Chapter 4

Chapter 4

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

MULTIPLE CHOICE QUESTIONS

Part 4 Nomenklatur -konformation
(Answers on pages 21-22) Uppgifter markerade * r verkurs
Topic: Nomenclature
1.

A)
B)
C)
D)
E)

OH

The IUPAC name for

6-Ethyl-3,4-dimethylheptane
2-Ethyl-4,5-dimethylheptane
3,4,6-Trimethyloctane
3,5,6-Trimethyloctane
2-(1-Methylpropyl)-4-methylhexane

is:

An IUPAC name for

5-Methyl-4-(1-methylpropyl)hexane
2-Methyl-3-(1-methylpropyl)hexane
2-Methyl-3-(2-methylpropyl)hexane
3-Methyl-4-(1-methylethyl)heptane
5-Methyl-4-(1-methylethyl)heptane

is:

5.
A)
B)
C)
D)
E)

Which of the following pairs of compounds represent pairs of constitutional isomers?

2-Methylbutane and pentane
2-Chlorohexane and 3-chlorohexane
sec-Butyl bromide and tert-butyl bromide
Propyl chloride and isopropyl chloride
All of the above

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

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

A)
B)
C)
D)
E)

Cl

4-propyl-5-chloro-3-heptanol
4-propyl-3-chloro-5-heptanol
4-(1-chloropropyl)-3-heptanol
5-chloro-4-propyl-3-heptanol
3-hydroxy-4-propyl-5-chloroheptane

Topic: Nomenclature

2.

A)
B)
C)
D)
E)

A)
B)
C)
D)
E)

2,5-Dimethyl-3-propylheptane
3,6-Dimethyl-5-propylheptane
6-Methyl-4-(1-methylethyl)octane
2-Methyl-3-(2-methylbutyl)hexane
3-Methyl-5-(1-methylethyl)octane

A)
B)
C)
D)
E)

I
II
III
IV
V

II

IV

III

7. Select the systematic name for

A)
B)
C)
D)
E)

87

Cl

Cl

cis-1,3-Dichlorocyclopentane
trans-1,4-Dichlorocyclopentane
cis-1,2-Dichlorocyclopentane
trans-1,3-Dichlorocyclopentane
1,1-Dichlorocyclopentane

88

Chapter 4

9.
A)
B)
C)
D)
E)

Chapter 4

Which isomer of C5H10 would you expect to have the smallest heat of combustion*?
Cyclopentane
Methylcyclobutane
1,1-Dimethylcyclopropane
cis-1,2-Dimethylcyclopropane
trans-1,2-Dimethylcyclopropane

Topic: Nomenclature

18.
A)
B)
C)
D)
E)

trans-1,2-Dibromocyclohexane is represented by structure(s):

I
II
III
II and III
I and II

19.
A)
B)
C)
D)
E)

cis-1,2-Dibromocyclohexane is represented by structure(s):

I
II
III
II and III
I and II

12. What is the common name for this compound?

Br

A)
B)
C)
D)
E)

Isobutyl bromide
tert-Butyl bromide
Butyl bromide
sec-Butyl bromide
Bromo-sec-butane

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

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

Br

3,6,7-trimethyl-4-bromo-1-octene
4-bromo-3-methyl-6-isopropyl-1-heptene
4-bromo-3,6,7-trimethyl-1-octene
4-bromo-6-isopropyl-3-methyl-1-heptene

Use the following to answer questions 18-19:

Br

H
Br

Br
H

Br

Br

Br

II

III

89

Br

Br
H

A)
B)
C)
D)

Br

Br
H
Br

Br

II

III

A)
B)
C)
D)
E)

I
II
III
II and III
I and II

21.
A)
B)
C)
D)
E)

CH3CHCH2!
CH2CH3 is:
An IUPAC name for the group
Isopentyl
Isoamyl
sec-Butylmethyl
2-Methylbutyl
2-Ethylpropyl

22.
A)
B)
C)
D)
E)

The neopentyl group has the alternative name:

1,1-Dimethylpropyl
1,2-Dimethylpropyl
2,2-Dimethylpropyl
1-Methylbutyl
2-Methylbutyl

90

Chapter 4

23.

