Optical Isomerism

1. Which two fischer formulas represent a pair of enantiomers?

CH3 CH3 C2H5 CH3
HO H H Cl Cl H HO H
H Cl HO H HO H Cl H
C2H5 C2H5 CH3 C2H5
I II III IV
(A) I & II (B) III & IV (C) I & IV (D) II & III
2. Among the following the correct statement about optical activity is
(A) A molecule containing two(or) more chiral centres is always optically active
(B) A molecule containing axial chirality is always optically active
(C) A molecule possessing alternating axis of symmetry is optically active
(D) an optically active molecule should have at least one chiral centre
3. Which of the following compounds have absolute configuration of ‘2R, 3S’?
OH H OH OH H
OH
OH
O HO O
O OH O
HO
H OH OH OH
OH H
(iv)
(ii) (iii)
(i)
(A) (i), (ii) & (iv) (B) (ii) & (iv) (C) (i) & (iii) (D) (i) & (ii)
4. Identify the correct statements in the following
(A) 1, 2–dimethyl cyclopentane has four optical isomers
(B) Both cis and trans 1, 4–dimethyl cyclohexanes are optically inactive
(C) Cis 1,3–dimethyl cyclo hexane is chiral
(D) 1,2–dimethyl cyclohexane has four resolvable optical isomers at ordinary temp
5. Which of the following compounds has absolute configuration (R)
H OH H3C HOOC
COOH CH3
SH

(A) H3C COOH

(B) H OH (C) H (D) HO H
6. Total number of geometrical isomers for the following compound Ph COOH
is ‘n’. How many of these are chiral? (assume that cyclobutane ring
is planar)
HOOC Ph
(A) 2 (B) 4 (C) 1 (D) None
7. Which of following compounds does not have center of symmetry.
(A) O O
H3C H3C NH
H
O
(B) H CH3
O NH
CH3
O
O
H H3C
HO OH H3C H
(C) (D)
H3C HO
CH3 OH
H H
8.
NO 2 NO 2

can show

CO2H CO2H
(A) Geometrical isomerism (B) optical isomerism
(C) both (A) and (B) (D) none of the above
9. The following compounds are H OH OH H
(A) Enantiomers (B) Diastereomers
(C) identical (D) geometrical isomers OH H H (ii) OH
(i)

10. Identify the correct statement about the following compounds

H3C H CH3 H3C CH3

CH3 H C H H
3
(i) (ii) (iii)
(A) (i) and (ii) are enantiomers (B) (i) and (iii) are identical compounds
(C) (ii) and (iii) are diastereomers (D) (i) & (ii) are optically active but (iii) is inactive
11. Total number of optical isomers possible for the compound CH3-CH=C=CH-CH(Cl)-CH3 is?
(A) 1 (B) 3 (C) 4 (D) 2
12. Which of the following compound is not chiral?
(A) DCH2CH2CH2Cl (B) CH3CHDCH2Cl
(C) CH3CHClCH2D (D) CH3CH2CHDCl
13. Which of the following pairs of compounds is not diasteriomers?
H CH3 OH CH3
HO CH3 H OH H3C H HO H
(A) HO H
and
H3C H
(B) H OH
and
HO CH3
CH3 OH CH3 H
CH3 H
H3C CH3 H3C H
H OH H3C OH
(C) and (D) and
H3C OH H3C H
H H H CH3
H OH

14. The correct statement about the compound given below is Cl

H
(A) The compound has C4-alternating axis of symmetry H
(B) The compound possesses centre of symmetry H3C Cl
(C) The compound possesses plane of symmetry CH3
(D) The compound possesses axis of symmetry

15. R and S configuration of compound (A) and (B) will be:

 CH2 O C2H5

CH2 CH2 O C2H5 H3C (CH2)4 (CH2)5 CH3

CH C HC
O H3C (CH2)4 (CH2)5 CH3
CH3
(A) (B)
(A) R, R (B) R, S (C) S, R (D) S, S
16. The compound QUINAP given beside is?
(A) An optically active compound having chiral centre N
(B) An optically inactive due to the presence of plane of symmetry
PPh2
(C) A meso compound
(D) An optically active compound without having chiral centre

