Chapter 5 Chapter 5

MULTIPLE CHOICE QUESTIONS Part 5: Stereochemistry

Answers on page 24-26 5. Pairs of enantiomers are:
CH3 CH3 H
Topic: Identifications and Comparisons
H3C Cl Cl CH3 H3C Cl
1. Which of the following is the enantiomer of the following substance? CH2CH2CH3 CH2CH2CH3 CH2CH2CH3
H H CH3 CH3 I II III

H Br Br H
CH3 H CH3 H H H Br CH2CH2CH3 CH2Cl
Br
I II III H3C Cl H H
A) I H CH2CH2CH3
B) II
C) III IV V
A) I, II and III, IV
D) It does not have a non-superposable enantiomer.
B) I, II
E) Both II and III
C) III, IV
D) IV, V
2. Which of the following molecules is achiral?
CO2H CO2H
E) None of the structures
CH3
H 3C H H OH H OH
Br HO Br 6. Chiral molecules are represented by:
C C C HO2C H HO H
H CH2CH3 CH3 CH3 H C2H5 CH2Cl
H CH3 OH Cl F
CO2H
H3C Cl Cl CH3 H 3C Cl H 3C Cl H H
I II III IV V C2H5 C2H5 H C 2H 5
C2H5
A) I IV V
I II III
B) II
C) III A) I, II, III, IV and V
D) IV B) I, II, III and IV
E) V C) I and II
D) III and IV
3. Hexane and 3-methylpentane are examples of: E) IV alone
A) enantiomers.
B) stereoisomers. 7. The molecules shown are:
H H
C) diastereomers.
D) constitutional isomers. H OH H OH
E) None of these H Br Br H
CH3 CH3
4. I and II are:
CH2CH3 CH2Cl A) constitutional isomers.
B) enantiomers.
H3C Cl H H
C) diastereomers.
H CH2CH3 D) identical.
I II E) None of these
A) constitutional isomers.
B) enantiomers.
C) non-superposable mirror images.
D) diastereomers.
E) not isomeric.

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The

8. The molecules shown are: 12. The molecules shown are:

Cl H H CH3 OH
H3CH2C H Cl CH2CH3 H
H Cl
and Cl H
are OH H H
CH2CH3 CH2CH3 CH3
A) enantiomers. A) constitutional isomers.
B) diastereomers. B) enantiomers.
C) constitutional isomers. C) diastereomers.
D) two conformations of the same molecule. D) identical.
E) not isomeric. E) None of these

9. The molecules shown are: 13. The molecules shown are:

H CH3
H H
H F
CH3 H F F
F H
A) constitutional isomers.
A) constitutional isomers.
B) enantiomers.
B) enantiomers.
C) diastereomers.
C) diastereomers.
D) identical.
D) identical.
E) None of these
E) None of these
10. The molecules below are:
F H H 14. The molecules below are:
CH3 H H
H
F H F H

F H CH3 CH3
A) constitutional isomers. CH3
B) enantiomers.
A) structural isomers.
C) diastereomers.
B) enantiomers.
D) identical.
C) diastereomers.
E) stereoisomers.
D) identical.
E) None of these
11. The molecules shown are:
CH3 H
15. Cis-trans isomers are:
Cl H Cl CH3 A) diastereomers.
B) enantiomers.
H Cl Cl H
C) stereoisomers.
CH3 CH3 D) constitutional isomers.
A) enantiomers. E) More than one of these
B) diastereomers. Ans: E
C) constitutional isomers.
D) two different conformations of the same molecule.
E) not isomeric.

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16. The molecules below are: 20. The molecules below are:
CH3 Cl H H
Cl F Br F H H
Br CH3 CH3 Cl

I II Cl CH3
A) constitutional isomers. A) constitutional isomers.
B) enantiomers. B) enantiomers.
C) diastereomers. C) diastereomers.
D) identical. D) identical.
E) None of these E) None of these

17. The molecules below are: 21. Which molecule is achiral?

CH3 CH3 H Cl H
H F F H Cl Br H Br Cl Br

H2N CH3 H3C F Br H H Cl Cl Br

F NH2 Cl Br Br
A) constitutional isomers. I II III
B) enantiomers. A) I
C) diastereomers. B) II
D) identical. C) III
E) None of these D) More than one of these
E) None of these
18. The molecules shown are:
H CH3
22. Which molecule is achiral?
H Br Br
F F
H Br Cl H Cl H
H Br Cl Br Br Cl
A) constitutional isomers.
B) enantiomers. Cl H H
C) diastereomers.
I II III
D) identical. A) I
E) None of these B) II
C) III
19. The molecules below are: D) More than one of the above
CH3 Cl
E) None of the above
F Cl F H
H CH3
A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these

