Chapter 7 Stereochemistry: Answers Prof.

Sivaguru Jayaraman

Chapter 7: Stereochemistry 
1. Which of the molecules below are chiral?

A) only II B) only III C) I and III D) II and III

Ans: D

2. Which of the molecules below are chiral?

A) only I B) I and III C) II and III D) I, II, and III

Ans: B

3. Identify the chiral compound(s) below.

A) only II B) II and III C) III and IV D) I, II, and IV

Ans: A

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

4. Which of the following molecules are chiral?

A) only II B) only III C) II and III D) I, II, and III

Ans: A

5. How many stereogenic centers are there in the following molecule?

A) only 1 B) two C) three D) four

Ans: B

6. How many stereogenic centers are there in the following molecule?

A) only 1 B) two C) three D) four

Ans: C

7. Give the configurations, respectively, of the following two molecules.

A) R and R B) R and S C) S and S D) S and R

Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

8. Give the configurations, respectively, of the following two molecules.

A) R and R B) R and S C) S and S D) S and R

Ans: A

9. Which one of the following groups has the highest rank as assigned by the Cahn-Ingold-
Prelog system for stereogenic carbons?
A) –CH=CH2 B) –CH2OH C) –CH=O D) –CH2SH
Ans: D

10. Give the configurations of carbons 1 and 2, respectively, in the structure shown below.

A) R and R B) R and S C) S and S D) S and R

Ans: B

11. What is the IUPAC name of the following compound?

A) (2S, 3S)-2,3-dibromopentane C) (2R, 3S)-2,3-dibromopentane

B) (2S, 3R)-2,3-dibromopentane D) (2R, 3R)-2,3-dibromopentane
Ans: D

12. Which of the following statements are true?

I. If a molecule has a plane of symmetry it is achiral.
II. If a molecule has a center of symmetry it is achiral.
III. If a molecule has one stereogenic center it is chiral.
A) I and II B) I and III C) II and III D) I, II, and III
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

13. What is the relationship between the following two molecules?

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

Ans: A

14. What are the configurations of carbons 2 and 3 in the Fischer projection below?

A) 2R, 3R B) 2R, 3S C) 2S, 3R D) 2S, 3S

Ans: D

15. Compound X, C5H10O, is optically active. The compound consumes one equivalent of
hydrogen to give C5H12O. The hydrogenation product is also optically active. Which
compound below matches the information?

A) A B) B C) C D) D
Ans: D

16. A pure sample of (S)-phenylalanine has a specific rotation of +70°. A mixture of the two
enantiomers of phenylalanine has a specific rotation of +7.0°. What are the percentages
of the S and R enantiomers in the mixture?
A) 95% S, 5% R C) 55% S, 45% R
B) 90% S, 10% R D) 52.5% S, 47.5% R
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

17. How many stereoisomers are there for the compound shown below?

A) two B) four C) six D) eight

Ans: A

18. Give the total number of stereoisomers of 2,3-dibromobutane.

A) none, only a single structure B) two C) three D) four
Ans: C

19. What is the relationship between the following two compounds?

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

Ans: D

20. What is the relationship between the following two compounds?

A) different conformations of the same compound

B) enantiomers
C) diastereomers
D) constitutional isomers
Ans: C

21. (+)–Tartaric acid has a specific rotation of +12.0°. What is the specific rotation of a
mixture of 75% (+)–tartaric acid and 25% (–)–tartaric acid?
A) +4.0° B) +6.0° C) +8.0° D) +9.0°
Ans: B

22. The addition of bromine, Br2, to trans-2-butene gives

A) (2R,3R)-2,3-dibromobutane.
B) (2S,3S)-2,3-dibromobutane.
C) a racemic mixture of (2R,3R) and (2S,3S)-2,3-dibromobutane.
D) meso-2,3-dibromobutane.
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

23. What is the relationship between the following two compounds?

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

Ans: B

24. In terms of stereochemistry, the following reaction gives

A) a single enantiomer. C) a nonracemic pair of enantiomers.

