Chapter 5

Chapter 5

MULTIPLE CHOICE QUESTIONS Part 5: Stereochemistry

Answers on page 24-26
Topic: Identifications and Comparisons

5. Pairs of enantiomers are:

CH3
H3C

1. Which of the following is the enantiomer of the following substance?

H

H
H
Br

A)
B)
C)
D)
E)

CH3

Br
H

CH3

CH3

CH3

Br
H

C C

HO2C
CH3

II

III

3. Hexane and 3-methylpentane are examples of:

A) enantiomers.
B) stereoisomers.
C) diastereomers.
D) constitutional isomers.
E) None of these
CH2CH3
Cl

A)
B)
C)
D)
E)

III

H
CO2H

IV

CH3
HO

Br

H
CH2CH3

I
II
constitutional isomers.
enantiomers.
non-superposable mirror images.
diastereomers.
not isomeric.

H
CH2CH2CH3

6. Chiral molecules are represented by:

CH3

CH2CH3

H3C

Cl

CH3

H 3C

C2H5

II
I
I, II, III, IV and V
I, II, III and IV
I and II
III and IV
IV alone

A)
B)
C)
D)
E)

7. The molecules shown are:

H

OH

Br

OH

Br

C2H5

CH3
Cl

C2H5

A)
B)
C)
D)
E)

CH2Cl

CH2Cl
H

Cl

IV
I, II and III, IV
I, II
III, IV
IV, V
None of the structures

CH3

4. I and II are:

OH

HO

H
Cl

I
II
III
IV
V

H3C

Br

OH

A)
B)
C)
D)
E)

CO2H

OH

II
CH2CH2CH3

A)
B)
C)
D)
E)

Cl

CO2H
H

H3C

CH2CH2CH3

H3C

2. Which of the following molecules is achiral?

H 3C

CH3
CH2CH2CH3

III

I
II
III
It does not have a non-superposable enantiomer.
Both II and III

Cl

CH2CH2CH3

H
Br

II

CH3

Cl

H
CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

Cl

H 3C

Cl

CH2Cl
H

C2H5

C 2H 5

III

IV

Chapter 5

Chapter 5

The

8. The molecules shown are:

12. The molecules shown are:

Cl
H3CH2C

Cl

and

Cl

CH2CH3

Cl

CH2CH3

A)
B)
C)
D)
E)

are

enantiomers.
diastereomers.
constitutional isomers.
two conformations of the same molecule.
not isomeric.

H
CH3

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

A)
B)
C)
D)
E)

10. The molecules below are:

F

OH

13. The molecules shown are:

CH3

OH
H

CH2CH3

9. The molecules shown are:

A)
B)
C)
D)
E)

CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

14. The molecules below are:

CH3

CH3

H
F

F
F

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
stereoisomers.

CH3

A)
B)
C)
D)
E)

11. The molecules shown are:

CH3
Cl
H
CH3

A)
B)
C)
D)
E)

H
H

Cl

Cl

Cl

CH3

CH3
H
CH3

enantiomers.
diastereomers.
constitutional isomers.
two different conformations of the same molecule.
not isomeric.
3

structural isomers.
enantiomers.
diastereomers.
identical.
None of these

15. Cis-trans isomers are:

A) diastereomers.
B) enantiomers.
C) stereoisomers.
D) constitutional isomers.
E) More than one of these
Ans: E

Chapter 5

16. The molecules below are:

20. The molecules below are:

Cl

CH3
Cl

Br

CH3

II

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
H

CH3

Cl

Cl

Br

Br

Cl

H3C

Br

Cl

Cl

F
F

A)
B)
C)
D)
E)

CH3

21. Which molecule is achiral?

CH3
CH3

Cl

CH3
Cl

17. The molecules below are:

H2N

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

Br

A)
B)
C)
D)
E)

Chapter 5

Cl

NH2

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

18. The molecules shown are:

H

CH3

Br

III

22. Which molecule is achiral?

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
Cl

CH3
F

Cl
H

A)
B)
C)
D)
E)

Br

Br

Cl

Cl

Br

Cl

Br

Br

A)
B)
C)
D)
E)

19. The molecules below are:

Br

H
Cl

H
Cl
H

II
I
II
III
More than one of the above
None of the above

III

CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

Br

Br

I
II
I
II
III
More than one of these
None of these

A)
B)
C)
D)
E)

Br

Chapter 5

Chapter 5

26. Which structure(s) represent(s) diastereomer(s) of I?

23. The molecules below are:
H

HO
HO

H
H

A)
B)
C)
D)
E)

