WADE7 Problems 05

Organic Chemistry, 7e (Wade)
Chapter 5 Stereochemistry
1) What term describes the structural relationship between cis-1,2-dimethylcyclopentane and

trans-1,3-dimethylcyclopentane?
A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: B
Diff: 2
Section: 5.1
2) What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane

and (2S,3S,5R)-2,3,5-trichloroheptane?
A) not isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: B
Diff: 2
Section: 5.1
3) What is the structural relationship between the two molecule shown below?
A) constitutional isomers
B) enantiomers
C) diastereomers
D) conformational isomers
E) not isomers
Answer: A
Diff: 2
Section: 5.1
1
4) __________ are isomers which have the same bonding sequence but differ in the orientation
of their atoms in space.
Answer: Stereoisomers
Diff: 1
Section: 5.1
5) How many asymmetric carbon atoms are present in the following compound?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: B
Diff: 1
Section: 5.2
6) How many asymmetric carbon atoms are present in the following compound?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: A
Diff: 1
Section: 5.2
2
7) How many enantiomers are there of the molecule shown below?
A) 0
B) 1
C) 2
D) 3
E) 6
Answer: B
Diff: 1
Section: 5.2
8) Which of the following incorrectly describes cis-1,2-dimethylcyclopentane?

A) It is a meso compound.
B) It is achiral.
C) It contains two asymmetric carbons.
D) Its diastereomer is trans-1,2-dimethylcyclopentane.
E) It has an enantiomer.
Answer: E
Diff: 1
Section: 5.2
9) Which of the statements below correctly describes an achiral molecule?

A) The molecule has a nonsuperimposable mirror image.
B) The molecule exhibits optical activity when it interacts with plane-polarized light.
C) The molecule has an enantiomer.
D) The molecule might be a meso form.
E) None of the above
Answer: D
Diff: 2
Section: 5.2
3
and (2S,3S,4R)-2,3,4-trichloroheptane?
A) not isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: C
Diff: 2
Section: 5.2
11) If possible, draw the structure of the enantiomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.2
12) Is the mirror image of the following molecule an enantiomer or is it superimposable with it?
Answer: Superimposable. The molecule is achiral.

Diff: 2
Section: 5.2
4
13) Circle each chiral molecule among those shown below.
Answer:
Diff: 2
Section: 5.2
14) Circle each chiral molecule among those shown below.
Answer:
Diff: 2
Section: 5.2
5
15) Draw the enantiomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.2
16) Circle all structures shown below that are chiral.
Answer:
Diff: 3
Section: 5.2
17) Is the molecule shown below chiral or achiral?
(CH3)3CCH(CH3)2
Answer: achiral
Diff: 1
Section: 5.2
6
18) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: the same compound