B) a racemic pair of enantiomers. D) two diastereomers.
Ans: D

25. Which of the following has a meso stereoisomer?

I. 2,4-dichloropentane
II. 1,3-dimethylcyclopentane
III. 2,3-dichloropentane
A) only I B) only II C) I and III D) I and II
Ans: D

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

26. Which of the following amines gives a pair of diastereomeric salts when reacted with
(S)-(-)-malic acid?

A) only I B) only II C) only III D) I and III

Ans: D

27. Which of the following C6H10 cycloalkenes would give a pair of diastereomeric
epoxides when reacted with peroxyacetic acid, CH3CO3H?
A) 1-methylcyclopentene C) 1,2-dimethylcyclobutene
B) 3-methylcyclopentene D) 3,3-dimethylcyclobutene
Ans: B

28. The addition of HBr to 1-octene gives

A) a racemic mixture of 2-bromooctane.
B) a nonracemic mixture of 2-bromooctane.
C) 1-bromooctane.
D) a racemic mixture of 1,2-dibromooctane.
Ans: A

29. Compound X, C6H10, is optically active. Hydrogenation of the compound gives

methylcyclopentane. Which compound below is compound X?

A) A B) B C) C D) D
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

30. Which of the following is the best method to make a racemic mixture of (+) and (–)–
2,3-dibromobutane?
A) photochemical bromination of 2-bromobutane
B) addition of HBr to racemic 3-bromo-2-butene
C) addition of Br2 to cis-2-butene
D) addition of Br2 to trans-2-butene
Ans: C

31. Which of the following compounds gives a pair of diastereomers upon epoxidation with
peroxyacetic acid, CH3CO3H?

A) A B) B C) C D) D
Ans: D

32. How many stereoisomers are there of D-fructose (including D-fructose), shown below?

A) four B) six C) eight D) twelve

Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

33. Which of the following Fischer projections corresponds to the compound shown below?

A) A B) B C) C D) D
Ans: A

34. The four isomeric dimethylcyclopropanes are shown below. Identify two of the isomers
which are related as diastereomers.

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

Ans: C

35. How many stereoisomers are there of 1-isopropyl-4-methylcyclohexane?

A) only 1 structure possible - no stereoisomers B) two C) three D) four
Ans: B

36. Which object below is achiral?

A) golf club (wood driver) B) baseball glove C) tennis shoe D) baseball bat
Ans: D

37. Which compound below has a meso form?

A) 1,2-dichlorobutane C) 2,3-dichlorobutane
B) 1,3-dichlorobutane D) 1,4-dichlorobutane
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

38. Which compound below has no stereoisomers?

A) 1,2-dichlorobutane C) 2,3-dichlorobutane
B) 1,3-dichlorobutane D) 1,4-dichlorobutane
Ans: D

39. Compound X (C7H12) is optically active. Hydrogenation of compound X gives two

isomeric 1,2-dimethylcyclopentanes, one is optically active and the other is optically
inactive. Of the following compounds, which is the only one that fits the data?

A) A B) B C) C D) D
Ans: C

40. Which sawhorse drawing below has the identical conformation as the following Fischer
projection?

A) A B) B C) C D) D
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

41. Which one of the following is a diastereomer of (R)-4-bromo-cis-2-hexene?

A) (S)-4-bromo-cis-2-hexene C) (R)-4-bromo-trans-2-hexene
B) (R)-5-bromo-cis-2-hexene D) (S)-5-bromo-trans-2-hexene
Ans: C

42. Which of the following statements is false?

A) Racemic mixtures are optically inactive.
B) Enantiomers have specific rotations which are equal, but have opposite signs.
C) Achiral molecules are optically inactive.
D) Meso compounds contain equal amounts of enantiomers.
Ans: D

43. Which reaction below gives a single enantiomer of a chiral product?

A) A B) B C) C D) D
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

44. Which reaction below gives a pair of diastereomers?

A) A B) B C) C D) D
Ans: A

45. Which one of the following isomeric dibromobutanes is shown below?

A) (2R, 3R)-2,3-dibromobutane C) meso-2,3-dibromobutane

B) (2S, 3S)-2,3-dibromobutane D) (R)-1,2-dibromobutane
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

46. The following isomer of dibromohexane can be synthesized by

A) addition of Br2 to trans-3-hexene. C) addition of HBr to trans-3-hexene.

B) addition of Br2 to cis-3-hexene. D) addition of HBr to cis-3-hexene.
Ans: A

47. What are the configurations of C(1) and C(2), respectively, for the stereoisomer of 2-
methylcyclopentanol shown below?

