Questions Chapter 1-10

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

(C) 5,6-Diethyl-3-methyl dec-4-ene
1.4
(B) 5,6-Diethyl-3-methyl dec-4-ene

(D) 2,4,5-Triethylnon-3-ene
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
1.6
The IUPAC name of the compound
will be :
(A) Tropyluim bromide

(C) 3-Bromocyclohepta-1,4,6-triene
(B) 1-Bromocyclohepta-2,4,6-triene
(D) 7-Bromocyclohepta-1,3,5-triene
Correct IUPAC name of the co,pound H3C CH2 O C

O
(A)
(B)
(C)
(D)
O C CH2 CH3
O
4-(Ethyl methanolyonxy)phenylpropanoate
Ethyl 4-propanoyloxybenzenecarboxylate
4-(1-Oxo-2-oxabutyl)phenylpropanoate
1-(1-Oxo-2-oxbutyl)-4-(1-oxopropoxy)benzene
O
Et
1.7
O is
Correct IUPAC name of the compound

Me
O
(A)
(B)
(C)
(D)
1.8
2-Ethyl-3-methylbut-2-ene-1,4-dioic anhydride
3-Ethyl_2-methylbut-2-enedioic anhydride
2-Ethyl-3-Methyl-1,4-diketobut-2-enoic anhydride
2-Ethyl-3-methylcyclopenatanoxy-1,4-dione
The IUPAC name of the following compound is
COOC2H5
COCl
(A) 2-(Ethoxycarbonyl) benzalychloride

(C) Ethyl 2-(chloromethanoyl)benzoate
(B) Ethyl 2-(Chloroformyl)benzoate

(D) Ethyl2-(Chorocarbonyl)benzene carboxylate.
Cl
1.9
CH3
IUAC name of
Br
(A)
(B)
(C)
(D)
1.10
C2H5
4-Bromo-6-chloro-2-ethyl-1-methylcyclohex-1-ene
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
O3
Zn/H2O
CH3 C CH C H + H C H + CH2 C C CH2 C H

CH3
(A)
CH3
(D)
(C)
(B)
H3C
1.12
In the given sequence reaction which of the following is the correct structure of compounds A.
H2 / Ni
A(C10H14)
O
H
(i) O3
(ii) Zn / H2O
+ HCHO
H
(A)
1.13
(B)
For the following reactions sequence HOOC

The structure consistent with X and Y are:
'Y'
(A)
(B)
(C)
(D)
(D)
(C)
'X'
COOH
O3
H2O2
H2 / Ni
C7H10
excess
Y
C7H 12
X
1.14
An organic hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Its
structure is
(A)
(B)
CO
1.15
(C)
and HCO
are
(A) Position isomers

(C) Functional isomers
1.16
(D)
(B) Chain isomers

(D) Metamers
In which reaction a chiral reactant is giving a chiral product.

CH3
C C2H5
HOC
CHO
KMnO4 / OH /
C=C
(B) H
(i) O3
(ii) Zn / H2O
Reductive ozonolysis
CH3
CH3
CH3
CH = CH2
H
CH2 CH3
H
O3/ Zn / H2O
Cl
C=O
(D)
H
CH2OH
H2 / Ni
Cl
CH3
Hint :
1.17
C = O + H2
H C OH
Which of the following statements is true abnout the follownig conformer (X)?
COOH
I
CH 3
(X)
I
CH3
COOH
(A) (X) is the most stable conformer of meso-2,3-Diiodo-2,3-dimethylbutanedioic acid

I
CH3
(B) The most stable conformation will be
CH3
I
COOH
(Y)
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 moleof2,4Dioxohexanedial. The possible structure\s of the hydrocarbon maybe
(A)
1.19
(B)
(C)
(D)
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:

CH3
COOH
(A) D
OH, HOOC
D
COOH
OH
OH3, HOOC
(C) H
CH3 , HO
(B) HO
CH3
CH3
(D) H
Ph
H
CH
1.22
OH
CH3
CH3
Ph
CH3
OH, HO
CH3
Ph
CH3
The stereochemical formula of deiastereomer 'Y' of optically active compound 'X' is:
X=2,3-Dihydroxbutanedioic acid.
OH
H
COOH
(A) HOOC
COOH
OH
(B) HOOC
OH
HO
COOH
H
(C) H
OH
OH
OH
H
COOH
(D) HO
COOH
COOH
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
(I)
CH CH3
OCH3
C2H5
CH2OCH3
CH3
(II)
(III)
(IV)
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
(I)
(II)
(III)
(A) (I)and (III)are structural isomers.

(C) (II)and (III)are strukctureal isomers
1.26
(B) (I)and (II)are geometrical diastereomers

(D) (I)and (II)are jidentical
Which of the following is\are a meso compoumd.

COOH
COOH
H
CH2OH
O
(A)
OH
F
(C)
CI
COOH
NH2
CH2OH(B)
OH
NH2
H
CI
Br
F
(D)
OH
H
H
HO
Br
COOH
1.27
Which of the following pair represents the correct relationship

I
NH2
II
OH
CI
Relationship
OH
(A)
Positional Isomers
NH2
CI
(B)
Chain Isomer
NH C3H7
H3C N C2H5
(C)
Functional Isomers
(D) CH3CH2CH2COCH3
O
CH3CH2COCH2CH3
Metamer Isomers
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:
CH3CHCOOH + CH3CHCH2CH3 CH3CHCOOCHCH2CH3+CH3CHCH2CH3

CI
OH
(+)excess
OH
(+)(Left unreacted)
CI
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
H2SO4
COOH + HO
H
D
Et
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
H
OH
OH
CH2OH
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
(D)
NH2
is the isomeric amide of oxime of next higher homolog of Z.
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
(A)
H
(B)
D
and
Cl
Cl
Br
OH
Br
D
and
H
Et
H
(C)
COOH
H
HOOC
1.35
and
(D) H
HOOC
H
OH
Br
CH3 and
C
H3C
Cl
H OH
H
Cl
Observe the following reaction

CH3
*
HOOC
(R')-1-Phenylethylamine
CH3
C*
NH2
Cl
(R' R) + (R' S)
(1)
H
(R+S)-2-Chloropropanoic acid
(R')+ (R)
(R')+ (S)
1.36
OH
Me
Br
COOH
OH
OH
Et
separation by
recrystallisation
(2)
hydrolysis
(3)
(R'R)
hydrolysis
(3)
(R'S)
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.
The number of chiral centres present in the following compound is
CH2OH
O H
H
H
OH
OH
H
HO
O
HOH2C
D (+) - Sucrose
OH
OH
CH2OH
(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
(p) Ozonolysis followed by reaction with
NH2 OH leads to more than one oxime
product
(A)
Ph CH = CH Ph
(B)
(CH3)2C = CH CH = Cl
(q) Can exhibit geometrical isomers
CH3
(r) Compounds with this structure formula

can be separated into different fractions
upon fractional distillation
CH2 = CH CH = CH2
CHO CH CH CHO
(s) Is capable of showing stereoisomerism

OH
OH
1.38
Column I
D
HO
(A)
Column II
CH3
OH
H3C
OH
OH
(p) can be separated by fractional
crystallisation
CHO
(B)
CH3
CH 3
CHO
CHO
CH3
CHO
C
(q) Can not be separated by
CH3
fractional crystallisation
COOH
OH
OH
COOH
(C)
COOH
H
OH H
COOH
OH
CH 3
Cl
H
(r) Optically resolvable
OH3
Br
(s) donot have identical boilling point
(D)
Br
D
OH2I
D
I
CH2Cl
SECTION-VII: SUBJECTIVE ANSWIR TYPE

SHORT SUBJECTIVE:
1.39
Total number of stereoisomes possible for molecule A will be

H3C
1.40
CH = CH
Cl2 / hv
Fractional
distillation
CH = CH
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

(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)
(A)x>Y>w>z
2.3
(w)
(z)
(y)
(B)y>x>w>z
(C)x>w>z>y
(D)z>x>y>w
Which of the following does not represent the resonating structure of

+
(A)
(C)
(B)
(D) +
2.4
The most stable resonating structure of CH3 O = CH = CH2 :

(A)
2.5
(B) H3C O = CH CH2 (C) H 3C O = CH CH 2 (D) H3C O = CH CH2
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
(A)
(B)
(C)
reason for this is

Double bond having partial triple bond charcter because of resonance
Doule bond undergo flipping
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

(A)
2.7
+
CH2 = CH N
O
O
(B)
+
CH2 = CH N
(C)
Cl
(B)
CH3
COCH3
(C)
H3C
CH3
+
Between
(A)
(B)
(C)
(D)
(D)
N
and
(ll)
N(I)has more 's' charcter in NCH3 bonds

N(II)has more 's' charcter in NH bonds
N(I)has less 's' charcter in NCH3 bonds
None of these
The acid strength order is:

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

2.11
H
H
CH3
(l)
2.10
CH3
CH3
2.9
(D)
+
+
CH2 CH = N
In which of the followig molecules all the effects namely inductive, mesomeric and hyperconjjgation
operate:?
(A)
2.8
+
+
CH2 CH N
(B)III> II> I> IV
(C) IV> III> II> I
N
H
(D)None of these
The acid dissociation constants of the following acids are given as under:
Compound
Ka
CICH2COOH
CH3CH2 C HCOOH
136 X 105
139 X 105
CI
CH3 C HCH2COOH 8.9 x105

CI
C H3CHCH2COOH 2.96 x105

CI
CH3CHCH2COOH
1.52 X 105
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
OH
(ll)
(l)
OH
COOH
OH
COOH
CH3
(lll)
COOH
CH3
(lV)
OH
(A) III> IV> I> II

2.13
(B) II> I> III> IV
(C)II> III> I> IV
(D)II> I> IV> III
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
2.14
If
CH 3 S
H
R
is mixed with NaOH solution. Acid base reaction occurs and HO snatches H from
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
H
2.16
(p)
NH(r)
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
2.17
N
H
I
H
II
H
III
N
IV
The order of basicity is

(A) I > IV > II > III
(C) III > II > IV > I
2.18
(B) I > II > IV > III

(D) II > III > IV > I
The correct basic strengtyh order is:

NH
CH3
NH
CH3
C
CH2
II
NH2 H2N
CH 3
III
(A) I > II > IV > III

(C) III > II > IV > I
2.19
IV
(B) IV > III > II > I

(D) III > IV > II > I
The correct order of acid and basic strength for the following pair of compounds should be?
COOH
COOH
CH3
Acid strength :
and
and
(I)
(II)
NH2
COOH
CH3
COOH
(III)
NH2
(IV)
NH2
NH2
CH3
CH3
and
Basic strength :
(V)
(A)
(B)
(C)
(D)
2.20
I
I
I
I
>
<
>
<
II
II
II
II
;
;
;
;
III
III
III
III
>
>
>
>
IV
IV
IV
IV
;
;
;
;
V
V
V
V
>
<
>
<
and
(VI)
VI
VI
VI
VI
;
;
;
;
VII
VII
VII
VII
<
>
>
<
(VII)
(VIII)
VIII
VIII
VIII
VIII
Observe the foolowing reaction :
O Na
COOH
OH
COONa
+
+
NO2
OH
NO2
ONa
+ NaHCO3
NO2
+ H2CO3
NO2
OH
ONa
+ H2CO3
+ NaHCO3
Which of the following is the correct order of acid strength :

