Organic Chemistry 10th Edition by SOLOMONS test bank

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Organic Chemistry 10th Edition by SOLOMONS test bank

Description

Chapter Five

MULTIPLE CHOICE QUESTIONS

Topic: Identifications and Comparisons
Section: 5.2
Difficulty Level: Easy

1. Cis-trans isomers are:
A) diastereomers.
B) enantiomers.
C) stereoisomers.
D) constitutional isomers.
E) More than one of these
Ans: E

Topic: General definitions
Section: 5.2C
Difficulty Level: Easy

2. Enantiomers are:
A) molecules that have a mirror image.
B) molecules that have at least one stereogenic center.
C) non-superposable molecules.
D) non-superposable constitutional isomers.
E) non-superposable molecules that are mirror images of each other.
Ans: E

Topic: General stereochemistry
Section: 5.4
Difficulty Level: Easy

3. How many stereogenic centers are there in Lovastatin ( Mevacor : a cholesterol-lowering drug) ?

A) 4
B) 5
C) 6
D) 7
E) 8
Ans: E

Topic: Identifications and Comparisons
Section: 5.1, 5.4
Difficulty Level: Easy

4. Which molecule is achiral?

A) I
B) II
C) III
D) More than one of these
E) None of these
Ans: A

Topic: Identifications and Comparisons
Section: 5.1, 5.4
Difficulty Level: Easy

5. Which molecule is achiral?

A) I
B) II
C) III
D) More than one of the above
E) None of the above
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4
Difficulty Level: Medium

6. Pairs of enantiomers are:

A) I, II and III, IV
B) I, II
C) III, IV
D) IV, V
E) None of the structures
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4
Difficulty Level: Medium

7. Chiral molecules are represented by:

A) I, II, III, IV and V
B) I, II, III and IV
C) I and II
D) III and IV
E) IV alone
Ans: D

Topic: General stereochemistry
Section: 5.2A, 5.4
Difficulty Level: Medium

8. What is the molecular formula for the alkane of smallest molecular weight which possesses a stereogenic center?
A) C4H10
B) C5H12
C) C6H14
D) C7H16
E) C8H18
Ans: D

Topic: Specific names
Section: 4.3, 5.7
Difficulty Level: Easy

9. (R)-2-Chlorobutane is represented by:

A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Specific names
Section: 4.3, 5.7
Difficulty Level: Easy

10. Which of the following represent (R)-2-butanol?

A) III and V
B) I, III, IV and V
C) I, IV and V
D) I and III
E) I, II, IV and V
Ans: C

Topic: Specific names
Section: 4.3, 5.7
Difficulty Level: Easy

11. Which structure represents (S)-1-chloro-1-fluoroethane?

A) I
B) II
C) III
D) More than one of the above
E) None of the above
Ans: D

Topic: Specific names
Section: 4.3, 5.7
Difficulty Level: Easy

12. Which structure represents (R)-1-chloro-1-fluoroethane?

A) I
B) II
C) III
D) More than one of the above
E) None of the above
Ans: B

Topic: Specific names
Section: 4.3, 5.7
Difficulty Level: Easy

13. Which structure represents (S)-2-bromobutane?

A) I
B) II
C) III
D) More than one of the above
E) None of the above
Ans: A

Topic: Identifications and Comparisons
Section: 5.3, 5.4, and 5.7
Difficulty Level: Easy

14. Which of the following is the enantiomer of the following substance?

A) I
B) II
C) III
D) It does not have a non-superposable enantiomer.
E) Both II and III
Ans: D

Topic: General stereochemistry
Section: 5.6, 5.7
Difficulty Level: Medium

15. What is the total number of compounds, stereoisomers included, designated by the general name dichlorocyclopentane?
A) 4
B) 5
C) 7
D) 8
E) 9
Ans: C

Topic: General definitions
Section: 5.8
Difficulty Level: Easy

16. Which of the following is NOT true of enantiomers? They have the same:
A) boiling point.
B) melting point.
C) specific rotation.
D) density.
E) chemical reactivity toward achiral reagents.
Ans: C

Topic: Optical activity
Section: 5.8
Difficulty Level: Medium

17. Which of these is a comparatively insignificant factor affecting the magnitude of specific optical rotation?
A) Concentration of the substance of interest
B) Purity of the sample
C) Temperature of the measurement
D) Length of the sample tube
E) All of the above are equally significant.
Ans: C