A) (1R, 2R) B) (1R, 2S) C) (1S, 2R) D) (1S, 2S)

Ans: B

48. Which one of the following is a diastereomer of (2R,3R)-2,3-dibromopentane?

A) (2S,3S)-2,3-dibromopentane C) R-1,2-dibromopentane
B) (2S,3R)-2,3-dibromopentane D) (2R,4R)-2,4-dibromopentane
Ans: B

49. Which of the following is the enantiomer of (2R,3R)-2,3-dibromopentane?

A) (2S,3S)-2,3-dibromopentane C) (2R,3S)-2,3-dibromopentane
B) (2S,3R)-2,3-dibromopentane D) (2R,4R)-2,4-dibromopentane
Ans: A

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

50. What is the IUPAC name of the following hydrocarbon?

A) (R)-4-ethylpentanane C) (S)-2-ethylpentane
B) (S)-3-methylhexane D) (R)-3-methylhexane
Ans: B

51. What is the total number of stereoisomers (including the one shown) for the following
alcohol?

A) zero (none are possible) B) two C) three D) four

Ans: B

52. Which of the following best describes a racemic mixture?

A) A mixture containing equal amounts of two diastereomers.
B) A mixture containing a meso stereoisomer.
C) A mixture containing unequal amounts of enantiomers.
D) A mixture containing equal amounts of enantiomers.
Ans: D

53. Which one of the isomeric C4H9Cl molecules is chiral?

A) 1-chlorobutane C) 1-chloro-2-methylpropane
B) 2-chlorobutane D) 2-chloro-2-methylpropane
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

54. Which of the following molecules is(are) chiral?

A) only I B) I and II C) II and III D) I, II, and III

Ans: A

55. How many stereoisomers of 2,3-pentanediol are possible?

OH

OH
A) 2 B) 3 C) 4 D) 6
Ans: C

56. How many stereoisomers are possible for this structure?

OH

A) 1 B) 4 C) 8 D) 16
Ans: C

57. How many stereoisomers of 2,4-pentanediol are possible?

HO OH

A) 2 B) 3 C) 4 D) 6
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

58. The tartaric acid found in fruits, when isolated, exhibits [α] = +12°. Which
configuration is NOT possible for this naturally-occurring material?

HO OH
tartaric acid
HO2C CO2H

A) R,R B) R,S C) S,S D) there is no way to tell

Ans: B

59. Which statement would be true of this reaction?

Br2
CH3CH2CH2CH3 CH3CH2CHBrCH3
light
A) The organic product is achiral.
B) The product is racemic.
C) The product is more of one enantiomer than the other.
D) There is no way to guess the stereochemistry.
Ans: B

60. The most specific description of the relationship between the following two molecules
is:

CH3 H
H H3C
C Br C CH2CH3
and
CH3CH2 Br

A) identical B) isomers C) enantiomers D) diastereomers

Ans: A

61. What are the R/S assignments in this molecule? (assume the carbons are numbered as
shown)

OH

3 CO2H
HO2C 2
OH
A) 2S, 3R B) 2S, 3S C) 2R, 3S D) 2R, 3R
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

62. What is the most important reason that chiral drugs are typically sold as single
enantiomers?
A) one enantiomer is typically a more effective drug
B) one enantiomer is typically cheaper to make
C) racemic mixtures have already been patented
D) one enantiomer is typically easier to separate
Ans: A

63. The free-radical bromination of (R)-2-chlorobutane could produce how many mono-
bromo 2-chlorobutanes? (count all isomers that could be formed, including
stereoisomers)

Br2
?
only (R) H Cl light

A) four B) five C) six D) eight

Ans: C

64. (-)-Fenchone can be purchased in 70% optical purity. What ratio of enantiomers is
present?

O
A) 70% (-) : 30% (+) C) 55% (-) : 45% (+)
B) 85% (-) : 15% (+) D) 60% (-) : 40% (+)
Ans: B

65. One stereoisomer of the structure below is a poison found in a certain mushroom. How
many stereoisomers of this structure are possible?

HO

N(CH3)3
H3C O
A) 4 B) 8 C) 16 D) 32
Ans: B

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.
Chapter 7 Stereochemistry: Answers Prof. Sivaguru Jayaraman

66. How many chiral centers are present in histrionicotoxin?

A) 2 B) 3 C) 4 D) 5
Ans: C

67. How many chiral centers are in this molecule?

HO
morphine

O
N
H
CH3
HO

A) 2 B) 4 C) 5 D) 6
Ans: C

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Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.