OH
COOH
(A)
>
OH
(B)
> H2CO3>
>
NO2
(C)
OH
>
> H2CO3
NO2
OH
COOH
OH
COOH
> H2CO3 >
>
NO2
OH
OH
(D)
OH
COOH
>
>
> H2CO3
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 electronwithdrawing 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
NO2
NO2
Br
(A)
(B)
(C)
(D)
All three C N bond are of same length

C1 N and C3 N bonds are of same length but longer than C3 N bond
C1 N and C5 N bonds are of same length but longer than C3 N bond
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 (oHydroxybenzoic 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
(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
(p)
(r)
(A)
(C)
2.32
The most stable carbocation is
2.33
correct heat of hydrogenation order is

1,3-Pentadiene
(q) 1,3-Butadiene
2,3-Dimethyl-1, 3-butadiene
(s) Propadiene
p > q > r > s
(B) s > q > p > r
q > s > p > r
(D) s > q > p > r
(A)
(B)
(C)
(D)
The most stable resonating structure of following compound is O = N
(A) O N
N=O
(B) O N
NO
(C) O = N
N=O
(D) O N
N=O
N=O
Comprehension # 2
2.34
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.
The correct resonation structre of 1, 3-butakiene is +
(A) CH2 CH CH = CH2
(C) CH2 CH = CH CH2
(B) CH2 CH CH = CH2

(D) None of these
2.35
The correct stable resonating structure of benzene is
(C) +
+
(A)
(B)
2.36
(D) None of these
Which resonating sturcture is not correct

+
(A) CH2=CHCH2
+
CH2 CH = CH2
(B) NH2CNH2
NH2 C = NH2
NH2
NH2
(C) CH3CNH
CH3C=NH
(D)
N
N+
SECTION - VI : MATRIX - MATCH TYPE

2.37
Match the following
CH3
CH3
(A)
(p) is more
N
CH3
CH3
Cl
+
N=O
(B) O2N
(q) is less
O
Cl
CH3
(C) O2N
(r) Larger C N compared to C NO2
NH2
CH3
CH3
CH3
(C) O2N
N
CH3
CH3
(s) Larger C N bond largteer compared to aniline
2.38
Match the pKa values with the given compounds

Acid
pKa
OH
NO2
NO2
(p) 4
(A)
NO2
(q) 9
(B) CH3COOH
O
NH
(C)
(r) 5
O
Phthalimide
COOH
(s) 0.74
(D)
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.
OH
HOOC
2.40
x mole NH2
CH
OHC
Br
C
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
I :
OCH3
II :
OCH3
NH2
NH2
+
O
III :
N
O
N
O
IV :
Cl
Cl
Reaction Mechanism
3.1
Read the following road map carefully

CH3
PhCH2CHOH
1-Phenyl-2-propanol
S.R = +33.02
K I
III TsCl
CH3
PhCH2CHOK + gas
CH3
PhCH2CHOTs
IV C2H5OK
II EtOTs
CH3
PhCH2CHOC2H5
ethyl1phenyl2propylether
(A)
(B)
(C)
(D)
3.2
CH3
PhCH2CHOC2H5
Ethyl1phenyl2propylether
Both the ethers obtained by the two routes have opposite but equal optical rotation.
One of the ether is obtained as a recemic mixture.
Step II & III both are SN2 reaction and both have inversion.
Step II has inversion but step III has retention.
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
(B)
(A)
CH3
Cl
Cl
CH3
(C)
3.3
(D)
Me2 SO4
PhOH
P, P is
NaOH
(A) PhOSO2OMe (B) PhOMe
(C) PhOSO2OPh
COCH2COCH3
3.4
NaOH
P=
Br
D
(D)
PhMe
Which of the following statement is correct

O
COCH2COCH3
(A) P =
(B) P =
OH
H
C CH3
O
CH3
(C) P =
H
(D) P =
Br
3.5
NaOH
OH
OH
OH
(A)
(B)
(C)
OH
3.6
(D)
CH3 CH2SH
(i) CH3O
(ii) ethylene oxide
(iii) H2O
OH
Product, Product is :
(A) CH3 CH2 S CH2 CH2 OH
(B) CH3 CH2O
(C) CH3 CH2 O CH2 CH2 OH
(D) CH3 CH2 S
CH2
CH2
Br
3.7
+ Ph CH2 NH2
Ph
EtO
Product, Product is
O
OEt
(A) Ph
(B) Ph
O
NH
Ph
Br
NH
(C) Ph
Ph
(D) Ph
NH
Ph
OH
CH 3
3.8
In the reaction
CH 3
OH
OH
conc. H2SO4
A. The product is -
CH3
CH3
(B)
(A)
O
CH 3
CH3
CH 3
CH3
(D)
(C)
CH3
COCH3
3.9
CH3(CH2)6
TsCl
C OH
Kl, DMSO
B (Major);
C2H5
(A) R
3.10
CH3
(B) S
NO2
NO2
OH
OH
(C) R,S both
CH3
H+
(D) None of these
A;
NO2
NO2
O
(A) CH3
(B) NO2
C
O
CH3
NO2
NO2
NO2
(A) CH3
CH(OH)
CH3
CH3
NO2
NO
H3O
3.11
The products of hydrolysis of
, is
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 HSO4
CH2
(A)
CH2
CH2
(B)
(C)
(D)
OH
3.13
(CH3)3CCI + (CH3)3COK+ 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
ONO2
OH
(A) (CH3)3CCH2ONO2 (B) (CH3)2C CH2CH3
3.15
(C) (CH 3)3CCH 2OH
(D) (CH3)2CCH2CH 3
The major end product of the following reaction is

CH2Cl
aq. AgNO3
OH
H3C
CH3
CH2 OH
(A)
H3C
3.16
(B)
OH
(C) H3C
(D)
CH3
H3C
The major product P of the following reaction is

NH2
CH3
CH3
NH2 CH3OH (P)
CH CH CH
Cl
NH2
(A)
CH3
NH2
CH3
C CH2 CH
NH2
CH3
CH CH2 C
(B)
(C)
CH3
NH2
OCH3
OCH3
NH2
CH3
CH3
CH CH CH
OCH3
NH2
NH2
(D)
CH3
CH3
CH CH = C
NH2
3.17
The product of following reacting is

O
H3O
14
O
Ar
OH
(A)
O
(B)
14
14
+ ArOH
O
OH
Ar
OH
(C)
14
+ ArOH
(D)
3.18
O
+
H /H2O
14
H2C
CH2
+ ArOH
14
18
Which can not be the product.

14
H2C
CH2
(A)
(B)
18
OH
3.19
CH2
OH
18
OH
14
CH2
CH2
(C)
18
(D) A and B both
18
OH
OH
CH2
OH
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

3.20
(C) P > R > S > Q (D) Q > P > R > S
The poduct in the given reaction is

Me
H
Br
ONa +
Ph
Ph
II
Me
(A)
Me
(B)
Ph
O
Me
H
(B)
H
O
Ph
Ph
Me
Me
Me
Ph
(C) H
Ph
Ph
Me
Me
Ph
Me
O
Ph
3.21
reaction
Rearranged most stable Carbocation is
Ph
(A)
(B)
(C)
Ph
Ph
3.22
(D)
Ph
Ph
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
CH3OH + (CH3)3S
HO + (CH3)3S
Trimethyl
sulphonium
ion
DMS
(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
CH3 CH CH CH2Br or CH3 CH CH CH2
O
I
Br
OH
CH3 CH CH CH2 OH
O
II
III
OH
EtO
(D)
OH
EtOH
OEt
OH
OEt
OEt
Cl
CH2CCl
OH
3.25
NaOH
1eq
OH
NaOH
LiAlH4
'S'
(A) R =
CH2 C Cl
OH
O
(B) Q =
O
OH
O
OH
C=O
(C) Q =
(D) S =
OH CH2Cl
OH
CH3C6H4
3.26
Ph
OH
NH2
HNO2
Ph
Ph
pCH3C6H5
(A)
Ph
O
Ph
(B)
3.27
Ph
pCH3C6H5
pCH3C6H5
Ph
pCH3C6H5 (C)
Ph
(D)
H
Ph
Ph
Which of the following reaction will go faster if the concentration of the nucleophile is increased?
H
Br
Br
+ CH3O
(A)
(CH3)3CCl
+ CH3S
(B)
H2O
CH3COOH
Br
Acetone
KI
SECTION - III : ASSERTION AND REASON TYPE

CH3
3.28
Statement-1 : (CH3)3C CH
H2SO4
CH3
(CH3)3CCH=CH2+
C=C
CH3
CH3
CH3
+ CH2=C
OH
40%
Statement-2 : It follows Hofmann's elimination by E2.
20%
40%
CH3
CH(CH3)2
Statement-1
3.29
Statement-1 : Ethers are prepared from alcohols in acid medium through SN1 or SN2 mechanisms
depending upon nature of alcohol.
+
R OH2
Statement-2 : ROH + H+
slow
+
R OH2
RO
+
R O R + H2O
ROR + H3O
H
+
or, R OH + H
R OH2
R +OR
RO R
slow
H2O
fast
R + H2O
+
R OR + H3O
Statement-1
SECTION - IV : TRUE AND FALSE TYPE

OH
3.30
CH3
Ph
H2SO4
Ph
CH3
Heat
(Elimination follows E1 mechanism.)

Comprehension # 1
Read the following reaction
O
+
3.31
Cl2
NaOEt /
NBS
NaOH
Compound 'T' is
OH
OH
(A)
(B)
OH
(C)
HO
OH
OH
OH
(D)
OH
3.32
Compound 'Q' is
OH
(A)
Ol
(B)
(C)
Cl
3.33
OH
OH
(D)
Cl
Cl
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
(A)
CH3
O
O
(B)
O
O
O
O
(C) CH3 C CH2 CH2 CH = O
3.35
(D) CHO CH = CH CHO
Compound W is
(A) COOH (CH2)2 COOH
(C)
COCH3
(B)
COOH
COOH
(D) CH3 CH2 CH COOH
COOH
3.36
CH = O
Compound 'X' is
(A)
CH3
(B)
CH3 CH3
CH3
(C)
CH3
(D)

3.37
Match the column I with column II

Column - (I)
Reactions
Column - (II)
Reactions
H
CH3
KNH2
C=C
(X)
Cl
Ph
(P)
-elimination
(Q)
SN
CH3
(Y)
OH
SOCl2
Ph
CH3
+
Ph
(Z)
N CH3
NaOH
(R)
-elimination
(S)
SN1
CH3
O
CH2CH2CH3
+
(W) CH3NCH2CH3CH3
NaOH
CH2CH3
3.38
Substrate
Stereochemistry of product
CH3CH2CH2
CBr + H2O
(A)
(p) Retention
H3C
CH2CH3
(B) CH3CHDCl + OH
(q) Racemisation
(C)
(r) Inversion
CBr + H2O
H3C
CH2CH3
CH3
(D) CH2=CHC Cl + SH / (CH3COCH3)

CH3
(s) Product with -bond shift

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
R and T B in periodic table.
(iv) Leaving group ability kincreased in moving from L
CH3
3.40
CH3CHCCH2Br
NaOH/H2O
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.
(i)
Br
Ph
Br
Ph
Ph
CH2Br
Br
(ii)
(iii)
Ph
3.42
Br
(iv)
In the given reaction following products are expected.