Topic: General definitions
Section: 5.3, 5.4, 5.8
Difficulty Level: Easy

18. Which of the following is true about any (R)-enantiomer?
A) It is dextrorotatory.
B) It is levorotatory.
C) It is an equal mixture of + and -.
D) It is the mirror image of the (S)-enantiomer.
E) (R) indicates a racemic mixture.
Ans: D

Topic: General definitions
Section: 5.3, 5.4, 5.8
Difficulty Level: Easy

19. Which of the following is true of any (S)-enantiomer?
A) It rotates plane-polarized light to the right.
B) It rotates plane-polarized light to the left.
C) It is a racemic form.
D) It is the mirror image of the corresponding (R)-enantiomer.
E) It has the highest priority group on the left.
Ans: D

Topic: Optical activity
Section: 4.13, 5.6, 5.8
Difficulty Level: Easy

20. Which compound would show optical activity?
A) cis-1,4- Dimethylcyclohexane
B) trans-1,4- Dimethylcyclohexane
C) cis-1,4- Dimethylcycloheptane
D) trans-1,4- Dimethylcycloheptane
E) More than one of these
Ans: D

Topic: Optical activity
Section: 4.13, 5.6, 5.8
Difficulty Level: Easy

21. Of the compounds which correspond to the general name dichlorocyclobutane, how many are optically active?
A) 0
B) 1
C) 2
D) 3
E) 4
Ans: C

Topic: Optical activity
Section: 5.7, 5.8
Difficulty Level: Easy

22. The compounds whose molecules are shown below would have:

A) the same melting point.
B) different melting points.
C) equal but opposite optical rotations.
D) More than one of the above
E) None of the above
Ans: D

Topic: Optical activity
Section: 5.8C
Difficulty Level: Easy

23. If a solution of a compound (30.0 g/100 mL of solution) has a measured rotation of +15 in a 2 dm tube, the specific rotation is:
A) +50
B) +25
C) +15
D) +7.5
E) +4.0
Ans: B

Topic: Optical activity
Section: 5.8, 5.9
Difficulty Level: Easy

24. What can be said with certainty if a compound has [] = -9.25 ?
A) The compound has the (S) configuration.
B) The compound has the (R) configuration.
C) The compound is not a meso form.
D) The compound possesses only one stereogenic center.
E) The compound has an optical purity of less than 100%.
Ans: C

Topic: Optical activity
Section: 5.8, 5.9
Difficulty Level: Medium

25. In the absence of specific data, it can only be said that (R)2bromopentane is:
A) dextrorotatory (+).
B) levorotatory ().
C) optically inactive.
D) achiral.
E) analogous in absolute configuration to (R)2chloropentane.
Ans: E

Topic: Optical activity
Section: 4.3, 5.8, 5.9
Difficulty Level: Easy

26. An alkane which can exhibit optical activity is:
A) Neopentane
B) Isopentane
C) 3Methylpentane
D) 3Methylhexane
E) 2,3Dimethylbutane
Ans: D

Topic: Optical activity
Section: 5.9B
Difficulty Level: Medium

27. What is the percent composition of a mixture of (S)-(+)-2-butanol,[] = +13.52, and (R)-(-)-2-butanol,[] = -13.52, with a specific rotation [] = +6.76?
A) 75%(R) 25%(S)
B) 25%(R) 75%(S)
C) 50%(R) 50%(S)
D) 67%(R) 33%(S)
E) 33%(R) 67%(S)
Ans: B

Topic: Reaction stereochemistry
Section: 5.10A
Difficulty Level: Medium

28. The reaction of with H2/Ni forms:
A) 2-methylheptane
B) (R)-2-methyl-5-heptanol
C) (S)-6-methyl-3-heptanol
D) (R and S)-6-methyl-3-heptanol
E) Achiral 6,6-dimethyl-3-hexanol
Ans: D

