Organic Chemistry 11th Edition by T. W. Graham Solomons Craig B. Fryhle Scott A. Snyder test bank

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Organic Chemistry 11th Edition by T. W. Graham Solomons Craig B. Fryhle Scott A. Snyder test bank

Description

Chapter Four

MULTIPLE CHOICE QUESTIONS

Topic: Nomenclature
Section: 4.2
Difficulty Level: Easy

1. Which of the following pairs of compounds represent pairs of constitutional isomers?
A) 2-Methylbutane and pentane
B) 2-Chlorohexane and 3-chlorohexane
C) sec-Butyl bromide and tert-butyl bromide
D) Propyl chloride and isopropyl chloride
E) All of the above
Ans: E

Topic: General
Section: 4.2
Difficulty Level: Easy

2. How many constitutional isomers are possible for the formula C6H14?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: D

Topic: General
Section: 4.2 and 4.3
Difficulty Level: Easy

3. What is the simplest alkane, i.e., the one with the smallest molecular weight, which possesses primary, secondary and tertiary carbon atoms?
A) 2-Methylpropane
B) 2-Methylbutane
C) 2-Methylpentane
D) 3-Methylpentane
E) 2,2-Dimethylbutane
Ans: B

Topic: General
Section: 4.2 and 4.3
Difficulty Level: Medium

4. How many alkanes of formula C7H16 possess a quaternary carbon atom?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: C

Topic: Nomenclature
Section: 4.3B
Difficulty Level: Easy

5. The IUPAC name for is:
A) 6-Ethyl-3,4-dimethylheptane
B) 2-Ethyl-4,5-dimethylheptane
C) 3,4,6-Trimethyloctane
D) 3,5,6-Trimethyloctane
E) 2-(1-Methylpropyl)-4-methylhexane
Ans: C

Topic: Nomenclature
Section: 4.3B
Difficulty Level: Medium

6. An IUPAC name for is:
A) 5-Methyl-4-(1-methylpropyl)hexane
B) 2-Methyl-3-(1-methylpropyl)hexane
C) 2-Methyl-3-(2-methylpropyl)hexane
D) 3-Methyl-4-(1-methylethyl)heptane
E) 5-Methyl-4-(1-methylethyl)heptane
Ans: D

Topic: Nomenclature
Section: 4.3B
Difficulty Level: Medium

7. A correct IUPAC name for the following compound is:

A) 2,5-Dimethyl-3-propylheptane
B) 3,6-Dimethyl-5-propylheptane
C) 6-Methyl-4-(1-methylethyl)octane
D) 2-Methyl-3-(2-methylbutyl)hexane
E) 3-Methyl-5-(1-methylethyl)octane
Ans: E

Topic: Nomenclature
Section: 4.3C
Difficulty Level: Easy

8. Which of these is the common name for the 1,1-dimethylpropyl group?
A) tert-Butyl
B) tert-Pentyl
C) Isopentyl
D) Neopentyl
E) sec-Pentyl
Ans: B

Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium

9. An IUPAC name for the group is:
A) Isopentyl
B) Isoamyl
C) sec-Butylmethyl
D) 2-Methylbutyl
E) 2-Ethylpropyl
Ans: D

Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium

10. The neopentyl group has the alternative name:
A) 1,1-Dimethylpropyl
B) 1,2-Dimethylpropyl
C) 2,2-Dimethylpropyl
D) 1-Methylbutyl
E) 2-Methylbutyl
Ans: C

Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium

11. Isopentyl is the common name for which alkyl group?
A)
B)
C)
D)
E)
Ans: C

Topic: Nomenclature
Section: 4.3C
Difficulty Level: Hard

12. Neglecting stereochemistry, which of these common group names is ambiguous, i.e., does not refer to one specific group?
A) Butyl
B) sec-Butyl
C) tert-Pentyl
D) Neopentyl
E) sec-Pentyl
Ans: E

