Organic Chemistry With Biological Topics 5Th Edition By Janice Smith - Test Bank

Organic Chemistry With Biological Topics 5Th Edition By Janice Smith – Test Bank

 

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Sample Questions Are Posted Below

 

Chapter 05 Test Bank: Stereochemistry

Student: ___________________________________________________________________________

 

1. What is the main carbohydrate in the seeds and roots of plants?
2. Starch
   B. Glucose
   C. Cellulose
   D. Glycogen

 

2. Which of the following statements about starch and cellulose is true?
3. Starch and cellulose are not stereoisomers.
   B. In cellulose, the O atom joins two rings using one equatorial and one axial bond.
   C. In starch, the O atom joins two rings using two equatorial bonds.
   D. In cellulose, the O atom joins two rings using two equatorial bonds.

 

3. Which of the following statements about constitutional isomers if not true?
4. They have different IUPAC names.
   B. They always have the same functional groups.
   C. They have different physical properties.
   D. They have different chemical properties.

 

4. Which of the following statements about stereoisomers is not true?
5. Stereoisomers have identical IUPAC names except for a prefix like cis or trans.
   B. Stereoisomers differ in configuration.
   C. Stereoisomers always have the same functional groups.
   D. Stereoisomers differ only in their structural formula.

 

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

 

1. Stereoisomers
   B. Constitutional isomers
   C. Identical
   D. Not isomers, different compounds

 

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

 

1. Constitutional isomers
   B. Identical
   C. Stereoisomers
   D. Not isomers, different compounds

 

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

 

1. Constitutional isomers
   B. Identical
   C. Stereoisomers
   D. Not isomers, different compounds

 

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

 

1. Constitutional isomers
   B. Stereoisomers
   C. Identical
   D. Not isomers, different compounds

 

9. Which of the following is the definition of chirality?
10. The existence of a molecule with a mirror image.
    B. The existence of a molecule with a carbon atom that has four different substituents.
    C. The existence of a molecule that is superimposable on its mirror image.
    D. The existence of a molecule that is not superimposable on its mirror image.

 

10. Which of the following statements is not true?
11. A molecule that is superimposable on its mirror image is said to achiral.
    B. A molecule that is not superimposable on its mirror image is said to be chiral.
    C. A molecule that is superimposable on its mirror image is said to be chiral.
    D. A carbon atom bonded to four different groups is a stereogenic center.

 

11. Which of the following statements is true?
12. Enantiomers are mirror images that are not superimposable.
    B. A molecule that is superimposable on its mirror image is chiral.
    C. A chiral molecule usually contains a plane of symmetry.
    D. An achiral molecule does not contain a plane of symmetry.

 

12. Which of the following statements is true?
13. Achiral molecules usually contain a plane of symmetry.
    B. With one tetrahedral stereogenic center, a molecule may or may not be chiral.
    C. With two or more stereogenic centers, a molecule is always chiral.
    D. Chiral molecules usually contain a plane of symmetry.

 

13. Which of the following is the correct definition for a pair of enantiomers?
14. A pair of stereoisomers that have a plane of symmetry.
    B. A pair of stereoisomers that are not mirror images of each other.
    C. A pair of stereoisomers that are not superimposable mirror images of each other.
    D. A pair of stereoisomers that are superimposable mirror images of each other.

 

14. Which of the following molecules has a plane of symmetry?

 

1. I
   B. II
   C. III
   D. IV

 

15. Which of the following statements is true?
16. The presence of a plane of symmetry makes a molecule chiral.
    B. An achiral molecule must have one or more stereogenic centers.
    C. All molecules that have stereogenic centers are chiral.
    D. Stereoisomers that are not superimposable on their mirror image are enantiomers.