Topic: Meso compounds
Section: 5.12
Difficulty Level: Easy

29. Which of the following is a meso compound?

A) I
B) II
C) III
D) IV
E) V
Ans: A

Topic: Meso compounds
Section: 5.12
Difficulty Level: Easy

30. Which of the following is(are) meso compound(s)?

A) I
B) II
C) III
D) Both II and III
E) Both I and III
Ans: E

Topic: Meso compounds
Section: 5.12
Difficulty Level: Easy

31. Which of the following is(are) meso?

A) I
B) II
C) III
D) IV
E) Two of the above
Ans: D

Topic: Meso compounds
Section: 5.12
Difficulty Level: Easy

32. Which molecule is a meso compound?

A) I
B) II
C) III
D) More than one of the above
E) None of the above
Ans: D

Topic: General stereochemistry
Section: 5.12
Difficulty Level: Easy

33. CH3CHBrCH2CHClCH3 is the generalized representation of what number of stereoisomers?
A) 3
B) 4
C) 5
D) 6
E) 7
Ans: B

Topic: General stereochemistry
Section: 5.12
Difficulty Level: Easy

34. For the generalized structure BrCH2CHClCH2CHClCH2Br there exists what number of stereoisomers?
A) 2
B) 3
C) 4
D) 6
E) 8
Ans: B

Topic: General stereochemistry
Section: 5.12
Difficulty Level: Easy

35. How many discrete dimethylcyclopropanes are there?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: C

Topic: General stereochemistry
Section: 5.12
Difficulty Level: Easy

36. How many chiral stereoisomers can be drawn for CH3CHFCHFCH(CH3)2?
A) 1
B) 2
C) 3
D) 4
E) 8
Ans: D

Topic: Meso compounds
Section: 5.12
Difficulty Level: Medium

37. Which statement is not true for a meso compound?
A) The specific rotation is 0.
B) There are one or more planes of symmetry.
C) A single molecule is identical to its mirror image.
D) More than one stereogenic center must be present.
E) The stereochemical labels, (R) and (S), must be identical for each stereogenic center.
Ans: E

Topic: Identifications and Comparisons
Section: 4.8A, 5.2, 5.4, 5.12
Difficulty Level: Medium

38. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 4.12, 5.2, 5.4, 5.12
Difficulty Level: Medium

39. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 4.12, 5.2, 5.4, 5.12
Difficulty Level: Medium

40. The structures

represent:
A) a single compound.
B) enantiomers.
C) meso forms.
D) diastereomers.
E) conformational isomers.
Ans: A

Topic: Identifications and Comparisons
Section: 4.12, 5.2, 5.4, 5.12
Difficulty Level: Medium

41. The two compounds shown below are:
are:
A) identical.
B) enantiomers.
C) diastereomers.
D) conformational isomers.
E) meso forms.
Ans: B

Topic: Identifications and Comparisons
Section: 4.12, 5.2, 5.4, 5.12
Difficulty Level: Hard

42. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 4.12, 5.2, 5.4, 5.12
Difficulty Level: Hard

43. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: General definitions
Section: 4.13, 5.4, 5.12
Difficulty Level: Medium

44. Which statement is true of 1,3-dimethylcyclobutane?
A) Only one form of the compound is possible.
B) Two diastereomeric forms are possible.
C) Two sets of enantiomers are possible.
D) Two enantiomeric forms and one meso compound are possible.
E) None of the previous statements is true.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

45. Hexane and 3-methylpentane are examples of:
A) enantiomers.
B) stereoisomers.
C) diastereomers.
D) constitutional isomers.
E) None of these
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

46. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

47. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

48. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) stereoisomers.
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

49. The molecules shown are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: E

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

50. The molecules below are:

A) structural isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

51. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

52. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

53. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

54. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Easy

55. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

56. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

57. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

58. The molecules below are:

A) enantiomers.
B) diastereomers.
C) constitutional isomers.
D) two different conformations of the same molecule.
E) not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

59. The molecules below are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

60. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: E

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

61. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

62. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

63. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

64. The molecules shown are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium
65. The
The molecules shown are:

A) enantiomers.
B) diastereomers.
C) constitutional isomers.
D) two conformations of the same molecule.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

66. The molecules shown are:

A) constitutional isomers.
B) enantiomers.
C) diastereomers.
D) identical.
E) None of these
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

67. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: C

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

68. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: C

Topic: General stereochemistry
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

69. Which of the compounds above (I-IV) represent enantiomers?
A) I and II
B) II and III
C) III and IV
D) II and IV
E) III and IV
Ans: B

Topic: General stereochemistry
Section: 5.2, 5.4, 5.12
Difficulty Level: Medium

70. Which compound above (I-IV) is a meso compound?
A) I
B) II
C) III
D) IV
E) None of these
Ans: D

Topic: General stereochemistry
Section: 5.2, 5.4, 5.7, 5.12
Difficulty Level: Medium