A)
B)
C)
D)
E)

24. The structures

OH
OH
CH3

A)
B)
C)
D)
E)

CH3
OH
H
OH
CH3

II

CH3
OH

HO

OH
OH
CH3

CH3
H
H
OH

CH3
OH

CH3

OH
H
CH3

IV

HO
H

III

H
H
HO

II
II and III
II and IV
III and V
IV and V

Cl
H

CH3

H
HO
H

H
H

II

Br

H
HO
HO

CH3
OH

HO
HO
H

H
H

CH3
H

CH3
OH

CH3

CH3

OH
H
CH3

III

IV

I and II
II and III
III and IV
III and V
IV and V

H
OH

H
H
HO

F
H
Br

A)
B)
C)
D)
E)

25. Which pair of structures represents the same compound?

CH3
OH

27. The two compounds shown below are:

CH3

CH3

represent:
A) a single compound.
B) enantiomers.
C) meso forms.
D) diastereomers.
E) conformational isomers.

H
H
H

H
H

II
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

CH3

CH3
OH
H
HO
OH
H
CH3
H

CH3

CH3
OH

Cl

enantiomers.
diastereomers.
constitutional isomers.
identical.
different but not isomeric.

28. The two compounds shown below are:

Br

Br

H
H

A)
B)
C)
D)
E)

Br

and
H

Br

are:

identical.
enantiomers.
diastereomers.
conformational isomers.
meso forms.

29. (2R,4S) 2,4Dichloropentane and (2S,4R)-2,4-dichloropentane are:

A) enantiomers
B) diastereomers
C) identical
D) conformational isomers
E) constitutional isomers

Chapter 5

Chapter 5

30. Which of the following is a meso compound?

H
HO
H3C
CH3
H

A)
B)
C)
D)
E)

H2
C

OH
CH3

H
H3C
HO

I
H

II

CH2OH

OH

33. Which of the following is(are) meso?

OH
CH3

CH2OH
H

OH

CH2OH

CH2OH

CH3

III
I
II
III
IV
V

IV

A)
B)
C)
D)
E)

Br

H
Br

Br

A)
B)
C)
D)
E)

II
I
II
III
IV
Two of the above

CH3

H
Cl

CH3

CH3

Cl

Cl

Cl

Cl

Cl

CH3

CH3

CH3

II

III

I
II
III
Both II and III
Both I and III

Br

Cl

H
H

Br

Br

III

A)
B)
C)
D)
E)

CH3

H
CH3
CH3

II
I
II
III
More than one of these
None of these

III

35. Which molecule has a plane of symmetry?

H

32. Which of the following molecules is achiral?

A) (2R,3R)-2,3-Dichloropentane
B) (2R,3S)-2,3-Dichloropentane
C) (2S,4S)-2,4-Dichloropentane
D) (2S,4R)-2,4-Dichloropentane
E) Two of these

CH3

A)
B)
C)
D)
E)

CH2CH3

CH3

HO

H
HO

CH3

II

IV

Cl

Br

Topic: Meso compounds

34. Which molecule has a plane of symmetry?

31. Which of the following is(are) meso compound(s)?

Cl

Br

III

I
II
III
More than one of these
None of these

10

Chapter 5

Chapter 5

36. Which compound does NOT possess a plane of symmetry?

H

Cl

H
CH3

39. Which of the following substances is achiral ?

Br

Br

Br

CH3

Cl
H

A)
B)
C)
D)
E)

Br

II

IV

III

I, II and V
I, III and IV
II, III and IV
III and IV
V

H3C

Br

H3C

Br

H
OH

H3C

CH3

CH3

OH

CH3

II

III

A)
B)
C)
D)
E)

CH3

Br

II

CH3

Br
H

HO

III

IV

I
II
III
IV
More than one of these

40. Which statement is not true for a meso compound?

A) The specific rotation is 0.
B) There are one or more planes of symmetry.
C) A single molecule is identical to its mirror image.
D) More than one stereogenic center must be present.
E) The stereochemical labels, (R) and (S), must be identical for each stereogenic
center.