CH2 Br
CH3
CH3OH
+
(I)
CH2OCH3
+
(II)
+
(III)
(IV)
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
Isomers = (X)
Total
Isomers = (Y)
KOH/DMSO
2
(SN )
Total number of 1 alcohols = (Z)
including stereoisomers
X
OCH3
OCH3
+
CH3
(V)
Grignard Reagent
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
(A) Ph C C CHO
(B) Ph
(C)
(D)
OH
Ph
O OH
4.2
Ph
O
Ph
Which of the following reactions will give 2 chiral alcohol as one or more of major organic
products?
H
(A) D
MgI
H3O
O2
(B) CH3MgI + H C OCH C2H5

(excess)
CH
H3O
CH3
O
H
(C)
H3O
MgBr + CH2 CH2
(D) None
CH3
4.3
CH3 C C CH3
H2O
PhMgBr
(excess)
No of product (X)
Fractional distillation
no. of fractios (Y)
O O
(A) 3,2
4.4
(B)3,3
(D) 4,3
(C)1,2-Diol
(D) -Hydroxy acid
The end product of following reaction is

O
CH3MgBr
PhMgBr
(1)
(2)
(A) ,-diketone
4.5
(C) 4,2
H
(3)
(B) -Hydroxy acid
Observe the following reaction sequence

O
Br2 / hv
Mg / Ether
dil.H2SO4
O3/Zn/H2O
X can be
CH3
(A)
(B)
(C)
(D)
4.6
SOCl2
(C2H5)2O
pyridine,
O
CH
OH
2
(x)
Product of the reaction is
(A)
CH2 C(CH3)2
O
Product
+
H
Mg
CH3
O
(B)
CH2 C CH2 CH3
CH2 CH C(CH3)2
O
OH
(C)
CH3
CH3
O
(D)
CH2 C CH2 OH
CH2 CH2 C OH
CH3
4.7
CH3
Observe the following sequence of reactions.

CH3CH2CH3
Br2/ hv
(1)
Mg/ether
(X)
(2)
(Y)
CH3Br
(3)
(Z)
Cl2 / hv
(W)
(4)
CH3OH
(5)
(R)
The product R is :
CH3
CH3
CH3
(A) CH3 CH CH2 OCH3 (B) CH3CH2CH2CH2OH (C) CH3CCH3 (D) CH3 C CH3
OCH3
4.8
Ph N = C = O
(i) CH3MgBr
(ii) H2O
LiAlH4
OH
(A) P is PhNHC CH3 and Q is PhNHCH2CH3

O
(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
4.9
CH3
Which of the following reduction methods is not suitable for preparing and alcohol?
(A) CH3COOC2H5+ NaBH4
(B) CH3COOC2H5+ Na/EtoH
(C) CH3CH2COCl+ LiAlB4
(D) CH3COOH + H2
4.10
CC
Li / NH3
X,
Br2 (1equivalent)
Ni
Ph CH
C=C
Br H
H
CH Ph
Br
'X' is :
(A)
(B)
(C) both
(D) none of these
Cl
O
C
Compound
N
on reduction with LiAIH4 produces
O
CH 2OH
CH2OH
(A)
N
CH2OH
(B)
R.coord
Energy
(A)
4.13
HO
OH
(C)
(D)
N
CH2OH
CH2OH
Which one is the correct energy profile for CI reaction ?

Energy
4.12
OH
CH 2OH (B)
HO
CH 2OH
CH2OH
(C)
Energy
4.11
R.coord
(D) All of these

R.coord
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
4.15
(D) 6,3
Which of the following is correct potential energy diagram for the given chin propagatiog step.
CH3 H+F
B.E.=435kJ/mol
CH3+ H F
B.E.=569kJ/mol
= 32 kcal/mol
4.16
Consider the following reaction

CH3CHCHCH3 + Br
D
'X' + HBr, X can be
CH3
(A) CH3CHCHCH2 (B) CH3CHCCH3

D
CH3
(C) CH3CCHCH3
CH3
(D) CH3CHCHCH3
D CH3
CH3

4.17
Br
Mg
14
(i) CH3COCH3
(ii) H
(iii)
NBS
AgNO3 / H2O
O3 / H2O
Zn
E+F
14 Br
(B) E is CH2 = O &
(A) Product C is
14 OH
(A) Product D is
14
CH2 = O
OH
14
OH
only
(D) F is
&
CH3
4.18
Ph CH2 CH CH3
Cl2 / h
(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
(A)
(i) Mg / Ether
+
tertiary alcohol
(ii) H3O
Cl
CO2
Mg
ether
(B)
F
COOH
H3O
MgF
Mg
ether
(C)
Cl
MgCl
O
(D)
HO
+ CH3 C CH
CH3MgBr
H 3O
C CH3
4.20
Point out the following incorrect Grignard synthesis.

OH
Br
(ii) Ph CH = O
(iii) H3O
(A)
N
H
CH Ph
(i) Mg, ether
N
H
(i) Mg, ether
(ii) PhCH = O
(B)
(iii) H3O
Br
HOCH2
MgBr
(C)
(i) CH3 C CH3
OH
(ii) H3O
HO
CH2CH3
(i) CH3CH2MgBr (1eq.)
(D)
OH
(ii) H3O
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
C6H5
O
(z)
O
(r)
(1)
(2)
(3)
(4)
(A)
4.27
LiAIH4 will reduced x, y, z, w, r

NaBH4 will reduced r
Na/C2H5OH will reduced r, w
(CH3)2CHOH + [(CH3)2CHO]3AI, (MPV) will reduced r
TFTF
(B) TTTT
(C) FTFT
(D) FFFT
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
CH CH
4.28
NaOCl
Mg
Ether
Cl
KOH
NaOH
T
H2O
'S' in the above reaction

CH2
(B)
CH2OH
H
C
(A)
(ii) Dil.KMnO4
CH2 OH
CH2
(i) H2 / Pd. BaSO4
OH
(C)
(D)
CMgBr
OH
HO
MgBr
CH2
CH2 OH
4.29
'U' is
CH2 OH
H
H
(A) H
H
OH
OH
OH
OH
CH2 OH
CH2 OH
H
H
(B) HO
HO
OH
OH
H
H
CH2 OH
CH2 OH
H
HO
(B) H
H
OH
H
OH
OH
CH2 OH
CH2 OH
(D) H
OH
COOH
4.30
'Q' is
(A) CIMgC CMgCI
(C) CIOC CMGCI
(B) CH C MgCI
(D) CIOC COCI
Comprehension # 2
considering the following reations (I,II,III) and give your answer for following questions
O
HO
CCl
(i) CH3MgBr
(ii) H3O+
O
COEt
(i) CH3MgBr (excess)
(ii) H3O +
CH2 Cl
O
(a)
EtO C OEt
(i) Ph MgBr (excess)

+
(ii) H
O
(b)
(i) CH3 MgBr (excess)
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
O
CH3
(A)
Cl
4.33
CH3 C CH3
(B)
OH
OH
CH3 C
(C)
CH2 Cl
CH3 C CH3
OEt
(D)
Cl
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
CH2 CH3
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
(B) CICN
(C) CH3COCI
(D) C2H5COOC2H5
4.35
(p) CH3CN
(q) CH3NH2
(r) C2H5COCH3
(s) CH3COCH3
Match the following :

O
Cl C
CH = CH2
O C CH3
COOH
(i) [Al(OiPr)3] + CH3 CH CH3

(1) (ii) H O
2
OH
(P)
(2) NaBH4(C2H5OH + H2O)
(Q)
Na/EtOH (low temp.)
(3)
(R)
Column - I
(4) (ii) H2O
(S)
Column - II
HOH2C
(P)
(i) LiAlH4 / Et2O
OH
CH = CH2
(X)
O C CH3
COOH
OH
Cl C
(Q)
CH = CH2
(Y)
O C CH3
COOH
O
(R)
O
OH
CH = CH2
HOH2C
(Z)
O C CH3
COOH
O
HOH2C
(S)
O
OH
H
C
CH = CH2
(W)
OH
COOH

Column A
Column B
Li
CH CH CI
3
2

?
(A) CH3CHCI
Cul
Li
(p) (CH3)2CHCH2CH(CH3)2
(CH )CH Br
3
2

?
(B) (CH3)2CHI
Cul
Li
(q) CH3CH2CH2CH3
CH CH Br
3
2

(C) CH3CH2C(CH3)2Br
Cul
Li
(r) (CH3)3CCH2CH3
CH CH Br
3
2

(D) (CH3)3CI
Cul
4.37
(s) CH3CH2C(CH3)2CH2CH3

Process
Graph
(A) Fluorination
(p)
Potential energy
4.36
B
C
Reaction CO-ordination
(B) Chlorination
(q)
B
C
(C) Bromination
(r)
B
A
C
(D) Iodination
(s)
C
A
Position (A) is for CH4,X,
(B) is for CH3, HX,
(C) is for CH3X,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 CH bonds for chlorination.
Degree of C H
Relative reactivity
for chlorination (RR)
1 C H
1
2 C H
3 C H
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
smelling liquid (Q)
(1)
(lce)
H2O
(2)
An alkyl halide (P)

ethereal solution
(R)
(II)
(I)
(III)
(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)

H
CH 3
(1) CH3 CH CH3
(2) CH3 C CH3

OH
OH
(3) H C C2H5
OH
C2H5
(4) C2H5 C C2H5
OH
CH3
(c) If R is
C CH3 then the numbers of monochlorination product are:

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

NH
5.1
Br2
The major product of the following reaction would be
Br
NH
N
(A)
(B)
Br
Br
5.2
(C)
H
(D)
Br
Br
In the following series of reactions the major products P and S are respectively.
Br2 / h
(P)
tBuO ,
(Q)
(i) HOBr/H+
(i) HOBr/H+
(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
(A)
H2O
ZnCl2HCl
OD
(B)
Mg/ether
(C)
D2O
(D)
D
OD
5.4
consider the following reactions

H5C2
C2H5
C=C
R1 R
2
H5C2C
CC2H5
R3
C=C
H5C2
H5C2 C
R4
H
C2H5
CH2 C2H5
O
2CH3 CH2 COOH
The correct set of reagents for these reactions is
R1
(A) H2 /Lindlar catalyst
(B) H2 /Lindlar catalyst
(C) (i) O3, (ii) H2O
(D) H2O,H2SO4,HgSO4
5.5
5.6
R2
Na / Iiq.NH3
Na / liq.NH3
H2O,H2SO4,HgSO4
H2/Lindlar catalyst
R3
(i) O3, (ii) H2O
H2O,H2SO4,HgSO4
Na / Iiq.NH3
(i) O3, (ii) H2O
The major product of the following reaction is :

Br
Cl
(A)
(B)
Br2 / h
(2)
Na / ether
(1)
C2H5O / C2H5OH,
(3)
(C)
(D)
Themost ap0propriatew major product of the followning sequence of reactions would be.
O
CH3
CH3CH2
C
CH3 C O O H
H3C
Me
Et
(A)
OH
()
(B)
Et
DH
()
Me
CH3
CH3
Me
Et
(C)
H3O
LiAlD4
Me
CH3CH2
OH
()
(D)
DH
OD
CH3
Me
5.7
R4
H2O,H2SO4,HgSO4
(I) O3, (ii) H2O
H2/Lindlar catalyst
Na / Iiq.NH3
Compound'P' of the following reaction swequence can be