71. Which compound above (I-IV) is (2R,3R)-2,3-butanediol?
A) I
B) II
C) III
D) IV
E) None of these
Ans: C

Topic: General stereochemistry
Section: 5.2, 5.4, 5.7, 5.12
Difficulty Level: Medium

72. Which compounds above (I-IV) form a set of stereoisomers?
A) I, II and III
B) II, III and IV
C) II and III
D) I, III and IV
E) I, II, III and IV
Ans: B

Topic: Meso compounds
Section: 5.1, 5.6, 5.12
Difficulty Level: Easy

73. Which of the following substances is achiral ?

A) I
B) II
C) III
D) IV
E) More than one of these
Ans: E

Topic: Meso compounds
Section: 5.6, 5.12
Difficulty Level: Easy

74. Which molecule has a plane of symmetry?

A) I
B) II
C) III
D) More than one of these
E) None of these
Ans: D

Topic: Meso compounds
Section: 5.6, 5.12
Difficulty Level: Easy

75. Which molecule has a plane of symmetry?

A) I
B) II
C) III
D) More than one of these
E) None of these
Ans: D

Topic: Meso compounds
Section: 5.6, 5.12
Difficulty Level: Easy

76. Which compound does NOT possess a plane of symmetry?

A) I, II and V
B) I, III and IV
C) II, III and IV
D) III and IV
E) V
Ans: D

Topic: Meso compounds
Section: 5.6, 5.12
Difficulty Level: Easy

77. Which molecule is a meso compound?

A) I and II
B) IV and V
C) II and III
D) I, II and III
E) None of the above
Ans: E

Topic: Optical activity
Section: 5.7, 5.12
Difficulty Level: Easy

78. The compounds whose molecules are shown below would have:

A) the same melting point.
B) different melting points.
C) equal but opposite optical rotations.
D) More than one of the above
E) None of the above
Ans: B

Topic: Meso compounds
Section: 5.7, 5.12
Difficulty Level: Medium

79. Which of the following molecules is achiral?
A) (2R,3R)-2,3-Dichloropentane
B) (2R,3S)-2,3-Dichloropentane
C) (2S,4S)-2,4-Dichloropentane
D) (2S,4R)-2,4-Dichloropentane
E) Two of these
Ans: D

Topic: Meso compounds
Section: 5.7, 5.12
Difficulty Level: Medium

80. Which is a meso compound?
A) (2R,3R)-2,3-Dibromobutane
B) (2R,3S)-2,3-Dibromopentane
C) (2R,4R)-2,4-Dibromopentane
D) (2R,4S)-2,4-Dibromopentane
E) (2R,4S)-2,4-Dibromohexane
Ans: D

Topic: Specific names
Section: 5.7, 5.12
Difficulty Level: Medium

81. The Cahn-Ingold-Prelog stereochemical designations used for the following substance are:

A) 2R,4S
B) 2S,4R
C) 2R,4R
D) 2S,4S
E) The R,S terminology doesnt apply in this case.
Ans: C

Topic: General stereochemistry
Section: 5.7 and 5.12
Difficulty Level: Medium

82. How many different compounds are there which correspond to the general name 3-(1-methylbutyl)cyclobutanol?
A) 2
B) 4
C) 6
D) 8
E) None of the above
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.7, 5.12
Difficulty Level: Medium

83. (2R,4S) 2,4Dichloropentane and (2S,4R)-2,4-dichloropentane are:
A) enantiomers.
B) diastereomers.
C) identical.
D) conformational isomers.
E) constitutional isomers.
Ans: C

Topic: Optical activity
Section: 5.6, 5.8, 5.12
Difficulty Level: Easy

84. The compounds whose molecules are shown below would have:

A) the same melting point.
B) different melting points.
C) equal but opposite optical rotations.
D) More than one of these
E) None of these
Ans: B

Topic: Optical activity
Section: 5.6, 5.8, 5.12
Difficulty Level: Easy

85. The compounds whose structures are shown below would have:

A) the same melting point.
B) different melting points.
C) equal but opposite optical rotations.
D) More than one of these
E) None of these
Ans: D

Topic: Optical activity
Section: 4.13A, 5.6, 5.12A
Difficulty Level: Medium

86. Which one of the following can exist in optically active forms?
A) cis-1,3-Dichlorocyclohexane
B) trans-1,3-Dichlorocyclohexane
C) cis-1,4-Dichlorocyclohexane
D) trans-1,4-Dichlorocyclohexane
E) cis-1,2-Dichlorocyclohexane
Ans: B