37. Which molecule is a meso compound?

H

A)
B)
C)
D)
E)

CH3

41. Which is a meso compound?

A) (2R,3R)-2,3-Dibromobutane
B) (2R,3S)-2,3-Dibromopentane
C) (2R,4R)-2,4-Dibromopentane
D) (2R,4S)-2,4-Dibromopentane
E) (2R,4S)-2,4-Dibromohexane

I
II
III
More than one of the above
None of the above

38. Which molecule is a meso compound?

H

CH3

CH3

OH

CH3

CH3

A)
B)
C)
D)
E)

II

III

IV

I and II
IV and V
II and III
I, II and III
None of the above

Topic: Specific names

42. (R)-2-Chlorobutane is represented by:

A)
B)
C)
D)
E)

11

CH3

CH3
H3C

Cl

Cl

CH3

H3C

CH2Cl

CH2CH3
Cl

H3C

Cl

CH2CH3

CH2CH3

CH2CH3

CH2CH3

II

III

IV

I
II
III
IV
V

12

Chapter 5

Chapter 5

43. Which of the following represent (R)-2-butanol?

H3C

OH

CH3

HO

CH2CH3

CH2CH3

CH3

II

III

IV

CH3

F
Cl

Cl
CH3

II

III

CH3
H

Cl

Cl
F

CH3

II
I
II
III
More than one of the above
None of the above

III

46. Which structure represents (S)-2-bromobutane?

Br
CH2CH3

A)
B)
C)
D)
E)

Br

48. The Cahn-Ingold-Prelog stereochemical designations used for the following substance
are:
H

Cl

Cl
Cl

2R,4S
2S,4R
2R,4R
2S,4S
The R,S terminology doesn't apply in this case.

49. Which of these is not a correct Fischer projection formula of the (S) form of
3-bromo-1,1-dichloro-2-propanol ?
H

A)
B)
C)
D)
E)

CHCl2
OH
CH2Br

HO

CH2Br
H
CHCl2

II

Cl2HC

CH2Br
OH

H3C

CH2CH3

II
I
II
III
More than one of the above
None of the above

Br
CH2CH3

III

13

OH
CHCl2
CH2Br

IV

III

I
II
III
IV
V

CH3

CH3
H

is properly named:
(3R,4S,5R)- 3,5-Dichloro-4-methylhexane
(2S,3S,4S)- 2,4-Dichloro-3-methylhexane
(2S,3R,4R)- 2,4-Dichloro-3-methylhexane
(2S,3R,4S)-2,4-Dichloro-3-methylhexane
(2S,3S,4R)- 2,4-Dichloro-3-methylhexane

A)
B)
C)
D)
E)

F
H

CH3

H
CH3

45. Which structure represents (R)-1-chloro-1-fluoroethane?

H

CH3

Cl

Cl

I
II
III
More than one of the above
None of the above

Cl

Cl

CH3

Cl

A)
B)
C)
D)
E)

44. Which structure represents (S)-1-chloro-1-fluoroethane?

OH

CH2CH3

III and V
I, III, IV and V
I, IV and V
I and III
I, II, IV and V

A)
B)
C)
D)
E)

CH2CH3

A)
B)
C)
D)
E)

A)
B)
C)
D)
E)

CH2CH3

CH3

HO

OH

CH2CH3

47.

CH3

14

BrH2C

OH
CHCl2
H

Chapter 5

Topic: Optical activity

Chapter 5

54. The compounds whose molecules are shown below would have:

50. What is the percent composition of a mixture of (S)-(+)-2-butanol,[!] 25

= +13.52,
D
and (R)-(-)-2-butanol,[!] 25
= -13.52, with a specific rotation [!] 25
= +6.76?
D
D
A) 75%(R) 25%(S)
B) 25%(R) 75%(S)
C) 50%(R) 50%(S)
D) 67%(R) 33%(S)
E) 33%(R) 67%(S)
51. Which one of the following can exist in optically active forms?
A) cis-1,3-Dichlorocyclohexane
B) trans-1,3-Dichlorocyclohexane
C) cis-1,4-Dichlorocyclohexane
D) trans-1,4-Dichlorocyclohexane
E) cis-1,2-Dichlorocyclohexane

OH

OH

A)
B)
C)
D)
E)

the same melting point.

different melting points.
equal but opposite optical rotations.
More than one of these
None of these

CH2CH3

CH2CH3

CH3

II

A)
B)
C)
D)
E)

the same melting point.

different melting points.
equal but opposite optical rotations.
More than one of the above
None of the above

53. The compounds whose molecules are shown below would have:
CH3
H

CH3
F

A)
B)
C)
D)
E)

CH3
F

H3C

F
H

the same melting point.

different melting points.
equal but opposite optical rotations.
More than one of the above
None of the above

15

H
OH
OH

55. The compounds whose structures are shown below would have:
CH3
Br

CH3

CH3

Br

A)
B)
C)
D)
E)

the same melting point.

different melting points.
equal but opposite optical rotations.
More than one of these
None of these

52. The compounds whose molecules are shown below would have:
CH3

Br

Br

CH3

(Ej .56. 57)

58. Which of these is a comparatively insignificant factor affecting the magnitude of
specific optical rotation?
A) Concentration of the substance of interest
B) Purity of the sample
C) Temperature of the measurement
D) Length of the sample tube
E) All of the above are equally significant.
59. What can be said with certainty if a compound has [!] 25
= -9.25 ?
D
A) The compound has the (S) configuration.
B) The compound has the (R) configuration.
C) The compound is not a meso form.
D) The compound possesses only one stereogenic center.
E) The compound has an optical purity of less than 100%.