A)
B)
C)
D)
E)

Chapter 4

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

Br
Cl is:
The correct IUPAC name for
2-Bromo-4-chloro-4-isopropylpentane
4-Bromo-2-chloro-2-isopropylpentane
5-Bromo-3-chloro-2,3-dimethylhexane
2-Bromo-4-chloro-4,5-dimethylhexane
2-(2-Bromopropyl)-2-chloro-3-methylbutane

24. Which of the following is a correct name which corresponds to the common name tertpentyl 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
Topic: Nomenclature
25. The correct IUPAC name for the following compound is:
OH

HO

A)
B)
C)
D)
E)

3-Hydroxymethylheptane
3-Hydroxymethylhexane
3-Methyloxyheptane
2-Ethyl-1-hexanol
2-Ethyl-1-heptanol

30.
A)
B)
C)
D)
E)

Which of these is the common name for the 1,1-dimethylpropyl group*?

tert-Butyl
tert-Pentyl
Isopentyl
Neopentyl
sec-Pentyl

31. 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
32. What is the correct IUPAC name for the following compound?
OH

A)
B)
C)
D)
E)

1-Hydroxy-3-sec-butylcyclopentane
3-sec-Butyl-1-cyclopentanol
1-sec-Butyl-3-cyclopentanol
4-sec-Butyl-1-cyclopentanol
3-Isobutyl-1-cyclopentanol

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

A)
B)
C)
D)
E)

A)
B)
C)
D)
E)

5-Ethyl-3-methylhexanol
5-Ethyl-3-methyl-1-hexanol
2-Ethyl-4-methyl-6-hexanol
3,5-Dimethyl-7-heptanol
3,5-Dimethyl-1-heptanol

3-Isobutyl-2-methylheptane
3-sec-Butyl-2-methyloctane
5-Isobutyl-6-methylheptane
2-Ethyl-3-isopropyloctane
4-Isopropyl-3-methylnonane

91

92

Chapter 4

33. Isopentyl is the common name for which alkyl group?

A) CH3CH2CH2CH

Chapter 4

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

CH3
B) CH3CH2CHCH2

HO

A)
B)
C)
D)
E)

CH3
C) CH3CHCH2CH2
CH3
D) CH3CH2CH

E)

CH3

CH2CH3

3-Hydroxymethyl-2-heptene
2-(1-methylethyl)-4-hexen-1-ol
5-(1-methylethyl)-2-hexen-6-ol
5-isopropyl-2,6-hexenol
2-(1-methylethyl)-4-hepten-1-ol

37. What is the correct IUPAC name for the following compound?
OH

CH3CCH2

CH3

A)
B)
C)
D)
E)

34.

A)
B)
C)
D)
E)

An IUPAC name for

3-Isobutyl-2,4-dimethylhexane
3-sec-Butyl-2,5-dimethylhexane
4-sec-Butyl-2,5-dimethylhexane
4-Isopropyl-2,5-dimethylheptane
4-Isopropyl-3,6-dimethylheptane

is:

5-Ethyl-3-fluorohexanol
5-Ethyl-3-fluoro-1-hexanol
2-Ethyl-4-fluoro-6-hexanol
3-fluoro-5-methyl-7-heptanol
3-fluoro-5-methyl-1-heptanol

38. A correct name for the following compound is:

Cl

A)
B)
C)
D)
E)

3-chloro-8-methylbicyclo[4.3.0]nonane
8-Methyl-3-chlorobicyclo[4.3.1]nonane
3-Methyl-7-chlorobicyclo[4.3.0]nonane
3-Methyl-7-chlorobicyclo[4.3.1]decane
3-chloro-8-methyl[4.3.0]bicyclononane

35. An IUPAC name for the following compound is:

A)
B)
C)
D)
E)

4-Isobutyl-3,4-dimethylheptane
4-sec-Butyl-2,4-dimethylheptane
2,4,5-Trimethyl-4-propylheptane
3,4,6-Trimethyl-4-propylheptane
4-Isobutyl-4,5-dimethylheptane

93

94

Chapter 4

Chapter 4

Topic: Conformational Analysis

Topic: Ring Strain 41-47

40. The least stable conformation of butane is:

H

H3C

H
H

H3C

H
CH3
CH3

H
H

H
H

CH3

H3C

CH3

CH3

CH3

IV

CH3

A)
B)
C)
D)
E)

H
H

IV

A)
B)
C)
D)
E)

I
II
III
IV
V

41.
A)
B)
C)
D)
E)

The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which:

the tert-butyl group is axial and the methyl group is equatorial.
the methyl group is axial and the tert-butyl group is equatorial.
both groups are axial.
both groups are equatorial.
the molecule exists in a boat conformation.

I
II
III
IV
V

CH3
H

H3C
H

CH3

CH3

H3C

II

III
H

CH3

H3C
H

CH3

H3C
H

IV

CH3
H

II

IV

III

A)
B)
C)
D)
E)

I
II
III
IV
V

45.
A)
B)
C)
D)
E)

Which isomer would have the largest heat of combustion*?