Topic: Nomenclature
Section: 4.3B/C
Difficulty Level: Easy

13. What is a correct name for the following compound?

A) 3-Isobutyl-2-methylheptane
B) 3-sec-Butyl-2-methyloctane
C) 5-Isobutyl-6-methylheptane
D) 2-Ethyl-3-isopropyloctane
E) 4-Isopropyl-3-methylnonane
Ans: E

Topic: Nomenclature
Section: 4.3B/C
Difficulty Level: Medium

14. An IUPAC name for is:
A) 3-Isobutyl-2,4-dimethylhexane
B) 3-sec-Butyl-2,5-dimethylhexane
C) 4-sec-Butyl-2,5-dimethylhexane
D) 4-Isopropyl-2,5-dimethylheptane
E) 4-Isopropyl-3,6-dimethylheptane
Ans: D

Topic: Nomenclature
Section: 4.3B/C
Difficulty Level: Medium

15. An IUPAC name for the following compound is:

A) 4-Isobutyl-3,4-dimethylheptane
B) 4-sec-Butyl-2,4-dimethylheptane
C) 2,4,5-Trimethyl-4-propylheptane
D) 3,4,6-Trimethyl-4-propylheptane
E) 4-Isobutyl-4,5-dimethylheptane
Ans: C

Topic: General
Section: 4.2, 4.3D
Difficulty Level: Medium

16. How many compounds with the formula C7H16 (heptanes) contain a single 3 carbon atom?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: C

Topic: Nomenclature
Section: 4.3E
Difficulty Level: Easy

17. What is the common name for this compound?

A) Isobutyl bromide
B) tert-Butyl bromide
C) Butyl bromide
D) sec-Butyl bromide
E) Bromo-sec-butane
Ans: A

Topic: Nomenclature
Section: 4.3E
Difficulty Level: Medium

18. The correct IUPAC name for is:
A) 2-Bromo-4-chloro-4-isopropylpentane
B) 4-Bromo-2-chloro-2-isopropylpentane
C) 5-Bromo-3-chloro-2,3-dimethylhexane
D) 2-Bromo-4-chloro-4,5-dimethylhexane
E) 2-(2-Bromopropyl)-2-chloro-3-methylbutane
Ans: C

Topic: Nomenclature
Section: 4.3F
Difficulty Level: Easy

19. What is the correct IUPAC name for the following compound?

A) 3-Hydroxymethylheptane
B) 3-Hydroxymethylhexane
C) 3-Methyloxyheptane
D) 2-Ethyl-1-hexanol
E) 2-Ethyl-1-heptanol
Ans: D

Topic: Nomenclature
Section: 4.3F
Difficulty Level: Easy

20. What is the correct IUPAC name for the following compound?

A) 5-Ethyl-3-methylhexanol
B) 5-Ethyl-3-methyl-1-hexanol
C) 2-Ethyl-4-methyl-6-hexanol
D) 3,5-Dimethyl-7-heptanol
E) 3,5-Dimethyl-1-heptanol
Ans: E

Topic: Nomenclature
Section: 4.3F
Difficulty Level: Easy

21. What is the correct IUPAC name for the following compound?

A) 5-Ethyl-3-fluorohexanol
B) 5-Ethyl-3-fluoro-1-hexanol
C) 2-Ethyl-4-fluoro-6-hexanol
D) 3-fluoro-5-methyl-7-heptanol
E) 3-fluoro-5-methyl-1-heptanol
Ans: E

Topic: Nomenclature
Section: 4.3F
Difficulty Level: Medium

22. Which of the following is a correct name which corresponds to the common name tert-pentyl alcohol?
A) 2,2-Dimethyl-1-propanol
B) 2-Ethyl-2-propanol
C) 2-Methyl-2-butanol
D) 3-Methyl-1-butanol
E) Methyl tert-butanol
Ans: C