16

Chapter 5

Chapter 5

60. An alkane which can exhibit optical activity is:

A) Neopentane
B) Isopentane
C) 3Methylpentane
D) 3Methylhexane
E) 2,3Dimethylbutane

67. Enantiomers are:

A) molecules that have a mirror image.
B) molecules that have at least one stereogenic center.
C) non-superposable molecules.
D) non-superposable constitutional isomers.
E) non-superposable molecules that are mirror images of each other.

61. In the absence of specific data, it can only be said that (R)2bromopentane is:
A) dextrorotatory (+).
B) levorotatory ().
C) optically inactive.
D) achiral.
E) analogous in absolute configuration to (R)2chloropentane.

68. Which of the following is NOT true of enantiomers? They have the same:
A) boiling point.
B) melting point.
C) specific rotation.
D) density.
E) chemical reactivity toward achiral reagents.

62. If a solution of a compound (30.0 g/100 mL of solution) has a measured rotation of +15
in a 2 dm tube, the specific rotation is:
A) +50
B) +25
C) +15
D) +7.5
E) +4.0

69. Which statement is true of 1,3-dimethylcyclobutane?

A) Only one form of the compound is possible.
B) Two diastereomeric forms are possible.
C) Two sets of enantiomers are possible.
D) Two enantiomeric forms and one meso compound are possible.
E) None of the previous statements is true.

63. Which compound would show optical activity?

A) cis 1,4- Dimethylcyclohexane
B) trans 1,4- Dimethylcyclohexane
C) cis 1,4- Dimethylcycloheptane
D) trans 1,4- Dimethylcycloheptane
E) More than one of these
64. Of the compounds which correspond to the general name "dichlorocyclobutane", how
many are optically active?
A) 0
B) 1
C) 2
D) 3
E) 4
Topic: General definitions
(Ej .65)
66. Which of the following is true of any (S)-enantiomer?
A) It rotates plane-polarized light to the right.
B) It rotates plane-polarized light to the left.
C) It is a racemic form.
D) It is the mirror image of the corresponding (R)-enantiomer.
E) It has the highest priority group on the left.

17

70. In which of the following reactions is the absolute configuration of the product likely to
be the same as that of the reactant?
Br
Br
A)
PBr3
(R)
OH
Br
O

B)
Br

(R)

OH

Br

OH

HA

C)
D)
E)

Br

OH

H2O

OH
(R)
All of the above
Answers A) and B) only

OH

Topic: Reaction stereochemistry

(Ej 71, 72)
73.
O
The reaction of
with H2/Ni forms:
A) 2-methylheptane.
B) (R)-2-methyl-5-heptanol
C) (S)-6-methyl-3-heptanol
D) (R,S)-6-methyl-3-heptanol
E) Achiral 6,6-dimethyl-3-hexanol

18

Chapter 5

74. CH3CHBrCH2CHClCH3 is the generalized representation of what number of

stereoisomers?
A) 3
B) 4
C) 5
D) 6
E) 7
75. For the generalized structure BrCH2CHClCH2CHClCH2Br there exists what number of
stereoisomers?
A) 2
B) 3
C) 4
D) 6
E) 8
76. How many discrete dimethylcyclopropanes are there?
A) 2
B) 3
C) 4
D) 5
E) 6
77. What is the molecular formula for the alkane of smallest molecular weight which
possesses a stereogenic center?
A) C4H10
B) C5H12
C) C6H14
D) C7H16
E) C8H18
78. How many chiral stereoisomers can be drawn for CH3CHFCHFCH(CH3)2?
A) 1
B) 2
C) 3
D) 4
E) 8
79. How many different compounds are there which correspond to the general name "3-(1methylbutyl)cyclobutanol?
A) 2
B) 4
C) 6
D) 8
E) None of the above

19

Chapter 5

80. How many stereogenic centers are there in Lovastatin ( Mevacor : a cholesterollowering drug) ?
HO

O
O

A)
B)
C)
D)
E)