+
O
O
(P)
[C8H6O3]
H2O
COOH
BH
[C16H21B]
HOO
[C8H8O]
(A)
CrO3 / Acetone / H2O
(B)
CH2 C
CH2 COOH
CH
(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
(A)
OH
CI
CI
5.9
CI
(B)
CI
CI
OH (D)
CI
(C)
HO
The end product 'W' in the follownign sequence of reactions is :

CH2CH3
alc. KOH
NBS
Hg(OAc)2
NaBH4
(X)
aq. KOH
W
CH3
CH3
CH3
(B) Ph CH O CH Ph
(A) Ph CH2 CH2 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.
CH = CH C2H5 PhCH = CH C2H5
C = CH CH3
CH3 C = CH2
CH3
CH3
(l)
(ll)
(A) lll > l > ll > IV
5.11
PhC CPh
(B) lV > lll > l > Il
Na/NH3
(D) lV > lll > lll > I
B ; B is
Ph
OH
H
(B) HO
Cl
Ph
5.12
(C) l > lll> lll > IV
(lV)
HOCl/H
Ph
H
(A)
Cl
(lll)
Ph
H
H
OH
Cl
(C) H
H
Ph
(D) B and C both
Ph
The most stable conformation of the product of followning reaction

C
CH
HBr / R2O2
Ph
H
(A)
Br
Ph
H
H
Br
HBr / dark
(1 eqivalent)
(B)
Ph
Br
H
H
H
Br
(C)
H
Br
Br
(D)
Br
Br
Br
Ph
H
CH 3
5.13
B2H6, THF
In the given reaction,
H2O2, NaOH
TSCl
tBuO K
(Y)
(X)
The product 'Y' is

(A) A positional isomer of X
(C) Chain isomer of X
5.14
(B) Identical to X
(D) An oxidation product of X.
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
O
(D)
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
(A) CH3 C
NaNH2
CH
(CH3)2 CHCHO
H3O+
OH
(B) (CH3)2CH CH C
NaNH2
CH
(C) CH3 C C CH CH2 CH3
NaNH2
CH3I
CH3I
OH
OH
(D) (CH3)2CH CH C
5.16
CH
CH 3MgI
CH3I
CH3
O
H3C C CH2 CH3

H3C CH2 CH2 N
(i) CH3I
(ii) AgOH,
H3C C CH3
CH3
In the above reaction the product will be
CH3 C Cl
AlCl3
X, X is
(A) CH3 CH CH2 Cl
(B) CH3 CH CH2 C CH3
COCH3
Cl
CH3
(B) CH3 CH CH2 C CH3
(C) CH3 CH C CH2 CH3

Cl
5.17
Cl
Fastest rate of electrophilic addition will take place in

(A) HO
CH = CH2
(C) CH3O
5.18
(B)ON
CH = CH2
(D)
CH = CH2
CH = CH2
Which of the following will be the correct product (P) for the given reaction ?
Conc. H3PO4
(P)
OH
OH
(A)
(B)
(C)
(D)
OH
CH2
5.19
HBr
R2O2
aq NaOH
X (major)
Y (major)
Identify the correct option

X
(A)
(B)
(C)
Y
CH3
Br
CH3
OH
CH3
CH3
Br
CH3
OH
CH3
CH3
CH2
CH3
Br
(D*)
CH3
Br
OH
CH2
OH
CH3
H2SO4/
Z (major)
5.20
(i) KMnO4 / H2O /
(ii) H3O
HOOC C CH2 CH2 CH2 CH2 COOH
X may be
COOH
COOH
(A)
(B)
(C)
COOH
(D)
O
O
5.21
D
H
CH3 C
CH3
CH3
OH OH
D
(CH3)3C
(A)
5.22
(2) CH3MgBr
(1) C6H5CO3H
C=C
(3) H2O/H
OH3OH3
H
(CH3)3C
(B)
Product; Product is :
OH OH3
(CH3)3C
(C)
OH3OH
(C)
(CH3)3C
The final product of the following reaction is

Ph
oCOCH3
Me
H
H
BrCl/CCl4
Ph
Ph
Ph
Cl
Br
H
(A) Me
Ph
Ph
Ph
Br
Cl
H
(B) Me
Cl
Me
H
(C) Br
Ph
Ph
Br
Me
H
(D) Br
Ph

5.23
Which statement is correct about the end product of the following reaction series,
HOCI (excess)
conc. NaOH,
(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
C CH
5.24
The following synthesis can not be carried out be:

I
CH = CH2
CH = CH2
CI
(A)
CI2
(1)
ICI / CH3COOH
(2)
(B)
HOCI / H
(1)
CI2 / Fe
(2)
I
ICI / CH3COOH
(3)
ICI / ZnCI2 (excess)
(3)
Zn dust
(4)
NaOH,
(4)
HOBr / H
(1)
(C)
(B)
5.25
CI2 / Fe
(2)
ICI / ZnCl2 (excess)

(3)
Zn dust, CH3COOH
(4)
Br2 / CH3COOH
CI2 / Fe
ICI / CH3COOH (excess)
NaNH2
(1)
(2)
(3)
(4)
Bu C
CH
LiNH2
(i) PhCHO
MnO2
(ii) H2O
Compound C of the above reaction can not be :

CHO
CHO
(A)
CC
CBu
(B)
(C)
C
CBu
(D)
CBu
C
5.26
CHO
CBu
Acetone (CH3COCH3) is the major product in :

H3O
CH2 = C = CH2
II
CH3C
CH
H2SO4 / HgSO4 / H2O
III
CH3C
CH
BH3- THF
H2O2 / OH
(A) I
(B) II
(D) none
(C) III
5.27
Br
HBr
Statement-1 :
CH2
40C
CH3
CH2
CH2
CH2
+
CH2
Br
Major
Minor
Br
CH2
20C
CH3
Statement-2 :
CH3
CH2
CH2
+
CH2
CH2
CH3
Allylic
cation
Br
Minor
Major
CH2
+ CH3
Br
Br
Br
CH2
CH3
major at low temp
CH3
CH2
Br
major at of high temp
Statement-1.
5.28
Statement-1 :
Me
Me
Me
NBS
Me
Me
+
Me
Br
Br
Statement-2 :
Me
Me
Me
Me
Br.
HBr
Me
Me
Br2
Br2
Me
Br
Me
Br
Me
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 80C to give 1, 2-adduct is kinetically controlled while that
at 40C 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
CH3 C CH = CH2
i)Hg(OAc)2. THF
HI (Conc.)
ii)CH3OH, NaBH4NaOH
B, Product B is :
CH3
(A) (CH3)3CCH CH3
(B) CH3I
(C) CH3CH2I
(D) (CH 3)3CCH CH 3
OH
5.34
NBr
O
CH3CH = CH2
1) Hg)OAc)2, THF
2) H2O
3) NaBH4, NaOH
OH
C.
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 :
(A)
OH
OH
OH
HO
(B)
(C)
OH
(D)
OH
Comprehension # 2
(A)
AI2O3
250C
HI
(B)
(C)
(ii) AgOH
AI2O3
150C
(B)
(i) B2H6
(ii) H2O2,OH
(A)
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) CH3CH2CH2CHCH3 (B) (CH3)2 CHCHOHCH3 (C) (CH3)3 CCH2OH (D) CH3CH2CHCH2CH3
OH
5.37
OH
Identify th structure of B
CH3
CH C C=CH2
(A) (CH3)2CHCH=CH2 (B) 3
(C)(CH3)2CH= CHCH3
CH3
(D) CH2=CHCHCH3
CH3
5.38
Identify the structure of C

CH3
(A) CH3CH2CH2CHCH3 (B) CH3CH2CCH3 (C) (CH3)3 CCH2OH (D) CH3 CH2 CHCH2 CH3
OH
OH
OH
SECTION - VI : MATRUX - MATCH TYPE

5.39
Match the column I with column II

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

SHORT SUBJECTIVE :
5.40
(a) CH3 CH C
OH
CH CH 3
OH
(X)
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 500C. Find out total no. of possible products.
CHCIBr2
5.42
(CH3)3 COK
m no. of products.
Et
5.43
CH3
CH3
H
CH3
+ CH2N2
Cold Dil
KMnO4
5.44
KMnO4
the products.
HIO4
Total no. of products.
NH2OH
(excess)
Total no. of isomers (including stereo) are formed in
Aromatic Compounds
SECTION-I : STRAIGHT OBJECTIVE TYPE
CH = CH COOH
HOCI / H
6.1
The major product is :

OH
CH = CH COOH
CH = CH COOH
(A)
(B)
CH = CH COOH
CH CH COOH
CI
CI
(C)
(D)
CI
CI
6.2
MeO
CI S
OH
Br2 / Fe
(2)
HCI
(1)
Me
H
(3)
The major product is

Br
Br
(A) MeO
Br
OH
(B) MeO
(C) MeO
(D) MeO
Br
6.3
The product is :
OH
O
||
O
product.
||
O
O
O
(A)
(B)
O
O
(C)
(D) None
OH
O
OH
6.4
Ph
OH
Me
Me
Ph
AgNO3
OH
Major product is
OH
NO3
CH3
Ph
(A) Ph
Me
(B) Ph
Me
Me
Ph
Me (C) Ph
Me (D) None of these
Ph
CH3
Me3CCI
6.5
PhCOCI
AICI3
Br2 / AICI3
AICI3
Me O
C Ph
Br
(A)
Product is
Me O
C Ph
(B)
(C)
(D)
C(Me)3
6.6
Me O
C Ph
Me O
C Ph
Br
C(Me)3
Br
Why does the reaction produce stable salt?

O
+ OH
CI
HCI
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
O
HNO3 + H2SO4
OMe
O
C
O
C
O
NO2
(A)
(B)
(C)
(D)
NO2
NO2
OMe
6.8
NO2 OMe
OMe
The end product of the folloowing reaction sequence is:

OCH3
|| O
+
Dry. AICI3
Zn Hg / HCI
SOCI2 / Pyridine
O
OH (tautomerises)
H2O
Dry. AICI3
OMe
OCH3OH
OCH3
(A)
6.9
OH
OH
CH3O
(B)
OH
CH3O
(C)
(D)
The end product of following reaction is

CH3COCI / AICI3
(1)
C2H5COCI / AICI3
(2)
CIO
(3)
COO
(B) OOC
(A) O = C
C C2H5
C2H5
O
COO
(C)
C
||
6.10
(D) OOC
COO
C2H5
The product of the followiing reactions is

O
||
C
CH3
O
||
CH3 C CI
AICI3
O
||
C CH3
(A)
O
||
C CH3
(B)
C=O
C CH3
CH3
O
O
||
C CH3
(C)
O
||
C CH3
O
(D) H3C C
H3C C
O
6.11
Which of the following is best sequence of reagents for the conversion of

CH3
Br
6.12
(A)
Br2 / Fe
conc. H2SO4
CH3CI / AICI3
(B)
CH3CI / AICI3
conc. H2SO4
(C)
CH3CI / AICI3
3CI2/ h
(D)
HNO3 + conc. H2SO4
Br2 / Fe
Br2 / Fe
CH3CI / AICI3
H3O
H3O
Zn / HCI
Sn / HCI
NaNO2 / HCI
CuBr
The intermediate product 'X' of following synthesis is identified as :

CI2/FeCI3 conc. H 2SO 4 Fuming HNO 3
'X'
NH3/Cu2O/
120C
dil.H 2So 4,
100C
2, 6-Dinitroaniline
CI
CI
(A)
HO3S
O2N
(B)
(C)
NO2
6.13
NO2
(D)
O2N
CI
NO2
CI
HO3S
SO3H
NO2
SO3H
SO3H
The major product of the following reaction sequence will be

