Docit - Tips - Organic Chemistry 3rd Edition Klein Test Bank Chirality Chemistry

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Klein, Organic Chemistry 3e
Chapter 5
1. What is the relationship between the following two compounds?
A. constitutional
constitutional isomers
isomers
B. stereoisomers
C. identical
D. not isomers; different compounds entirely
Answer: A
Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including
an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and
disubstituted cycloalkanes
Difficulty: Easy
A. constitutional
isomers
B. stereoisomers
C. identical
Answer: C
Difficulty: Easy

Thanks.
A. constitutional
isomers
B. stereoisomers
C. identical
Answer: B
Difficulty: Easy
A. constitutional
isomers
B. stereoisomers
C. identical
Answer: B
Difficulty: Easy
A. constitutional
isomers
B. stereoisomers
C. identical
Thanks.
Answer: C
Difficulty: Easy
A. constitutional
isomers
B. stereoisomers
C. identical
Answer: A
Difficulty: Easy
7. Is the following alkene cis, trans, or neither?
Answer: trans
Difficulty: Easy

Thanks.
Answer: neither
Difficulty: Easy
Answer: trans
Difficulty: Easy
Answer: cis
Difficulty: Easy

Thanks.
Answer: neither
Difficulty: Medium
12. Is the alkene on the left in the molecule below cis, trans, or neither?
Answer: trans
Difficulty: Medium
13. Shown below is the structure of Crestor ®

® (rosuvastatin), a medication used to
reduce cholesterol. Is the highlighted alkene of rosuvastatin cis, trans, or
neither?
Answer: trans
Difficulty: Medium
Thanks.
14. Shown below is the structure of Singulair ®
® (montelukast), a medication used to
manage athsma. Is the alkene of montelukast cis, trans, or neither?
Answer: trans
Difficulty: Medium
15. Draw all the isomers with molecular formula C 4H8.
Answer:

Difficulty: Hard
16. Draw all the isomers with molecular formula C 4H6.
Answer:
Thanks.
Difficulty: Hard
17. Locate the chirality center(s) in the following compound.
Answer:
Learning Objective: 5.2 Describe the most common cause of chirality in a molecule,
and draw a pair of enantiomers
Difficulty: Medium
18. Shown below is the structure of the drug nicotine. Locate the chirality center(s)
in the following compound.
Answer:
Thanks.
Difficulty: Easy
Answer:
Difficulty: Easy
Answer:
Thanks.
Difficulty: Easy
Answer:
Difficulty: Easy
22. Identify the relationship between the following two structures.
A. enantiomers
enantiomers
B. identical
C. neither
Thanks.
Answer: B
Difficulty: Easy
A. enantiomers
enantiomers
B. identical
C. neither
Answer: A
Difficulty: Easy
A. enantiomers
enantiomers
B. identical
C. neither
Answer: B
Difficulty: Easy

Thanks.
A. enantiomers
enantiomers
B. identical
C. neither
Answer: A
Difficulty: Easy
A. enantiomers
enantiomers
B. identical
C. neither
Answer: B
Difficulty: Medium
27. Draw the enantiomer of the following compound.
Answer:
Thanks.
Difficulty: Medium
Answer:
Difficulty: Medium
Answer:
Thanks.
Difficulty: Medium
Answer:
Difficulty: Medium
Answer:
Thanks.
Difficulty: Medium
32. Assign the absolute configuration of the chirality center as R or

or S .
Answer: S
Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned
using the Cahn-Ingold-Prelog system
Difficulty: Easy

or S .
Answer: S
Difficulty: Easy

or S .
Thanks.
Answer: R
Difficulty: Easy

or S .
Answer: S
Difficulty: Easy

or S .
Answer: R
Difficulty: Easy

or S .
Thanks.
Answer: R
Difficulty: Easy
38. Drawn below is the structure of Crestor ®

reduce cholesterol. Assign the absolute configurations of the two chirality
centers as R or
or S .
Answer: Left (allylic)

