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ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

IIT JEE: 2016

CRASH COURSE (C 8 A 1)
TOPIC: ISOMERISM, REACTION MECHANISM

SECTIONI (Single Choice Questions)


This section contains 10 multiple choice questions. Each question has 4 choices (A), (B), (C)
and (D) for its answer, out which ONLY ONE is correct.
1.

Which molecule is (R, Z)-7-methoxy-2, 7-dimethyl-4-propylnona-1, 4-diene?


H3CO

H3C
H3C

CH3

H3C

CH3

OCH 3
CH3

CH2
CH3

(A)
H3CO

CH2
CH3

(B)
H3CO

CH3

H3C

CH3

OCH3

H3C

CH3

CH2

(C)
2.

CH3

CH2
CH3

(D)

Which type of isomerism is observed between I and II?


CH3 CH 2 NH CHO

CH 3 CH CHO
NH 2

(I)

3.

4.

(II)

(A) Chain isomers


(C) Functional group isomers

(B) Position isomers


(D) Metamers

Meso-tartaric acid and d-tartaric acid are


(A) Positional isomers
(C) Diastereomers

(B) Enontiomers
(D) Racemic mixture

How many stereoisomers of the following molecule are possible?


HOOC.CH C CH.COOH
(A) only two optical isomers
(B) only two geometrical isomers
(C) two optical and two geometrical isomers
(D) none

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5.

What of the following pair of isomers can not be separated by fractional distillation?
(A) Maleic acid and fumaric acid
(B) (+) - Tartaric acid and meso-tartaric acid
CH3 CH COOH
NH 2

(C)

and H 2 N CH 2 CH 2 COOH

(D) (+) - lactic acid and () - lactic acid


6.

Identify specific rotation of a mixture have 5g of (+) 2-butanol and 7g of () 2-butanol, if specific
rotation of 100% pure compound is +13.5 o.
(A) 2.25o
(B) 1.6o
(C) 12.2o
(D) 4.45 o

7.

How many 1, 2-hydride shifts are involved during following reaction:


OH
CH3

conc.H 2SO 4

(A) 1

(B) 2

(C) 3

(D) 4

8.
H3C

CH3
OH

P
low Temp.

The product P is :
CH3
H3C

CH3

H3C

CH3

CH3

CH3

CH3
OH

(A)
9.

10.

(B)

(C)

(D)

In the given reaction :


HI/
C 6 H5 O CH 2 CH3
X Y
X & Y will be :
(A) C 6 H 5 I & CH 3 CH 2 I

(B) C 6 H 5 OH & CH 3CH 2 I

(C) C 6 H 5 I & CH 3 CH 2OH

(D) C 6 H 5OH & CH 2 CH 2

Identify correct reactivity order for E2 reaction with alcoholic KOH.


CH3

(i)H3C

CD3
Cl

CH3

(A) i ii iii

(B) iii ii i

(ii) D3C

Cl
CD3

(C) ii iii i

CT3

(iii) T3C

Cl
CT3

(D) iii i ii

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SECTION-II (Multiple Choice Questions)


This section contains 20 multiple choice questions. Each question has 4 choices (A), (B), (C)
and (D) for its answer, out which ONE OR MORE is/are correct.
11.

Which of the following are optically active?


Me
Me

(B) Me

Cl

(A)

Me

OH

H3C

H3C
H

(C)
12.

Cl

(D)

Identify the compound that give trans product on reaction with Zn dust and heat.
Cl
CH3
H

Cl

Cl

CH3

CH3

(A)

CH3

CH3

Cl

13.

Cl

(B)

Cl

CH 3

Cl

(C)

CH3

Cl
T

(D)

C2 H5

Identify the structure of meso compounds?

D
CH 3

CH3

H
D

CH3

H
CH3

(A)

(B)

Cl
D

CH3
OH

Cl
(C)

Me

CH3

(D)

D
OH

CH3

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14.

Identify compounds that show geometrical isomerism.


CH3

Cl

Me
S

(A) H

H
CH2

(C) H3C
15.