Diff: 1
Section: 5.2

Diff: 1
Section: 5.2
Answer: enantiomers
Diff: 1
Section: 5.2
21) How many asymmetric carbons are present in the compound below?
Answer: 1
Diff: 1
Section: 5.2
7
Answer: none
Diff: 1
Section: 5.2
Answer: 5
Diff: 1
Section: 5.2
CH3CH2CH(CH3)CH2CH3
Answer: achiral
Diff: 2
Section: 5.2
Answer: achiral
Diff: 2
Section: 5.2
Answer: chiral
Diff: 2
Section: 5.2
8
Answer: achiral
Diff: 2
Section: 5.2
Answer: achiral
Diff: 2
Section: 5.2
Answer: chiral
Diff: 2
Section: 5.2
Answer: enantiomers
Diff: 2
Section: 5.2
9
Answer: 2
Diff: 2
Section: 5.2
3-ethyl-2,2,4-trimethylpentane
Answer: 1
Diff: 2
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
10
Answer: enantiomers
Diff: 3
Section: 5.2
Answer: 5
Diff: 3
Section: 5.2
38) Does the molecule shown below contain asymmetric carbon atoms? Is this molecule chiral?
Answer: Yes, the molecule contains 4 asymmetric carbon atoms. No, the molecule is not chiral
since it is superimposable with its mirror image.
Diff: 3
Section: 5.2
11
39) Which of the following configurations corresponds to the structure below?
A) (4R, 5R)
B) (4R, 5S)
C) (4S, 5R)
D) (4S, 5S)
Answer: A
Diff: 3
Section: 5.3
40) Label each asymmetric carbon in the molecule below as having the R or S configuration.
Answer:
Diff: 2
Section: 5.3
41) Assign the proper configurational label, R or S, to the chiral carbon in the molecule shown
below.
Answer: S
Diff: 2
Section: 5.3
12
42) Assign the proper configurational label, R or S, to each chiral carbon in the molecule below.
Answer:
Diff: 2
Section: 5.3
43) For the structure shown below, draw the stereoisomer having a configuration of (1R,3S,4S) in
a perspective structure.
Answer:
Diff: 3
Section: 5.3
13
44) Captopril is used to treat high blood pressure and congestive heart failure. Label the chiral
centers as R or S.
Answer:
Diff: 3
Section: 5.3
45) Label each asymmetric carbon in the compound below as R or S.
Answer:
Diff: 1
Section: 5.3
46) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate three-
dimensional stereochemical detail properly.
Answer:
Diff: 1
Section: 5.3
47) Draw the structure of (S)-2-bromobutane. Take particular care to indicate stereochemistry
properly.
Answer:
Diff: 1
Section: 5.3
14
Answer:
Diff: 2
Section: 5.3
Answer:
Diff: 2
Section: 5.3
50) Draw the structure of (2R,3S)-2,3-dichloropentane. Take particular care to indicate three-
dimensional stereochemical detail properly.
Answer:
Diff: 2
Section: 5.3
51) Draw the structure of the enantiomer of (2S, 3R)-2,3-dichloropentane. Take particular care to
indicate three-dimensional stereochemical detail properly.
Answer:
Diff: 2
Section: 5.3
15
52) Draw the structure of any diastereomer of (2S, 3R)-2,3-dichloropentane. Take particular care
to indicate three-dimensional stereochemical detail properly.
Answer:
Diff: 2
Section: 5.3
53) Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate
stereochemistry properly.
Answer:
Diff: 2
Section: 5.3
54) Draw the structure of (S)-3-chloro-3-methylhexane. Take particular care to indicate

stereochemistry properly.
Answer:
Diff: 2
Section: 5.3
55) Draw the structure of (1R, 2S, 3S)-1,2-dibromo-3-ethylcyclohexane. Take particular care to
indicate stereochemistry properly.
Answer:
Diff: 2
Section: 5.3
16
Answer:
Diff: 3
Section: 5.3
57) Label each assymetric carbon in the compound below as R or S.
Answer:
Diff: 3
Section: 5.3
58) Which of the following statements correctly pertains to a pair of enantiomers?

A) They rotate the plane of polarized light by exactly the same amount and in opposite
directions.
B) They rotate the plane of polarized light by differing amounts and in opposite directions.
C) They rotate the plane of polarized light by differing amounts and in the same direction.
D) The have different melting points.
E) They have the same melting point, but they have different boiling points.
Answer: A
Diff: 2
Section: 5.4
17
59) If (S)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (R)-
glyceraldehyde?
A) 0.0°
B) -8.7°
C) +8.7°
D) cannot be determined from the information given
Answer: C
Diff: 2
Section: 5.4
60) Which of the following statements is (are) true for the compound (R)-2-butanol?
A) This compound is chiral.
B) This compound is optically active.
C) This compound has an enantiomer.
D) all of the above
E) none of the above
Answer: D
Diff: 2
Section: 5.4
61) Predict the specific rotation of the compound shown.
A) It is impossible to predict; must be determined experimentally.