Topic: Nomenclature
Section: 4.3B/E/F
Difficulty Level: Medium

23. A correct IUPAC name for the following compound is:

A) 4-propyl-5-chloro-3-heptanol
B) 4-propyl-3-chloro-5-heptanol
C) 4-(1-chloropropyl)-3-heptanol
D) 5-chloro-4-propyl-3-heptanol
E) 3-hydroxy-4-propyl-5-chloroheptane
Ans: D

Topic: Nomenclature
Section: 4.3F and 4.4
Difficulty Level: Hard

24. The correct IUPAC name for the following compound is:

A) 1-Hydroxy-3-sec-butylcyclopentane
B) 3-sec-Butyl-1-cyclopentanol
C) 1-sec-Butyl-3-cyclopentanol
D) 4-sec-Butyl-1-cyclopentanol
E) 3-Isobutyl-1-cyclopentanol
Ans: B

Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium

25. The most stable conformation of 3-bromo-2-methylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):

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

Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium

26. The least stable conformation of 3-bromo-2-methylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):

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

Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium

27. The most stable conformation of 2,3-dimethylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):

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

Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium

28. The least stable conformation of 2,3-dimethylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):

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

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

29. Which of the following is bicyclo[3.2.2]nonane?

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

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

30. Which compound is a bicycloheptane?

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

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

31. Which is the correct name for the compound shown below?

A) Bicyclo[2.2.0]hexane
B) Bicyclo[2.2.0]butane
C) Bicyclo[2.2.2]hexane
D) Bicyclo[2.2.1]hexane
E) Disquarane
Ans: A

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

32. What is the name of this compound?

A) Bicyclo[2.2.2]octane
B) Bicyclo[3.2.1]octane
C) Bicyclo[4.1.1]octane
D) Bicyclo[4.2.0]octane
E) Bicyclo[3.3.0]octane
Ans: D

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

33. Which of the above is bicyclo[3.3.1]nonane?
A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

34. Which of the above is bicyclo[5.2.0]nonane?
A) I
B) II
C) III
D) IV
E) V
Ans: E

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

35. Which of the above is bicyclo[4.3.0]nonane?
A) I
B) II
C) III
D) IV
E) V
Ans: A

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy

36. Which of the following structures represents bicyclo[3.2.1]octane?

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

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard

37. A correct name for the following compound is:

A) 2-Methylbicyclo[4.3.0]nonane
B) 1-Methylbicyclo[4.3.1]nonane
C) 7-Methylbicyclo[4.3.0]nonane
D) 2-Methylbicyclo[4.3.1]nonane
E) 1-Methylbicyclo[4.3.0]nonane
Ans: A

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard

38. What is the correct name of the following compound?

A) 1-Chlorobicyclo[4.1.1]octane
B) 2-Chlorobicyclo[4.1.0]octane
C) 2-Chlorobicyclo[4.1.1]octane
D) 2-Chlorobicyclo[4.1.1]heptane
E) 5-Chlorobicyclo[4.1.1]octane
Ans: C

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard

39. A correct name for the following compound is:

A) 3-chloro-8-methylbicyclo[4.3.0]nonane
B) 8-Methyl-3-chlorobicyclo[4.3.1]nonane
C) 3-Methyl-7-chlorobicyclo[4.3.0]nonane
D) 3-Methyl-7-chlorobicyclo[4.3.1]decane
E) 3-chloro-8-methyl[4.3.0]bicyclononane
Ans: A

Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard

40. A correct name for the following compound is:

A) 4-bromo-3,8-dimethylbicyclo[5.2.2]nonane
B) 3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane
C) 4-bromo-3,8-dimethylbicyclo[5.2.1]decane
D) 7-bromo-2,6-dimethylbicyclo[5.2.0]nonane
E) 4-bromo-3,8-dimethylbicyclo[5.2.0]nonane
Ans: E