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

23. The molecules below are:
H H CH3 CH3 CH3 CH3 CH3
H F F H H OH H OH H OH HO H H OH
HO H HO H H OH HO H H OH
H F H H
HO H H OH H OH H OH HO H
H H H F CH3 CH3 CH3 CH3 CH3
H H
I II III IV V
I II
A) constitutional isomers. A) II
B) enantiomers. B) II and III
C) diastereomers. C) II and IV
D) identical. D) III and V
E) None of these E) IV and V

24. The structures 27. The two compounds shown below are:
CH3 H Br F
H CH3
H CH3 Cl H
CH3 H F Cl
H Br
represent:
A) a single compound. A) enantiomers.
B) enantiomers. B) diastereomers.
C) meso forms. C) constitutional isomers.
D) diastereomers. D) identical.
E) conformational isomers. E) different but not isomeric.
25. Which pair of structures represents the same compound? 28. The two compounds shown below are:
CH3 CH3 CH3 CH3 CH3 Br
H OH H OH H OH HO H H OH
Br H and H
H OH HO H HO H HO H H OH
H Br H Br
H OH H OH HO H H OH HO H are:
CH3 CH3 CH3 CH3 CH3 A) identical.
B) enantiomers.
I II III IV V C) diastereomers.
D) conformational isomers.
A) I and II E) meso forms.
B) II and III
C) III and IV 29. (2R,4S) –2,4–Dichloropentane and (2S,4R)-2,4-dichloropentane are:
D) III and V A) enantiomers
E) IV and V B) diastereomers
C) identical
D) conformational isomers
E) constitutional isomers

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30. Which of the following is a meso compound? 33. Which of the following is(are) meso?
H OH Br H Br Br Br
H2 H OH Br H
CH3
C CH3
HO H3C H
H3C H Br Br H H H
HO H Br
I II I II III IV
CH3 CH2OH CH2OH
A) I
H OH H H H OH B) II
CH2OH CH2OH CH3 C) III
D) IV
III IV V E) Two of the above
A) I
B) II Topic: Meso compounds
C) III 34. Which molecule has a plane of symmetry?
D) IV F H
Cl H
E) V Cl H H

H H CH3
31. Which of the following is(are) meso compound(s)? Cl
H CH3
CH3
H CH3 CH3
Cl CH3 Cl H H Cl I II III
H Cl H Cl H Cl A) I
B) II
CH3 CH3 CH3
C) III
I II III D) More than one of these
A) I E) None of these
B) II
C) III 35. Which molecule has a plane of symmetry?
D) Both II and III H CH3 CH2CH3 H H
E) Both I and III H
HO CH3 HO CH3 F F
32. Which of the following molecules is achiral?
A) (2R,3R)-2,3-Dichloropentane I II III
B) (2R,3S)-2,3-Dichloropentane
C) (2S,4S)-2,4-Dichloropentane A) I
D) (2S,4R)-2,4-Dichloropentane B) II
E) Two of these C) III
D) More than one of these
E) None of these

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36. Which compound does NOT possess a plane of symmetry? 39. Which of the following substances is achiral ?
CH3 Cl H H Br CH3
Cl H H Br H F
H H Br
H CH3 F H Br H HO
F F H CH3 Br H Br
H3C I II III IV
I II III IV V
A) I, II and V A) I
B) I, III and IV B) II
C) II, III and IV C) III
D) III and IV D) IV
E) V E) More than one of these

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

37. Which molecule is a meso compound? A) The specific rotation is 0º.
CH3 H H B) There are one or more planes of symmetry.
H Br H3C OH H3C F C) A single molecule is identical to its mirror image.
H Br H CH3 H F D) More than one stereogenic center must be present.
E) The stereochemical labels, (R) and (S), must be identical for each stereogenic
CH3 OH CH3
center.
I II III

A) I 41. Which is a meso compound?

