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CSIR-UGC-NET/JRF | GATE CHEMISTRY

TEST : REACTIVE INTERMEDIATE (BATCH-A)

Time 00: 45 Hour Date : 29-09-2017

M.M. : 60
INSTRUCTION :
1. There are Two Parts. Part-A contains 10 objective type questions, each question carry 2 marks
and Part-B contains 10 objective type questions, each question carry 4 marks.
2. There is negative marking, @ 25% will be deducted for each wrong answer.
3. Attempt all the questions, use of calculator is not allowed.

PART - A
1. Product (P) formed in the following reaction
N
N
EtO2C
(P)
heat

H
N2
(a) (b)
CO2Et
CO2Et

CO2Et N NH CO2Et
(c) (d)

2. Correct order of carbocations (I-IV) in terms of stability is

(I) H3C C O (II) Ph CH2 (III) CH (IV) Tropylium cation

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(a) IV > I > II > III (b) IV > II > III > I (c) II > IV > III > I (d) IV > III > II > I
3. Correct order of stability of carbanion is
(a) Ph  CH 2  Ph 2 CH  CH 2  CH  HC  C
(b) Ph 2 CH  Ph  CH 2  HC  C  CH 2  CH
(c) Ph 2 CH  Ph  CH 2  CH 2  CH  HC  C
(d) HC  C  Ph 2 CH  PhCH 2  CH 2  CH
4. Correct order of stability of free radicals (I-IV) is
• • • •
(I) H2C CH CH2 (II) Me2CH (III) Ph (IV) Ph3C
(a) I > IV > II > III (b) IV > I > III > II (c) IV > III > I > II (d) IV > I > II > III

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Cl Cl
SbCl5
(P)
5.
Cl Cl

The major product (P) in the above reaction is

Cl Cl
Cl Cl
Cl

(a) (b) (c) (d)

Cl Cl Cl Cl Cl Cl
6. Spin trapping technique is used for detection of
(a) carbonium ion (b) Free radical (c) Benzyne (d) Carbanion
7. The correct order of the stability of carbanion is
O O
O O O O
(A) (B) (C) MeO OMe
(D)
O O
(a) A > B > C > D (b) D > A > B > C (c) B > A > C > D (d) C > B > A > D
8. The given reaction/rearrangement is popularly known as
O
(i) 
R C N3 R NH Cbz
(ii)
Ph OH
(a) Lossen rearrangement (b) Curtius rearrangement
(c) Hofmann rearrangement (d) Wolf rearrangement
9. Which of the following readicals have pyramidal shape
•
(I) CH3 (II) CF3 (III) CD3 (IV)
(a) I, II (b) I, II, IV (c) III, IV (d) II and IV
10. The major product formed in the following reaction is
Me Me
+ :CH2(Singlet)
H H
Me Me Me H
(a) (b)
H H H Me
Me CH2CH3

(c) 50 : 50 mixture of above two compounds (d)

H H

PART - B
11. The correct order of stability of carbocation is

(A) (B) (C)

(a) A > B > C (b) C > B > A (c) B > C > A (d) A = B > C
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North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-65462244, 65662255
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12. Product (P) in the following reaction is
CO2H
(i) HNO2
(P)

NH2 Ph
(ii)
Ph
O
Ph
Ph

O O
Ph Ph Ph
Ph

(a) (b) Ph

Ph
Ph Ph

Ph

Ph Ph Ph

(c) (d)
Ph
Ph Ph
Ph

* N2
13. hv
(P)
H2O

The major product (P) in the above reaction is

O

OH
* *
(a) (b) COOH (c) (d) COOH

O OMe
TMS

14. CsF, CH3CN

(X)
N OTf
The major product, intermediate and mechanism involve in the above synthetic transformation are
OMe

(a) O , Benzyne, [2+2] cycloaddition

N

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OMe

(b) O , Benzyne, [4+2] cycloaddition

N

O
OMe , Benzyne, [2+2] cycloaddition
(c)
N

OMe
O
(d) , Carbene, electrophilic addition

15. Products (B) in the given reaction is

CO2Me (i) KOH
(ii) (COCl)2 Ag(Obz)2
(A) (B)
(iii) CH2N2 MeOH

O O
C
HC OH CO2Me

(a) (b) (c) (d)

16. Products (P) in the following reaction is

O
Rh2(OAc)4
Product (P)
NH
O N2 CO2Bn

O
O

(a) (b) NH
N O C
O CO2Bn O
O O

(c) (d)
N N
O CHO O O

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North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-65462244, 65662255
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17. In the given reactions,

NBS, CCl4 NBS

(P) (Q)
hv H2O

Products (P) and (Q) are respectively,

Br Br

Br Br

(a) , (b) ,

Br OH
Br Br

Br

(c) , (d) , both (P) and (Q)

OH
18. The products (A) and (B) are, respectively
Br2, hv
A (<1%) yield + B(>99%) yield

Br Br
(a) , Br (b) Br , Br
Br
Br
(c) Br , Br
(d) Br ,
19. In the following reactions
CHBr3
Z  2  butene 
t  BuOK
 P
CHBr3
E  2  butene  t  BuOK
  Q
The correct statement(s) about products (P) and (Q) is/are
(I) P and Q, both are identical (II) P and Q are diastereomers
(III) P is chiral and Q is achiral (IV) P is achiral and Q is chiral
(a) I and IV (b) II and III (c) I, III and IV (d) II and IV only
20. Product (P) in given reaction

Cu metal
+ N2 CO2Et (P)

CO2Et CO2Et

(a) (b)

CO2Et
CO2Et

(c) (d)

South Delhi : 28-A/11, Jia Sarai, Near-IIT Hauz Khas, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-65462244, 65662255
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CSIR-UGC-NET/JRF | GATE CHEMISTRY Date : 29-09-2017

TEST : REACTIVE INTERMEDIATE (BATCH-A)

[ANSWERS]

PART-A

1. (c) 2. (a) 3. (b) 4. (b) 5. (c) 6. (b) 7. (c)

8. (b) 9. (d) 10. (a)

PART-B

11. (a) 12. (c) 13. (d) 14. (b) 15. (c) 16. (a) 17. (c)
18. (d) 19. (d) 20. (a)

South Delhi : 28-A/11, Jia Sarai, Near-IIT Hauz Khas, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-65462244, 65662255