 

16. Which of the following molecules are chiral?
    I. cis-1,3-Dibromocyclohexane
    II.1-Bromo-1-methylcyclohexane
    III.trans-1-Bromo-3-methylcyclohexane
    IV.cis-1-Bromo-3-methylcyclohexane
17. I, II
    B. II, III
    C. I, IV
    D. III, IV

 

17. Which of the following molecules are chiral?
    I.2-Chlorobutane
    II.3-Bromopentane
    III.1-Bromo-2-methylpropene
    IV.2-Bromo-3-methylbutane
18. I, II
    B. I, IV
    C. II, III
    D. III, IV

 

18. Which of the following molecules are achiral?

 

1. II, III
   B. I, II
   C. I, IV
   D. III, IV

 

19. Which of the following molecules are chiral?

 

1. II, III
   B. I, II
   C. I, IV
   D. III, IV

 

20. How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?

 

1. 0
   B. 1
   C. 2
   D. 3

 

21. How many stereogenic centers are present in the following compound?

 

1. 0
   B. 1
   C. 2
   D. 3

 

22. How many stereogenic centers are present in fructose, a simple sugar?

 

1. 1
   B. 2
   C. 3
   D. 4

 

23. How many stereogenic centers are present in the following compound?

 

1. 1
   B. 2
   C. 3
   D. 4

 

24. How many stereogenic centers are present in menthol?

 

1. 1
   B. 2
   C. 3
   D. 4

 

25. How many stereogenic centers are present in the following compound?

 

1. 1
   B. 2
   C. 3
   D. 4

 

26. How many stereogenic centers are present in the following molecule?

 

1. 1
   B. 2
   C. 4
   D. 5

 

27. How many stereoisomers are possible for a molecule with formula CH₃CHBrCH(OH)CH₃?
28. 1
    B. 2
    C. 3
    D. 4

 

28. How many stereoisomers can be drawn for a molecule with formula CH₃CH(OH)CH(OH)CH₃?
29. 1
    B. 2
    C. 3
    D. 4

 

29. What is the total number of possible stereoisomers for the following molecule?

 

1. 2
   B. 4
   C. 6
   D. 8

 

30. How many isomers can be drawn (constitutional and stereoisomers) for dimethylcyclopropane in which the cyclopropane remains intact? QC_CS-66408
31. 2
    B. 3
    C. 4
    D. 6

 

31. How many chiral stereoisomers can be drawn for dimethycyclopropane?
32. 1
    B. 2
    C. 3
    D. 4

 

32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

 

1. 0
   B. 1
   C. 2
   D. 3

 

33. How many stereogenic centers are present in the following compound?

 

1. 0
   B. 1
   C. 2
   D. 3

 

34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. III > I > II > IV
   B. I > II > IV > III
   C. III > II > IV > I
   D. III > IV > II > I

 

35. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > II > III > IV
   B. II > I > IV > III
   C. II > I > III > IV
   D. I > II > IV > III

 

36. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > III > IV > II
   B. III > IV > I > II
   C. IV > III > I > II
   D. IV > I > III > II

 

37. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > II > IV > III
   B. IV > II > I > III
   C. IV > I > II > III
   D. III > II > I> IV

 

38. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. IV > III > I > II
   B. IV > I > III > II
   C. III > IV > I > II
   D. II > I > III > IV

 

39. Which of the following compounds has a plane of symmetry?

 

1. I and II
   B. II and III
   C. II, III, and IV
   D. III and IV

 

40. Which of the following structures has a different configuration from the other three?

 

1. I
   B. II
   C. III
   D. IV

 

41. Which of the following structures has a different configuration from the other three?

 

1. I
   B. II
   C. III
   D. IV

 

42. Which of the following structures has the S configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

 

43. Which of the following structures has the R configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

 

44. Which of the following structures has the R configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

 

45. Which of the following is the definition for a pair of diastereomers?

 

1. A pair of stereoisomers with stereogenic centers but is not chiral.
   B. A pair of stereoisomers that are superimposable mirror images of each other.
   C. A pair of stereoisomers that are not superimposable mirror images of each other.
   D. A pair of stereoisomers that are not mirror images of each other.