(allylic) alcohol
alcohol is S ; right alcohol is R
Difficulty: Medium
39. Drawn below is the structure of Singulair ®

manage athsma. Assign the absolute configuration of the chirality center as R or
or
S .
Answer: R
Difficulty: Medium
Thanks.
40. Drawn below is the structure of Plavix ® (clopidogrel), a medication used to
manage blood clots. Assign the absolute configuration of the c
chirality
hirality center as
R or
or S .
Answer: S
Difficulty: Medium
41. Drawn below is the structure of Cymbalta ® (duloxetine), a medication used to

manage depression. Assign the absolute configuration of the chirality center as
R or
or S .
Answer: S
Learning Objective: 5.3 Describe how the configuration
configuration of a chirality center is assigned
Difficulty: Medium
42. Provide an IUPAC name of the following compound.
Answer: (S )-4-methyl-2-pentanol
)-4-methyl-2-pentanol
Thanks.
Difficulty: Medium
43. Provide an IUPAC name of the following compound.
Answer: (S )-3-octanol
)-3-octanol
Difficulty: Medium
44. Which of the following is the correct structure for the compound ( R )-2-pentanol?
)-2-pentanol?
A. I
B. II
C. III
D. IV
Answer: C
Difficulty: Medium
45. Which of the following is the correct structure for the compound ( S )-3-
)-3-
methylheptane.
Thanks.
A. I
B. II
C. III
D. IV
Answer: B
Difficulty: Medium
46. Draw the structure of the compound ( S )-3-methylheptane.

)-3-methylheptane.
Answer:
Difficulty: Medium
47. Draw the structure of the compound ( R )-4-ethyloctane.

)-4-ethyloctane.
Answer:
Difficulty: Medium
Thanks.
48. Which of the following is the correct IUPAC name of the following structure?
A. (S )-3-ethyl-2-methylhexane
)-3-ethyl-2-methylhexane
B. (R )-3-ethyl-2-methylhexane
)-3-ethyl-2-methylhexane
C. (S )-3-ethyl-2-methylpentane
)-3-ethyl-2-methylpentane
D. (R )-3-ethyl-2-methylpentane
)-3-ethyl-2-methylpentane
Answer: B
Difficulty: Medium
49. Which of the following is the correct IUPAC name of the following structure?
A. (S )-2-ethylhexane
)-2-ethylhexane
B. (S )-3-methylheptane
)-3-methylheptane
C. (R )-2-ethylhexane
)-2-ethylhexane
D. (R )-3-methylheptane
)-3-methylheptane
Answer: D
Learning Objective: 5.3 Describe how the configuration
configuration of a chirality center is assigned
Difficulty: Medium
50. Redraw the structure below as a wedge-dash structure

structure and label any/all
stereocenters with their absolute configuration.
Answer:
Thanks.
Difficulty: Hard
51. Redraw the structure below as a wedge-dash structure and label all
stereocenters with their absolute configuration.
Answer:
Difficulty: Hard
52. Identify the relationship between these two structures.

Thanks.
A. diastereomers
diastereomers
B. enantiomers
C. the same compound
D. different compounds
Answer: A
Difficulty: Hard
53. Rank the following from highest to lowest priority according to the Cahn-Ingold-
Cahn-Ingol d-
Prelog system.
I. -F II. -H III. -OH IV. -SH
Answer: IV > I > III > II

Difficulty: Easy
Cahn-Ingol d-
Prelog system.
I. -CH3 II. -CN III. -CH 2OH IV. -Br
Answer: IV > III > II > I

Difficulty: Easy
Cahn-Ingol d-
Prelog system.
I. -CH2CH3 II. -CHCH2 III. -CCH IV. -CH 3
Answer: III > II > I > IV

Difficulty: Easy
Thanks.
56. What is the % ee of a sample of carvone that exhibits a specific rotation of −20,
given that the specific rotation of ( R )-
)-carvone is −61?
Answer: 33%
Learning Objective: 5.4 Compare the effects of a pair of enantiomers on plane-
polarized light, discussing how the relative amounts of the two enantiomers affect the
observed rotation of plane-polarized light
Difficulty: Medium
57. What is the % ee of a sample of carvone that exhibits a specific rotation of −40,
given that the specific rotation of ( R )-
)-carvone is −61?
Answer: 66%
Difficulty: Medium
58. If a sample of carvon e gives a specific rotation of −60 and the specific rotation of
(R )-
)-carvone is −61, does the unknown sample primarily have the R or or S absolute
absolute
configuration?
Answer: R
Difficulty: Medium
59. If a sample of carvone gives a specific rotation of 0 and the specific rotation
rotation of
pure (R )-
)-carvone is −61, what is the configuration of the unknown sample?
Answer: neither, it is a racemic

racemic mixture
Difficulty: Medium
Thanks.
60. What is the specific rotation of pure ( S )-carvone