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Medium

87. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (1R,3S)-1-methylcyclopentane-1,3-diol

Topic: Identifications and Comparisons
Section: 4.8A, 5.2, 5.4, 5.12, 5.13
Difficulty Level: Easy

88. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 4.8A, 5.2, 5.4, 5.12, 5.13
Difficulty Level: Hard

89. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 4.8A, 5.2, 5.4, 5.12, 5.13
Difficulty Level: Hard

90. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 4.8A, 5.2, 5.4, 5.12, 5.13
Difficulty Level: Hard

91. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, and 5.13
Difficulty Level: Easy

92. I and II are:

A) constitutional isomers.
B) enantiomers.
C) non-superposable mirror images.
D) diastereomers.
E) not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Easy

93. The two compounds shown below are:

A) enantiomers.
B) diastereomers.
C) constitutional isomers.
D) identical.
E) different but not isomeric.
Ans: A

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Easy

94. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Medium

95. Which pair of structures represents the same compound?

A) I and II
B) II and III
C) III and IV
D) III and V
E) IV and V
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, and 5.13
Difficulty Level: Medium

96. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Medium

97. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Medium

98. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Medium

99. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Hard

100. Which structure(s) represent(s) diastereomer(s) of I?

A) II
B) II and III
C) II and IV
D) III and V
E) IV and V
Ans: B

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, and 5.13
Difficulty Level: Hard

101. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: D

Topic: Identifications and Comparisons
Section: 5.2, 5.4, 5.12, 5.13
Difficulty Level: Hard

102. I and II are:

A) constitutional isomers.
B) enantiomers.
C) identical.
D) diastereomers.
E) not isomeric.
Ans: B

Topic: Specific names
Section: 4.3, 5.7, 5.12, 5.13
Difficulty Level: Medium

103. is properly named:
A) (3R,4S,5R)- 3,5-Dichloro-4-methylhexane
B) (2S,3S,4S)- 2,4-Dichloro-3-methylhexane
C) (2S,3R,4R)- 2,4-Dichloro-3-methylhexane
D) (2S,3R,4S)-2,4-Dichloro-3-methylhexane
E) (2S,3S,4R)- 2,4-Dichloro-3-methylhexane
Ans: D

Topic: Specific names
Section: 4.3, 5.7, 5.13
Difficulty Level: Medium

104. Which of these is not a correct Fischer projection formula of the (S) form of
3-bromo-1,1-dichloro-2-propanol ?

A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Reaction stereochemistry
Section: 5.15
Difficulty Level: Easy

105. Which reaction must take place with retention of configuration at the stereogenic center?
A)
B)
C)
D) More than one of the above
E) None of the above
Ans: D

Topic: Reaction stereochemistry
Section: 5.15
Difficulty Level: Medium

106. In which of the following reactions is the absolute configuration of the product likely to be the same as that of the reactant?
A)
B)
C)
D) All of the above
E) Answers A) and B) only
Ans: E

Topic: Reaction Stereochemistry
Section: 5.15
Difficulty Level: Medium

107. Which of the following reactions must occur with retention of configuration?
A)
B)
C)
D)
E)
Ans: D

Topic: Optical activity
Section: 5.18
Difficulty Level: Medium

108. A solution of which of these allenes will rotate plane-polarized light?

A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Optical activity
Section: 5.18
Difficulty Level: Medium

109. How many optically active compounds are represented by the following generalized formula?

A) 0
B) 1
C) 2
D) 3
E) 4
Ans: C

Topic: Identifications and Comparisons
Section: 5.1, 5.4, 5.12A and 5.18
Difficulty Level: Medium

110. Which of the following molecules is achiral?

A) I
B) II
C) III
D) IV
E) V
Ans: B

SHORT ANSWER QUESTIONS

Topic: General stereochemistry
Section: 5.1, 5.2
Difficulty Level: Easy

111. An achiral molecule is one that is __________________ upon its mirror image.
Ans: superposable

Topic: General stereochemistry
Section: 5.2
Difficulty Level: Easy

112. Enantiomers are stereoisomers whose molecules are ____________________.
Ans: nonsuperposable mirror images

Topic: General stereochemistry
Section: 5.2C
Difficulty Level: Medium

113. When discussing the stereochemical relationship of cis/trans isomers of cyclic compounds, we refer to them as __________________.
Ans: diastereomers