OH
PhCOCI / Pyridine
(1)
CH3COCI/AICI3
(2)
O C
(A) CH3CH2
Zn Hg / HCI /
(3)
(B) H3CCH2
Br2/Fe
(4)
O C
Br
Br
CH2 CH3
(C) Br
(D) CH3 CH2
O CH2
Br
6.14
In the following reactions X, Y and Z are respectively :

NH2
(x)
Br2/KOH,
H2/Ni
(Z)
OMe
NaNH2/NH3(l)
(Y)
X
CH = NOH
CONH2
CI
(A)
,
OMe
OMe
OMe
CI
NO2
(B)
CONH2
OMe
OMe
CONH2
,
(C)
MeO
CN
NO2
,
MeO
MeO
CN
(D)
OMe
COO NH4
,
CI
,
OMe
OMe
OMe
NH2
CH3COCI
6.15
Br2 + H2O
H3O
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

p Nitro phenol
(X)
(?)
(C2H5)2SO4 / NaOH
(1)
(A) X
6.17
NaNO2/ HCI
(7)
(B) Y
(3)
Sn / HCI
(6)
(W)
C6H5OH
NaNO2 / HCI
(Y)
(2)
NaNO2
CuNO2
(8)
HI
(9)
Sn / HCI
(4)
NaOH / C2H5Br
(5)
(C) Z
(Z)
(D) W
Consider the following reaction sequence

HNO3+H2SO4
NaNO2+HCI
Sn+HCI
Cu2(CN)2+HCN
H2O
(6H)
Product
Product is:-
CN
CH2OH
(A)
COOH
(B)
NH2
(C)
CN
(D)
OH
6.18
The products R and S are respectively

NO2
(X)
KMnO4/ OH /
Sn/HCI
KMnO4/ OH /
(Y)
(W)
(Z)
Br2 / Fe
Br2 / Fe
(R)
(S)
NH2
HOOC
(A)
HOOC
HOOC
HOOC
Br
and
Br
(B)
: R and S are same products

HOOC
HOOC
Br
HOOC
(C)
HOOC
NO2
NO2
NO2
HOOC
and
Br
HOOC
Br
HOOC
(D)
HOOC
and
HOOC
Br
HOOC
Br
6.19
The end product 'Z' of the reaction sequence is

CI
CI
6.20
AICI3
X
Zn/Hg
Conc. HCI
Se/
(A)
(B)
(C)
(D) Both A and B
NO2
+
KCN/C2H5OH
H3O
NaOH+CaO
distilation
C. Product 'C' is
Br
COONa
NO2
COONa
(A)
(B)
(C)
Br
(D) None of these
Br
NH2
HNO2
6.21
B, Product 'B' is
NH2
+
N2 CI
N
N
(B)
(A)
N
H
N
N
(C)
N
H
(D) All of these

NO2
6.22
(1) Sn/HCI
(2) KMnO4
'x'
KMnO4
[O]
'y'
'x' and 'y' are respectively :

NO2
COOH
B
(A)
COOH
and
NH2
A
(B)
and
COOH
COOH
COOH
COOH
COOH
COOH
NO2
COOH
and
and
(D)
COOH
6.23
COOH
COOH
COOH
(C)
NH2
B
COOH
COOH
COOH
Which of the following electophilic substitution reaction represent correct product.

NO2
NO2
Br2/FeBr3
(A)
Br
OCH3
OCH3
Br
Br2/FeBr3
(B)
O
COOCH3
COOCH3
OCH3
(C)
Br2/FeBr3
OCH3
Br
CCH3
(D)
Br2/FeBr3
CCH3
O
Br
6.24
Which of the followning reactions give alkylation product:

OH
(A)
(C)
+ CH3COCI
H
AICI3
(B)
(D)
+ Me3C COCI
AICI3
6.25
The following conversion reafction can be carried out by using reaction sequence/s.
O
COOH
OH
(A)
Zn / Hg / HCI,
(B)
NaBH4
(C)
Heat
Br2 / h
H3O,
KCN
O3 / H2O (oxidative)
AI2O3,
I2/NaOH,
(D) KMnO4 / OH / heat
6.26
Which of the following ion will be aromatic in nature?

(A)
CI
H
H
(B)
N
|
H
(C)
(D)
+
N

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
(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.
6.30
AIBr3
Statement-1 : Ar C(CH3 )3 Br2
ArBr CH3 2 C CH2
AIBr
but
3
ArCH2 CH3 Br2
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
NOH
OH
||
Statement-2: Former exist in
||
which gives
NOH where
at later exists in
OH
NOH
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
is 4

Comprehension # 1
COOH
SOCI2
Solid N2O5
(CH3)2 CuLi
Fe / H
(i) NaNO2 / H
(U)
(ii) PhOH / OH
6.34
The product U is
CH3
(A)
O
||
(B) H3C C
C
H
N=N
N=N
(C)
H3C C
O
N=N
OH
OH
OH
(D)
N=N
CH2CH3
OH
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
(A)
(B)
(C) CHCI3
COONa
6.36
NO2
(D)
COOH
CH2COONa
T on reaction with NaNO2/HCI followed by reaction with H3PO2 will give.

COCH3
CH2COCH3
(A)
COCH3
(B)
COCH3
(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 CH2 CI
(A)
CH2 CI
CH2 CI
(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
(A)
CH2 NC
(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
O
CH2 CO
AICI3
(1)
C10H10O3
(X)
Zn(Hg) HCI/
(2)
(C10H12O2)
(Y)
SOCI2
(3)
(Z) (C10H11OCI)
(C10H8) + H2
(T)
Pt, heat
(7)
(C10H10)
(S)
H2SO4 /
(6)
(C10H12O)
(R)
H2 / Pt
(5)
(C10H10O)
(W)
AICI3
(4)
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
6.41
Ph
What product is obvtained when (X) is heated with conc. H2SO4

O
O
O
(A)
(B)
(C)
6.42
(D)
What product is obtained when W is heated with KMnO4 / OH.

COOH
(A)
COOH
(B)
COOH
COOH
O
(C)
(D)

6.43
Match the following

Column - I
Column - II
:e
(A)
e:
(p)
Anti aromatic
(q)
Aromatic
(r)
Non aromatic
(s)
G.F = CnHn
(Non-Planar)
(B)
:e
(C)
(Planar)
(D)
(Planar)
6.44
NO2
(1)Sn/HCI
(2) (CH3CO)2O
HNO3
H2SO4
Dil.
B
H2SO4
C
Br2
H3PO2
(1) CuBr
(2)Sn/HCI
(3) NaNO2, HSO4 E
NaNO2
H2SO4
HBF4,
H
Write the correct combinations

Column-I
Column-II
Br
(A) A
(p)
Br
Br
Br
(q)
Br
Br
(B) B
NHCOCH3
(C) G
(r)
NO2
(s)
(D) H
NHCOCH3
6.45
Match the correct properties of compounds of column I with column II.

(I)
(II)
OCH=CH2
(A)
(p) Gives Benzoic acid with hot alkaline KMnO4

CH=CH2
(B)
(q) o/p directing and activating for E

CHCH3
(C)
(r) Gives fastest reaction with an electrophile
OH
O
C
(s) Gives an ester on reductive ozonolysis
CH3
(D)

SHORT SUBJECTIVE:
NO2
(C2H5)2SO4
6.46
(I)
Zn/HCI/
(2)
OH (1)
(II)
NaNO2, HCI
5C (3)
(III)
Phenol
NaOH (4)
(IV)
Br2/H2O
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)
6.47
Assign the correct numbers to the type of reactions as follows w x y z

Observe the following reaction sequence
(1)
Phenol
NaOH (1 eq)
Me
(2) D
(X)
HCN, HCI/AICI3
(3)
(Y)
NH2NHPh
(4)
(Z)
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
(5)
(V)
6.48
CH3CI/AICI3
Br2/h (1 eq.)
Na/ether
(1)
(2)
(3)
(4)
(monobromination)
(5)
alc.KOH
(i) O3
(P)
(2 moles)
Br2/h (1 eq.)
(ii) Zn/CH3COOH
Find the structure formula and molecular weight 'P'.

6.49
Indicate the most probable sites for ArSE reactions.
O
O
(A)
NO2
(B)
NO2
CH2
(C)
(D)
NHCOCH3
(E)
NH
NH
O
||
C
6.50
+ (CH2)2
C
||
O
CI
CI
AICI3/
Na/C2 H5OH
Se/
Find the molecular weingt of the compound C and D.

6.51
In the following sequence of reaction how many nucleophilic substitution taking place.
O
OH
SOCI2
alc.KOH
CI C CI
AICI3
CH3MgBr
H
HBr
Carbonyl Compounds
SECTION-I : STRIGHT OBJECTIOVE TYPE
7.1
OH
OH
PhCOCHBr2 A B
C
The compound'C' is
(A) PhCH(OH)CHO
(B) PhCH(OH)COOH
(C) PhCOCBr2
(D) PhCCH2OH
O
7.2
The product/s of the following reaction is

Ph
O
||
C C Me
PhCO3H
Me
Ph
(A)
H
O
||
C C O Me
Ph
C O C Me
(A)
Me
H
Me
Ph
(B)
O
||
C O C O Me
(D)
Me
C = O + HO C Me
Me
7.3
Ph
Which step is not feasible in the following loop?

Br
CH2(Br)CH2CHO
EtOH, H
a
CH2 CH2CH(OEt)2
d alc. KOH
b alc. KOH
+
CH2=CHCHO
(A) step - a
7.4
COCHO
H2SO4
CH2 =CHCH(OEt)2
(B) step - b
CH3
2Q
H2O, H
OH
(C) step - c
(D) step - d
H3O
The product R is :
O
||
C
(A) CH3
CH(OH)COOH
(B) CH3
CH
O
CH
C
||
O
CH3
O
(C) CH3
(D) CH3
CH = CH COOH
CH
O
7.5
CH3 C (CH2)4 C CH3

||
||
O
O
The product 'C' is
(A)
PhMgBr
O
||
(C)
CH3COONa
HBr
(A) PhCH = CHCH2Br
(D)
Br
(D) PhCH= CH COBr
The number of stereoisomeric products formed in the following reaction is

Ph
Ph
+ H
CHO
(Optical pure)
(A) 1
7.8
Ph
(B) PhCH CH2 COOH
(C) PhCH2 CH(Br) COOH
7.7
Ph
(B)
PhCHO + (CH3CO)2O
The product B is
ZnHg
Conc.HCI
Ph
Ph
7.6
OH/
OH
MgBr
H2O
Ether
CH3
Optical pure
(B) 8
(C) 4
(D) 2
The end products of following reaction would be,

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

O
O
||
||
H3C C (CH2)2 C CH3
NH2
Ph
H3C
(A)
(B)
CH3 N
7.11
O
||
OH
CH3
CH3
(C)
(D)
N
|
Ph
CH3 N CH3
Ph
CH3
H/
N
|
Ph
H3C
The possible number of stereoisomers of the product of following reaction would be :

Ph CH = CH CH CHO
NH2OH
CH3
(A) 2
7.12
(B) 4
(C) 6
(D) 8
Which of the following ketone recemises in aqueous solution containing some acidic or basic
impurities.
CH3CH CH C CH3
(A)
Ph
C2H5 CH C CH3
(B)
Ph
CH3 O
O
CH3
(C)
Ph
C6H5 C C C2H5
Me
(D) Me
O Ph
7.13
The final product (X) of the following reactions would be

