Chemistry by Prof.

Ajay Y Kapoor Sir

TOPIC : REACTION INTERMEDIATE (Carbocation) : SINGLE TYPE QUESTIONS


Q.1 H (X).


Product (X) is

(A) (B)

(C) (D)

Q.2 Which one of following carbonyl compound when treated with dilute acid forms the more stable
carbocation?
O
||
(A) CH 3  C  CH 3 (B)

O
||
(C) (D) C6 H 5  C  C 6 H 5

Q.3 How many 1,2-Shifts are involved during the course of following reaction:

conc. H SO
 24 

(A) 1 (B) 2 (C) 3 (D) 4

Q.4 HNO
2  A (Major)

Product 'A' is:

(A) (B)

(C) (D)

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 Chemistry by Prof. Ajay Y Kapoor Sir
Q.5 Most appropriate transition state in dehydration of alcohol is (In acidic medium).

Low ve charge High ve charge

density on R density on R

H  
H
 
(A) R ------ O (B) R ------------ O
H H

H  
(C) R ----- O (D) R ----- O – H
H

O
||
H
Q.6 (B)

(A)

Give structure of (B)

O

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

O

CH 3 CH 3
| | H
Q.7 CH 3 — C — C — CH 3 

(P) (Major)
| |
OH OH

Major product (P) is:

O CH 3 CH 3 CH 3
|| | | |
(A) CH 3 — C — C — CH 3 (B) CH 2  C — CH — CH 3
|
CH 3

CH3 O O
||
(C) (D) CH 3  C  CH 3
CH3 CH3

Me
Q.8 O3
 A+ B ;

Total two type of Molozonides are formed identify relation between them?
(A) Diastereoisomers (B) Geometrical isomers
(C) Enantiomer (D) Identical

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Q.9 Which of following on ozonolysis give 2-different product ?

(A) (B)

CH 3
|
(C) (D) CH 3  C  CH  CH  CH 2

OH

Q.10 Reaction-Ist Ph /
H
Br / CCl
 (A) Major product 2 4  (B)

Br / CCl
Reaction-IInd Stereoisomer of "A" 2 4  (C)
Identify relationship between (B) and (C) products.
(A) Enantiomers (B) Diastereo isomers (C) Identical (D) Geometrical isomers

Ph Ph Ph Ph MeO

Q.11
Ph
(I) (II) (III) (IV)
Order of rate of electrophilic addition reaction with HBr will be
(A) IV > I > III > II (B) I > II > III > IV
(C) I > III > II > IV (D) IV > I > II > III

—
Q.12  A. Here A is:
Cl

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

Ph 14 Ph
C—C Conc. H SO
  
2
4 
Q.13 OH OH  A, A is:
MeO CH3

Ph Ph
Ph Ph
C= C 14
(A) 14
(B) MeO C– C=O
MeO CH3

CH3

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 Chemistry by Prof. Ajay Y Kapoor Sir
Ph Ph O
14 14
(C) CH3 C – C–Ph (D) Ph–C—C Me
O

OMe OMe

AgNO
Q.14 Ph  C(OH )  C(I)Me 2  3  ?
| 
Me
Major product is

OAg
|
(A) Ph C(OH)  C( NO3 )Me 2 (B) Ph C  C( NO3 )Me 2
| |
Me Me

(C) Ph CO  CMe 3 (D) Ph C (Me2) CO Me


Q.15 H
 ? Product is:

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

NaNO
Q.16  
2  A
HCl,

A is

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

Q.17 from the two pairs (a) and (b) of resonance structures given below, designate the ones that would
contribute most to the resonance hybrid.

(a) (b)

(A) I & III (B) I & IV (C) II & III (D) II & IV

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 Chemistry by Prof. Ajay Y Kapoor Sir
Q.18 Correct order of rate of hydrolysis for following compounds is

[I] [II] [III] [IV]

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

Q.19 HCl
 ?
(1eq.)

Major product of this reaction at 40°C is:

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

Q.20 CH2=CH–CH2–CH2–CH2–CH2–SH Br


2 ?
CCl 4

Major product of this reaction is:

(A) Br2  CH 2  CH  CH 2  CH 2  CH 2  CH 2  SH
|
Br

(B) Br2  CH 2  CH  CH 2  CH 2  CH 2  CH 2  SH
|
CCl 3

(C) Br2  CH 2  CH  CH 2  CH 2  CH 2  CH 2  SH
|
Cl

(D)

Q.21 What will be the product of hydration of 3-chloro-1-fluoro- propyne?

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

Q.22 Predict the major product P in following reaction:

NaNO
 2  P
HCl,

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(A) (B)

(C) (D)

Q.23 Which of the following will not decolourize bromine water

(A) (B) CH2= CH2 (C) Me–CCH (D)

Q.24 The most appropriate starting material for one step synthesis of compound (I) are

(I)

(A) (B)

(C) (D)

Q.25 The incorrect statement regarding the product of reaction

Br2
A 
 B
CCl 4

(alkene)
(A) A is trans and B is a meso compound if R = R'
(B) A is trans and B is a racemic mixture if R  R'
(C) A is trans-alkene and B is always racemic mixture irrespective of the face whether R and R' are the
same or different.
(D) B is optically inactive due to external compensation if R  R' and optically inactive due to internal
compensation if R=R'.