 

46. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

47. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

48. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

49. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

50. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

51. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

52. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

53. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

 

54. Which of the following statements about meso compounds is not true?
55. A meso compound generally has a plane of symmetry.
    B. A meso compound and its mirror image are identical.
    C. A meso compound is achiral.
    D. A meso compound is chiral.

 

55. Which of the following compounds is a meso compound?
56. (2R, 3S)-dichlorobutane
    B. (2R, 3R)-dichlorobutane
    C. (2R, 3S)-3-chloro-2-butanol
    D. (2R, 3R)-3-chloro-2-butanol

 

56. Which of the following compounds are meso?

 

1. Only I
   B. Only II
   C. I and II
   D. Neither

 

57. Which of the following compounds can have a meso stereoisomer?

 

1. I
   B. II
   C. III
   D. IV

 

58. How many stereoisomers of 1,3-dibromocyclopentane exist?
59. 1
    B. 2
    C. 3
    D. 4

 

59. Which of the following compounds does not have a plane of symmetry?

 

1. Only I and II
   B. Only II
   C. Only III and IV
   D. Only I, II, and IV

 

 

60. Which of the following cyclic molecules is a meso compound?

 

1. I
   B. II
   C. III
   D. IV

 

61. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
62. 3
    B. 4
    C. 5
    D. 6

 

62. A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H₂O. What is the specific rotation of this compound?
63. -10°
    B. +100°
    C. +10°
    D. -100°

 

63. A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer?
64. +50°
    B. -40°
    C. +40°
    D. -50°

 

64. How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer?
65. 3.0 g
    B. 3.5 g
    C. 6.5 g
    D. 7.0 g

 

65. A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?
66. +5.6°
    B. +11.2°
    C. +2.8°
    D. +1.4°

 

66. What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other?
67. 70
    B. 85
    C. 40
    D. 30

 

67. If a mixture has an ee of 90%, what is the percentage of each enantiomer?
68. 65% : 35%
    B. 55% : 45%
    C. 80% : 20%
    D. 95% : 5%

 

68. A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture?
69. 75
    B. 40
    C. 65
    D. 50

 

69. Which of the following compounds are chiral?
70. I and II
    B. II and III
    C. III and IV
    D. I and IV

 

 

70. Which of the following compounds is identical to compound A?
71. I and II
    B. II and III
    C. I and III
    D. II

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Chapter 05 Test Bank: Stereochemistry Key

1. What is the main carbohydrate in the seeds and roots of plants?
2. Starch
   B.Glucose
   C. Cellulose
   D. Glycogen

Accessibility: Keyboard Navigation
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.01
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry
 

2. Which of the following statements about starch and cellulose is true?
3. Starch and cellulose are not stereoisomers.
   B.In cellulose, the O atom joins two rings using one equatorial and one axial bond.
   C. In starch, the O atom joins two rings using two equatorial bonds.
   D. In cellulose, the O atom joins two rings using two equatorial bonds.

Accessibility: Keyboard Navigation
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.01
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry
 

3. Which of the following statements about constitutional isomers if not true?
4. They have different IUPAC names.
   B.They always have the same functional groups.
   C. They have different physical properties.
   D. They have different chemical properties.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

4. Which of the following statements about stereoisomers is not true?
5. Stereoisomers have identical IUPAC names except for a prefix like cis or trans.
   B.Stereoisomers differ in configuration.
   C. Stereoisomers always have the same functional groups.
   D. Stereoisomers differ only in their structural formula.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

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

 

1. Stereoisomers
   B. Constitutional isomers
   C. Identical
   D. Not isomers, different compounds

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

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

 

1. Constitutional isomers
   B. Identical
   C. Stereoisomers
   D. Not isomers, different compounds

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

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

 