)-carvone if a sample of ( R )-carvone
)-carvone of
85% ee has a specific rotation of −52?
A. −61
B. 64
C. 0
D. 61
Answer: D
Difficulty: Medium
61. What is the specific rotation of a sample of carvone that is an equal mixture of
the R and
and S enantiomers?
enantiomers? ( R )-
)- carvone has a specific rotation of −61.
A. −61
B. 64
C. 0
D. 61
Answer: C
Difficulty: Medium
62. What is the percentage of the R enantiomer in a sample of carvone that has a
specific rotation of 10, given that the specific rotation of ( R )-
)-carvone is −61?
A. 42
B. 84
C. 16
D. 58
Answer: D
Thanks.
Difficulty: Hard
)-carvone is −61?
A. 26%
B. 51%
C. 49%
D. 75%
Answer: A
Difficulty: Medium
64. What is the percentage of the S enantiomer in a sample of carvone that has a
)-carvone is −61?
A. 42
B. 84
C. 16
D. 58
Answer: A
Difficulty: Hard
65. What is the percentage of the S enantiomer in a sample of carvone that has a
)-carvone is −61?
A. 25.5%
B. 51%
Thanks.
C. 49%
D. 74.5%
Answer: D
Difficulty: Medium
specific rotation of −20, given that the specific rotation of ( R )-
)-carvone is −61?
A. 20%
B. 66.5%
C. 33.5%
D. 61%
Answer: B
Difficulty: Medium
67. What is the percentage of the R enantiomer

enantiomer in a sample of limonene that has a
specific rotation of −38, given that the specific rotation of ( S )-
)-limonene is −116?
Answer: 66%
Difficulty: Medium
68. The structure of Crestor (rosuvastatin), a medication used to reduce cholesterol,

is shown below. If the specific rotation for this compound is known to be +100,
what would be the specific rotation for the stereoisomer shown at the right?
Thanks.
A. +100
B. -100
C. 0
D. Impossible to predict
Answer: D
Difficulty: Medium
69. What is the relationship of the following two structures?
A. enantiomers
enantiomers
B. diastereomers
C. constitutional isomers
D. identical
Answer: B
Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how
many stereoisomers a compound can have
Difficulty: Medium
Thanks.
A. enantiomers
enantiomers
B. diastereomers
D. identical
Answer: A
Difficulty: Medium
A. enantiomers
enantiomers
B. diastereomers
D. identical
Answer: A
Difficulty: Medium

Thanks.
A. enantiomers
enantiomers
B. diastereomers
D. identical
Answer: D
Difficulty: Medium
A. enantiomers
enantiomers
B. diastereomers
D. identical
Answer: B
Difficulty: Medium

Thanks.
Answer:

Difficulty: Medium
Answer: none. There is no stereocenter,

stereocenter, so the compound
compound is not chiral and thus does
not have an enantiomer.
Difficulty: Medium
Answer:

Thanks.
Difficulty: Medium
77. Draw a diastereomer of the following compound.
Answer:

Difficulty: Hard
Answer: None. There is only one stereocenter,

stereocenter, so the compound
compound does not have a
diastereomer.
Difficulty: Hard

Thanks.
Answer:

Difficulty: Hard
80. Draw all the stereoisomers of the following compound.
Answer:

Difficulty: Hard
81. Draw all the stereoisomers of the following compound.
Answer:
Thanks.

Difficulty: Hard
82. Which of the following choices is a diastereomer of the first structure shown?
A. I
B. II
C. III
D. IV
Answer: C
Difficulty: Medium
83. Which of the following choices is a diastereomer of the first structure shown.
Thanks.
A. I
B. II
C. III
D. IV
Answer: D
Difficulty: Medium
84. Which of the following choices is a diastereomer of the first structure shown?
A. I
B. II
Thanks.
C. III
D. IV
Answer: B
Difficulty: Medium
85. Is the following a meso compound?
Answer: No
Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and
how an axis of symmetry and plane of symmetry affects chirality and whether a meso
compound is chiral or achiral
Difficulty: Medium
86. Which of the following can exist as a meso isomer?
A. I
B. II
C. III
D. IV
Answer: A
Thanks.
Difficulty: Medium
87. Does the following contain a plane of symmetry?
Answer: yes
Difficulty: Easy
88. Draw in the plane of symmetry in the following compound.
Answer:
Difficulty: Easy
89. Draw in the plane of symmetry in the following compound.

Thanks.
Answer: none
Difficulty: Hard
90. Draw all of the possible stereoisomers of the following compound.
Answer: 7
Difficulty: Hard
91. How many stereoisomers are possible for 2,3-dimethylbutane?

2,3-dimethylbuta ne?
Answer: None. It has no stereocenters.

stereocenters.
Difficulty: Hard
92. Draw all possible stereoisomers of 1,3,5-trimethylcyclohexane.

