Organic Chemistry 6th Edition By Brown Foote Iverson – Test Bank
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Sample Test
CHAPTER 3–STEREOISOMERISM AND CHIRALITY
Student: ___________________________________________________________________________
1. Which
of the following is the definition of a pair of enantiomers?
2. A
pair of structures that are superposable mirror images of one another
3. A
pair of stereoisomers that are non-superposable mirror images of one another
4. A
pair of stereoisomers that are not mirror images of one another
5. A
pair of stereoisomers that have equal specific rotations
2. Which
of the following is the definition of a pair of diastereomers?
3. A
pair of structures that are superposable mirror images of one another
4. A
pair of stereoisomers that are non-superposable mirror images of one another
5. A
pair of stereoisomers that are not mirror images of one another
6. A
pair of stereoisomers that have equal specific rotations
3. Which
of the following is the definition of chirality?
4. The
non-superposability of an object on its mirror image
5. The
superposability of an object on its mirror image
6. A
molecule that has a carbon atom with four different substituents
7. A
molecule with a mirror image
4. Which
of the following is the definition of a meso compound?
5. A
molecule with stereocenter centers which is chiral
6. A
molecule with stereocenter centers which is not chiral
7. A
diastereomer with no stereocenter centers
8. A
chiral compound with more than one stereocenter center
5. Which
of the following statements is not true regarding pairs of enantiomers?
6. They
have identical melting points
7. They
have identical boiling points.
8. They
rotate plane polarized light in opposite directions
9. They react
at identical rates with chiral reagents
6. Which
of the following statements is true?
7. All
mirror images are enantiomers
8. All
molecules that have stereocenter centers are chiral
9. Isomers
that are not superposable on their mirror images are enantiomers
10. Superposable
structural isomers are enantiomers
7. Which
of the following structures is different from the other three?
1. 1
2. 2
3. 3
4. 4
8. Which
of the following structures is different from the other three?
1. 1
2. 2
3. 3
4. 4
9. Which
of the following compounds is/are chiral?
1. only
1
2. only
1 and 2
3. only
2 and 3
4. 1, 2
and 3
10. Which
of the following compounds is/are chiral?
1. only
1
2. only
1 and 2
3. only
2 and 3
4. 1, 2
and 3
11. Which
of the following have the S configuration?
1. only
1
2. only
2
3. only
1 and 2
4. 1, 2
and 3
12. Which
of the following have the R configuration?
1. only
1
2. only
2
3. only
1 and 2
4. 1, 2
and 3
13. What
is the configuration of the two chiral centers in the following molecule?
1. 3R,5R
2. 3R,5S
3. 3S,5R
4. 3S,5S
14. What
is the configuration of the two chiral centers in the following molecule?
1. 3R,5R
2. 3R,5S
3. 3S,5R
4. 3S,5S
15. Which
of the following Newman projections represents (2R,3R)-dibromobutane?
1. 1
2. 2
3. 3
4. 4
16. Which
of the following Newman projections represents meso-2,3-dibromobutane?
1. 1
2. 2
3. 3
4. 4
17. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
18. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
19. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
20. Which
of the following compounds is a meso compound?
21. (2R,3R)-dibromobutane
22. (2R,3S)-dibromobutane
23. (2R,3S)-3-bromo-2-butanol
24. (2R,3R)-3-bromo-2-butanol
21. How
many stereoisomers of 2,3-dimethylbutane, (CH3)2CHCH(CH3)2, exist?
22. 1
23. 2
24. 3
25. 4
22. How
many stereoisomers of 3-chloro-2-methylbutane, (CH3)2CHCHClCH3, exist?
23. 1
24. 2
25. 3
26. 4
23. How
many stereoisomers of 3-bromo-2-butanol, CH3CH(OH)CHBrCH3, exist?
24. 1
25. 2
26. 3
27. 4
24. How
many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist?