1. Constitutional isomers
   B. Identical
   C. Stereoisomers
   D. Not isomers, different compounds

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

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

 

1. Constitutional isomers
   B. Stereoisomers
   C. Identical
   D. Not isomers, different compounds

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.02
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

9. Which of the following is the definition of chirality?
10. The existence of a molecule with a mirror image.
    B.The existence of a molecule with a carbon atom that has four different substituents.
    C. The existence of a molecule that is superimposable on its mirror image.
    D. The existence of a molecule that is not superimposable on its mirror image.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry
 

10. Which of the following statements is not true?
11. A molecule that is superimposable on its mirror image is said to achiral.
    B.A molecule that is not superimposable on its mirror image is said to be chiral.
    C. A molecule that is superimposable on its mirror image is said to be chiral.
    D. A carbon atom bonded to four different groups is a stereogenic center.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry

11. Which of the following statements is true?
12. Enantiomers are mirror images that are not superimposable.
    B.A molecule that is superimposable on its mirror image is chiral.
    C. A chiral molecule usually contains a plane of symmetry.
    D. An achiral molecule does not contain a plane of symmetry.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry
 

12. Which of the following statements is true?
13. Achiral molecules usually contain a plane of symmetry.
    B. With one tetrahedral stereogenic center, a molecule may or may not be chiral.
    C. With two or more stereogenic centers, a molecule is always chiral.
    D. Chiral molecules usually contain a plane of symmetry.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

13. Which of the following is the correct definition for a pair of enantiomers?
14. A pair of stereoisomers that have a plane of symmetry.
    B.A pair of stereoisomers that are not mirror images of each other.
    C. A pair of stereoisomers that are not superimposable mirror images of each other.
    D. A pair of stereoisomers that are superimposable mirror images of each other.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

14. Which of the following molecules has a plane of symmetry?

 

1. I
   B. II
   C. III
   D. IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

15. Which of the following statements is true?
16. The presence of a plane of symmetry makes a molecule chiral.
    B.An achiral molecule must have one or more stereogenic centers.
    C. All molecules that have stereogenic centers are chiral.
    D. Stereoisomers that are not superimposable on their mirror image are enantiomers.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

16. Which of the following molecules are chiral?
    I. cis-1,3-Dibromocyclohexane
    II.1-Bromo-1-methylcyclohexane
    III.trans-1-Bromo-3-methylcyclohexane
    IV.cis-1-Bromo-3-methylcyclohexane
17. I, II
    B.II, III
    C. I, IV
    D. III, IV

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

17. Which of the following molecules are chiral?
    I.2-Chlorobutane
    II.3-Bromopentane
    III.1-Bromo-2-methylpropene
    IV.2-Bromo-3-methylbutane
18. I, II
    B. I, IV
    C. II, III
    D. III, IV

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

18. Which of the following molecules are achiral?

 

1. II, III
   B. I, II
   C. I, IV
   D. III, IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

19. Which of the following molecules are chiral?

 

1. II, III
   B. I, II
   C. I, IV
   D. III, IV

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Difficulty: Medium
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

20. How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?

 

1. 0
   B. 1
   C. 2
   D. 3

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

21. How many stereogenic centers are present in the following compound?

 

1. 0
   B. 1
   C. 2
   D. 3

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

22. How many stereogenic centers are present in fructose, a simple sugar?

 

1. 1
   B. 2
   C. 3
   D. 4

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

23. How many stereogenic centers are present in the following compound?

 

1. 1
   B. 2
   C. 3
   D. 4

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

24. How many stereogenic centers are present in menthol?

 

1. 1
   B. 2
   C. 3
   D. 4

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.05
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

25. How many stereogenic centers are present in the following compound?

 

1. 1
   B. 2
   C. 3
   D. 4

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

26. How many stereogenic centers are present in the following molecule?

 

