Chapter 6 Chirality

Multiple Choice
1. Which compounds contain stereocenters? (Sec. 6.3)
I) 1-chloropentane
II) 2-chloropentane
III) 3-chloropentane
IV) 1,2-dichloropentane
a)
b)
c)
d)

I, II
III, IV
I, III
II, IV

2. Which compounds contain stereocenters? (Sec. 6.3)

I) 2-methylpentane
II) chlorocyclohexane
III) 3-methyl-2-butanol
IV) 2-hydroxypropanoic acid
a)
b)
c)
d)

I, II
III, IV
I, III
II, IV

3. Which compounds contain stereocenters? (Sec. 6.3)

OH OH
I.

HO

OH
O

III.

CH3CCH2CH3

CH CH2

II.

IV.

H3C
H3C

a)
b)
c)
d)

I, II
III, IV
I, III
II, IV

61

OH
CHCHCH3

Chapter 6 Chirality

4. Which compounds have multiple stereocenters? (Sec. 6.3, 6.5)

HO CH3
I. CH3CHCHCH3

HO OH O
II. CH3CHCH COH
O

Cl OH
III. CH3CHCHCH3

CH2COH

IV.

HO C

COH

CH2O
COH
O
a)
b)
c)
d)

I, II
III, IV
II, III
I, III

5. How many stereoisomers are possible for 1,2-dichlorocyclopentane? (Sec. 6.3)

a)
b)
c)
d)

1
2
3
4

6. How many stereoisomers are possible for 2,3-butanediol? (Sec. 6.3)

a)
b)
c)
d)

1
2
3
4

7. How many stereoisomers are possible for the following structure? (Sec. 6.2-6.3)

OH

CH3CHCHCOH
NH2
a)
b)
c)
d)

1
2
3
4

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Chapter 6 Chirality

8. Which structures are chiral? (Sec. 6.3)

H
Cl

H
C

Cl
H2C

H2C

CH2CH2CH3

CH2CH2CH3

I.

II.

CHCH2CH3
Cl
III.
H

H
H2C

H2C

CH2CHCH3
IV.

a)
b)
c)
d)

CH2CH2CH2

Cl

V.

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

9. Which pair of structures are enantiomers? (Sec. 6.3)

CH3
H
HOC

I.

OH

H O
HO
H3C

O
Cl
Br

II.

a)
b)
c)
d)

COH

Br

H3C
CH3
CH2CH3 H3CH2C
H

III.

OH

Cl

CH3
CH3

OH

I, II
II, III
I, III
I, II, III

63

Cl

Chapter 6 Chirality

10. What is the relationship between these two structures? (Sec. 6.3, 6.5)

NH2
H

CH3

H3C

NH2

NH2

H2N

CH3

CH3
a)
b)
c)
d)

Identical structures
Enantiomers
Diastereomers
Constitutional isomers

11. What is the relationship between these two structures? (Sec. 6.3, 6.5)

a)
b)
c)
d)

Cl

Br

Cl

Br

identical structures
enantiomers
diastereomers
constitutional isomers

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Chapter 6 Chirality

12. Which are meso compounds? (Sec. 6.5)

O
CH2OCH3

CH

OH

OH

OH

OH

CH2OH

CH
O

I.

II.
CH2OH

a)
b)
c)
d)

CH2OH

OCH3

H3CO

OCH3

CH2OH

III.

IV.

13. How many stereoisomers are possible for Prilosec? (Sec. 6.7)

H
N

CH3
O
a)
b)
c)
d)

OCH3

CH2OH

I, II
I, III
II, III
III, IV

.HCl

CH3

OH

4
8
16
32

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Chapter 6 Chirality

14. How many pairs of enantiomers are possible for cortisone acetate? (Sec. 6.7)

OH O

CH3

CH3

O
a)
b)
c)
d)

32
64
128
256

15. Which forms of lactic acid are R forms? (Sec. 6.4)

COH
HO
H3C

CH3
H
HOC

CH3

COH
HO

OH

H
CH3 HO

O
I.

a)
b)
c)
d)

II.

III.

COH
O

IV.

I, II
III, IV
I, III
II, IV

16. What is the R,S configuration for the following structure of isocitric acid? (Sec. 6.4)

O
HOCCH2
HO

COH
H
C
#1
C
H

a)
b)
c)
d)

COH
O

2-R, 3-R
2-R, 3-S
2-S, 3-R
2-S, 3-S

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Chapter 6 Chirality
17. The specific rotation of dextrorotatory tartaric acid is +12.7 degrees. A mixture of dextrorotatory and
levorotatory tartaric acid has a specific rotation of +6.35 degrees. What is the optical purity of the mixture?
(Sec. 6.9)
a)
b)
c)
d)

25%
33 1/3%
50%
75%

18. Rank the following substituents in order of increasing priority. (Sec. 6.4)

OH

Cl

I.
a)
b)
c)
d)

CH3

II.

III.

IV.

I, III, II, IV
II, I, III, IV
III, I, II, IV
IV, III, I, II

19. Rank the following substituents in order of increasing priority. (Sec. 6.4)

H
C

OCH3

II.

III.