1,3,5-trim ethylcyclohexane.
Thanks.
Answer:
Difficulty: Medium
93. Draw the meso isomer of the following compound.
Answer:
Difficulty: Hard

Thanks.
Answer:
Difficulty: Hard
Answer:
Difficulty: Medium
96. How many possible stereoisomers are there for Crestor ® (rosuvastatin), a
medication used to reduce cholesterol?
Thanks.
A. 2
B. 4
C. 6
D. 8
Answer: D
Difficulty: Hard
97. Draw the Fischer projection of the following compound.
Answer:
Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

Difficulty: Hard

Thanks.
Answer:

Difficulty: Hard
Answer:

Difficulty: Hard

Thanks.
Answer:

Difficulty: Hard
101. Convert the following Fischer projection into a wedge/dash drawing.
Answer:

Difficulty: Hard

Thanks.
Answer:

Difficulty: Hard
Answer:

Difficulty: Hard

Thanks.
Answer:

Difficulty: Hard
105. Which of the following is a correct Fischer projection of the following compound?
A. I
B. II
C. III
D. IV
Answer: A
Difficulty: Hard
Thanks.
A. I
B. II
C. III
D. IV
Answer: C
Difficulty: Hard
Thanks.
A. I
B. II
C. III
D. IV
Answer: A
Difficulty: Hard
108. Which of the following structures is the correct wedge/dash drawing of the
following Fischer projection?
A. I
B. II
C. III
D. IV
Thanks.
Answer: B
Difficulty: Hard
109. Which of the following structures is a correct wedge/dash

wedge/dash drawing of the following
Fischer projection?
A. I
B. II
C. III
D. IV
Answer: B
Difficulty: Hard
110. What is the relationship between the following two molecules?

Thanks.
A. enantiomers
enantiomers
B. diastereomers
C. identical
D. constitutional Isomers
Answer: A
Difficulty: Easy
A. enantiomers
enantiomers
B. diastereomers
C. identical
Answer: B
Difficulty: Easy
A. enantiomers
enantiomers
Thanks.
B. diastereomers
C. identical
Answer: C
Difficulty: Medium
113. Assign the following stereocenter as having the R or

or S absolute
absolute configuration.
Answer: S
Difficulty: Medium

or S absolute
Answer: S
Difficulty: Hard

or S absolute
Answer: Neither – no stereocenter

Difficulty: Medium
Thanks.
116. Provide an IUPAC name for the following compound.
Answer: (R )-2-butanol
)-2-butanol
Difficulty: Medium
117. Which of the following is the IUPAC name for the following compound?
A. (S )-2-pentanol
)-2-pentanol
B. (S )-2-butanol
)-2-butanol
C. (R )-2-pentanol
)-2-pentanol
D. (R )-2-butanol
)-2-butanol
Answer: A
Difficulty: Hard
118. Identify the relationship between these two structures.
A. diastereomers
diastereomers
Thanks.
B. enantiomers
C. identical
D. unrelated compounds
Answer: C.
Difficulty: Hard
119. What is the relationship between the two structures shown?
A. identical
B. enantiomers
C. diastereomers
D. none of these
Answer: A
Learning Objective: 5.8 Describe conformationally mobile systems
Difficulty: Hard
A. same compound

compound
B. enantiomers
C. diastereomers
D. none of these
Answer: B
Difficulty: Hard
Thanks.
A. same compound

compound
B. enantiomers
C. diastereomers
D. none of these
Answer: C
Difficulty: Hard
122. What is the relationship between

between the two structures shown?
A. same compound

compound
B. enantiomers
C. diastereomers
D. none of these
Answer: D
Difficulty: Hard

Thanks.
A. same compound

compound
B. enantiomers
C. diastereomers
D. none of these
Answer: C
Difficulty: Hard
124. Stereoisomers that result from the hindered rotation of a single bond are called
___________.
___________.
Answer: atropisomers
atropisomers
Learning Objective: 5.9 Discuss ways in which a compound can be chiral without
containing a chiral center
Difficulty: Medium
A. same compound

compound
B. enantiomers
C. diastereomers
D. none of these
Answer: B
Difficulty: Medium
Thanks.
126. Identify the hybridization of the middle carbon of an allene.
A. sp
B. sp2
C. sp3
D. sp4
Answer: A
Difficulty: Medium
127. Which of the following strategies will NOT be an effective way to separate
enantiomers?
A. chiral chromatogra