25. 1
26. 2
27. 3
28. 4
25. How
many stereoisomers of 2,4-dimethylpentane, (CH3)2CHCH2CH(CH3)2, exist?
26. 1
27. 2
28. 3
29. 4
26. How
many stereoisomers of 4-chloro-2-methylpentane (CH3)2CHCH2CHClCH3, exist?
27. 1
28. 2
29. 3
30. 4
27. How
many stereoisomers of 4-bromo-2-pentanol, CH3CH(OH)CH2CHBrCH3, exist?
28. 1
29. 2
30. 3
31. 4
28. How
many stereoisomers of 2,4-pentanediol, CH3CH(OH)CH2CH(OH)CH3, exist?
29. 1
30. 2
31. 3
32. 4
29. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
30. 3
31. 4
32. 5
33. 6
30. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclohexane?
31. 3
32. 5
33. 6
34. 9
31. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclopentane?
32. 3
33. 5
34. 7
35. 9
32. How
many isomers (constitutional and stereoisomers) exist for dimethylpentane?
33. 2
34. 3
35. 4
36. 5
33. Which
of the following statements regarding optical rotation is not true?
34. All
(+) enantiomers are dextrorotatory.
35. All R
enantiomers are dextrorotatory.
36. All
(-) enantiomers rotate plane-polarized light in a counterclockwise direction.
37. All
(+) and (-) enantiomers rotate plane-polarized light in opposite directions.
34. How
much of the R enantiomer is present in 10 g of a mixture which has an
enantiomeric excess of 20% of the S isomer?
35. 1 g
36. 2 g
37. 4 g
38. 6 g
35. How
much of the R enantiomer is present in 10 g of a mixture which has an
enantiomeric excess of 60% of the R isomer?
36. 2 g
37. 4 g
38. 6 g
39. 8 g
36. A
solution containing 0.2 g/mL of a pure R enantiomer in a 1 dm polarimeter
rotates plane polarized light by +3°.
What is the specific rotation of the R isomer?
37. +0.6°
38. +15°
39. +67°
40. +150°
37. A
solution containing 0.04 g/mL of a pure S enantiomer in a 1 dm polarimeter
rotates plane polarized light by +2°.
What is the specific rotation of the R isomer?
38. -50°
39. -20°
40. +10°
41. +50°
38. A
solution containing 0.2 g/mL of a pure R enantiomer in a 1 dm polarimeter
rotates plane polarized light by +2.8°. What
is the rotation of a solution containing 0.4 g/mL of the R isomer in the same
polarimeter?
39. +0.7°
40. +1.4°
41. +2.8°
42. +5.6°
39. A
solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane
polarized light by +4.8°.
What is the rotation observed on this solution in a 2 dm polarimeter?
40. +2.4°
41. +4.8°
42. +9.6°
43. +19.2°
40. A
pure sample of the R enantiomer of a compound has a specific rotation, [a], of
+20°. A
solution containing 0.2 g/mL of a mixture of enantiomers rotates plane
polarized light by -2° in a
1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?
41. 25% R
42. 40% S
43. 50% S
44. 70% R
41. A
pure sample of the R enantiomer of a compound has a specific rotation, [a], of
-15°. A
solution containing 0.6 g/mL of a mixture of enantiomers rotates plane
polarized light by -3° in a
1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?
42. 33% R
43. 33% S
44. 50% R
45. 75% R
42. Which
of the following structures has a center of symmetry?
1. 1
2. 2
3. 3
4. 4
43. Which
of the following structures has a center of symmetry (i.e., center of
inversion)?
1. 1
2. 2
3. 3
4. 4
44. Which
of the following structures have a plane of symmetry?
1. only
1 and 2
2. only
2 and 4
3. only
3 and 4
4. 1, 2,
3 and 4
45. Which
of the following structures does not have a plane of symmetry?
1. only
2
2. only
1 and 2
3. only
3 and 4
4. only
1, 2 and 4
46. How
many stereogenic centers are there in the following molecule (the naturally
occurring stereoisomer is the male hormone testosterone)?