C6H5 C C6H5
||
O
(A) Br
NH2OH.HCI
PCI5
Br2/Fe
(1)
(2)
(3)
C
||
N
CI
C
||
O
C
||
O
(B)
NH
Br
OH
(C)
(X)
NH
Br
C
||
O
(D)
NH2
Br
7.14
CH3COCH3
CH3C CNa
H2O
H2,Pd+CaCO3
AI2O3
W, W is :
(A) CH2=CHCH=CH2
(B) CH3 CH = CH CH = CH2
CH3
(C)
CH = CHC = CH2
(D) CH3CH=CHCH=CHCH3
CH3
CH3
7.15
LiAIH4
HBr(excess)/
AICI3
Alc.KOH
Pd,
W
H2
CH3
Identify X, Y, Z and W
X
Z
CH3
Br
(A)
W
CH3
C6H5 C = CH (CH2)2 OH
C6H5 C (CH2)3 OH
CH3
CH3
OH
Br
(B)
CH3
Br
C6H5 C (CH2)3 OH
CH3
CH3
Br
(C)
C6H5 C (CH2)3 OH
CH3
(D) C6H5 C = CH (CH2)2 OH
C6H5 C (CH2)3 OH
CH3
CH3
CH3
Br
CH3
CH3
O
||
C OC2H5
CH3
Br
CH3
Br
7.16
(1) HCI
(2) CH2OH
(i) LiAIH4/Et2O
(ii) H2O
H3O
CH2OH
X
(A)
O
||
COC2H5 O
O
||
COC2H5
Y
O
||
COC2H5
Z
HO
CH2OH
COOH
HO
CH2OH
CH2OH
CH2OH
CH2OH
HO
COOH
(B)
O
(C)
O
||
COC2H5
O
(D)
O
O
CH3
CH2OH
O
O
O
O
HO
Z, Identify X, Y and Z
C4H9Li
7.17
S
R'X
C4H9Li
R''X
HgCI2, H
H2O
The final product U is
(A) S
H
(B) S
R'
R'
(C)
R''
S
H
O
||
C
(D)
Li
R'
7.18
O3
Zn,H2O
Y+Z
CH=CHC
OH
Compound X in the above reaction is
C=CHCH3
(A)
CH2CH=CH
(C)
CH3
C=CH
(B)
CHCH=CH2
(D)

COOH
7.19
H
Ar
1.PCI5
2.CH3MgBr
NH2OH.HCI
H2SO4
Et
X, Y, Z are
CH3
COCH3
(A) H
C=N
Ar
(B) H
Et
Ar
Et
Ar
Et
NHCOCH3
(C) H
OH
NHCOCH3
(D) H
Et
Ar
R''
7.20
Which of the following products is/are correctly mentioned in the following reactions.
NaOD
(A) HCOH
HCOONa + CH3OD
NaOEt
(C) HCDO DCOOEt + DCH2ONa
7.21
NaOH
(B) HCDO
DCOONa + CH2DOH
NaOD
(D) D2CO DCOONa + CD3OD
The correct statement/s about the following reaction sequence is / are

CI2 / FeCI3
HNO3 + H2SO4
HNO3 + H2SO4
(1)
(2)
(3)
(P)
NH2NH2,
(4)
O2N
CH = N NH
(R)
NO2
(5)
(Q)
(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 ?

HOOC
1. NaOH,
CHO
2. H3O
(A) A diacid
7.24
(B) A monoacid
(C) A diol
(D) An alcohol
Which of these carbony compounds on reduction winth Zn Hg / HCI will give th3e same
compound as product
(A)
O
||
HC
CH2CH(CH3)2
(B)
O
||
C CH(CH3)2
H3C
O
||
C C(CH3)2
HC=O
(C) H3C
(D) H3C
CH2 C CH3
H
7.25
whic one of the followning compound will not show enolisation ?
(A)
O
Me
Ph
OH
(B)
(C)
O
OH
O
O
Me
(D) O
O
Ph
OH

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.
7.27
Statement-1 : CH3O
CHO + HCHO
KOH
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 hemiacetalacetal equilibria towards acetal.
OH
(III) Conc. KOH changes PhCCPh to PhCCOO

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

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
C
OH
R'
R' C = N R
H2O
R'C = N R
OH2
R'
OH
R'C NH R
O
It is interisting to note that the migration of group is completely Retentive and no loss of optical
activity is seen.
7.32
O2 N
Me
C=N
OH
H
Br
C NH Me
NH C Me
Br
(A)
Br
(B)
O2N
O2N
O
O
C NH CH3
NH C Me
NO2
(C)
Br
Br
(D)
NO2
7.33
CH3CHO + NH2OH
Br2 /KOH
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
H
H3C
OH
C=N
dil. H2SO4
C
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
1Ehtylcyclopent1ene on reductive ozonolysis followed by aq. HaOH/ gives

O
CH3
(A)
(B)
(C)
(D)
O
O
7.36
CH3
Which of the following compound on reaction with O3/Zn, H2O followed by aq. HaOH/ will form
O
(A)
(B)
(C)
O
(D)
O
CH3CCH2CH2CH2CH2CH
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
OAc
Ph
(ll)
(l)
O
O
=
O
Ph
Ph
Ph
(lV)
(lII)
O
H
4
H
O
Ph
O
C
OH + ACO
H+
Ph
(V)
(Vl)
Reaction -2
Ph
7.38
+ ACO
Ph
The intermediate product similar to (IV) following in the reation-(2) :

Ph
Ph
O
O
Ph
Ph
(A)
O
Ph
(B)
O
Ph
(C)
O
Ph
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
18
(C) Ph CH= CH C O H
(D) H O C O18 H
O
(D)
Ph
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
OH (excess)
R C CH3
R C CI3
I2 (excess)
OH
7.41
R C CI3
R C OH + CI3
OH
R C O + CHI3
Whichof the following compound show haloform reaction and recemisation in OD- / D2O.
O
Me
(A) CH3CH2OH
(B) Et
Me
Me
Ph
(C)
(D) CH3 C CH Ph
O
Et
Et
7.42
(1) I2 /OH +
Ph C C C CH3
(2) H+
(3)
O Me O
product is
O
Ph
O
7.43
(1) NaIO
product is
(2) H ,

7.44
Column-I
Coulmn-II
(p) 1, 4-addition
PhCH2CCH=CH2
(q) Tautomerism
OHC
(r) AgNO3/NH4OH
CH3CH=CHCH=CH2
CH 3CCH 2CH
O
(s) 2,4 DNP test
7.45
Column-I
Coulmn-II
O
NaCN + H2SO4 (A)
(A)
LiAlH4
(p) Formation of six fmember ring take place

(B)
HNO2
Product
O
NH2OH
(B)
(A)
(B) LiAlH4
(C) CH3CCH2CH2CH2CH
O
Product
(q) Final product is ketone
(r) Final product formed will give positive tollen's test
O
Ph
(D)
OH
Product
Product
CH3
OH OH
7.46
Column-I
Coulmn-II
alkaline KCN
(A) PhCH
(s) Final product will react with 2, 4 DNP
Product
(p) Final product formed give positive tollen test
(1) OH
(B)
Product
(q) Final product give test with 2, 4 DNP
(C) CH3COEt
(1) C2H5ONa
Product
(r) Final product react with NaOCO3 and

liberated CO2 gas
(1) KOH
(D) PhCH=O
(2) H
Product
(s) Final product react with Na and liberated H2 gas

SHORT SUBJECTIVE :
7.47
A compound (A) of molecular formula C14H10O12 is formed formed from C14H14O2 by oxidation
Cr2O72. (A) upon treatment with OHgives (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] ?
7.51
CH3CH=O + PhCH2CH=O
mixture of aldols
(z) total number of aldols including stereoisomers
Carboxylic Acid/Acid Derivatives

SECTION - I : STRAIGHT ONJECTIVE TYPE
8.1
PhCOOH, PhMe can be separated by

(A) KMnO4
(C) H2O
(B) aq. NaHCO3 + n-hexane

(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
(A) Ph
(B) Ph
CH
ONaO
C ONa
OHO
(D) Ph C CH2ONa
(C) Ph C C ONa
O O
8.4
In the given reaction, the number of isomeric products formed is+
CH3CHClCOOH
(Racemic mixture)
(A) 1
8.5
CH3 CHDOH
(optically pure d-isomer)
(B) 2
(CH3CO)2O, Pyridine
NH2
ester
(C) 3
(II)
(i) LiAlH4
(ii) H2O
(D) 4
(III) ;
(I)
The basicity order of I, II and III is

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

O
(A) CH3 CH CH2 C OH and CH3 CH CH2 O H
OH
CO2H
(B) CH3 CH2 CH CO2H and (CH3)2 C(OH)CO2H

OH
(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
(A)
(C)
SOCl2
CH2N2
COH
CH2 C OH
NO2
NO2
Ag
H2O
SOCl2
CH2N2
Ag
H2O
(B)
(D)
SOCl2
Ag
H2O
CH2N2
SOCl2
Ag
H2O
CH2N2
8.10
+ 18
H /H2O
X+Y
X, Y are
O
18
OH
18
OH,
(A)
(B)
18
OH
OH
O
OH
18 ,
OH
(C)
(D) All of these
8.11
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
PCl5
8.12
H2O
H3O
N
OH
The product(s) Z is.

O
, CH3NH2
(A)
N
(B)
, CH3OH
NH2
CH3
CH3
(C) NH2 (CH2)5 CH COOH, CH3NH2
8.13
(D) NH2 (CH2)5 CH COOH only
O
Cl
NaN3
(2) OH
Product
Product is/are
(A)
NH2 only
(B)
NH2, HCOOH
O
(C)
CONH2
(D)
+
C OH + NH4
8.14
O
O
AlCl3
Zn/Hg
HCl
SOCl2
AlCl3
W , Product 'W' is :
O
O
(A)
(B)
(C)
(D)
8.15
CCl
NaOEt
CH2(COOEt)2 +
(1 eq.)
Final product is
C
O
OEt
O
COOEt
C CH
COOEt
(A)
(B)
C
COOH
(C)
COOH
CH COOH
C
CH3
(D)
COOH
COOH
OEt
8.16
CH2 COOH
Which of the following undergoes decarboxylation most readily on being heated ?

O
(A)
(B)
OH
O
OO
HO
O
(C) HO
(D)
OH
OH
O
HO
CN
8.17
CN
CN
H3O
A ; product (A) of the reaction is
CN
O
C
(A)
(B)
C
O
8.18
(C)
COOH
O
C
O
Which statement is correct about the following reaction

COCl
H
Br
CH3
NaOH (1 eq.)
COOH
COOH
(D)
CN
CN
COOH
(A)
(B)
(C)
(D)
8.19
There is inversion of configuration at asymmetric C* atom

There is No change of configuration at asymmetric C* atom
There is 100% racemisation at C* atom
% inversion > % retention at C* atom
Identify C in the following sequence of reactions :

CO3H
SOCl2
NH3
CN
OH
(A)
]
CH3
(D)
(C)
CH3
CH3
OMe
CO2Et
EtOOC
H3O
(A), Product (A) obtained is :
O
CO2Et
O
(A)
8.21
CN
CN
(B)
CH3
MeO
heat
CH3
8.20
P4O10
(B)
CO2H
(C)
(D)
Which of the following acid remains unaffected on heating ?