Topic: Nomenclature
Section: 4.5
Difficulty Level: Medium

41. A correct IUPAC name for the following compound is:

A) 3,6,7-trimethyl-4-bromo-1-octene
B) 4-bromo-3-methyl-6-isopropyl-1-heptene
C) 4-bromo-3,6,7-trimethyl-1-octene
D) 4-bromo-6-isopropyl-3-methyl-1-heptene
E) 4-bromo-6-isopropyl-3,6-dimethyl-1-hexene
Ans: C

Topic: Nomenclature
Section: 4.5
Difficulty Level: Hard

42. What is the correct IUPAC name for the following compound?

A) trans-3-Hydroxymethyl-2-heptene
B) trans-2-(1-methylethyl)-4-hexen-1-ol
C) trans-5-(1-methylethyl)-2-hexen-6-ol
D) cis-5-isopropyl-2,6-hexenol
E) cis-2-(1-methylethyl)-4-hepten-1-ol
Ans: B

Topic: Nomenclature
Section: 4.6
Difficulty Level: Easy

43. Give the IUPAC name for

A) 3-Methyl-4-hexyne
B) 4-Methyl-2-hexyne
C) 2-Ethyl-3-pentyne
D) 4-Ethyl-2-pentyne
E) 3-Methyl-2-hexyne
Ans: B

Topic: Nomenclature
Section: 4.6
Difficulty Level: Easy

44. The IUPAC name for diisobutylacetylene is
A) 2,7-Dimethyl-4-octene
B) 2,7-Dimethyl-4-octyne
C) 3,6-Dimethyl-4-octyne
D) 2,5-Diethyl-3-hexyne
E) 2,2,5,5-Tetramethyl-3-hexyne
Ans: B

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy

45. The least stable conformation of butane is:

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy

46. The most stable conformation of butane is:

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy

47. The least stable conformation of butane is:

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy

48. The most stable conformation of 1,2-dibromoethane is:

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

49. Which conformation(s) of 1,2-dibromoethane does not illustrate one or more gauche interactions?

A) I and II only
B) II, III, and V only
C) I, III, and IV only
D) All but one above
E) All the above
Ans: D

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

50. The most stable conformation of 3-bromo-2-methylpentane, viewed through the
C-3C-4 bond (i.e., C-3 in the front, C-4 in the back):

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

51.
The most stable conformation of 2,3-dibromobutane, viewed through the C-2C-3 bond :

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

52.
Which conformation(s) show(s) the bromines in a gauche orientation for 2,3-dibromobutane, viewed through the C-2C-3 bond?

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

53. The least stable conformation of 3-bromo-2-methylpentane, viewed through the
C-3C-4 bond (i.e., C-3 in the front, C-4 in the back):

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

54. Consider the graph below, which is a plot of the relative energies of the various conformations of hexane, viewed through the C-2C-3 bond. The conformations corresponding to the 60o and 300o are:

A) Eclipsed
B) Staggered and gauche
C) Staggered and anti
D) More stable than the conformation at 180o
E) None of the above
Ans: B

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium

55. Consider the graph below, which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane, viewed through the C-2C-3 bond. The conformations corresponding to the 120o and 240o are:

A) Eclipsed, more stable than the conformation at 0o
B) Eclipsed, more stable than the conformation at 180o
C) Staggered, more stable than the conformation at 0o
D) Staggered, less stable than the conformation at 180o
E) Two of the above are true
Ans: A

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

56.
Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrates the following boxed compound?

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

57.
Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrates the following boxed compound?

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

58.
Which staggered Newman projection(s), looking down the C-3C-4 bond (C-3 in front and C-4 in back), illustrate(s) the following boxed compound?

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

59.
Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrate(s) the following boxed compound?

