 : A mixture os p-methylbenzoic acid and picric acid is separated by NaHCO3
solution .
Statement -2 : p-Methylbenzoic acid is soluble in NaHCO3 because it give effervesence of CO2
Statement-1.

10.27 Give the correct order of initials T or F for following statements. Use T if statement is true and
F if it is false. X (molecular formula, C7H6O2) is and aromatic white solid which liberates
colourless, odourless gas on rescting with NaHCO3.
S1 : Only three of th3e five functional isomers of X (including 'X' itself) will give positive 2, 4-DNP
test.
S2 : The liberated colourles, odourless gas will contaning radioactive 14C.
S3 : Except 'X', no other functional isomer will liberate colourless odourless gas with NaHCO3.
S4 : The DU of higher homolog of 'X' will be four.
(A) TTTF (B) FTTF (C) FTTT (D) TTFF

Comprehension # 1
Observe the following sequence of reactions
O3 / Zn,H2O
P (C9H9Br) R + Q
reductive (i) Tollen's Reagent
+
(ii) H
(s) + Ag
P shows geometrical isomersm. Q gives positive Tolen's test and the oxidation product of
Tollen's test followed by acidification is the strongest acid among its all position isomers. R gives
positive lab tests with 2,4-DNP, Fehling solution and I2/NaOH reagents.
10.28 The compound P can be

CH2– CH = CH2 CH= CH – CH3
Br Br
(A) (B)
CH= CH – CH3
CH= CH – CH3
Br
(C) (C)
Br
10.29 What could be the structure of Q ?
CHO COOH CHO CHO
Br
(A) (B) (C) (D)
Br CH3
CH3
10.30 Identify the structure of R
(A) HCOOH (B) CH3CHO (C) BrCH2 – CHO
Comprehension # 2
An aromatic compound T (C10H10O2) give 2 moles of CHI3 and compound U (C8H4O4Na2) On
treatment with I2 and NaOH. After acidification U gives two mononitro produicts on nitration.
10.31 Compound (T) can aoso be obtained by ozonolysis of V, in this ozonolysis one mole of OHC
– CHO is obtained alongwith (T). Possible structure for Compound V could be
CH3
CH3
CH3
(A) (B)
CH3
CH3
CH3
(C) (D)
CH3
CH3
10.32 Which of the following statement is true
O O
H3 C C CH3
(A) T is C
(B) Compound (V) decolourises pink colour of diluted solution lkof KMnO4.
(C) All isomers (only acidic) of U after acidification gives one mole of CO2 with NaHCO3
(D) After acidification of (U), it is most acidic in its all other isomers.
10.33 Compound U is
COONa COONa COONa COONa

COONa
(A) (B) (C) (D)
COONa
O H COONa
C
||
O
10.34 X(C8H14) by ozonolysis forms Y[C8H14O2]. Y on reaction with NaOI followed by acidification gives
CHI3 and compound Z on strong heating forms W.
Column-I Column-II
(A) Compound X (p) Bayer's Test

(B) Compound Y (q) NaHCO3
(C) Compound Z (r) 2, 4-DNP
(D) Compound W (s) Iodoform Test
(t) Na Metal
10.35 Match the following : (More than one option in column - II may match with single option in
column-I)
C C–H
(A) Sodium metal (X)
O
CH3
C – CH3
(B) Sodium bicarbonate (Y)
OH
C CH
(C) 2, 4-Dinitrophenylhydrazine (Z)
OHC COOH
CH = CH2
(D) Lucas reagent
(W) H3CO
C OH
O

SHORT SUBJECTIVE :
10.36 A water insoluble organic mixture contained following compounds
(1) = Benzoic acid (2) = salicylaldehyde
(3) = p-Hydroxybenzaldehyde (4) =a-Naphthylamine
(5) = Naphthalene
The following sequence of reagents are uksed to separate this mixture
1 + 2 + 3 + 4 + 5 mixture
(Step-X) aq. HCI
[Insoluble] [Soluble]*
(Step-Y) aq. NaHCO3
[Insoluble] [Soluble]*
(Step-Z) aq. NaOH
[Insoluble]* [Soluble]
(Step-W) Steam distillation
[distilled]* [left behind]
Fill up the serial number of starred compound ontained in the steps X, Y, Z and W reapectively.
X Y Z W
10.37 How many acidic H is present in given compound.