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

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

CH2 COOH
8.23
Ph(CH2)5 C Cl
(A) X is
AlCl3
CH2
(CH2)4
C
(X)
Na2Cr2O7, H heat
(Y)
heat
(Z)
COOH
(B) Y is
COOH
O
CHO
CO
O
(C) z is
(D) Y is
COOH
CO
8.24
trans-2-methylcyclohexanol + acetyl chloride X
X + NaOH (aq) Y + sodium acetate.
(D) Y is
(B) X is
CH3 H
(A) X is
CH3 O C CH3
O C CH3
O
(C) Y is
(D) Y is
CH3 OH
8.25
CH3 H
OH
In which of the following reactions cprrect ,akpr [rpdict os ,emtopmed ?

O
O
(A)
+ CH3OH
OCH3
HO
O
OH
(B)
COOH
+ CH3COCCH3
O
OCCH3
H2SO4
+ CH3COOH
fast
COOH
(asprin)
CH2CH3
CH2CH3
(C) CH3COC
H
O
CH3
CH3COH + HOC
1. OH
2. H
CH3
H
(D) CH3CCH3 + PhCOH

OH
O
H2SO4
CH3CCH3
OCPh
18
18

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
+
Br + RNC=O
CNBr
RN=C=O
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement1.
Statement-1.
8.27
Statement-1 : The base catalysed hydrolysis of ester order is

(1) CH3COOCH3>CH3COOC2H5>CH3COOCH(CH3)2.
COOC2H5
COOC2H5
>
(2)
NO2
COOC2H5
>
Cl
COOC2H5
>
CH3
OCH3
Statement-2 : SN2 Th is sterically as well as electronically controlled reaction.

Statement-1.
8.28
Statement-1 : CO 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)
CH3
(B)
CH3CH2COOH > CH3CHCOOH > CH3
CH3
OH
(C)
CH3
OH
>
COOH (Rate of esterification)
OH
>
(Rate of esterification)
ON2
O
(D)
CH3CCOOH > CH3CCH2COOH > PhCH2COOH (Rate of decarboxylation)

Comprehension # 1
Observe the esterfication mechanisms for primary and tertiary alcohols.
O
Type.1
CH3COOH + CH3CH2CH2OH
Propyl = Pr
Conc. H2SO4
CH3COCH2CH2CH3
Mechanism
O
CH3C
H
CH3C
Step 1.
OH
OH
OH
CH3C
OH
CH3C
OH
H
Step 2
CH3COH
OH
O
Pr H
CH3
OH
Type. 2
Pr
Step 3
CH3COCH2CH2CH3
H
H2O
CH3
+ CH3COH
OH
CH3
Conc. H2SO4
CH3COCCH3
CH3 O
OH
CH3
CH3
H
Mechanism CH3COH
Step 1.
CH3C
+ H2O
CH3COCCH3
CH3
CH3
8.31
CH3
CH3C
CH3 O
Conc.H2SO 4
CH3 COOH + C2H518OH
(P)
Conc.H2SO 4
OH
(Q)
In the above reaction (P) and (Q) are respectively :
CH3 COOH + (CH3)3C
O
18
18
CH3
(A) CH3COC2H5, CH3COCCH3
CH3
18
(B) CH3COC2H5, CH3COCC2H3
CH3
O
O
18
CH3
O
CH3
(C) C2H5COCH3, CH3COCCH3
O
18
18
CH3
(D) CH3COC2H5, CH3COCCH3

CH3
CH3
8.32
CH3COOH + D
OH
Conc.H2SO4
(X)
Conc.H2SO4
(X)
CH3
CH3
CH3COOH + PhCOH
C2H5
(A)
(B)
(C)
(D)
8.33
(X) is optically active while (Y) is optically inactive

Both (X) and (Y) are optically active
(X) is optically inctive while (Y) is optically active.
(X) is optically inactive while (Y) is optically active.
(+) 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
Phenylacetylene
8.34
CH3MgBr
CH4
i) CO2
H2O/H2SO4
HgSO4
Compound z is
O
(B) Ph CH
(A) Ph CH2 C COOH
COOH
COOH
O
(D) Ph CH2 COOH
(C) Ph C CH2COOH
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
R C NH2 + NaOH + Br2
hydrolysis
RN=C=O
isocyanate
R NH2
Mech :
OH
R C NH2
R C NH
Br Br
O
CO2 +RNH
O C NH R
R C NH Br
OH
R C N Br
OH
OH
OC=NR
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
(A)
C C NH2
CH3O
O
(B) CH3CH2CNHPh
O
C
(C) NO 2
8.38
O
NH2
(D) PhCNH2
Arrange the following amides according to their relative reactivity when react with Br2 in excess
of strong base
O
C NH2
C NH2
H3C
II
O
C NH2
C2N
C NH2
Cl
IV
IV
(A) IV > I > II > III

8.39
(B) II > I > III > I
(C) II > IV > III > I
(D) II > I > IV > III
D O
15
Br2/KOH
H3CH2CCHCNH2+ CH3CH2CCNH2
CH3
(R)
Products
CH3
(S)
D
15
(A) H3CH2CCHNH2 & H3CH2CCHNH2
CH3
(S)
CH3
(R)
D
15
(C) H3CH2CCHNH2 & H3CH2CCHNH2
CH3
(R)
D
15
(B) H3CH2CCNH2 & H3CH2CCHNH2
CH3
(S)
(D) B & C both are correct
CH3
(S)

8.40
Column-I
Column-II
O
(A) C 2H 5COH
C2H5O
(p) Hydrolysis
C2H5OH/H
(q) Esterification
H 3O
(r) Saponification
OH
(s) Acid base reaction
O
(B) C 2H 5COH
O
(C) C2H5COC2H5
O
(D) C2H5CO C2H5
CH3
(R)
8.41
Match the column I with column II.

Column-I
Column-II
CH3
HOOC
(A)
COOH
(p) Diastereomer
D
Ph
COOH
H
D
(B) H C
3
1. AgOH /
(q) Racemic mixture
2. Br2 / CCl4
Ph
CH3
COOH
(C) HOOC
(r) Optically active
Et
(D) PhCCDCOH
O CH3 O
(s) CO2 gas will evolve
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.
O S
8.43
H2O
O S O
Me
Et
Et
(Products)
warm
Me
The total number of products obtained in above reaction is.

8.44
Cl
CH2COOH
C2H5OH
(i) C2H5ONa
(ii) CH3l
(i) OH +
(ii)H
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
8.46
When
CH3
C
NH2, CH3 C NH2,and H

O
then how many products are obtained.
C
D
NH2,
is mixed and reacted with Br2/KOH
Biomolecules
(Carbohydrates, Amino acids & Polymers)

9.1
CHO
H
H
HO
H
H
OH
OH
H
OH
H
OH
H
OH
HO
H
HO
H
H
OH
H
OH
OH
H
HO
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
H
H
(A) 1
9.3
9.4
OH
OH
CH2OH
(B) 2
Glycoside linkage is :
(A) an acetal linkage (B) an ether linkage
(C) 3
(D) 4
(C) an ester linkage (D) an amide linkage
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
(Histidine)
N
NH2
IV
CH3 CH CH COOH
(Valine)
CH3
Codes :
(A) only I
9.6
HOOC CH2
(B) only II
(C) IandIII
(D) I, III, IV
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
9.8
Polymer which has amide linkage is

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

(A) Polystyrene
(B) PVC
(C) Polyester
(D) Bakelite
(D) Teflon
Which of the following aldohexoses give the same osazone derivative ?

CHO
H
HO
H
H
CHO
OH
H
OH
OH
CH2OH
1
HO
H
HO
H
(A) I and IV
9.10
CHO
H
OH
H
OH
CH2OH
ll
HO
HO
H
H
(B) I and III
CHO
H
H
OH
OH
CH2OH
lll
HO
HO
HO
H
(C) II and III
H
H
H
OH
CH2OH
lV
(D) III and IV
Which of the following is a non-reducing sugar ?

H
CH2OH
OH
HO
O
CH2OH O
(A)
HO
HO
(C) HOHO
OH
O
(B) HO
O
HO
O
H
OH H
HO
CH2OH
OH H
CH2OH O
CH2OH O
OH
OH
H
CH2OH O
O
CH2
OH O
HO
CH2OH
OH
HO
(D) HO
OH H
HO
HO
OH
OH
H
OH
9.11
9.12
Basic solution of fructose contains :

(A) Only fructose
(C) Fructose and glucose
(B) Only glucose

(D) Glucose, fructose and mannose
Which of the following is a nonreducing sugar ?

CH2OH
OH
OH
CH2OH
H
OH
OH
OH
(D)
H
OH
O
H
OH
OH
Which one of the following is non-reducing sugar ?

(A) Glucose
(B) Mannose
(C) Fructose
Glucose and mannose are :
(A) Anomers
(B) Positional isomers
OH
OH
OH
OH
H
OH
9.14
9.13
OH
H
OH
O
H
(C)
CH2OH
CH2OH
O
H
CH2OH
OH
OH
(B)
(A) OHCH2 C (CHOH)3 CH2OH
H
OH
CH2OH
O
9.9
(D) Sucrose
(C) Functional isomers
(D) Epimers
9.15
9.16
Basic solution of fructose contains :

(A) Only fructose
(B) Only glucose
fructose and mannose
(D) Glucose,
How many moles of acetic anhydride (Ac2O) is needed to react completely with tataric acid,
ribose and glucose respectively.
Tataric acid
Ribose
OH
OH
Glucose
CH2OH
CHO
OH
OH
H
COOH
H
H
HO
COOH
O HO
H
H
OH
H
H
HO
CH2OH
(A) 2,4, 5
9.17
(C) Fructose and glucose
OH
(B) 2, 3, 4
(C) 4, 5, 6
(D) 4, 5, 5
Which of the following amino acid is most basic :

O
(A) H2NCNHCH2CH2CH2CHCOOH
NH
(B) H2N CH C NH CH2 COOH
NH2
CH3
CO2H
(D) HS
(C) HOOC CH2 CH COOH
NH2
NH2
9.18
9.19
Glucose on reduction with Na/Hg and water gives ?

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

O
(A) H N
NH
N
(B)
Me
H
O
Me
H
(C)
NH
O
(D)
NH
NH

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.
H
HO
CH2OH
O
H
OH H
H
CH2OH
dil. HCl
OH
Salicin
The correct statement (s) is (are)

(A) P is D- glucose
(B) Q is 2-hydroxybenzylalcohol
P
+Q
Carbohydrate
(C) Q can be converted to a modern anlgesic (pain killer), aspirin

(D) The above reaction occurs through a carbocation
F
9.21
O2N
+ H2N
O
C
NH
CH3
NO2
COOH
2. dil. NaOH
CH2
Ph
The products can be
O2N
NO2
NH
NO2
NH
H
(V)
COO
COO
CH3
O2N
CH2Ph
NHAC
NO2
H
(D) NH2
COOH
CH2Ph
NO2
9.22
Glucosazone is osazone derivative very similar to that formed from

(A) Fructose
(B) Galactose
(C) mannose
(D) glucose
9.23
The
(A)
(B)
(C)
9.24
The
(A)
(B)
(C)
(D)
9.25
Observe the following reaction and mark the correct statements (s) given below-
correct statements about peptides are

A dipeptide has one peptide link between two amino acids.
By convention N-Terminus is kept at left and C-terminus at right in the structure of a peptide
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
correct statements about anomers are
Anomers have different stereochemistry at anomeric carbon atom
a-D-glucopyranose and b-D-glucopyranose are anomers
a-D-glucopyranose and b-D-glucopyranose are diastereomer
When pure a-D-glucopyranose is dissolved in water its optical rotation slowly changes
CHO
H
OH
HO
OH
OH
CH2OH
D-glucose
MeO
OMe
H
MeOH
dry HCl
HO
H
OH
H O
OH
H
C
HO
+
OH
H O
OH
H
CH2OH
CH2OH
(A)
(B)
(C)
(D)
Methyl glucosides do not react with Fehling's or Tollen's reagent.