Topic: General stereochemistry
Section: 5.3
Difficulty Level: Easy

114. A chiral molecule is defined as one that is _____________________ on its mirror image.
Ans: nonsuperposable

Topic: General stereochemistry
Section: 5.2, 5.3
Difficulty Level: Easy

115. To be superposable, when one object is placed on top of another, _________________.
Ans: all parts of each object must coincide

Topic: General stereochemistry
Section: 5.4
Difficulty Level: Easy

116. The molecule of aspartame ( Nutrasweet ), depicted below, has ___________ ( how many? ) stereogenic centers.

Ans: two

Topic: General stereochemistry
Section: 5.6
Difficulty Level: Easy

117. All molecules with a plane of symmetry are _________.
Ans: achiral

Topic: General stereochemistry
Section: 5.7
Difficulty Level: Easy

118. When using the Cahn-Ingold-Prelog rules for prioritizing groups on a stereogenic carbon, priority is first assigned on the basis of ____________________.
Ans: atomic number

Topic: Nomenclature
Section: 4.3, 5.7
Difficulty Level: Easy

119. Draw a dash-wedge structure for (R)-2,3,5-trimethylhexane
Ans:

Topic: Nomenclature
Section: 4.4, 5.7
Difficulty Level: Easy

120. Draw a dash-wedge structure for (1R)-1-bromo-1,3,3-trimethylcyclohexane
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 5.7
Difficulty Level: Medium

121. Draw a dash-wedge structure for (3R)-3-methyl-5-hexen-3-ol
Ans:

Topic: Nomenclature
Section: 4.3, 4.6, 5.7
Difficulty Level: Easy

122. Draw a dash-wedge structure for (R)-5-methylhept-2-yne
Ans:

Topic: Nomenclature
Section: 4.3, 4.6, 5.7
Difficulty Level: Medium

123. Draw a dash-wedge structure for (S,trans)-5-fluoro-2,2-dimethylhex-3-ene
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 4.6, 5.7
Difficulty Level: Medium

124. Draw a dash-wedge structure for (R,cis)-hept-3-en-5-yn-2-ol
Ans:

Topic: General stereochemistry
Section: 5.8
Difficulty Level: Easy

125. Enantiomers have ______________ physical properties.
Ans: identical

Topic: General stereochemistry
Section: 5.8B
Difficulty Level: Medium

126. The device that is used for measuring the effect of optically active compounds on plane-polarized light is called a ________________.
Ans: polarimeter

Topic: General stereochemistry
Section: 5.8C
Difficulty Level: Easy

127. True or false: A sample consisting of the pure R enantiomer of a compound will always rotate plane-polarized light in a clockwise direction.
A) True
B) False
Ans: B

Topic: General stereochemistry
Section: 5.9A
Difficulty Level: Easy

128. An equimolar mixture of two enantiomers is called a ________________.
Ans: racemic mixture

Topic: General stereochemistry
Section: 5.12A
Difficulty Level: Easy

129. A molecule that contains stereogenic carbons but is nonetheless achiral is referred to as a ______________.
Ans: meso compound

Topic: General stereochemistry
Section: 5.12A
Difficulty Level: Medium

130. A meso compound has __________ chiral center(s), and is __________ upon its mirror image.
Ans: two or more, superposable

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Medium

131. Draw a dash-wedge structure for (2S,3S)-3-methylpent-4-en-2-ol
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Medium

132. Draw a dash-wedge structure for (3R,6R)-3-bromo-6-methylcyclohex-1-ene
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Medium

133. Draw a dash-wedge structure for (3R,4R)-4-bromo-1,3-dimethylcyclohex-1-ene
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Easy

134. Draw a dash-wedge structure for (2R,3S)-2-chloro-3-methylpentane
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Easy

135. Draw a dash-wedge structure for (3R,4S)-4,6-dimethylheptan-3-ol
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Easy

136. Draw a dash-wedge structure for (2R,3S)-2-bromo-3-chlorohexane
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Medium

137. Draw a dash-wedge structure for (3S,4R)-4-fluoro-2,4-dimethylheptan-3-ol
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Hard

138. Draw a dash-wedge structure for (2R,3R)-3-phenylbutan-2-ol
Ans:

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Hard

139. Draw a dash-wedge structure for (2R,4S)-2,4-dibromo-2-chloropentane
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Medium

