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Organic Chemistry, 8e (Wade)
Chapter 5 Stereochemistry
1) ________ 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
2) 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
4) What is the structural relationship between the two molecule shown below?
A) constitutional isomers
B) enantiomers
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C) diastereomers
D) conformational isomers
E) not isomers
Answer: A
Diff: 2
Section: 5.1
A) 0
B) 1
C) 2
D) 3
E) 6
Answer: B
Diff: 1
Section: 5.2
7) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
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8) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
9) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: enantiomers
Diff: 1
Section: 5.2
(CH3)3CCH(CH3)2
Answer: achiral
Diff: 1
Section: 5.2
11) 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
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12) 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
13) How many asymmetric carbons are present in the compound below?
Answer: 1
Diff: 1
Section: 5.2
14) How many asymmetric carbons are present in the compound below?
Answer: none
Diff: 1
Section: 5.2
15) How many asymmetric carbons are present in the compound below?
Answer: 5
Diff: 1
Section: 5.2
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16) How many asymmetric carbon atoms are present in the molecule shown?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: A
Diff: 1
Section: 5.2
17) How many asymmetric carbon atoms are present in the molecule shown?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: A
Diff: 1
Section: 5.2
18) How many asymmetric carbon atoms are present in the molecule shown?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: B
Diff: 1
Section: 5.2
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19) How many asymmetric carbon atoms are present in the molecule shown?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Diff: 1
Section: 5.2
20) What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and
(2S,3S,4R)-2,3,4-trichloroheptane?
A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: C
Diff: 2
Section: 5.2
21) If possible, draw the structure of the enantiomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.2
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22) Is the mirror image of the following molecule an enantiomer or is it superimposable with it?
Answer:
Diff: 2
Section: 5.2
24) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: enantiomers
Diff: 2
Section: 5.2
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25) 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
Answer:
Diff: 2
Section: 5.2
Answer:
Diff: 2
Section: 5.2
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28) Is the molecule shown below chiral or achiral?
CH3CH2CH(CH3)CH2CH3
Answer: achiral
Diff: 2
Section: 5.2
Answer: achiral
Diff: 2
Section: 5.2
Answer: chiral
Diff: 2
Section: 5.2
Answer: achiral
Diff: 2
Section: 5.2
Answer: achiral
Diff: 2
Section: 5.2
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33) Is the molecule shown below chiral or achiral?
Answer: chiral
Diff: 2
Section: 5.2
34) How many asymmetric carbons are present in the compound below?
Answer: 2
Diff: 2
Section: 5.2
35) How many asymmetric carbons are present in the compound below?
3-ethyl-2,2,4-trimethylpentane
Answer: 1
Diff: 2
Section: 5.2
36) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: enantiomers
Diff: 3
Section: 5.2
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37) Circle all structures shown below that are chiral.
Answer:
Diff: 3
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
Answer: achiral
Diff: 3
Section: 5.2
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41) Which of the following structures are achiral and meso?
A) 1, 2, 3 & 4
B) 1 &2
C) 2 & 3
D) 1 & 4
Answer: D
Diff: 3
Section: 5.2
42) 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
43) How many asymmetric carbons are present in the compound below?
Answer: 5
Diff: 3
Section: 5.2
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44) Label each asymmetric carbon in the compound below as R or S.
Answer:
Diff: 1
Section: 5.3
45) 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
Diff: 1
Section: 5.3
Diff: 2
Section: 5.3
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48) Label each asymmetric carbon in the molecule below as having the R or S configuration.
Answer:
Diff: 2
Section: 5.3
49) Assign the proper configurational label, R or S, to the chiral carbon in the molecule shown below.
Answer: S
Diff: 2
Section: 5.3
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50) Assign the proper configurational label, R or S, to each chiral carbon in the molecule below.
Answer:
Diff: 2
Section: 5.3
Answer:
Diff: 2
Section: 5.3
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52) Label each asymmetric carbon in the compound below as R or S.
Answer:
Diff: 2
Section: 5.3
53) 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
54) 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
55) 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
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56) Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate
stereochemistry properly.
Answer:
Diff: 2
Section: 5.3
57) Draw the structure of (S)-3-chloro-3-methylhexane. Take particular care to indicate stereochemistry
properly.
Answer:
Diff: 2
Section: 5.3
58) 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
Answer:
Diff: 2
Section: 5.3
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60) Label each asymmetric carbon in the compound below as R or S.
