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CSIR-UGC-NET/JRF | GATE CHEMISTRY

TEST : STEREOCHEMISTRY

Time : 00: 45 Hour Date : 06-09-2018

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. Fumaric acid is converted to S-2-hydroxybutanedioic acid by the enzyme fumarase such as
H H
HOOC HO
HOOC
COOH COOH
H
100%
Which of the following statement is true about above enzymatic conversion
(a) The hydroxyl group is added stereospecifically from ‘Si’ face of the double bond
(b) The hydroxyl group is added stereospecifically from ‘Re’ face at the double bond
(c) The ‘Si’ and ‘Re’ face gives the same product.
(d) The enzyme fumarase is not able to distinguish between these two faces. Therefore, the product should be
racemic mixture.
2. Among the following which compound is resolvable?
CH3 H NH2 H
SH NO2

OH NH2 H H H CH3
HOOC H
OH COOH Br COOH Cl NO2
(a) (b) (c) (d)
H COOH CH3 CH3 CH3 H
CH3 Br
1
3. Which of the following pair can be distinguishable by H NMR spectroscopy
Ph H Ph H
,
(a) (H3C)2HC COOH HOOC CH(CH3)2
HO H H OH
(b) HOOC , HOOC
COOH COOH
(c) (D)–(+)-glyceraldehyde and (L)(–)-glyceraldehyde
OH OH

(d) and

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4. Which of the following pairs of compound are enantiomers
CHO CH2OH
H Cl
H NH2 H OH H H H CH3

, and
(a) HO H H NH2 (b) Cl Ph H Ph
CH2OH CHO CH3 H

HO (CH2)3CH3 H
(c) (d) and
and
OH
H3C(H2C)3

O H
5. C CH2OH
H OH HO H
H OH and HO H
H OH H OH
H H CHO
OH

The above pair is the case of

(a) Enantiomers (b) Anomer (c) Epimer (d) Identical
6. Which of the following pair containing enantiotopic and ‘distereotopic Ha and Hb proton respectively.
Hb
Ha
Cl Ha H2C CH2 COOH
Br
C C C Hb and Hb
(a) and Ha (b) Ha
H Hb
H2C CH2 CH3 H

Cl Ha Ha Hb Ha Cl
Br Ha and C C
C C C C
(c) (d) and
H Hb
H Hb Cl Cl Cl Hb

7. Which of the following compound is achiral

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

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8. Among A-C, the compounds which can exhibit optical activity are

CO2H
Ph OH O H O
OMe
CO2H Ph
N Cl Cl
OH
CO2H
H
(A) (B) (C) (D)

(a) A, B and C (b) B and C (c) C and D (d) B and D

9. The compounds given below are
D
D
D

D
(a) Regioisomers (b) Identical (c) Enantiomers (d) Diastereomers
10. The correct statements about the following compounds (A-D) are

Br H H H H Br Br Br

H Br Br Br Br H H H
(A) (B) (C) (D)
(I) A and B are identical (II) C and D are homomers
(III) A and B are diastereomers (IV) C and D are enantiomers
(V) A and C are enantiomers (VI) C and D are diastereomers
(a) I, III, V (b) II, VI (c) I, IV and VI (d) III, V and VI

PART - B
11. Amongst the following the correct statement for the compound P, Q and R is
Br
H Cl

Cl H

H Cl
(P) (Q) (R)
Br
(a) P and Q are achiral and R is chiral (b) P is chiral and Q and R are achiral
(c) P and Q are chiral and R is achiral (d) P is achiral and Q and R are chiral.
12. Consider the following molecules
H Ha Hb
Ha
Ha
H2
Br H3C C C CH3
Hb
(I) (II) Hb (III)

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Identify Ha and Hb hydrogen in the above compound
(a) Diastereotopic, enantiotopic, homotopic respectively
(b) Enantiotopic, diastereotopic, homotopic respectively
(c) Homotopic, diastereotopic, diastereotopic respectively
(d) Diastereotopic, enantiotopic, diastereotopic respectively
13. Among the following, the optically inactive compounds is

P H3C
N
H3C •
Et
(a) (b) (c) (d)
CH3 CH3
H COOH
HO
14. Which of the following statement is incorrect for cis-1, 2 dibromocyclopentane?
(a) it contains two chiral centres but is optically inactive
(b) it can exist in two enantiomeric forms but can not be optically active
(c) It is with two chiral centres and is optically active
(d) it is a meso compound
15. Consider the following statements
(A) Diastereomers are more or less easy to separate from one another by conventional crystalization,
distillation or sublimation
Cl O Br
CH3 N
H H
CH3
H
(B) Cl H, H C CH3 ,
3 N
Cl
O Br Br
All these compounds are chiral
OCH3
H
H 
(C) Ph CH3 + Cl (P)
NH2 Ph
O
(R, S) (R)
The product (P) of the above reaction will be diastereo isomers
H3C H
(D) HOOC (X) . The compound, (X) having ‘S’ configuration
Among the statement mentioned above the correct one is/are
(a) A, B, C (b) B and D (c) A, C and D (d) All
16. The correct statements for compounds (A–C) are
H Me
Me
H Me Me Br
N
(A) (B) (C)
Me H
O HO
H Me

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(I) A has 4-fold rotation-reflection axis of symmetry and is achiral
(II) B has 2-fold rotation axis and is chiral
(III) C has plane of symmetry and is achiral
(a) I only (b) all are correct (c) II only (d) II and III
17. The number of asymmetric center and configuration in D-glucose
(a) 4 and 2R, 3R, 4S, 5R (b) 5 and, 1S, 2R, 3S, 4R, 5R
(c) 4 and 2R, 3S, 4R, 5R (d) 5 and, 1S, 2R, 3R, 4R, 5R
OH

18. m-CPBA
P

Which of the following statement is correct about product ‘P’

(a) The number of asymmetric center is increased by one unit in the product.
(b) The number of assymmetric center is increased by two units in the product.
(c) There is no change in asymmetric center in the product
(d) In product the number of asymmetric center will be two.

CH3 CH3 CH3

I I C2H5 F
C2H5 F I Br
19. F H3C Cl
Cl Cl
Br Br Br Cl F
C2H5 I F Cl CH3
C2H5 C2H5 I
(A) (B) (C) (D) (E) Br

The correct option about above compounds is

(a) A/B are homomer, C/D are enantiomers (b) D/E are diastereomers, A/C are homomer
(c) A/C are enantiomers and A/E are homomer (d) B/E are diastereomers and C/D are homomer
20. Which of the following statements for meso compound is incorrect
(a) The meso compound has either a plane or point of symmetry
(b) The meso compound has atleast one pair of similar stereocentre
(c) The meso compound is formed when equal amount of two enantiomer are mixed
(d) The meso compound is optically inactive.

South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, 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: 011-27653355, 27654455
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CSIR-UGC-NET/JRF | GATE CHEMISTRY Date : 06-09-2018

TEST : STEREOCHEMISTRY

[ANSWERS]

PART-A

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

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

PART-B

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

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North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455