(D) H2C

CH2

Which of the following can show tautomerism?


O

(A)

CH4

(B)

(C)
16.

CH3

(B)

(D)

The correct conformation of the following compound can be :


Et
Me

CMe3

CMe3

Me
Me 3 C
Me
Et

Et

(A)

(B)

Me
Me3C

Me3C

(C)

Me
Et

(D)

Et

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17.

Identify compound having highest heat of combustion.


Me

Me

t-Bu

t-Bu

(A)

(B)
t-Bu

Me

(C)
18.

19.

Me

Me

(D)

Which of the following is not a isomer of Butanal?


(A) Butanol
(B) Butanone
(C) Diethyl ether

(D) Butenol

The Fischer projection of the given Newmann projection can not be :


H
Me

CHO
OH

Ph
D
Ph
HO

(A)
20.

Ph

H
Ph

CHO

CH3

CH3

OHC

CHO
D

(B)

OH

H
OH

Me

OH

Ph

CHO

CH3

(C)

(D)

The dihedral angle between two methyl groups in partially eclipsed conformation of n-butane is :
(A) 180 o
(B) 120 o
(C) 90o
(D) 109 o28

21.
CH3
OH

1eq.
OH
CH3

Correct statements for the given reaction :


(A) Product mixture is resolvable
(B) Products can be separated by fractional distillation of mixture.
(C) Two products possible and both are optically active
(D) Products are diastereomers
22.

Which of the following reaction are nucleophilic substitution reaction?


(A) R CHO R 'MgX
R CH R '
OH
CH3

(B)

CH3

H C
Br NH 3
3

H3C
CH3

(C)

H3C

NH2
CH3

H 2 O
H C
3

CH3
OH

CH 3 CH CH 3
(D) CH3 CH CH 2 H3O
OH
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23.
OH

OH

Me

Me

Major product is :
OH
H2C

CH2

H2C

(A)
H3C

OH

H3C

H3C

(C)
24.

Me

(B)

OH
CH3

(D)

The possible structure of the alcohol is


H 2SO4
R OH

Alcohol

CH 2

OH

OH
OH

(A)
25.

(B)

(C)

OH
(D)

Which of the following can be formed during given reaction?


Cl
Aq. NaOH

Cl
OH

OH

OH
O

Ph

(A)
26.

Ph
Cl

Ph

Ph
OH

(B)

Ph

Ph
H

(C)

(D) Ph

Ph

Which of the following solvents favour SN2 reaction?


O

O
Me

(A) Me
27.

Me

(B) Me

H
Me

(C)

Me

(D) CCl4

Select correct statement for given reaction :


OH

(A) Double bond equivalent of final product is odd number


(B) Reaction proceed via E2 mechanism
(C) only two 1, 2-shifts will take place
(D) product is spiro compound.
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28.

Consider the reactions :


C 2 H5 OH
CH3 2 CHCH 2OC 2 H5 HBr
i CH 3 2 CHCH 2 Br

C HO
CH 3 2 CHCH 2 OC 2 H 5 Br
ii CH3 2 CHCH2 Br
2

The mechanisms of reaction (i) and (ii) are respectively :


(A) SN2 and SN1
(B) SN2 and SN2
(C) SN1 and SN2
29.

Which will dehydrate at faster rate by H 3PO4 :


(A) 2-methyl butan-2-ol
(C) Butan-1-ol

30.

(D) SN1 and SN1

(B) 3-methyl butan-2-ol


(D) 2-methyl butan-1-ol

Which of the following is correct about product P?


OH

'P '

OH

(A) It is a spiro compound


(C) It can show tautomerism

(B) It is a ketone
(D) Its Double bond equivalent is 3

SECTION III (Integer Answer Type)


This section contains 20 questions. The answer to each of the questions is a single digit integer,
ranging from 0 to 9. The correct digit below the question number in the ORS is be bubbled.
31.

Number of optically active alcohols with molecules formula C5 H12O is

32.

How many chiral centers are present in given compound?


OH

CH3

CH3
Me

H3C

N
CH3

33.