Answer:
Diff: 2
Section: 5.3
A) (4R, 5R)
B) (4R, 5S)
C) (4S, 5R)
D) (4S, 5S)
Answer: A
Diff: 3
Section: 5.3
62) 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
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63) 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
Answer:
Diff: 3
Section: 5.3
Answer:
Diff: 3
Section: 5.3
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66) Phantasmidine, shown below, is found in poisonous frog skin and has analgesic properties (J. Nat.
Prod. 2010, 331). Assign each chiral center as having either R or S configuration.
Answer:
Diff: 3
Section: 5.3
67) Compounds that rotate the plane of polarized light clockwise are called ________.
Answer: dextrorotatory
Diff: 1
Section: 5.4
68) 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
70) 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
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71) Predict the specific rotation of the compound shown.
73) 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
74) Given that glucose has a specific rotation of +52.8°. Predict the concentration of a glucose aqueous
solution contained in a 10 cm long polarimetry tube if a rotation of +15.8° was observed.
A) 0.299 g/mL
B) .0299 g/mL
C) 3.34 g/mL
D) .334 g/mL
Answer: A
Diff: 2
Section: 5.4
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75) 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).
A) -10.5∘
B) +25.6∘
C) +79.5∘
D) -105∘
E) +256∘
Answer: D
Diff: 3
Section: 5.4
76) 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
78) 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
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79) 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
80) A mixture of two enantiomers with a composition of 65.0% R has an observed rotation of -25.3° in a
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
81) 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
82) (-)-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
83) 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
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84) 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
85) Is the molecule shown below chiral or achiral? Explain what this means.
86) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: enantiomers
Diff: 3
Section: 5.9
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
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88) Draw the Fischer projection of (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH.
Answer:
Diff: 1
Section: 5.10
Diff: 2
Section: 5.10
Answer:
Diff: 3
Section: 5.10
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91) Provide a Fischer projection of (2R,3R,4S)-2,3,4-trichloroheptane.
Answer:
Diff: 3
Section: 5.10
Diff: 3
Section: 5.10
93) 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
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94) Stereoisomers which are not mirror image isomers are ________.
Answer: diastereomers
Diff: 1
Section: 5.11
95) 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
96) 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
97) What term describes the structural relationship between (E)- and (Z)-2-pentene?
A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11
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98) What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,2-
dimethylcyclopentane?
A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11
99) If possible, draw the structure of any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
100) If possible, draw the structure of any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
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101) Draw any diastereomer of the molecule shown below.
Answer:
Diff: 2
Section: 5.11
102) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: diastereomers
Diff: 2
Section: 5.11
103) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
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104) One of the stereoisomers of the following oblongolide structure is a natural product isolated from a
fungus and has been found to contain antiviral and cytotoxic activities (J. Nat. Prod. 2010, 55). How
many stereoisomers exist for this structure?
A) 6
B) 12
C) 32
D) 64
Answer: D
Diff: 2
Section: 5.11
105) Which of the following statements is (are) true for the compound (3R, 4R)-3,4-dimethylhexane?
A) This compound is chiral.
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
E) none of the above
Answer: D
Diff: 2
Section: 5.11
106) What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and
(2R,3R,4R)-2,3,4-trichloroheptane?
A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers
Answer: D
Diff: 2
Section: 5.11
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107) 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
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110) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Answer: diastereomers
Diff: 3
Section: 5.11
111) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
112) 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
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113) Can the molecule shown below be properly described as a meso compound?
Answer: Yes
Diff: 1
Section: 5.13
114) Can the molecule shown below be properly described as a meso compound?
Answer: Yes
Diff: 1
Section: 5.13
115) 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
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116) If possible, draw the structure of the enantiomer of the molecule shown below.
118) Which of the following statements is (are) true for the compound cis-1,2-dichlorocyclopropane?
A) This compound is chiral.
B) The enantiomer of this compound is trans-1,2-dichlorocyclopropane.
C) This compound contains no asymmetric carbons.
D) all of the above
E) none of the above
Answer: E
Diff: 2
Section: 5.13
119) 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
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120) Can the molecule shown below be properly described as a meso compound?
(CH3)2CHCH2CH3
Answer: No
Diff: 2
Section: 5.13
121) Can the molecule shown below be properly described as a meso compound?
Answer: No
Diff: 2
Section: 5.13
122) Can the molecule shown below be properly described as a meso compound?
Answer: No
Diff: 2
Section: 5.13
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125) 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
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