B) Because both asymmetric centers are R, the compound is dextrorotatory.
C) Because both asymmetric centers are S, the compound is levorotatory.
D) Zero; the compound is achiral.
E) Because this compound represents a racemic mixture, the compound is dextrorotatory.
Answer: D
Diff: 2
Section: 5.4
18
62) A student measured the optical activity of an unknown sugar at two different concentrations.
The results of his measurements are shown below. Given that the sample cell had a path length
of 10.0 cm, calculate the specific rotation for the unknown sugar. (Hint: consider each
measurement of plane polarized light has a true reading and a "ghost" reading 180° from the true
reading).
concentration observed rotation

2.00 g sugar in 10.0 mL water +159.1°
5.00 g sugar in 10.0 mL water +127.8°
A) -10.5°
B) +25.6°
C) +79.5°
D) -105°
E) +256°
Answer: D
Diff: 3
Section: 5.4
63) Compounds that rotate the plane of polarized light clockwise are called __________.
Answer: dextrorotatory
Diff: 1
Section: 5.4
64) Would a 50:50 mixture of (2R,3R)-2,3-dibromobutane and (2R,3S)-2,3-dibromobutane be

optically active? Explain.
Answer: Yes, the mixture would be optically active. This is not a racemic mixture but a mixture
of diastereomers. The specific rotations of diastereomers are not the same in magnitude nor
necessarily opposite in sign.
Diff: 2
Section: 5.4
65) Can one predict whether a compound with a single asymmetric carbon is dextro- or
levorotatory based on the R/S assignment at this asymmetric carbon? Explain briefly.
Answer: No. R/S assignment is purely a convention of nomenclature and is completely
independent of the direction in which plane-polarized light is rotated by the compound.
Diff: 2
Section: 5.4
66) A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10
mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this
natural product?
Answer: +2.57°
Diff: 3
Section: 5.4
19
67) A mixture of equal amounts of two enantiomers __________.
A) is called a racemic mixture
B) is optically inactive
C) implies that the enantiomers are meso forms
D) both A and B
Answer: D
Diff: 2
Section: 5.6
68) If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of
the mixture?
A) 100
B) 75
C) 50
D) 25
E) 3
Answer: C
Diff: 2
Section: 5.7
69) A mixture of two enantiomers with a composition of 65.0% R has an observed rotation of
-25.3° in a 10.0 cm polarimeter tube. If the mixture has a concentration of 2.038 g/mL at 25°C,
what is the predicted [α]25D of an optically pure sample of the S enantiomer?
A) -25.3°
B) -53.5°
C) +12.4°
D) +41.3°
E) +53.5°
Answer: D
Diff: 3
Section: 5.7
70) Calculate the e.e. of a mixture containing 8.0 g of (-)-glyceraldehyde and 2.0 g of
(+)-glyceraldehyde.
Answer: 60%
Diff: 2
Section: 5.7
71) The specific rotation of pure (-)-2-butanol is -13.5°. What % of a mixture of the two
enantiomeric forms is the (+)-form if the specific rotation of this mixture is +7.0°?
Answer: 76%
Diff: 3
Section: 5.7
20
72) (-)-Lactic acid has a specific rotation of -3.8°. What is the specific rotation of a solution
containing 7.5 g of (-)-lactic acid and 2.5 g of (+)-lactic acid?
Answer: -1.9°
Diff: 3
Section: 5.7
73) Explain the stereochemical relationship, if any, among the following two structures and
describe whether or not they could be theoretically isolated from each other. (Note: Some H
atoms are omitted for clarity.)
Answer: These structures are conformationally dependent diastereomers. They could not be
isolated because they are actually the same molecule.
Diff: 3
Section: 5.8
74) Can a molecule be chiral if it contains no asymmetric carbons? Explain briefly.

Answer: Yes. The presence of asymmetric carbons is not required for a molecule to be chiral.
The only requirement is that the molecule be nonsuperimposable with its mirror image.
Structural features other than asymmetric carbons can lead to chirality.
Diff: 2
Section: 5.9
Answer: enantiomers
Diff: 3
Section: 5.9
21
76) Why is the following structure not a meso compound?
Answer: The functional group at the top (aldehyde) is different from the bottom (alcohol) and
thus there is no internal reflective plane in the molecule
Diff: 1
Section: 5.10
77) Draw the Fischer projection of (2R,4R)-2,4-dibromopentane.