17. The absolute configuration of numbered chiral carbon centre are? OCH3

(A) 2–S, 3–S (B) 2–S, 3–R H 2 O

3
(C) 2–R, 3–S (D) 2–R, 3–R Et

18. (S)-(–)-2-Methyl-1-butanol can be converted to (+)-2-Methylbutanoic acid without breaking any of

the bonds to the asymmetric carbon. The configuration of (–)-2-Methylbutanoic acid is
(A) S (B) R (C) S or R (D) Can’t be determined
19. Which of the following compounds has a stereoisomer that is a meso compound?
(A) 1, 3-dimethylcyclohexane (B) 2, 3-dimethylpentane
(C) 1, 2-dibromocyclopropane (D) 2, 4-dimethylhexane
20. Which of the following object(s) is(are) chiral?
(A) A mug with DAD written on one side of the handle
(B) A mug with DAD written opposite the handle
(C) A mug with MOM written on one side of the handle
(D) A mug with MOM written opposite the handle
21. HOOC – CH = CH – COOH exhibit
(A) Chain isomerism (B) Stereoisomerism (C) Geometrical (D) Functional
22. A solution prepared by mixing 10 ml of a 0.1M solution of the R enantiomer and 30 ml of a 0.1M
solution of the S enantiomer was found have an observed specific rotation of +4.0. What is the
specific rotation of (–)-isomer?
23. You are provided with a set of compounds. What is the number of compounds that are expected to
show geometrical isomerism.
CH3
CH3
CH3
H3C CH2CH N OH H2C CH CH CH CH3
CH3
(I) (II) (III) (IV)
O2N

Br C C H Ph CH C CH Ph H3C CH N NH NO2 H3C C N NH2

Cl F CH3
(V) (VI) (VII) (VIII)

24. How many isomeric benzene derivatives are possible with molecular formula C7H9N?
25. The number of asymmetric carbons with ‘R’ O OH OH H OH OH
configuration in glucose is……….
H H H OH H
H3C CH3
26. Tetracycline is called a broad-spectrum antibiotic OH N
H3C
because it is active against a wide variety of bacteria. OH
How many asymmetric carbons does tetracycline
NH2
have?
OH
OH O OH O O

27. O

H2 ? The Number of isomeric compounds

Ni
O
28. No. of Isomeric products possible by mono halogenation of CH4, if it is considered to have a
pyramidal structure with rectangular base
29. Find the number of geometrical isomers of the given compound
C6H5 – CH=CH–CH2–CH=CH–CH=CH–COOH
30. What will be the number configurational isomers of the compound
CH2 CH CH CH CH2
OH OH OH OH OH
31. How many stereo isomers are possible for 1, 3–dichloro cyclopentane
32. Total number of trichloro derivatives of cyclopentane (Excluding stereoisomers) will be
33. How many optically active stereo isomers are possible for butane –2, 3–diol
34. what will be the total number of possible structural isomers with formula C7H12Br2 fulfilling the
following conditions
(I) it should contain 6 membered ring
(II) none of the isomer should contain both bromine atom either on same or adjacent carbon atom
(III) none of the isomer should contain bromine atom on tertiary carbon atom
35. 24g of optically pure tartaric acid is dissolved in water to make 240ml solution. It is kept in 20cm
long tube and plane polarized light is passed through it to produce rotation of -2.40.
i) If a mixture of ‘d’ & ‘l’ tartaric acid has the specific rotation of -4.00. Calculate the % of optical
purity of the mixture?
A) 50% B) 66.67% C) 33.33% D) 75%
ii) If original solution is diluted by two times and length of the polarimeter tube is increased four
times the previous length. What will be the specific rotation?
A) -4.80 B) +4.80 C) -6.00 D) -12.00

Answers
1. B 2. B 3. C 4. B 5. C
6. D 7. C 8. B 9. C 10. C
11. D 12. A 13. C 14. D 15. D
16. D 17. C 18. B 19. A, C 20. B, D
21. A, B, C, D 22. 8 23. 6 24. 5 25. 3
26. 5 27. 4 28. 1 29. 8 30. 4
31. 4 32. 5 33. 2 34. 7 35. C, D