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

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

60. The graph below is a plot of the relative energies of the various conformations of:

A) Ethane
B) Propane
C) Chloroethane
D) 1-Chloropropane (C1-C2 rotation)
E) Butane (C1-C2 rotation)
Ans: D

Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard

61. The graph below is a plot of the relative energies of the various conformations of:

A) 2-chloropropane
B) 1,3-dichloropropane
C) 2-methylpropane
D) Butane (C1-C2 rotation)
E) Butane (C2-C3 rotation)
Ans: E

Topic: Conformational Analysis
Section: 2.13 and 4.8A
Difficulty Level: Medium

62. The most stable conformation for 1,2-ethanediol (ethylene glycol) is shown below. It is the most stable conformation because:

A) this corresponds to an anti conformation.
B) in general, gauche conformations possess the minimum energy.
C) it is stabilized by intramolecular hydrogen bonding.
D) it is a staggered conformation.
E) it has the highest energy of all the possibilities.
Ans: C

Topic: Ring Strain
Section: 4.10
Difficulty Level: Easy

63. Which cycloalkane has the greatest ring strain?
A) Cyclopropane
B) Cyclobutane
C) Cyclopentane
D) Cyclohexane
E) Cycloheptane
Ans: A

Topic: Ring Strain
Section: 4.10
Difficulty Level: Easy

64. Which cycloalkane has the least ring strain?
A) Cyclopropane
B) Cyclobutane
C) Cyclopentane
D) Cyclohexane
E) Cycloheptane
Ans: D

Topic: Ring Strain
Section: 4.11
Difficulty Level: Easy

65. Which is the most stable conformation of cyclohexane?
A) Chair
B) Twist
C) Boat
D) One-half chair
E) Staggered
Ans: A

Topic: Conformational Analysis
Section: 4.11
Difficulty Level: Easy

66. The least stable conformation of cyclohexane is the:
A) boat.
B) twist boat.
C) chair.
D) half-chair.
E) twist chair.
Ans: D

Topic: Conformational Analysis
Section: 4.12
Difficulty Level: Medium

67. The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the molecule exists in a boat conformation.
Ans: D

Topic: Nomenclature
Section: 4.13
Difficulty Level: Easy

68. Select the systematic name for

A) cis-1,3-Dichlorocyclopentane
B) trans-1,4-Dichlorocyclopentane
C) cis-1,2-Dichlorocyclopentane
D) trans-1,3-Dichlorocyclopentane
E) 1,1-Dichlorocyclopentane
Ans: D

Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium

69. trans-1,2-Dibromocyclohexane is represented by structure(s):
A) I
B) II
C) III
D) II and III
E) I and II
Ans: D

Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium

70. cis-1,2-Dibromocyclohexane is represented by structure(s):
A) I
B) II
C) III
D) II and III
E) I and II
Ans: A

Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium

71. cis-1,3-Dibromocyclohexane is represented by structure(s):

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

Topic: Conformational Analysis
Section: 4.13
Difficulty Level: Medium

72. What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?

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

Topic: Conformational Analysis
Section: 4.13
Difficulty Level: Medium

73. The twist boat conformation is the preferred conformation for this compound.
A) cis-1,4-Di-tert-butylcyclohexane
B) trans-1,4-Di-tert-butylcyclohexane
C) cis-1,3-Di-tert-butylcyclohexane
D) trans-1,2-Di-tert-butylcyclohexane
E) None of these
Ans: A

Topic: Nomenclature
Section: 4.5, 4.13
Difficulty Level: Easy

74. Select the structure for cis-3-methyl-6-vinylcyclohexene.

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

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

75. The most stable conformation of cis-1-tert-butyl-2-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the twist boat conformation is adopted.
Ans: B

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

76. The most stable conformation of trans-1-tert-butyl-2-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the molecule is in the half chair conformation.
Ans: D

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

77. The most stable conformation of trans-1-tert-butyl-3-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the twist boat conformation is adopted.
Ans: B

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

78. In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are:
A) one axial, one equatorial.
B) both axial.
C) both equatorial.
D) alternating between being both axial and both equatorial.
E) None of the above
Ans: A