1. Three
2. Four
3. Six
4. Seven
47. How
many stereogenic centers are there in the following molecule (the naturally
occurring stereoisomer is camphor, a pungent moth repellent)?
1. Two
2. Three
3. Four
4. Five
48. Which
of the following is the best definition of a pair of atropisomers?
49. A
pair of enantiomers which do not interconvert.
50. A
pair of enantiomers which lack chiral centers.
51. A
pair of enantiomeric structures which lack chiral centers and interconvert by
rotation around carbon-carbon single bonds.
52. A
pair of enantiomers which lack chiral centers and do not interconvert because
of hindered rotation around carbon-carbon single bonds.
49. Which
of the following structures is chiral?
1. 1
2. 2
3. 3
4. 4
50. Which
of the following substituents has the highest priority according to the Cahn-Ingold-Prelog
system used in assigning R and S configurations?
51. -COOH
52. -CHO
53. -CH2OH
54. -CH3
51. Which
of the following substituents has the highest priority according to the
Cahn-Ingold-Prelog system used in assigning R and S configurations?
52. -NH2
53. -NHCH3
54. -CH2NH2
55. -CH2NHCH3
52. What
is the correct order of the Cahn-Ingold-Prelog ranking of the following
substituents as used in assigning R and S configurations of chiral centers?
(higher ranking > lower ranking)
1. -C°CH
2. -CH2NH2
3.
-NHCH3
4. -CN
1. 3
> 4 > 2 > 1
2. 4
> 3 > 1 > 2
3. 3
> 4 > 2 > 1
4. 4
> 3 > 2 > 1
53. What
is the correct order of the Cahn-Ingold-Prelog ranking of the following
substituents as used in assigning R and S configurations of chiral centers?
(higher ranking > lower ranking)
1. -CH2OH
2.
-CHO
3.
-OCH3
4. -OCOCH3
1. 3
> 4 > 1 > 2
2. 4
> 3 > 1 > 2
3. 3
> 4 > 2 > 1
4. 4
> 3 > 2 > 1
54. What
is the relationship between the following pair of structures?
1. They
are enantiomers
2. They
are diastereomers
3. The
are constitutional isomers
4. They
are identical
55. What
is the relationship between the following pair of structures?
1. They
are enantiomers
2. They
are diastereomers
3. The
are constitutional isomers
4. They
are identical
56. What
is the relationship between the following pair of structures?
1. They
are enantiomers
2. They
are diastereomers
3. The
are constitutional isomers
4. They
are identical
57. Complete
the following diagram so that it represents (S)-2-butanol.
58. Complete
the following diagram so that it represents (S)-2-butanol.
59. Complete
the following diagram so that it represents (R)-2-bromobutane.
60. Complete
the following diagram so that it represents (R)-2-bromobutane.
61. Complete
the following Fischer diagram so that it represents (2R,3S)-butane-2,3-diol.
62. Complete
the following Fischer diagram so that it represents (2R,3R)-butane-2,3-diol.
63. Complete
the following Fischer diagram so that it represents (2R,3R)-3-bromobutan-2-ol.
64. Complete
the following Fischer diagram so that it represents (2R,3S)-3-bromobutan-2-ol.
65. Complete
the following zig-zag structure so that it represents
(2R,3S)-3-chlorobutan-2-ol.
66. Complete
the following zig-zag structure so that it represents (2R,3R)-3-chlorobutan-2-ol.
67. Complete
the following zig-zag structure so that it represents (2R,3S)-2,3-butanediol.
68. Complete
the following zig-zag structure so that it represents (2S,3R)-2,3-dibromobutane.
69. Complete
the following Newman projection so that it represents
(2R,3R)-2,3-dibromobutane.
70. Complete
the following Newman projection so that it represents (2R,3S)-2,3-dibromobutane.
