STEREOISOMERISM

S.M.TRIPATHI

TOPIC : OPTICAL ISOMERISM

1. Which of the above descriptions may be applied to these isomeric structural formulae?
OH OH
and

(A) They are diastereomers (B) They are tautomers

(C) They are enantiomers (D) They are identical

2. A solution of (+)-2-chloro-2-phenylethane in toluene racemises slowly in the presence of a small

amount of SbCl5, due to the formation of
(A) Carbanion (B) Carbene (C) Free radical (D) Carbocation

3. Et

H3C OH
has chiral (*)center it is

H
(A) R (B) S (C) both (D) none

Cl

4. Number of chiral carbon atoms in is

CH3
(A) 2 (B) 3 (C) 4 (D) 1

5. Iso pentane, (CH3)2CH.CH2.CH3 can form four isomeric monochloro derivatives. How many these are
optically active?
(A) 1 (B) 2 (C) 3 (D) 4

6. Meso-Tartaric acid is optically inactive due to the presence of

(a) Molecular symmetry (b) Molecular asymmetry
(c) External compensation (d) Two asymmetric C-atoms

7. Which of the following compounds is optically active

(a) CH3CH2COOH (b) CH3CHOHCOOH (c) HOOC.CH2.COOH (d) CH3.CO.COOH

8. The necessary and sufficient condition for a molecule to exhibit optical activity is
(A) Molecular symmetry (B) Molecular dissymmetry or chirality
(C) Presence of chiral carbon atoms (D) Tetrahedral nature of carbon atoms

9. Optical isomers which are non-superimposable mirror images of each other are called
(A) Enantiomers (B) Diastereomers (C) Tautomers (D) Geometrical isomers

10. Which of the following statements is not applicable to enantiomers?

(A) They have identical melting and boiling points
(B) They have identical chemical properties except towards optically active reagents
(C) They can be separated by fractional crystallization
(D) They rotate the plane polarized light in different directions but to the same extents

11. Which of the following will show optical isomerism?

Cl CHBr - CH3 H3C Cl
(A) C C (B) C C
H Cl H CH2 - CH3
H3C CH3 H3C H
(C) C C (D) C C
Br CH2Br H CH3

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S.M.TRIPATHI

12. What is the possible number of stereoisomers for tartaric acid?

(A) four (B) three (C) two (D) one

13. Racemic mixture is optically inactive because of

(A) molecular symmetry (B) external compensation
(C) internal compensation (D) molecular asymmetry or chirality

14. The optical isomers which are not mirror images of each other are called
(A) diastereomers (B) Tautomers (C) Enantiomers (D) Metamers

15. The two isomers given below are

CO2H CO 2H

H OH H OH
and
HO H H OH

CO2H CO 2H
(A) Enantiomers (B) Diastereomers (C) Mesomers (D) Positional isomers

16. If optical rotation produced by compound(l) is +52o then that produced by compound (ii) is
CH3 CH3

Cl H H Cl

H Cl Cl H

CH3 CH3
(i) (ii)
(A) – 52o (B) + 52o (C) 0o (D) Unpredictable

17. The correct statements about the compounds A, B, C

COOMe COOH COOMe
H OH H OH H OH
is
H OH H OH HO H
COOH COOMe COOCH 3
(A) (B) (C)
(A) A and B are identical (B) A and B are diastereomers
(C) A and C are diastereomers (D) A and B are enantiomers

18. The following two compounds are

CH3 CH3
H OH HO H
H OH HO H
C2H5 C2H5
(A) Enantiomers (B) Diastereomers (C) Identical (D) geometrical isomers

19. An optically active alkene with the M.F. C 6H12 which upon hydrogenation gives optically inactive
alkane is
(A) 2-Hexene (B) 3-Methyl-2-pentene (C) 2-Methyl-2-pentene (D) 3-Methyl-1-pentene

20. Which of the following does not show enantiomerism?

(A) 1, 2-propadiene (B) 2, 3-pentadiene (C) sec-Butyl alcohol (D) All the three above

21. The configuration at C2 and C3 of the compound given below is

CH3
H Cl
Cl H
C2 H5
(A) 2R, 3S (B) 2S, 3R (C) 2S, 3S (D) 2R, 3R

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 STEREOISOMERISM
S.M.TRIPATHI

22. The R-isomer among the following are:

CHO H CH3 COOH

H OH D OH H OH H3C NH2

CH 2OH CH3 CH 2 - CH 3 H
(I) (II) (III) (IV)
(A) (i) and (ii) (B) (i) and (iii) (C) (ii) and (iii) (D) (iii) and (iv)

23. The specific rotation of a pure enantiomer is +12 o. What will be the observed rotation if it is isolated
from a reaction with 80% racemization and 20% inversion?
(A) +9.6o (B) –2.4o (C) +2.4o (D) –9.6o
24. The lowest molecular weight alkanes which are optically active are
(A) 3-Methylhexane (B) 2, 3-Dimethylpentane
(C) 2, 3, 3-Trimethylbutane (D) 2-Methylhexane

25. Which of the following have finite dipole moment?

(A) Propylene (B) 1-Butene (C) cis-2-Butene (D) trans-2-pentene

26. The compounds given below are

HO CH3 HO CH3

(A) Enantiomers (B) Identical

(C) Regiomers (D) Diastereomers

27. The optically active compound among the following is

(A) OH (B) O
CN

(C) HO OH (D)
O

28. Which of the following compounds is chiral?

(A) Br Br (B) Br Br

(C) Br Br (D) Br

29. Mark the chiral carbon in Salbutamol

H
H
N OH H
H
H
H OH
OH

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