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

79. Which conformation of trans-1-isopropyl-3-methylcyclohexane would be present in greatest amount at equilibrium?
A) The conformation with the methyl group equatorial and the isopropyl group axial.
B) The conformation with the methyl group axial and the isopropyl group equatorial.
C) The conformation with both groups axial.
D) The conformation with both groups equatorial.
E) The twist boat conformation.
Ans: B

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

80. Which conformation represents the most stable conformation of trans-1-bromo-4-methylcyclohexane?

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

Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium

81. Which of the following will have the same energy after undergoing ring flip?

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

Topic: Cis-Trans Isomers
Section: 4.12 and 4.13
Difficulty Level: Easy

82. Which of the following can be described as cis isomers?

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

Topic: Cis-Trans Isomers
Section: 4.12 and 4.13
Difficulty Level: Easy

83. Which of the following can be described as trans isomers?

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

Topic: Ring Strain
Section: 4.14
Difficulty Level: Medium

84. Which of these C10H18 isomers is predicted to be the most stable?

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

Topic: Alkane Synthesis
Section: 4.16
Difficulty Level: Easy

85. Select the reagents necessary to convert cyclopentene into cyclopentane.
A) H2 and Ni
B) H2O
C) Heat
D) Zn, H3O+
E) Light
Ans: A

Topic: Catalytic hydrogenation
Section: 4.16
Difficulty Level: Easy

86. Which alkene would yield 3-methylpentane when subjected to catalytic hydrogenation?
A)
B)
C)
D)
E)
Ans: B

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

87. Catalytic hydrogenation of which of the following will yield 2-methylpentane?
A) 2-methyl-1-pentene
2
B) 2-methyl-2-pentene
C) 4-methyl-2-pentene
D) 4-methyl-1-pentene
E) All of the above
Ans: E

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

88. How many moles of hydrogen (H2) will react with (trans, trans)-hepta-3,5-dien-1-yne?
A) 1
2
B) 2
C) 3
D) 4
E) 5
Ans: D

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

89. How many moles of hydrogen (H2) will react with 3-cyclobutylpropan-1-ol?
A) 1
2
B) 2
C) 3
D) 4
E) None of the above
Ans: E

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

90. How many moles of hydrogen (H2) will react with 5-chlorocyclohex-3-en-1-ol?
A) 1
2
B) 2
C) 3
D) 4
E) None of the above
Ans: A

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

91. How many moles of hydrogen (H2) will react with cylohexa-2,5-diene-1,4-diol?
A) 1
2
B) 2
C) 3
D) 4
E) None of the above
Ans: B

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

92. How many moles of hydrogen (H2) will react with 3-vinylcyclo-2-penten-1-ol?
A) 0
2
B) 1
C) 2
D) 3
E) 4
Ans: C

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

93. How many moles of hydrogen (H2) will react with trans-1,2-dimethylcyclohexane?
A) 0
2
B) 1
C) 2
D) 3
E) 4
Ans: A

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium

94. How many moles of hydrogen (H2) will react with cis-2,3,3-trimethylhepta-1,5-diene?
A) 0
2
B) 1
C) 2
D) 3
E) 4
Ans: C

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Easy

95. What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H2?
A) No reaction
2
B) cis-1,2-dimethylcyclohexane
C) trans-3,4-dimethylhexane
D) trans-1,2-dimethylhexane
E) None of the above
Ans: A

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium

96. What product is formed when cis-2,3,3-trimethylhepta-1,5-diene is reacted with Pd/C and H2?
A) cis-5,5,6-trimethylhept-2-ene
2
B) 2,3,3-trimethylhept-1-ene
C) 5,5,6-trimethylheptane
D) 2-isopropyl-2-methylhexane
E) None of the above
Ans: E

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium

97. What product is formed when 3-cyclobutylpropan-1-ol is reacted with Pd/C and H2?
A) 3-cyclobutylpropane 2
B) 1-propanol
C) No reaction
D) hexane
E) None of the above
Ans: C