chromatography
phy
B. distillation
C. crystallization
D. chiral resolving agents
Answer: B
Learning Objective: 5.10 Describe resolution and methods to separate enantiomers
Difficulty: Medium
128. When a racemic mixture is reacted with a single enantiomer of another

compound, then a pair of _________ is formed.
A. identical compounds

compounds
B. enantiomers
C. diastereomers
D. none of the above
Answer: B
Difficulty: Medium
129. In chiral column chromatography, __________ adsorbent is used to separate

separate a
pair of enantiomers.
Thanks.
A. an achiral
achiral
B. a polar
C. a nonpolar
D. a chiral
Answer: D
Difficulty: Medium
130. Is the following alkene E , Z , or neither?
Answer: E
Learning Objective: 5.11 Describe how stereodiscriptors
stereodiscripto rs are assigned for certain
trisubstituted and tetrasubstituted alkenes
Difficulty: Medium
Answer: neither
Learning Objective:
Objective: 5.11 Describe how how stereodiscriptors
stereodi scriptors are assigned for certain
Difficulty: Medium
Answer: E
Thanks.
Difficulty: Medium
Answer: Z
Learning Objective:
stereod iscriptors are assigned for certain
Difficulty: Medium
Answer: neither
Difficulty: Medium
135. Is the alkene on the left in the molecule below E , Z , or neither?
Answer: E
Difficulty: Medium
Thanks.
Answer: Z
Learning Objective:
Difficulty: Medium
Answer: E
Difficulty: Medium
Answer: E
Learning Objective:
Difficulty: Medium

Thanks.
Answer: Z
Difficulty: Medium
140. Shown below is the structure of Crestor ®

reduce cholesterol. Is the highlighted alkene of rosuvastatin E , Z , or neither?
Answer: E
Difficulty: Medium
141. Shown below is the structure of Singulair ®

manage athsma. Is the alkene of montelukast E , Z , or neither?
Answer: E
Thanks.
Difficulty: Medium

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

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

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

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

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

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

7. Is the following alkene cis, trans, or neither?

8. Is the following alkene cis, trans, or neither?

9. Is the following alkene cis, trans, or neither?

10. Is the following alkene cis, trans, or neither?

11. Is the following alkene cis, trans, or neither?

13. Shown below is the structure of Crestor ®

15. Draw all the isomers with molecular formula C 4H8.

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including

16. Draw all the isomers with molecular formula C 4H6.

17. Locate the chirality center(s) in the following compound.

19. Locate the chirality center(s) in the following compound.

20. Locate the chirality center(s) in the following compound.

21. Locate the chirality center(s) in the following compound.

22. Identify the relationship between the following two structures.

23. Identify the relationship between the following two structures.

24. Identify the relationship between the following two structures.

25. Identify the relationship between the following two structures.

26. Identify the relationship between the following two structures.

27. Draw the enantiomer of the following compound.

28. Draw the enantiomer of the following compound.

29. Draw the enantiomer of the following compound.

30. Draw the enantiomer of the following compound.

31. Draw the enantiomer of the following compound.

32. Assign the absolute configuration of the chirality center as R or

33. Assign the absolute configuration of the chirality center as R or

34. Assign the absolute configuration of the chirality center as R or

35. Assign the absolute configuration of the chirality center as R or

36. Assign the absolute configuration of the chirality center as R or

37. Assign the absolute configuration of the chirality center as R or

38. Drawn below is the structure of Crestor ®

Answer: Left (allylic)

39. Drawn below is the structure of Singulair ®

41. Drawn below is the structure of Cymbalta ® (duloxetine), a medication used to

42. Provide an IUPAC name of the following compound.

43. Provide an IUPAC name of the following compound.

46. Draw the structure of the compound ( S )-3-methylheptane.

47. Draw the structure of the compound ( R )-4-ethyloctane.

50. Redraw the structure below as a wedge-dash structure

52. Identify the relationship between these two structures.

I. -F II. -H III. -OH IV. -SH

Answer: IV > I > III > II

I. -CH3 II. -CN III. -CH 2OH IV. -Br

Answer: IV > III > II > I

I. -CH2CH3 II. -CHCH2 III. -CCH IV. -CH 3

Answer: III > II > I > IV

Answer: neither, it is a racemic

60. What is the specific rotation of pure ( S )-carvone

67. What is the percentage of the R enantiomer

68. The structure of Crestor (rosuvastatin), a medication used to reduce cholesterol,

69. What is the relationship of the following two structures?

71. What is the relationship of the following two structures?

72. What is the relationship of the following two structures?

73. What is the relationship of the following two structures?

74. Draw the enantiomer of the following compound.

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how