71. Complete
the following Newman projection so that it represents (2S,3S)-2,3-butanediol.
72. Complete
the following Newman projection so that it represents (2R,3S)-2,3-butanediol.
73. What
mass of (S)-(–)-mandelic acid is present in a 10 g sample which has an
enantiomeric excess of 20% of the S-enantiomer?
74. What
mass of (S)-(–)-mandelic acid is present in a 10 g sample which has an
enantiomeric excess of 30% of the S-enantiomer?
75. The
specific rotation of the S-enantiomer of a compound is -120°. What is the
enantiomeric excess of a sample of the compound that has a measured specific
rotation of -30°.
76. The
specific rotation of the S-enantiomer of a compound is -120°. A student determines
that a sample of the compound has a specific rotation of +60°. What mass of the
S-enantiomer is present in 10 g of the sample
CHAPTER 3–STEREOISOMERISM AND CHIRALITY Key
1. Which
of the following is the definition of a pair of enantiomers?
2. A
pair of structures that are superposable mirror images of one another
3. A
pair of stereoisomers that are non-superposable mirror images of one another
4. A
pair of stereoisomers that are not mirror images of one another
5. A
pair of stereoisomers that have equal specific rotations
2. Which
of the following is the definition of a pair of diastereomers?
3. A
pair of structures that are superposable mirror images of one another
4. A
pair of stereoisomers that are non-superposable mirror images of one another
5. A
pair of stereoisomers that are not mirror images of one another
6. A
pair of stereoisomers that have equal specific rotations
3. Which
of the following is the definition of chirality?
4. The
non-superposability of an object on its mirror image
5. The
superposability of an object on its mirror image
6. A
molecule that has a carbon atom with four different substituents
7. A
molecule with a mirror image
4. Which
of the following is the definition of a meso compound?
5. A
molecule with stereocenter centers which is chiral
6. A
molecule with stereocenter centers which is not chiral
7. A
diastereomer with no stereocenter centers
8. A
chiral compound with more than one stereocenter center
5. Which
of the following statements is not true regarding pairs of enantiomers?
6. They
have identical melting points
7. They
have identical boiling points.
8. They
rotate plane polarized light in opposite directions
9. They
react at identical rates with chiral reagents
6. Which
of the following statements is true?
7. All
mirror images are enantiomers
8. All
molecules that have stereocenter centers are chiral
9. Isomers
that are not superposable on their mirror images are enantiomers
10. Superposable
structural isomers are enantiomers
7. Which
of the following structures is different from the other three?
1. 1
2. 2
3. 3
4. 4
8. Which
of the following structures is different from the other three?
1. 1
2. 2
3. 3
4. 4
9. Which
of the following compounds is/are chiral?
1. only
1
2. only
1 and 2
3. only
2 and 3
4. 1, 2
and 3
10. Which
of the following compounds is/are chiral?
1. only
1
2. only
1 and 2
3. only
2 and 3
4. 1, 2
and 3
11. Which
of the following have the S configuration?
1. only
1
2. only
2
3. only
1 and 2
4. 1, 2
and 3
12. Which
of the following have the R configuration?
1. only
1
2. only
2
3. only
1 and 2
4. 1, 2
and 3
13. What
is the configuration of the two chiral centers in the following molecule?
1. 3R,5R
2. 3R,5S
3. 3S,5R
4. 3S,5S
14. What
is the configuration of the two chiral centers in the following molecule?
1. 3R,5R
2. 3R,5S
3. 3S,5R
4. 3S,5S
15. Which
of the following Newman projections represents (2R,3R)-dibromobutane?
1. 1
2. 2
3. 3
4. 4
16. Which
of the following Newman projections represents meso-2,3-dibromobutane?
1. 1
2. 2
3. 3
4. 4
17. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
18. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
19. Which
of the following structures represent the same stereoisomer?
1. only
1 and 2
2. only
1 and 3
3. only
2 and 3
4. 1, 2
and 3
20. Which
of the following compounds is a meso compound?