Answer:
Diff: 2
Section: 5.10
78) Provide a Fischer projection of (2R,3R,4S)-2,3,4-trichloroheptane.

Answer:
Diff: 3
Section: 5.10
22
79) Provide a Fischer projection of (2S,3S,4S)-2,3,4-trichloroheptane.
Answer:
Diff: 3
Section: 5.10
80) Draw the Fischer projection of (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH.

Answer:
Diff: 1
Section: 5.10
81) How many diastereomers are there of the molecule shown below?
A) 0
B) 1
C) 2
D) 3
E) 6
Answer: C
Diff: 1
Section: 5.11
23
82) Which of the following terms best describes the stereochemical relationship of the two
compounds shown below in Fischer notation?
A) enantiomers
B) diastereomers
C) constitutional isomers
D) cis/trans - isomers
E) meso - same structure
Answer: B
Diff: 2
Section: 5.11
83) Which of the following statements is (are) true for the compound (3R, 4R)-3,4-
dimethylhexane?
B) The enantiomer of this compound is (3S, 4S)-3,4-dimethylhexane.
C) This compound is a diastereomer of (3R, 4S)-3,4-dimethylhexane.
D) all of the above
Answer: D
Diff: 2
Section: 5.11
84) Which of the following terms correctly describe(s) the structural relationship between cis-
1,3-dimethylcyclopentane and trans-1,3-dimethylcyclopentane?
A) enantiomers
B) diastereomers
C) geometric isomers
D) both A and C
E) both B and C
Answer: E
Diff: 2
Section: 5.11
24
85) What term describes the structural relationship between (E)- and (Z)-2-pentene?
A) not isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11
86) What term describes the structural relationship between cis-1,2-dimethylcyclopentane and
trans-1,2-dimethylcyclopentane?
A) not isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11

and (2R,3R,4R)-2,3,4-trichloroheptane?
A) not isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11
25
88) How many diastereomers are there of the molecule shown below?
A) 0
B) 1
C) 2
D) 3
E) 6
Answer: E
Diff: 3
Section: 5.11
Use the following three structures to answer the questions below.
89) The relationship between I and III is:

A) same compound
B) enantiomers
C) diastereomers
D) constitutional isomers
Answer: C
Diff: 3
Section: 5.11
90) The relationship between I and II is:

A) same compound
B) enantiomers
C) diastereomers
D) constitutional isomers
Answer: C
Diff: 3
Section: 5.11
26
91) Which of the structures above are meso structures?
A) I
B) II
C) III
D) II & III
E) None of the previous
Answer: A
Diff: 3
Section: 5.13
92) Stereoisomers which are not mirror image isomers are __________.
Answer: diastereomers
Diff: 1
Section: 5.11
93) If possible, draw the structure of any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
27
94) If possible, draw the structure of any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
95) Draw any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
28
Diff: 2
Section: 5.11

Diff: 2
Section: 5.11
Diff: 3
Section: 5.11

Diff: 3
Section: 5.11
29
100) Which of the following molecules, if isolated in its pure form, would demonstrate optical
activity ?
A) both IV and V
B) both I and III
C) only II
D) both III and IV
E) both I and V
Answer: A
Diff: 3
Section: 5.12
101) Which of the following statements is (are) true for the compound cis-1,2-
dichlorocyclopropane?
B) The enantiomer of this compound is trans-1,2-dichlorocyclopropane.
C) This compound contains no asymmetric carbons.
D) all of the above
Answer: E
Diff: 2
Section: 5.13
30
102) How many enantiomers are there of the molecule shown below?
A) 0
B) 1
C) 2
D) 3
E) 6
Answer: A
Diff: 2
Section: 5.13
103) If possible, draw the structure of the enantiomer of the molecule shown below.
Answer: The compound is an achiral, meso compound; it has no enantiomer.