B) II A) (2R,3R)-2,3-Dibromobutane
C) III B) (2R,3S)-2,3-Dibromopentane
D) More than one of the above C) (2R,4R)-2,4-Dibromopentane
E) None of the above D) (2R,4S)-2,4-Dibromopentane
E) (2R,4S)-2,4-Dibromohexane
38. Which molecule is a meso compound?
H H H F H H H CH3 F CH3 Topic: Specific names

OH F F H H F H CH3 F CH3 42. (R)-2-Chlorobutane is represented by:

CH3 CH3 H CH2CH3 CH2Cl
I II III IV V H3C Cl Cl CH3 H3C Cl H3C Cl H H
CH2CH3 CH2CH3 CH2CH3 H CH2CH3
A) I and II
B) IV and V I II III IV V
C) II and III
D) I, II and III A) I
E) None of the above B) II
C) III
D) IV
E) V

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43. Which of the following represent (R)-2-butanol? 47. CH2CH3

H CH3 H CH3 CH2CH3 H Cl
H3C OH H OH HO CH3 HO H H OH H CH3
CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH3 Cl H
I II III IV V CH3 is properly named:
A) (3R,4S,5R)- 3,5-Dichloro-4-methylhexane
A) III and V B) (2S,3S,4S)- 2,4-Dichloro-3-methylhexane
B) I, III, IV and V C) (2S,3R,4R)- 2,4-Dichloro-3-methylhexane
C) I, IV and V D) (2S,3R,4S)-2,4-Dichloro-3-methylhexane
D) I and III E) (2S,3S,4R)- 2,4-Dichloro-3-methylhexane
E) I, II, IV and V
48. The Cahn-Ingold-Prelog stereochemical designations used for the following substance
44. Which structure represents (S)-1-chloro-1-fluoroethane? are:
F F CH3 H
Cl H H Cl H Cl Cl
Cl
CH3 CH3 F H
I II III Cl Cl
A) I
B) II A) 2R,4S
C) III B) 2S,4R
D) More than one of the above C) 2R,4R
E) None of the above D) 2S,4S
E) The “R,S” terminology doesn't apply in this case.
45. Which structure represents (R)-1-chloro-1-fluoroethane?
F F CH3 49. Which of these is not a correct Fischer projection formula of the (S) form of
Cl H H Cl H Cl 3-bromo-1,1-dichloro-2-propanol ?
CHCl2 CH2Br H OH OH
CH3 CH3 F
H OH HO H Cl2HC CH2Br H CHCl2 BrH2C CHCl2
I II III CH2Br CHCl2 OH CH2Br H
A) I
I II III IV V
B) II
A) I
C) III
B) II
D) More than one of the above
C) III
E) None of the above
D) IV
E) V
46. Which structure represents (S)-2-bromobutane?
CH3 CH3 H
H Br Br H H3C Br
CH2CH3 CH2CH3 CH2CH3

I II III
A) I
B) II
C) III
D) More than one of the above
E) None of the above

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Topic: Optical activity 54. The compounds whose molecules are shown below would have:
H
H H H
50. What is the percent composition of a mixture of (S)-(+)-2-butanol,[!] 25D
= +13.52º,
and (R)-(-)-2-butanol,[!] 25 = -13.52º, with a specific rotation [!] 25 = +6.76º? OH
D D OH OH
A) 75%(R) 25%(S) OH
B) 25%(R) 75%(S)
C) 50%(R) 50%(S) A) the same melting point.
D) 67%(R) 33%(S) B) different melting points.
E) 33%(R) 67%(S) C) equal but opposite optical rotations.
D) More than one of these
51. Which one of the following can exist in optically active forms? E) None of these
A) cis-1,3-Dichlorocyclohexane
B) trans-1,3-Dichlorocyclohexane 55. The compounds whose structures are shown below would have:
CH3
C) cis-1,4-Dichlorocyclohexane
Br CH3
D) trans-1,4-Dichlorocyclohexane Br
E) cis-1,2-Dichlorocyclohexane Br
CH3 Br
CH3
52. The compounds whose molecules are shown below would have:
CH3 CH2CH3
H F H F A) the same melting point.
B) different melting points.
CH2CH3 CH3
C) equal but opposite optical rotations.
I II D) More than one of these
E) None of these
A) the same melting point.
B) different melting points. (Ej .56. 57)
C) equal but opposite optical rotations.
D) More than one of the above 58. Which of these is a comparatively insignificant factor affecting the magnitude of
E) None of the above specific optical rotation?
A) Concentration of the substance of interest
53. The compounds whose molecules are shown below would have: B) Purity of the sample
CH3 CH3 C) Temperature of the measurement
H F F H D) Length of the sample tube
H CH3 H3C F E) All of the above are equally significant.
F H
59. What can be said with certainty if a compound has [!] 25
D
= -9.25º ?
A) the same melting point. A) The compound has the (S) configuration.
B) different melting points. B) The compound has the (R) configuration.
C) equal but opposite optical rotations. C) The compound is not a meso form.
D) More than one of the above D) The compound possesses only one stereogenic center.
E) None of the above E) The compound has an optical purity of less than 100%.