1. 1
   B. 2
   C. 4
   D. 5

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry

27. How many stereoisomers are possible for a molecule with formula CH₃CHBrCH(OH)CH₃?
28. 1
    B. 2
    C. 3
    D. 4

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

28. How many stereoisomers can be drawn for a molecule with formula CH₃CH(OH)CH(OH)CH₃?
29. 1
    B.2
    C. 3
    D. 4

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

29. What is the total number of possible stereoisomers for the following molecule?

 

1. 2
   B. 4
   C. 6
   D. 8

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.04
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

30. How many isomers can be drawn (constitutional and stereoisomers) for dimethylcyclopropane in which the cyclopropane remains intact? QC_CS-66408
31. 2
    B. 3
    C. 4
    D. 6

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.05
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

31. How many chiral stereoisomers can be drawn for dimethycyclopropane?
32. 1
    B.2
    C. 3
    D. 4

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.05
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

 

1. 0
   B. 1
   C. 2
   D. 3

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.05
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

33. How many stereogenic centers are present in the following compound?

 

1. 0
   B. 1
   C. 2
   D. 3

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Hard
Difficulty: Medium
Gradable: automatic
Section: 05.05
Subtopic: Chiral vs Achiral Molecules
Subtopic: Stereogenic/Chirality Carbon Centers
Topic: Stereochemistry
 

34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. III > I > II > IV
   B. I > II > IV > III
   C. III > II > IV > I
   D. III > IV > II > I

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry
 

35. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > II > III > IV
   B. II > I > IV > III
   C. II > I > III > IV
   D. I > II > IV > III

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry

36. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > III > IV > II
   B. III > IV > I > II
   C. IV > III > I > II
   D. IV > I > III > II

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry

37. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. I > II > IV > III
   B. IV > II > I > III
   C. IV > I > II > III
   D. III > II > I> IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry
 

38. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

1. IV > III > I > II
   B. IV > I > III > II
   C. III > IV > I > II
   D. II > I > III > IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry
 

39. Which of the following compounds has a plane of symmetry?

 

1. I and II
   B. II and III
   C. II, III, and IV
   D. III and IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.08
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

40. Which of the following structures has a different configuration from the other three?

 

1. I
   B. II
   C. III
   D. IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry
 

41. Which of the following structures has a different configuration from the other three?

 

1. I
   B. II
   C. III
   D. IV

Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry
 

42. Which of the following structures has the S configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry

43. Which of the following structures has the R configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry

44. Which of the following structures has the R configuration?

 

1. Only I
   B. Only II
   C. Only I and II
   D. I, II, and III

 

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.09
Subtopic: R and S Nomenclature
Topic: Stereochemistry

45. Which of the following is the definition for a pair of diastereomers?
46. A pair of stereoisomers with stereogenic centers but is not chiral.
    B.A pair of stereoisomers that are superimposable mirror images of each other.
    C. A pair of stereoisomers that are not superimposable mirror images of each other.
    D. A pair of stereoisomers that are not mirror images of each other.

Accessibility: Keyboard Navigation
Bloom’s Level: 2. Understand
Chapter: 05
Difficulty: Easy
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

46. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

47. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

48. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

49. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Hard
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

50. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

51. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

52. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

53. What is the relationship between the following compounds?

 

1. Constitutional isomers
   B. Diastereomers
   C. Enantiomers
   D. Identical

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.07
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

54. Which of the following statements about meso compounds is not true?
55. A meso compound generally has a plane of symmetry.
    B.A meso compound and its mirror image are identical.
    C. A meso compound is achiral.
    D. A meso compound is chiral.