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium

98. What product is formed when 5-chlorocyclohex-3-en-1-ol is reacted with Pd/C and H2?
A) 5-chlorocyclohexanol
2
B) 3-chlorocyclohexanol
C) 5-chloro-3-hexanol
D) 2-chloro-4-hexanol
E) None of the above
Ans: B

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium

99. What product is formed when 3-vinylcyclo-2-penten-1-ol is reacted with Pd/C and H2?
A) 3-vinylcyclopentanol
2
B) 3-ethylcyclo-2-penten-1-ol
C) 4-ethylcyclopentanol
D) 3-ethylcyclopentanol
E) None of the above
Ans: D

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium

100. What product is formed when 2,3,3-trimethylhept-1-en-6-yne is reacted with Pd/C and H2?
A) 2,3,3-trimethylheptan-6-yne
2
B) 2,3,3-trimethylheptan-1-ene
C) 5,5,6-trimethylheptan-6-yne
D) 2,3,3-trimethylheptane
E) None of the above
Ans: D

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Hard

101. What product is formed when cylohexa-2,5-diene-1,4-diol is reacted with Pd/C and H2?
A) hexane-1,4-diol
2
B) cyclohexa-2-ene-1,4-diol
C) cyclohexane-1,4-diol
D) hexane-1,4-diol
E) None of the above
Ans: C

Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Hard

102. What product is formed when (trans, trans)-hepta-3,5-dien-1-yne is reacted with Pd/C and H2?
A) heptane
2
B) 1-heptyne
C) 1-ethylpentane
D) trans-2-heptene
E) None of the above
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

103. What is the index of hydrogen deficiency (or degree of unsaturation) of benzene (C6H6)?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: C

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

104. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

105. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

106. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: B

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

107. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: C

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

108. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

109. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

110. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

111. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C6H2O2?
A) 3
B) 4
C) 5
D) 6
E) 7
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

112. What is the index of hydrogen deficiency (or degree of unsaturation) for retinol?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy

113. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug lidocain?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: C

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Easy
114. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C8H3Br5O2?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

115. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug Cetilistat?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

116. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug THC?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

117. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Ans: B

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

118. What is the index of hydrogen deficiency (or degree of unsaturation) of the following compound?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

119. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C21H30O5?
A) 3
B) 4
C) 5
D) 6
E) 7
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

120. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C14H14Cl4?
A) 3
B) 4
C) 5
D) 6
E) 7
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

121. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C9H18N2?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

122. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C7H7NOS?
A) 2
B) 3
C) 4
D) 5
E) 6
Ans: D

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Medium

123. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C6H5BrClN?
A) 0
B) 1
C) 2
D) 3
E) 4
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Hard

124. What is the index of hydrogen deficiency (or degree of unsaturation) of the hormone cortisol?

A) 3
B) 4
C) 5
D) 6
E) 7
Ans: E

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Hard

125. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C11H20Br3F4N3O3?
A) 0
B) 1
C) 2
D) 3
E) 4
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Hard

126. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of H6N4O3?
A) 0
B) 1
C) 2
D) 3
E) 4
Ans: A

Topic: Index of Hydrogen of Deficiency
Section: 4.17
Difficulty Level: Hard

127. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug morphine?

A) 6
B) 7
C) 8
D) 9
E) 10
Ans: D

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A and 4.17
Difficulty Level: Medium

128. Which statement(s) is/are true about a molecule with the molecular formula C10H20, that when subjected to catalytic hydrogenation there is no consumption of hydrogen?
A) The molecule has no degrees of unstaturation.
2
B) There is one degree of unsaturation, which happens to be a pi-bond.
C) There are two degrees of unsaturation where one is a ring and the other is a pi-bond.
D) There is one degree of unsaturation, which happens to be a ring.
E) None of the above.
Ans: D

Topic: Alkane Synthesis, Nomenclature
Section: 4.16A and 4.17
Difficulty Level: Medium