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60. An alkane which can exhibit optical activity is: 67. Enantiomers are:
A) Neopentane A) molecules that have a mirror image.
B) Isopentane B) molecules that have at least one stereogenic center.
C) 3–Methylpentane C) non-superposable molecules.
D) 3–Methylhexane D) non-superposable constitutional isomers.
E) 2,3–Dimethylbutane 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)–2–bromopentane is: 68. Which of the following is NOT true of enantiomers? They have the same:
A) dextrorotatory (+). A) boiling point.
B) levorotatory (–). B) melting point.
C) optically inactive. C) specific rotation.
D) achiral. D) density.
E) analogous in absolute configuration to (R)–2–chloropentane. 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 +15º 69. Which statement is true of 1,3-dimethylcyclobutane?
in a 2 dm tube, the specific rotation is: A) Only one form of the compound is possible.
A) +50º B) Two diastereomeric forms are possible.
B) +25º C) Two sets of enantiomers are possible.
C) +15º D) Two enantiomeric forms and one meso compound are possible.
D) +7.5º E) None of the previous statements is true.
E) +4.0º
70. In which of the following reactions is the absolute configuration of the product likely to
63. Which compound would show optical activity? be the same as that of the reactant?
A) cis 1,4- Dimethylcyclohexane A) Br PBr3 Br
B) trans 1,4- Dimethylcyclohexane (R) OH Br
C) cis 1,4- Dimethylcycloheptane B) O
D) trans 1,4- Dimethylcycloheptane Br Br
E) More than one of these OH
(R) OH O
HA
64. Of the compounds which correspond to the general name "dichlorocyclobutane", how O
C) Br H2O OH
many are optically active?
A) 0 (R) OH OH
B) 1 D) All of the above
C) 2 E) Answers A) and B) only
D) 3
E) 4 Topic: Reaction stereochemistry
(Ej 71, 72)
Topic: General definitions 73.
(Ej .65)
The reaction of O with H2/Ni forms:
66. Which of the following is true of any (S)-enantiomer? A) 2-methylheptane.
A) It rotates plane-polarized light to the right. B) (R)-2-methyl-5-heptanol
B) It rotates plane-polarized light to the left. C) (S)-6-methyl-3-heptanol
C) It is a racemic form. D) (R,S)-6-methyl-3-heptanol
D) It is the mirror image of the corresponding (R)-enantiomer. E) Achiral 6,6-dimethyl-3-hexanol
E) It has the highest priority group on the left.

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74. CH3CHBrCH2CHClCH3 is the generalized representation of what number of

stereoisomers? 80. How many stereogenic centers are there in Lovastatin ( Mevacor® : a cholesterol-
A) 3 lowering drug) ?
B) 4 HO O
C) 5 O
D) 6
E) 7 O

75. For the generalized structure BrCH2CHClCH2CHClCH2Br there exists what number of
stereoisomers?
A) 2 (Lovastatin)
B) 3
A) 4
C) 4
B) 5
D) 6
C) 6
E) 8
D) 7
E) 8
76. How many discrete dimethylcyclopropanes are there?
A) 2
B) 3
81. What is the total number of compounds, stereoisomers included, designated by the
C) 4
general name "dichlorocyclopentane"?
D) 5
A) 4
E) 6
B) 5
C) 7
77. What is the molecular formula for the alkane of smallest molecular weight which
D) 8
possesses a stereogenic center?
E) 9
A) C4H10
B) C5H12
Use the following to answer questions 82-85:
C) C6H14
Consider the following compounds:
D) C7H16
E) C8H18 CH2OH H CH3 CH3
H OH HO CH3 HO H H OH
78. How many chiral stereoisomers can be drawn for CH3CHFCHFCH(CH3)2?
A) 1 H H H CH3 HO CH3 H3C H
B) 2 CH3 OH H OH
C) 3
D) 4 I II III IV
E) 8
82. Which of the compounds above (I-IV) represent enantiomers?
79. How many different compounds are there which correspond to the general name "3-(1- A) I and II
methylbutyl)cyclobutanol”? B) II and III
A) 2 C) III and IV
B) 4 D) II and IV
C) 6 E) III and IV
D) 8
E) None of the above