Q.26 When reacts with Br2/CCl4, the major product obtained is

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

HOCl
Q.27 HCCH  A
( excess )

CH3–CCH HOCl
 B
( excess )

A & B are respectively

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 Chemistry by Prof. Ajay Y Kapoor Sir

(A) Cl2CH–CHO & CH3–CCl2–CHO (B) Cl2CH–CHO & CH 3C  CHCl 2

||
O

(C) Cl2CH–COOH & CH3CCl2COOH (D) Cl2CHCOOH & CH 3C  CHCl 2

||
O

Q.28 + Br2  A. A is

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


Q.29 H X


X is:

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

Q.30 The major product formed upon addition of 1 mole of HBr in the following reaction is :

Major Product ?

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

Q.31 The major product formed in the following reaction is :

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

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Q.32 Find out the correct order of rate of dehydration for given compounds with conc. H2SO4.

OH OH
OH OH

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

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


H
H2O A
(i) Hg(OAc)2 / THF, H2O
Q.33 
B
(ii)NaBH4, OH
(i) B2H6/THF
(ii)H2O2/NaOH
C

Select the correct statement about products A, B & C.

(A) A is a secondary alcohol
(B) B is a tertiary alcohol
(C) C is a primary alcohol
(D) A & C are tertiary alcohol

HBr
Q.34 HCl
 (1eq )
 X (major) 
 Y (major)
ROOR ,  ROOR

Y is
Cl Br Br Cl

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

Br Cl Cl Br

Q.35 Polymer of 2-methyl-1, 3-butadiene (isoprene) would give which product on (reductive) ozonolysis.
O O
|| ||
(A) CH 3  CH  C  CH 3 (B) OHC  CH 2  CH 2  C  CH 3
|
CHO

(C) OHC – CH2 – CH2 – CH2 – CHO (D) CH 3  C  CH 2  C  CH 3

|| ||
O O

Q.36 Which molecule will give the following dicarboxylic acid on heating with acidic solution of KMnO4?
O

HOOC || CH2COOH
O

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

conc. H SO
OH    4  Product major is
2
Q.37


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

Br (1eq.)
Q.38  Major product is
2 
CCl 4

Me Me Me
Br Br
Br
Br Br Br
(A) (B) (C) (D)
Br
Br
Br
Br

Ph Me
Cl 2
Q.39   
 Major product is
18
H H CH 3OH ( excess ),

Ph Ph Ph Ph
18
H Cl H Cl H Cl H OCH3
18 18
(A) CH3 Cl (B) H OCH3 (C) CH3O H (D) Cl H

H CH3 CH3 CH3

Ph Ph

Q.40 (
i ) BD3 . THF
  Product is
(ii ) HCOOD / D 2O
H H 

Ph Ph Ph Ph
H D D H H D H H
(A) D H (B) H H (C) H D (D) D D
Ph Ph Ph Ph

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 Chemistry by Prof. Ajay Y Kapoor Sir
CH2–OH
Conc.H SO
Q.41   2 
4
Major Product is


CH3
CH2 CH3 CH2–HSO4

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

OH

Cl
O / Zn 
Na
Q.42  A 
3
 B Mg
  /
Hg
 C H Product is
Dry ether H 2O (ii ) H  
Cl

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

Q.43 Which of the following represent correct order of leaving group nature.
(A) I  > F  > Cl  > Br 

(B) I  > Cl > F  > Br 
 
(C) I  > Br > Cl > F 
 
(D) Br  > F > Cl > I 

Q.44 Which of the following alcohol undergoes dehydration most easily.

OH OH OH

(A) (B) (C) (D) CH2 = CH – OH

conc . H SO
Q.45 (I)   
2
4  A (major)

OH OH

conc . H SO
(II)   
2
4  B (major)

OH OH
A & B are :
(A) Enantiomers (B) Positional isomers
(C) Functional isomers (D) Metamers

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(1) B2H6
Q.46
(2) NaOH / H2O2
Major product is
(A) Cis (B) Trans
(C) Mixture of cis and trans in equal amount (D) Mixture of cis and trans in unequal amount


dil. H
Q.47
Potential energy diagram for the formation of major product in above reaction.

(A) (B)

(C) (D)

Q.48 Br

2 Incorrect about product mixture is:
CCl 4
(A) Product mixture is optically inactive.
(B) Product mixture is having only achiral components.
(C) Product mixture is resolvable.
(D) Overall anti addition takes place in this reaction

Me NH2
Ph
Q.49 Me
NaNO
 2  (Major product in hemiacetal form)
/ HCl
Ph
O
Me

Me Me Me Me
Ph Me Ph Me
Me Ph Me Ph
Me Ph Ph Me
(A) (B) (C) (D)
Ph Me Me Ph
O O O O
OH OH OH OH

Q.50 Find out the number of 1-2- shifts during the conversion of





(A) 2 (B) 3 (C) 4 (D) 5
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 Chemistry by Prof. Ajay Y Kapoor Sir
Q. No. Answer Q. No. Answer
1 A 26 D
2 C 27 D
3 C 28 A
4 A 29 A
5 B 30 B
6 B 31 C
7 A 32 C
8 C 33 C
9 A 34 A
10 B 35 B
11 D 36 D
12 C 37 A
13 B 38 D
14 D 39 D
15 D 40 C
16 D 41 B
17 D 42 D
18 A 43 C
19 C 44 A
20 D 45 D
21 C 46 B
22 A 47 A
23 D 48 B
24 D 49 B
25 C 50 B

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