The reaction passes through a carbocation
The two forms of glucosides are enantiomers
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 H2NOH
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).
HOH2C
H
CH2OH
O
H HO
HO
H
(I)
OCH3
HO
CH2OH
H
H
O
H
OH H
H
OCH3
OH
(II)
Staftement-2 : The intermediate carbocation in case of I is more stable than in case of II.
Statement-1.

9.31
9.32
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 Dfructose 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
The true/false statements about the following compounds are :
H
CH2OH
O
H
OH H
CH2OH
O
H
OH H
OH
CH2OH
O
H
OH H
H
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
l
ll
lll
lV
9.33
9.34
Aspartic acid
Glutamic acid
Lysine
Arginine
P Ka1
P Ka2
P Ka3 (side chain)
1.88
2.19
2.18
2.17
9.6
9.67
8.95
9.04
3.65
4.25
10.53
12.48
In the table given above the acidic amino acids are

(A) I, II
(B) I, III
(C) II, III
(D) I, II, IV
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
O H
H
H
OH
O H
OH
OH
OH
OH
H
(H2 O)
CH2OH
O H
H
H
OH
Dimerisation
H
OH
OH
H
CH2OH
CH2OH
H
OH
OH
H
OH
OH
O H
OH
(I)
OH
(II)
Polymerisation
Starch (polymer) (III)
9.36
9.37
9.38
What is true abouit compound (I)

(A) It has an acetal strukctukre
(C) It has a hemiacetal structure
(B) It has tertiary hydroxy group

(D) It's degree of unsatkuration is two
Compound (II) is/has

(A) A polysaccharede
(C) Monosaccharide
(B) Oligosacharide
(D) Hydrogen deficiency index is three
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
(A)
CH2OH
O H
H
H
(B)
H
OH
H
OH
OH
OH
CH2OH
(C)
OH
OH
CH2OH
O H
H
OH
O H
(D)
O
H
OH
OH

9.39
Match the following column-I with column-II :

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

Column-I
(A)
(B)
(C)
(D)
9.41
Natural rubber
Nylon-66
Bakelite
Buna-S
Column-II
(p)
(q)
(r)
(s)
(t)
Match the Column-I with Column-II.

Column-I
(A)
(B)
(C)
(D)
Fructose
Zwitterion
Peptide linkage
Hydrolysis of cane sugar
Thermosetting polymer
Homopoluymer
Butadiene & styrne
Polyamide
Copolymer
Column-II
(p)
(q)
(r)
(s)
(t)
Protein
Inversion
-Amino acid
Carbohydroate
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 -
9.43
The pka1, pka2 and pka3 values for the amino acid cysteine
HSCH2CHCOOH
NH2
are
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
(a) (Ser, Hyp, Pro, Thr)
H3O
Ser, Thr + Thr, Hyp + Pro, Ser
A B C D
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
(B) CH3 CH C C CH3
(A) CH3 C C CH3
CH3
(C) CH3 CH2 CH = CH2
(D) All of these

(i) Na metal
10.2
(ii) Cl2/h
Compound C4H10O
(iii) Lucas reagent
No H2 gas evolved
3-monochloro
products
Ve test
Compound is
O
(A)
10.3
(B)
(C)
(D)
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'
OH
OCH3
CH2 CH2 OH
(A)
(B)
CH3
OH
CH2CH3
(C)
(D)
CH3
CH3
Br2/H2O
10.4
C4H6
(X)
Bayer's reagent
Na metal
(A) H3C C
C CH3
(B) CH2 = CH CH = CH2

C
(C) CH3 CH2 C
CH
(D)
CH
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
(A) HCH and PhCH
O
D
H and H
(B)
O
O
(C)
Me
C=O
(D) PhCPh and MeCMe
and
O
Me
10.7
C=O
Observe the4 following compound and select +Ve & Ve tests respectively
(i) Na metal
HO
CH
(ii) NaHCO3
(iii) 2,4-DNP
OHC
COOH
(A) + + +
10.8
(iv) Lucas reagent
(B) + + + +
(C) + +
(D) + +
Consider following compounds and decide as to which of the following statements are true ?
CH3
CH2 = CH C COOH
H
(I)
CH3
CH3 C OCH3
CH3
(II)
CH3
CH3OC
CH
(III)
CH3 C CH2OCH3
OH
(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
COOH
(A)
COCH3
(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 CH3
OH
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
4Amino2, 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
O
(A)
OO
(B)
OO
(C)
(D)
10.14 A set of reagents (1 to 8) are successively reacted with the followit compound
O
OH
OH
1. NaHCO3
5. Fehling's solution
The reagents which
(A) 1, 2, 3, 4, 5
and 8
2.2, 4, DNP
3.Na metal
4. AgNO3 +OH
6.Cu2CI2 + NH4OH
7. Br2/H2O
8. NaNO2 + HCI
give positive test with the given compound are :
(B) 3, 4, 5, 6, 8
(C) 1, 2, 3, 4, 8
(D) All reagents except 1
10.15 Compounds (C8H8O) X will give following laboratory tests.

Isomers
FeCl3
AgNO3 / NH4OH
Coloured solution
Negative
Na metal
1/2 H2
X can be :
OCH3
CH2OH
(A)
(B)
CH = O
H3C
OH
(C)
CHO
O
O
(D)
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)2C CH2OH
OH
(B) OHC(H2C)2HC = HC COOH
OH
(D)
(C)
CHO
10.18 In compound A (C30H60O) following tests are observed negatively, A can be :

Br2 / H2O
C30H60O
2, 4 DNP
Na metal
(A)
-Ve
-Ve
-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
(A) CH3(CH2)8CHO
NH2
and
COOH
COOH
(B)
and
NH2
NO2
CHO
and
(C)
NO2
CHO
(D)
CHO
and

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
Br2water
Nametal
Lucas reagent
lodoform test negative
The compound X and Y are
(A)
OH
(B)
positive
positive
turbidity after some time
negative
OH
(C)
OH
negative
negative
negative
(D)
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
(C)
OH
CH = CH CH3
(D)
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
(lll) C6H5 CH2 C CH3
O
(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
aq.NaOH
(A)

aq.HCI
aq.NaHCO3
(B)

aq.NaOH
aq.NaHCO3
(C)

aq.NaOH
aq.HCI
(D)


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
P (C9H9Br)
O3 / Zn,H2O
reductive
R + Q
(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
(A)
Br
CH= CH CH3
(B)
Br
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)
CH3
Br
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
(C)
CH3
(D)
CH3
CH3
10.32 Which of the following statement is true

O
H3 C
(A) T is C
O
C CH3
(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
C
||
O
COONa

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
(B) Compound Y
(C) Compound Z
(D) Compound W
(p) Bayer's Test

(q) NaHCO3
(r) 2, 4-DNP
(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)
Column - I
Column - II
C
(A) Sodium metal
CH
(X)
O
CH3
(B) Sodium bicarbonate
C CH3
(Y)
OH
C
(C) 2, 4-Dinitrophenylhydrazine
CH
(Z)
COOH
OHC
CH = CH2
(D) Lucas reagent
(W) H3CO
OH

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
10.37 How many acidic H is present in given compound.

OH
O
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.
NNH
CHO
H
Hint :
OH
HO
OH
OH
NNH
3PhNHNH2
CH2OH
HO
OH
OH
CH2OH
10.40 How many CHI3 will be released from given compound.

O
||
O
||
H2N
OCH3
O
O
+ PhNH2 + NH3

Questions Chapter 1-10

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Questions Chapter 1-10

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General Organic Chemistry-I

SECTION - I : STRAIGHT OBJECTIVE TYPE

IUPAC name of compound

Which of the following structure\s is the correct structure of 3-ethyl-5, 5-diisopropyl-7-methlnonane

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

Correct IUPAC name of the following compound is :

(A) 3-(Hepta-2,4,6-trienyl)-4 bromo cyclopenta-2, 4, -dien-1-ol

The IUPAC name of the compound

(A) Tropyluim bromide

Correct IUPAC name of the co,pound H3C CH2 O C

Correct IUPAC name of the compound

The IUPAC name of the following compound is

(A) 2-(Ethoxycarbonyl) benzalychloride

(B) Ethyl 2-(Chloroformyl)benzoate

Identify the structure of x,

CH3 C CH C H + H C H + CH2 C C CH2 C H

For the following reactions sequence HOOC

(A) Position isomers

(B) Chain isomers

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

(A) (X) is the most stable conformer of meso-2,3-Diiodo-2,3-dimethylbutanedioic acid

(B) The most stable conformation will be

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

How manyh assymmetric carbon atoms are present in

Which of the following statements is not correct?

Identify the pair of enantiomers amongst the given pairs:

SECTION-II : MULTIPLE CORRECT ANSWER TYPE

Which of the followning statements are not correct?

Consider following compounds

Choose the correct statement(s)from the following

(A) (I)and (III)are structural isomers.

(B) (I)and (II)are geometrical diastereomers

Which of the following is\are a meso compoumd.

Which of the following pair represents the correct relationship

Statement-1:Restricted rotation about a bond is the necessary condition for geometrical

Statement-1: Aracemic mixture of 2-Chloropropanoic acid is treated with excess of (+)-2-Butanol.

CH3CHCOOH + CH3CHCH2CH3 CH3CHCOOCHCH2CH3+CH3CHCH2CH3

SECTION-IV : TRUE & FALSE STATEMENT TYPE

The products(ester)of following reactiongive diastereomers

(D) Nuclear Isomers

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

Which of the following statement is true

is the isomeric amide of oxime of next higher homolog of Z.

The pair showing identical species is

Observe the following reaction

Which statement is not correct about the above observation.

(q) Can exhibit geometrical isomers

(r) Compounds with this structure formula

(s) Is capable of showing stereoisomerism

(p) can be separated by fractional

(q) Can not be separated by

(r) Optically resolvable

(s) donot have identical boilling point

SECTION-VII: SUBJECTIVE ANSWIR TYPE

Total number of stereoisomes possible for molecule A will be

Number of possible fractions of B are:

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

General Organic Chemistry-II

SECTION-I: STARINGT OBJECTIVE TYPE

Choose the correct statement

The correct stability order of following species is :

Which of the following does not represent the resonating structure of

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

(B) H3C O = CH CH2 (C) H 3C O = CH CH 2 (D) H3C O = CH CH2

reason for this is

Most contributing structure in nitroethene is

N(I)has more 's' charcter in NCH3 bonds

The acid strength order is:

(A)I> IV> II> III

(B)III> I> II> IV

(C)II >III> I>IV

(D)I >III >II> IV

Acid strenght of the conjugate acids of the following are-

(A)I> II> III >IV