140. Draw a dash-wedge structure for (2S,3R)-3-bromo-6,6-dimethyl-7-en-2-ol
Ans:

Topic: Nomenclature
Section: 4.4, 4.5, 5.7, 5.12B
Difficulty Level: Hard

141. Draw a dash-wedge structure for (1R,2S,3S)-3-bromo-2-vinylcyclohexanol
Ans:

Topic: Nomenclature
Section: 4.3, 4.6, 5.7, 5.12B
Difficulty Level: Medium

142. Draw a dash-wedge structure for (3S,4R)-4-chloro-3,5-dimethylhex-1-yne
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Medium

143. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (3S,4S)-3,4-dimethylhex-1-ene

Topic: Nomenclature
Section: 4.3, 4.5, 5.7, 5.12B
Difficulty Level: Hard

144. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (2S,4S)-4-chlorohex-5-en-2-ol

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B
Difficulty Level: Hard

145. Draw a dash-wedge structure for (1R,4R)-1,4-dibromo-1-chloro-1-fluoropentane
Ans:

Topic: Nomenclature
Section: 4.3, 4.5, 4.6, 5.7, 5.12B
Difficulty Level: Hard

146. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (S)-pent-1-en-4-yn-3-ol

Topic: Nomenclature
Section: 4.3, 4.8A, 5.7, 5.12B
Difficulty Level: Hard

147. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (3R,4R)-3,4-dimethylhexan-1-ol

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Easy

148. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (1S)-1-ethyl-1,3,3-trimethylcyclopentane

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Medium

149. Draw a dash-wedge structure for (1S,3R)-1-ethyl-1,3-dimethylcyclopentane
Ans:

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Medium

150. Draw a dash-wedge structure for (1R,3R)-1,3-dibromo-1,3-dimethylcyclohexane
Ans:

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Medium

151. Draw a dash-wedge structure for (1S,2S,5R)-5-methyl-2-propylcyclohexanol
Ans:

Topic: Stereoisomers
Section: 4.4, 5.7, 5.12B
Difficulty Level: Medium

152. Draw dash-wedge structures for all stereoisomers of 1-bromo-3-isopropylcyclohexane, giving stereochemical details for each structure.
Ans:

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Hard

153. Draw a dash-wedge structure for (1S,2R,3R)-1-tert-butyl-3-chloro-2-methylcyclohexane
Ans:

Topic: Nomenclature
Section: 4.4, 5.7, 5.12B
Difficulty Level: Hard

154. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (1S,3S)-methylcyclohexanol

Topic: Nomenclature
Section: 4.5, 5.7, 5.12B
Difficulty Level: Medium

155. Draw a dash-wedge structure for (3S,5R)-5-chloro-3-isopropylcyclohex-1-ene
Ans:

Topic: Fischer projections
Section: 5.7, 5.13
Difficulty Level: Hard

156. Which Fischer projection illustrates compound A:

A) I.
B) II.
C) III.
D) IV.
E) V.
Ans: A

Topic: Nomenclature
Section: 4.3, 5.7, 5.12B, 5.13
Difficulty Level: Medium

157. What is the complete IUPAC name of the following substance? (Remember to give stereochemical details, as relevant.)

Ans: (3R,4S)-4-bromo-2,3-dimethylhexane

Topic: Fischer projections
Section: 4.3, 5.7, 5.12B, 5.13
Difficulty Level: Hard

158. Draw Fischer projection formulas for all stereoisomers of 2,4-dibromohexane, giving stereochemical details for each structure.
Ans:

Topic: Fischer projections
Section: 4.3, 5.7, 5.12B, 5.13
Difficulty Level: Hard

159. Draw the Fischer projection of the following compound with the lowest priority groups on each chiral carbon in the back: (3R,4S)-4-bromo-4-chloro-3-heptanol.
Ans:

Topic: Fischer projections
Section: 4.3, 4.5, 5.7, 5.12B, 5.13
Difficulty Level: Medium

160. Draw a Fischer projection formula of (3R)-6-Bromo-1-hexen-3-ol.
Ans:

Topic: Fischer projections
Section: 4.4, 5.7, 5.12B, 5.13
Difficulty Level: Hard

161. Draw Fischer projection formulas for all stereoisomers of 2,4-dimethyl-3-hexanol, giving stereochemical details for each structure.
Ans:

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