Accessibility: Keyboard Navigation
Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.08
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

55. Which of the following compounds is a meso compound?
56. (2R, 3S)-dichlorobutane
    B.(2R, 3R)-dichlorobutane
    C. (2R, 3S)-3-chloro-2-butanol
    D. (2R, 3R)-3-chloro-2-butanol

Accessibility: Keyboard Navigation
Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Hard
Gradable: automatic
Section: 05.08
Subtopic: R and S Nomenclature
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

56. Which of the following compounds are meso?

 

1. Only I
   B. Only II
   C. I and II
   D. Neither

Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Hard
Gradable: automatic
Section: 05.08
Subtopic: R and S Nomenclature
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

57. Which of the following compounds can have a meso stereoisomer?

 

1. I
   B. II
   C. III
   D. IV

Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Hard
Gradable: automatic
Section: 05.08
Subtopic: R and S Nomenclature
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

58. How many stereoisomers of 1,3-dibromocyclopentane exist?
59. 1
    B.2
    C. 3
    D. 4

Accessibility: Keyboard Navigation
Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.10
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

59. Which of the following compounds does not have a plane of symmetry?

 

1. Only I and II
   B. Only II
   C. Only III and IV
   D. Only I, II, and IV

 

Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.08
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

60. Which of the following cyclic molecules is a meso compound?

 

1. I
   B. II
   C. III
   D. IV

Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.08
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

61. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
62. 3
    B.4
    C. 5
    D. 6

Accessibility: Keyboard Navigation
Bloom’s Level: 4. Analyze
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.10
Subtopic: Stereogenic/Chirality Carbon Centers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

62. A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H₂O. What is the specific rotation of this compound?
63. -10°
    B.+100°
    C. +10°
    D. -100°

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

63. A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer?
64. +50°
    B.-40°
    C. +40°
    D. -50°

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

64. How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer?
65. 3.0 g
    B. 3.5 g
    C. 6.5 g
    D. 7.0 g

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

65. A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?
66. +5.6°
    B. +11.2°
    C. +2.8°
    D. +1.4°

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

66. What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other?
67. 70
    B.85
    C. 40
    D. 30

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

67. If a mixture has an ee of 90%, what is the percentage of each enantiomer?
68. 65% : 35%
    B.55% : 45%
    C. 80% : 20%
    D. 95% : 5%

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

68. A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture?
69. 75
    B.40
    C. 65
    D. 50

Accessibility: Keyboard Navigation
Bloom’s Level: 5. Evaluate
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.12
Subtopic: Optical Activity
Subtopic: Physical Properties of Stereoisomers
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry
 

69. Which of the following compounds are chiral?
70. I and II
    B. II and II
    C. III and IV
    D. I and IV

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Medium
Gradable: automatic
Section: 05.03
Subtopic: Chiral vs Achiral Molecules
Topic: Stereochemistry
 

70. Which of the following compounds is identical to compound A?
71. I and II
    B. II and III
    C. I and III
    D. II

Bloom’s Level: 3. Apply
Chapter: 05
Difficulty: Hard
Gradable: automatic
Section: 05.11
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)
Topic: Stereochemistry

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Chapter 05 Test Bank: Stereochemistry Summary

Category	# of Questions
Accessibility: Keyboard Navigation	29
Bloom’s Level: 2. Understand	40
Bloom’s Level: 3. Apply	14
Bloom’s Level: 4. Analyze	7
Bloom’s Level: 5. Evaluate	7
Chapter: 05	70
Difficulty: Easy	30
Difficulty: Hard	6
Difficulty: Medium	37
Gradable: automatic	70
Section: 05.01	2
Section: 05.02	6
Section: 05.03	12
Section: 05.04	9
Section: 05.05	5
Section: 05.07	9
Section: 05.08	7
Section: 05.09	10
Section: 05.10	2
Section: 05.11	1
Section: 05.12	7
Subtopic: Chiral vs Achiral Molecules	28
Subtopic: Optical Activity	7
Subtopic: Physical Properties of Stereoisomers	7
Subtopic: R and S Nomenclature	13
Subtopic: Stereogenic/Chirality Carbon Centers	39
Subtopic: Stereoisomers (Enantiomers, Diastereomers, Meso)	33
Topic: Stereochemistry	70