129. Which statement(s) is/are true about a molecule with the molecular formula C10H14O, that when subjected to Pd/C and H2 in ethyl acetate, there is a consumption of 2 moles of hydrogen?
A) The molecule has no degrees of unsaturation.
2
B) There are four degrees of unsaturation, where two come from either two alkenes or one alkyne and the other two are either two rings or one ring and a carbonyl.
C) There are two degrees of unsaturation where they were either two alkenes or one alkyne.
D) There are four degrees of unsaturation, which come from a mixture of alkenes and alkynes, that is why four hydrogens are added.
E) None of the above.
Ans: B

SHORT ANSWER QUESTIONS

Topic: Nomenclature
Section: 4.1
Difficulty Level: Easy

130. Alkanes in which some or all of the carbon atoms are arranged in a ring are called ___________________________.
Ans: cycloalkanes

Topic: Nomenclature
Section: 4.3
Difficulty Level: Easy

131. What is the fundamental principle of the IUPAC system of nomenclature for organic compounds?
Ans: Each different compound should have an unambiguous name.

Topic: Nomenclature
Section: 4.3
Difficulty Level: Easy

132. Give the IUPAC name corresponding to the following structure:

Ans:

Topic: Nomenclature
Section: 4.3
Difficulty Level: Medium

133. Give the IUPAC name corresponding to the following structure:

Ans:

Topic: General
Section: 4.3B
Difficulty Level: Easy

134. To determine the parent name for an alkane, we begin by finding the ___________________________.
Ans: longest continuous chain of carbons

Topic: Nomenclature
Section: 4.3B
Difficulty Level: Easy

135. When more than one substituent is present on the parent chain, how do we organize the names of the substituents in the name of the compound? ___________________________.
Ans: alphabetical order

Topic: Nomenclature
Section: 4.3B
Difficulty Level: Medium

136. What are the four possible parts of an IUPAC name?
Ans: locant, prefix, parent name, suffix

Topic: Nomenclature
Section: 4.3 and 4.4A
Difficulty Level: Hard

137. Give the IUPAC name corresponding to the following structure:

Ans:

Topic: General
Section: 4.4B
Difficulty Level: Easy

138. A compound containing two fused or bridged rings is referred to as a ___________________________.
Ans: bicycloalkane

Topic: General
Section: 4.4B
Difficulty Level: Easy

139. In a bicyclic compound, the carbon atoms common to both rings are called ___________________________.
Ans: bridgeheads

Topic: General
Section: 4.6
Difficulty Level: Easy

140. A compound containing a triple bond between the first two carbons in the chain is called a ___________________________.
Ans: terminal alkyne

Topic: Nomenclature
Section: 4.6
Difficulty Level: Medium

141. Draw the bond-line structural formula corresponding to the name: 2,5,9-trimethyl-2-decen-7-yne
Ans:

Topic: General
Section: 4.8A
Difficulty Level: Easy

142. When non-bonded atoms/groups are closely positioned, the repulsive interactions between their electron clouds are referred to as ___________________________.
Ans: steric hindrance

Topic: Alkane Conformations
Section: 4.8A
Difficulty Level: Easy

143. Draw the Newman projection formula for the gauche conformation of the C-2C-3 bond in pentane.
Ans:

Topic: Alkane Conformations
Section: 4.8A
Difficulty Level: Easy

144. Draw the Newman projection formula for the most stable conformation of the C2-C3 bond in 3-methylpentane.
Ans:

Topic: General
Section: 4.9A
Difficulty Level: Easy

145. _____________________ have the same molecular formula and connectivity but different arrangements of atoms in three-dimensional space.
Ans: Stereoisomers

Topic: Nomenclature
Section: 4.11 and 4.13
Difficulty Level: Easy

146. Give the IUPAC name corresponding to the following structure:

Ans:

Topic: Nomenclature, Conformations
Section: 4.11, 4.12, and 4.13
Difficulty Level: Hard

147. Draw the bond-line structural formula corresponding to the most stable conformation of the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane
Ans:

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