Propylcyclopropane
Ethylcyclobutane
Methylcyclopentane
Cyclohexane
Since they are all isomers, all would have the same heat of combustion.

I
II
III
IV
V

III

44. Which cycloalkane has the lowest heat of combustion per CH2 group*?

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

A)
B)
C)
D)
E)

II

III

H
H

II
H

43. Which cycloalkane has the largest heat of combustion per CH2 group*?

95

96

Chapter 4

46.
A)
B)
C)
D)
E)
47.
A)
B)
C)
D)
E)

Chapter 4

Which is the most stable conformation of cyclohexane?

Chair
Twist
Boat
One-half chair
Staggered

50. The most stable conformation of 2,3-dibromobutane, viewed through the C-2C-3
bond :
CH3
Br
Br

I
H3C
H3C

48. The most stable conformation of butane is:

H3C

H
H

A)
B)
C)
D)
E)

H
H

H 3C

H
CH3
CH3

H
H

I
II
III
IV
V

H 3C

II

H
CH3

III

IV

CH3
CH3

CH3

CH3
H

A)
B)
C)
D)
E)

CH3

III
Br

H3C

Br
H

Br

CH3

IV

51. 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):
CH3
Br

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

H
Br

Br

H
H

I
II
III
IV
V

Br

I
II
III
IV
V

A)
B)
C)
D)
E)

Br

II
Br

Topic: Conformational Analysis

H

H3C
Br
Br

H3C
H3C

H
CH3

Which cycloalkane has the greatest ring strain?

Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Cycloheptane

H
H

H
H
Br
Br

H
H

H
Br

Br

Br

Br

Br

III

IV

97

III
CH3
Br

CH(CH3)2

I
II
III
IV
V

CH3
CH(CH3)2

II

A)
B)
C)
D)
E)

Br

H
Br

II

H
CH3
CH(CH3)2

H
H

H
CH(CH3)2

Br

Br
H

CH3

H
CH3

CH2CH3

IV

98

Chapter 4

Chapter 4

52. 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):
H
H

CH3

Br
CH3

Br
H
H
H3C

CH3

H
CH3
CH2CH3

CH3
CH(CH3)2

II

III

CH3

CH3

Br

Br

CH2CH3

CH3

55. 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.

CH2CH3

53. 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):
CH3

H
CH3

CH2CH3

CH2CH3
H

H
H3C

CH3

H
CH(CH3)2

II
CH3
H

H3CH2C

A)
B)
C)
D)
E)

CH3

CH3
H

CH3

CH3

III
H3C

CH3

CH3
CH(CH3)2

IV

CH3

I
II
III
IV
V

99

Which cycloalkane has the least ring strain?

Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Cycloheptane

Topic: Conformational Analysis

I
II
III
IV
V

54.
A)
B)
C)
D)
E)

H
CH3

IV

A)
B)
C)
D)
E)

Br

Topic: Ring Strain

56. 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.
57. 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.
58.
A)
B)
C)
D)
E)

In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are:

one axial, one equatorial.
both axial.
both equatorial.
alternating between being both axial and both equatorial.
None of the above

100

Chapter 4

OH

62. Consider the graph below, which is a plot of the relative energies of the various
conformations of hexane, viewed through the C2-C3 bond. The conformations
corresponding to the 60o and 300o are:
Relative energy

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

Chapter 4

OH
H

A)
B)
C)
D)
E)

this corresponds to an anti conformation.

in general, gauche conformations possess the minimum energy.
it is stabilized by intramolecular hydrogen bonding.
it is a staggered conformation.
it has the highest energy of all the possibilities.

0o

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

60o 120o 180o 240o 300o 360o

Relative energy

Ethane
Propane
Chloroethane
1-Chloropropane (C1-C2 rotation)
Butane (C1-C2 rotation)

Relative energy

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

0o

0o

A)
B)
C)
D)
E)

60o 120o 180o 240o 300o 360o

Angle of rotation

A)
B)
C)
D)
E)

Eclipsed
Staggered, and gauche
Staggered and anti
More stable than the conformation at 180o
None of the above

63. Consider the graph below, which is a plot of the relative energies of the various
conformations of 2,3-dimethylbutane, viewed through the C2-C3 bond. The
conformations corresponding to the 120o and 240o are:

Angle of rotation

A)
B)
C)
D)
E)

Angle of rotation

A)
B)
C)
D)
E)

Relative energy
0o

60o 120o 180o 240o 300o 360o

2-chloropropane
1,3-dichloropropane
2-methylpropane
Butane (C1-C2 rotation)
Butane (C2-C3 rotation)
Ans: E
101