21. (2R,3R)-dibromobutane
22. (2R,3S)-dibromobutane
23. (2R,3S)-3-bromo-2-butanol
24. (2R,3R)-3-bromo-2-butanol
21. How
many stereoisomers of 2,3-dimethylbutane, (CH3)2CHCH(CH3)2, exist?
22. 1
23. 2
24. 3
25. 4
22. How
many stereoisomers of 3-chloro-2-methylbutane, (CH3)2CHCHClCH3, exist?
23. 1
24. 2
25. 3
26. 4
23. How
many stereoisomers of 3-bromo-2-butanol, CH3CH(OH)CHBrCH3, exist?
24. 1
25. 2
26. 3
27. 4
24. How
many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist?
25. 1
26. 2
27. 3
28. 4
25. How
many stereoisomers of 2,4-dimethylpentane, (CH3)2CHCH2CH(CH3)2, exist?
26. 1
27. 2
28. 3
29. 4
26. How
many stereoisomers of 4-chloro-2-methylpentane (CH3)2CHCH2CHClCH3, exist?
27. 1
28. 2
29. 3
30. 4
27. How
many stereoisomers of 4-bromo-2-pentanol, CH3CH(OH)CH2CHBrCH3, exist?
28. 1
29. 2
30. 3
31. 4
28. How
many stereoisomers of 2,4-pentanediol, CH3CH(OH)CH2CH(OH)CH3, exist?
29. 1
30. 2
31. 3
32. 4
29. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
30. 3
31. 4
32. 5
33. 6
30. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclohexane?
31. 3
32. 5
33. 6
34. 9
31. How
many isomers (constitutional and stereoisomers) exist for dimethylcyclopentane?
32. 3
33. 5
34. 7
35. 9
32. How
many isomers (constitutional and stereoisomers) exist for dimethylpentane?
33. 2
34. 3
35. 4
36. 5
33. Which
of the following statements regarding optical rotation is not true?
34. All
(+) enantiomers are dextrorotatory.
35. All R
enantiomers are dextrorotatory.
36. All
(-) enantiomers rotate plane-polarized light in a counterclockwise direction.
37. All
(+) and (-) enantiomers rotate plane-polarized light in opposite directions.
34. How
much of the R enantiomer is present in 10 g of a mixture which has an enantiomeric
excess of 20% of the S isomer?
35. 1 g
36. 2 g
37. 4 g
38. 6 g
35. How
much of the R enantiomer is present in 10 g of a mixture which has an
enantiomeric excess of 60% of the R isomer?
36. 2 g
37. 4 g
38. 6 g
39. 8 g
36. A
solution containing 0.2 g/mL of a pure R enantiomer in a 1 dm polarimeter
rotates plane polarized light by +3°.
What is the specific rotation of the R isomer?
37. +0.6°
38. +15°
39. +67°
40. +150°
37. A
solution containing 0.04 g/mL of a pure S enantiomer in a 1 dm polarimeter
rotates plane polarized light by +2°.
What is the specific rotation of the R isomer?
38. -50°
39. -20°
40. +10°
41. +50°
38. A
solution containing 0.2 g/mL of a pure R enantiomer in a 1 dm polarimeter
rotates plane polarized light by +2.8°.
What is the rotation of a solution containing 0.4 g/mL of the R isomer in the
same polarimeter?
39. +0.7°
40. +1.4°
41. +2.8°
42. +5.6°
39. A
solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane
polarized light by +4.8°.
What is the rotation observed on this solution in a 2 dm polarimeter?
40. +2.4°
41. +4.8°
42. +9.6°
43. +19.2°
40. A
pure sample of the R enantiomer of a compound has a specific rotation, [a], of
+20°. A
solution containing 0.2 g/mL of a mixture of enantiomers rotates plane
polarized light by -2° in a
1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?
41. 25% R
42. 40% S
43. 50% S
44. 70% R
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