O OH
O
OH
10.38 How many CHI3 will be released from the given compound.
O O
|| || l2 / NaOH
10.39 How many molecule of phenyIhydrazine is used to form osazone from glucose.
N––NH
CHO
H OH
N––NH
HO H 3Ph–NH–NH2
Hint : HO H + Ph––NH2 + NH3
H OH
H OH
H OH OH
H
CH2OH
CH2OH
10.40 How many CHI3 will be released from given compound.
O O
|| ||
H2N OCH3
O
O

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General Organic Chemistry-I

1.3 The correct IUPAC name of the folllowing compound is

(A) 5,6-Diethyl-8-methyl dec-6-ene (B) 5,6-Diethyl-3-methyl dec-4-ene

1.4 Correct IUPAC name of the following compound is :

1.5 The IUPAC name of the compound will be :

(A) Tropyluim bromide (B) 1-Bromocyclohepta-2,4,6-triene

(A) 2-Ethyl-3-methylbut-2-ene-1,4-dioic anhydride

1.11 Identify the structure of x,

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

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

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

1.15 C–O and H–C–O are

1.16 In which reaction a chiral reactant is giving a chiral product.

(B) The most stable conformation will be COOH

1.18 An unsaturated hydrocarbon on jcomplete hydrogenation gives 1-isopropyl-3 methylcyclohexane,

1.19 How manyh assymmetric carbon atoms are present in

1.20 Which of the following statements is not correct?

1.21 Identify the pair of enantiomers amongst the given pairs:

COOH OH CH3 CH3

SECTION-II : MULTIPLE CORRECT ANSWER TYPE

1.24 Consider following compounds

1.26 Which of the following is\are a meso compoumd.

(B) Chain Isomer

NH – C3H7 H3C – N – C2H5

(C) Functional Isomers

(D) CH3–CH2–CH2–C–OCH3 CH3–CH2–C–OCH2–CH3 Metamer Isomers

SECTION-IV : TRUE & FALSE STATEMENT TYPE

1.31 compound(V)and (W)are

1.32 Compound (Y)can give........ type of oximes on treatment with NH2-OH

1.33 Which of the following statement is true

1.34 The pair showing identical species is

1.38 Column I Column II

CHO CH 3 CHO CHO (q) Can not be separated by

1.40 Cl2 / hv Fractional

Number of possible fractions of B are:

1.42 Number of sp2-sp2 sigma bonds in viven compound A is:

2.2 The correct stability order of following species is :

(A)x>Y>w>z (B)y>x>w>z (C)x>w>z>y (D)z>x>y>w

(A) (B) (C) – + (D) + –

2.4 The most stable resonating structure of CH3 – O = CH = CH2 :

The reason for this is

(A) Cl (B) CH3 (C) COCH3 (D)

2.8 Between and

(A) N(I)has more 's' charcter in N–CH3 bonds

2.9 The acid strength order is:

2.10 Acid strenght of the conjugate acids of the following are-

(l) N NH (ll) N NH (lll) (lV) N

2.12 The correct order of acidic strength is :

2.13 Which one of the following reaction is not possible?

The correct basicity order of atoms p,q and r is :

2.18 The correct basic strengtyh order is:

(I) (II) (III) (IV)

NH2 NH2 NH2 NH2

(V) (VI) (VII) (VIII)

2.20 Observe the foolowing reaction :

(A) > > H2CO3> (B) > > > H2CO3

2.22 Which of the following statement regarding resonance is NOT correct?

SECTION-II: MULTIPLE CORRECT ANSWER TYPE

2.24 Choose the incorrect statement:

2.27 Resonance structures of a molecule should have.

SECTION-III : ASSERTION AND REASON TYPE

SECTION - IV : TURE AND FALSE TYPE