C O
H

I.
a)
b)
c)
d)

OH
H

IV.

III, II, IV, I

I, IV, II, III
IV, I, III, II
I, II, III, IV

20. Rank the following substituents in order of decreasing priority (highest first). (Sec. 6.4)

OCH3
I.
a)
b)
c)
d)

COH

CH

OCH2CH3

II.

III.

IV.

II, III, IV, I

III, IV, I, II
IV, III, II, I
IV, I, II, III

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Chapter 6 Chirality

21. Rank the following substituents in order of increasing priority. (Sec. 6.4)

H
C

C
H

H
I.

CH3

CH3

CH3

CH3

CH3

II.

III.

C
H

H3C
IV.

a) III, II, IV, I

b) IV, I, II, III
c) I, III, II, IV
d) IV, II, I, III
22. Which structures represent R-3-methylhexane? (Sec. 6.4)

H3C

I.
a)
b)
c)
d)

CH3

CH3

II.

H
III.

CH3

IV.

II, III
I, III
I, II
III, IV

23. Which structure is correctly named 3R,4S-3,4-dimethylhexane (Sec. 6.4)

H3C

H3C

I.
a)
b)
c)
d)

CH3

H3C H

H CH3

H3C

II.

H
III.

II
I, III
III
III, IV

24. Which statement about enantiomers is false? (Sec. 6.8)

a)
b)
c)
d)

enantiomers have the same boiling and melting points.

enantiomers have the same chemical properties.
enantiomers have the same atom connectivity.
enantiomers have the same three dimensional orientation.

68

H CH3
H3C

H
IV.

Chapter 6 Chirality
25. Which statements about stereoisomers are true? (Sec. 6.8, 6.9)
I) enantiomers and diastereomers have the same physical properties.
II) 50/50 mixtures of R and S enantiomers are called racemic mixtures.
III) meso isomers rotate the plane of plane polarized light.
IV) dextrorotatory compounds rotate plane polarized light to the right.
a)
b)
c)
d)

I, II
II, III
II, IV
III, IV

Fill in the Blank

1. The following structure contains ___________ stereocenters. (Sec. 6.7)

OH
OH
O

Nadolol (beta-blocker)

OH
N

2. The following structure contains __________ stereocenters. (Sec. 6.7)

CH3
N
morphine
O

OH

3. The priority order for the following groups are (highest = 1),

CH3
C CH3
CH3

CH3
C C

CH3
C C H

C H
CH3

(Sec. 6.4)

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Chapter 6 Chirality

4. The priority order for the following groups is (highest = 1),

Br

Cl

C H
CH3

C Cl
CH3

Cl

OH

C OH
CH3

C H
CH3

(Sec. 6.4)
5. The following structure is the _____________ configuration. (Sec. 6.4)

OH

OH
6. The following structure is the _____________ configuration. (Sec. 6.4)

NH2
OH
Br
7. The structure of the R,R enantiomer of 2,3-butanediol is,

(Sec. 6.4)
8. The structure of the S,R enantiomer of 3-bromo-4-chlorohexane is,

(Sec. 6.4)

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Chapter 6 Chirality

9. The following structures are __________________ (what type of stereoisomer). (Sec. 6.3, 6.5)

NH2

OH

NH2

OH

10. The following structures are ________________ (what type of stereoisomer). (Sec. 6.3, 6.5)

True-False
1. The following structures are enantiomers. (Sec. 6.3)

Cl

H
Cl
HO

CH3

H
HO

CH3

2. The following structures are diastereomers. (Sec. 6.5)

Cl

Br

Cl

Br

3. The name of the following structure is 2S,3S-2,3-dibromobutane. (Sec. 6.4)

Br

Br
4. The diastereomer of 2R,3R-dichlorobutane is achiral. (Sec. 6.5)
5. The following groups are listed in decreasing order of priority. (Sec. 6.4)

O
OH >

OCH3 >

>
CH3

OH

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Chapter 6 Chirality

6. The following groups are listed in decreasing order of priority. (Sec. 6.4)

OH >

NH2

>

Br

>

CH3

7. Enantiomers have the same physical properties (m.p., b.p., index of refraction, density). (Sec. 6.8)
8. Meso compounds rotate plane polarized light the same magnitude as enantiomers, but in opposite directions.
(Sec. 6.5)
9. Diastereomers are achiral. (Sec. 6.5)
10. Enantiomers and meso compounds are diastereomers. (Sec. 6.5)

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Chapter 6 Chirality
Answers
Multiple Choice
1. d
2. b
3. d
4. c
5. c
6. c
7. d
8. d
9. a
10. a
11. c
12. c
13. b
14. a
15. a
16. b
17. c
18. d
19. b
20. d
21. d
22. c
23. c
24. d
25. c
Fill in the Blank
1.
2.
3.
4.
5.
6.
7.

3
5
2, 3, 1, 4
2, 1, 3, 4
2R, 3R
1S, 2S

OH

OH
8.

Cl

Br
9. enantiomers
10. diastereomers

73

Chapter 6 Chirality
True-False
1. T
2. T
3. F
4. T
5. F
6. F
7. T
8. F
9. F
10. T

74