Diff: 2
Section: 5.13
104) Can the molecule shown below be properly described as a meso compound?
Answer: Yes
Diff: 1
Section: 5.13
31
Answer: Yes
Diff: 1
Section: 5.13
106) Draw the structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to
indicate three-dimensional stereochemical detail properly.
Answer:
Diff: 2
Section: 5.13
(CH3)2CHCH2CH3
Answer: No
Diff: 2
Section: 5.13
Answer: No
Diff: 2
Section: 5.13
Answer: No
Diff: 2
Section: 5.13
32
110) Is it theoretically possible to separate the pair of compounds below by distillation? Explain
briefly.
Answer: Yes. The molecules are related as diastereomers and hence have different boiling
points.
Diff: 2
Section: 5.15
111) The process by which enantiomers are separated is called __________.

Answer: resolution
Diff: 1
Section: 5.16
112) Can one separate a mixture of enantiomers by gas chromatography? Explain.

Answer: Provided the compounds can be volatilized, a mixture of enantiomers can be separated
by GC if an appropriate chiral column can be found. Enantiomers will be retained differently by
the chiral stationary phase of the column.
Diff: 3
Section: 5.16
113) Briefly describe how two enantiomers might be separated.

Answer: The two compounds can be converted to diastereomers, separated based on different
physical properties of these diastereomers, and subsequently returned to their original forms after
separation. Another method involves the chromatographic separation using a chiral stationary
phase.
Diff: 2
Section: 5.16
33

WADE7 Problems 05

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Organic Chemistry, 7e (Wade)

1) What term describes the structural relationship between cis-1,2-dimethylcyclopentane and

2) What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane

8) Which of the following incorrectly describes cis-1,2-dimethylcyclopentane?

9) Which of the statements below correctly describes an achiral molecule?

Answer: Superimposable. The molecule is achiral.

14) Circle each chiral molecule among those shown below.

16) Circle all structures shown below that are chiral.

17) Is the molecule shown below chiral or achiral?

Answer: the same compound

Answer: the same compound

24) Is the molecule shown below chiral or achiral?

25) Is the molecule shown below chiral or achiral?

26) Is the molecule shown below chiral or achiral?

28) Is the molecule shown below chiral or achiral?

29) Is the molecule shown below chiral or achiral?

33) Is the molecule shown below chiral or achiral?

34) Is the molecule shown below chiral or achiral?

35) Is the molecule shown below chiral or achiral?

45) Label each asymmetric carbon in the compound below as R or S.

49) Label each asymmetric carbon in the compound below as R or S.

54) Draw the structure of (S)-3-chloro-3-methylhexane. Take particular care to indicate

57) Label each assymetric carbon in the compound below as R or S.

58) Which of the following statements correctly pertains to a pair of enantiomers?

61) Predict the specific rotation of the compound shown.

A) It is impossible to predict; must be determined experimentally.

concentration observed rotation

64) Would a 50:50 mixture of (2R,3R)-2,3-dibromobutane and (2R,3S)-2,3-dibromobutane be

74) Can a molecule be chiral if it contains no asymmetric carbons? Explain briefly.

77) Draw the Fischer projection of (2R,4R)-2,4-dibromopentane.

78) Provide a Fischer projection of (2R,3R,4S)-2,3,4-trichloroheptane.

80) Draw the Fischer projection of (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH.

87) What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane

Use the following three structures to answer the questions below.

89) The relationship between I and III is:

90) The relationship between I and II is:

95) Draw any diastereomer of the molecule shown below.

Answer: the same compound

Answer: the same compound

Answer: The compound is an achiral, meso compound; it has no enantiomer.

111) The process by which enantiomers are separated is called __________.

112) Can one separate a mixture of enantiomers by gas chromatography? Explain.

113) Briefly describe how two enantiomers might be separated.

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