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83. Which compound above (I-IV) is a meso compound? SHORT ANSWER QUESTIONS Answers on p. 25-26
A) I
B) II
C) III 86. The molecule of aspartame ( Nutrasweet® ), depicted below, has ___________ ( how
D) IV many? ) stereogenic centers.
E) None of these O
HO O
84. Which compound above (I-IV) is (2R,3R)-2,3-butanediol? HN
A) I O
H2N O
B) II
C) III
Aspartame
D) IV
E) None of these
87. True or false: A sample consisting of the pure R enantiomer of a compound will always
85. Which compounds above (I-IV) form a set of stereoisomers? rotate plane-polarized light in a clockwise direction.
A) I, II and III A) True
B) II, III and IV B) False
C) II and III
D) I, III and IV 88. Draw a dash-wedge structure for (3R)-3-methyl-5-hexen-3-ol
E) I, II, III and IV
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 CH3

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93. What is the complete IUPAC name of the following substance? (Remember to give
stereochemical details, as relevant.) Svar Part 5: Stereochemistry
H Fråga Svar Rätt/Fel Fråga Svar Rätt/Fel
OH 1 D 44 D
2 B 45 B
3 D 46 A
H3C OH 4 A 47 D
5 C 48 C
94. Draw Fischer projection formulas for all stereoisomers of 2,4-dibromohexane, giving 6 D 49 D
stereochemical details for each structure. 7 B 50 B
8 B 51 B
9 B 52 D
95. Draw dash-wedge structures for all stereoisomers of 1-bromo-3-isopropylcyclohexane, 10 A 53 B
giving stereochemical details for each structure. 11 A 54 B
12 B 55 D
Topic: Fischer projections 13 E 56 C
14 C 57 C
96. Draw Fischer projection formulas for all stereoisomers of 2,4-dimethyl-3-hexanol, 15 E 58 C
giving stereochemical details for each structure. 16 D 59 C
17 C 60 D
18 A 61 E
97. Draw a Fischer projection formula of (3R)-6-Bromo-1-hexen-3-ol. 19 D 62 B
20 B 63 D
21 A 64 C
22 C 65 D
23 A 66 D
24 A 67 E
25 D 68 C
26 B 69 B
27 A 70 E
28 B 71 D
29 C 72 D
30 A 73 D
31 E 74 B
32 D 75 B
33 E 76 C
34 D 77 D
35 D 78 D
36 D 79 B
37 D 80 E
38 E 81 C
39 E 82 B
40 E 83 D
41 D 84 C
42 C 85 B
43 C

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Answer 86 – 97 96:
CH3 CH3 CH3 CH3

86: two H3C H H3C H H3C H H3C H

87: B H OH HO H H OH HO H
H3C H H CH3 H CH3 H3C H
88: OH
H H H H H H H H
CH3 CH3 CH3 CH3
89: 3S,4S 3R,4R 3S,4R 3R,4S
Br
2,4-dimethyl-3-hexanol
97: H2C H
90:
H OH
Br *
Br
H H
OH
Br H H
CH2Br
91: CH3
C2H5 (3R)-6-Bromo-1-hexen-3-ol.

H CH3
92: (1S)-1-ethyl-1,3,3-trimethylcyclopentane
93: (1R,3S)-1-methylcyclopentane-1,3-diol

94: CH3 CH3 CH3 CH3

Br H H Br H Br Br H
H H H H H H H H
Br H H Br Br H H Br
H H H H H H H H
CH3 CH3 CH3 CH3
2R,4S 2S,4R 2S,4S 2R,4R
2,4-dibromohexane
95: 1-bromo-3-isopropylcyclohexane
H H
H H

H Br Br H H Br Br H

1S, 3R 1R, 3S 1S, 3S 1R, 3R

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