Ph
HO

Number of primary amides for molecules formula C5 H11ON

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34.

Number of molecules that show geometrical isomerism :


CH3
CH3

CH3

H3C

H2C
CH3
CH3

H3C

CH3

CH2

CH3

CH3

CH3

Cl
N

CH3

H2C
Cl

CH3

H3C

H3C

H3C

CH3

CH3

F
C

OH

Br

C
Cl

F
C

HN

NH

35.

Total number of vicinal diol for molecular formula C 4 H10O 2 is :

36.

How many of the given compounds are Z-form?


OH
H3C

CH3 H3C

Me

OH

Et

OMe

CN

CN

H2N

NH2

CH3

OH

CH2
HC

CH3

Br

Cl

37.

CH3

Me

H3C

Me

CH3

CH3

CH3

CH3

How many chiral carbons are present in given compound?


CH3

CH3
CH3

N
H3C
Cl
S
OH

38.

Number of hyperconjugating structures (involving CH bond) for given compound :


CH3

39.

How many stereoisomers are possible for the given compound?

OH
H 3C

CH3

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40.
CH3

Br

Br

CH3

H3C
Br

CH3

II

If

x Number of stereoisomers of I
y Number of stereoisomers of II

Find value of 2 x y
41.

Total number of stereoisomers of the following compound are :


CH3
CH3

H3C

42.

Number of plane of symmetry in Benzene.

43.

How many 1, 2-shifts are involved during the course of following rearrangement :

44.
CH3
NBS

Total number of allylic brominated products in the given reaction :


45.

How many of the following carbocations undergo re-arrangement?


CH3
H3C

CH3

CH3

H3C

H3C

CH3

H3C
CH3
H3C

OH

CH3

H3C

CH3

CH2

CH3

46.

Total number of alkene products when 3-chloro-3-mthylheptane react with alcoholic KOH and heat.

47.

If x is the total number of -H present in alkene formed as major product when 2, 3-dimethyl
butanol react with conc. H2SO4/ . Find x .
2

48.

Calculate percentage of recemic mixture, if (R)-2-chloro butane on reaction with NaOH gives 98%
inverted product.

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49.

CH3
Aq. KOH

C onc. H SO

2
4
A
B
CH3

H3C
I

Considering B as the major product of the above reaction, if :


x no. of carbon in principal chain in B
y no. of ' CH 3 ' units present in B
Find x y .
50.

How many of the following is correct regarding stability of carbocation?


F

CH3

CH3

CH3

H3C

H3C

CH 3

iii

CH3

CH3

H3C

H3C

CH 3

iv

CH3

CH3

ii

NO2

CT 3

CH3

vi
CH 3

CH3

CT 3

CT3

CH3

vii

viii

H3C

CH3

CH2

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA / PUNE # 10

ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

IIT JEE: 2016

CRASH COURSE (C 8 A 1)
TOPIC: ISOMERISM, REACTION MECHANISM

ANSWER KEY
1.

(A)

2.

(C)

3.

(C)

4.

(A)

5.

(D)

6.

(A)

7.

(B)

8.

(D)

9.

(B)

10.

(A)

11.

(AD)

12.

(ABC)

13.

(ABC)

14.

(ABD)

15.

(D)

16.

(BD)

17.

(C)

18.

(AC)

19.

(BCD)

20.

(B)

21.

(AC)

22.

(BC)

23.

(D)

24.

(AB)

25.

(ABD)

26.

(ABC)

27.

(AC)

28.

(B)

29.

(A)

30.

(ABCD)

31.

(6)

32.

(9)

33.

(5)

34.

(6)

35.

(6)

36.

(4)

37.

(5)

38.

(7)

39.

(4)

40.

(4)

41.

(8)

42.

(7)

43.

(4)

44.

(9)

45.

(2)

46.

(5)

47.

(6)

48.

(4)

49.

(8)

50.

(6)

CENTERS: MUMBAI / DELHI / AKOLA / KOLKATA / LUCKNOW / NASHIK / GOA / PUNE # 11