(Lovastatin)
4
5
6
7
8

81. What is the total number of compounds, stereoisomers included, designated by the
general name "dichlorocyclopentane"?
A) 4
B) 5
C) 7
D) 8
E) 9
Use the following to answer questions 82-85:
Consider the following compounds:
CH2OH
H

OH

CH3

HO

CH3

HO

CH3

HO

CH3

CH3
H

OH

H3C

CH3

OH

OH

II

III

IV

82. Which of the compounds above (I-IV) represent enantiomers?

A) I and II
B) II and III
C) III and IV
D) II and IV
E) III and IV

20

Chapter 5

83. Which compound above (I-IV) is a meso compound?

A) I
B) II
C) III
D) IV
E) None of these

Chapter 5

SHORT ANSWER QUESTIONS Answers on p. 25-26

86. The molecule of aspartame ( Nutrasweet ), depicted below, has ___________ ( how
many? ) stereogenic centers.
O
O

HO

84. Which compound above (I-IV) is (2R,3R)-2,3-butanediol?

A) I
B) II
C) III
D) IV
E) None of these
85. Which compounds above (I-IV) form a set of stereoisomers?
A) I, II and III
B) II, III and IV
C) II and III
D) I, III and IV
E) I, II, III and IV

HN
O
O

H2N

Aspartame

87. True or false: A sample consisting of the pure R enantiomer of a compound will always
rotate plane-polarized light in a clockwise direction.
A) True
B) False
88. Draw a dash-wedge structure for (3R)-3-methyl-5-hexen-3-ol
89. Draw a dash-wedge structure for (1R)-1-bromo-1,3,3-trimethylcyclohexane
90. Draw a dash-wedge structure for (1R,3R)-1,3-dibromo-1,3-dimethylcyclohexane

91. Draw a dash-wedge structure for (1S,3R)-1-ethyl-1,3-dimethylcyclopentane

92. What is the complete IUPAC name of the following substance? (Remember to give
stereochemical details, as relevant.)
H
C2H5
H3C

21

CH3

22

Chapter 5

93. What is the complete IUPAC name of the following substance? (Remember to give
stereochemical details, as relevant.)
H
OH

H3C

OH

94. Draw Fischer projection formulas for all stereoisomers of 2,4-dibromohexane, giving
stereochemical details for each structure.
95. Draw dash-wedge structures for all stereoisomers of 1-bromo-3-isopropylcyclohexane,
giving stereochemical details for each structure.
Topic: Fischer projections
96. Draw Fischer projection formulas for all stereoisomers of 2,4-dimethyl-3-hexanol,
giving stereochemical details for each structure.
97. Draw a Fischer projection formula of (3R)-6-Bromo-1-hexen-3-ol.

23

Chapter 5

Svar Part 5: Stereochemistry

Frga
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43

Svar
D
B
D
A
C
D
B
B
B
A
A
B
E
C
E
D
C
A
D
B
A
C
A
A
D
B
A
B
C
A
E
D
E
D
D
D
D
E
E
E
D
C
C

Rtt/Fel

Frga
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85

Svar
D
B
A
D
C
D
B
B
D
B
B
D
C
C
C
C
D
E
B
D
C
D
D
E
C
B
E
D
D
D
B
B
C
D
D
B
E
C
B
D
C
B

24

Rtt/Fel

Chapter 5

Chapter 5

96:

Answer 86 97
86:
87:

CH3

two
B

H3C
H
OH

88:

89:

CH3

H
OH

CH3

CH3

H3C

H3C

HO

OH

H3C

CH3

CH3

3S,4S

3R,4R

3S,4R

3R,4S

H2C
*

OH

92:
93:

Br

OH

H
CH2Br

C2H5

(3R)-6-Bromo-1-hexen-3-ol.

CH3

(1S)-1-ethyl-1,3,3-trimethylcyclopentane
(1R,3S)-1-methylcyclopentane-1,3-diol
CH3

94:
Br

CH3

CH3

Br

Br

Br

Br

Br

Br

CH3

CH3

2R,4S

95:

CH3

Br

H
H

CH3

CH3

2S,4R
2S,4S
2,4-dibromohexane

2R,4R

1-bromo-3-isopropylcyclohexane
H

H
H

Br

1S, 3R

H
Br

1R, 3S

Br

1S, 3S

25

Br

H
CH3

90:

CH3

CH3

2,4-dimethyl-3-hexanol

91:

H3C

CH3

97:

Br

HO

CH3
Br

Br

H3C

1R, 3R

26