60o 120o 180o 240o 300o 360o

Angle of rotation
Eclipsed, more stable than the conformation at 0o
Eclipsed, more stable than the conformation at 180o
Staggered, more stable than the conformation at 0o
Staggered, less stable than the conformation at 180o
Two of the above are true

102

Chapter 4

Chapter 4

Topic: Conformational Analysis

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

64. 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.
65. Which conformation represents the most stable conformation of trans-1-bromo-4methylcyclohexane?
CH3

Br

Br

A)
B)
C)
D)
E)

Br

II

CH3

CH3

Br

CH3

H3C

Br

IV

III

Br

HO

Cl

Br

A)
B)
C)
D)
E)

II

CH3

CH3

CH3

HO

III

CH2CH3

IV

I
II, V
III, IV
I, III and IV
None of the above are trans isomers.

Topic: Conformational Analysis

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

I
II
III
IV
V

OH

HO

Topic: Cis-Trans Isomers

Cl

Br

II

CH3

CH3

CH2CH3

HO

CH2CH3

III

A)
B)
C)
D)
E)

I
II
III
IV
V.

69.
A)
B)
C)
D)
E)

The least stable conformation of cyclohexane is the:

boat.
twist boat.
chair.
half-chair.
twist chair.

IV

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

Br

HO

A)
B)
C)
D)
E)

Cl

Br

II

CH3

III

I
II, V
III, IV
I, III and IV
None of the above are cis isomers.

CH3

CH3

HO

CH2CH3

IV

70. Express, quantitatively, the difference in stability of the two structures shown below.
CH3
CH3

H3C

A)
B)
C)
D)
E)

103

H3C

II

I is more stable than II by 7.5 kJ mol-1.

I is more stable than II by 15 kJ mol-1.
II is more stable than I by 7.5 kJ mol-1.
II is more stable than I by 15 kJ mol-1.
The two are equal in stability.

104

Chapter 4

Chapter 4

Topic: Conformational Analysis

71.
A)
B)
C)
D)
E)

The twist boat conformation is the preferred conformation for this compound.
cis-1,4-Di-tert-butylcyclohexane
trans-1,4-Di-tert-butylcyclohexane
cis-1,3-Di-tert-butylcyclohexane
trans-1,2-Di-tert-butylcyclohexane
None of these

Topic: Ring Strain

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

A)
B)
C)
D)
E)

Topic: Alkane Synthesis, Nomenclature

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

II

III

IV

I
II
III
IV
V
Ans: E

Topic: General
75.
A)
B)
C)
D)
E)

How many constitutional isomers are possible for the formula C6H14?
2
3
4
5
6

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

105

Topic: Alkane Synthesis, Nomenclature

78. The synthesis of an alkyne precursor to 2,2-dimethylheptane is accomplished most
effectively by the reaction between these two reagents:
A) CH3CH2CH2C!CNa and (CH3)3CBr
B) CH3CH2C!CNa and (CH3)3CCH2Br
C) (CH3)3CC!CNa and CH3CH2CH2Br
D) (CH3)3CCH2CH2C!CH and CH3CH2I
E) HC!CNa and (CH3)3CCH2CH2Br
79. The reaction of the Na salt of 3-methyl-1-pentyne with 1-bromo-3-methylbutane
produces which of these?
A) 3,8-dimethyl-4-nonyne
B) 2,7-dimethyl-4-nonyne
C) 3,8-dimethyl-5-nonyne
D) 3,7-dimethyl-4-nonyne
E) 3,7-dimethyl-5-nonyne
Topic: General
80. 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
81.
A)
B)
C)
D)
E)

How many alkanes of formula C7H16 possess a quaternary carbon atom?

1
2
3
4
5

106

Chapter 4

Svar Part 4 - Nomenklatur, konformation

SHORT ANSWER QUESTIONS

Topic: Nomenclature
92. Give the IUPAC name corresponding to the following structure.
Br

OH

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

Br
HO

94.

Chapter 4

Give the IUPAC name corresponding to the following structure:

Br
F

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

HO

96. Draw the bond-line structural formula corresponding to the most stable conformation of
the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane
97. Draw the bond-line structural formula corresponding to the name: 2,5,9-trimethyl-2decen-7-yne
Topic: Alkane Conformations
98. Draw the Newman projection formula for the gauche conformation of the C2-C3 bond
in pentane.
99. Draw the Newman projection formula for the most stable conformation of the C2-C3
bond in 3-methylpentane.

107

Frga
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40

Svar
C
D
E
D
E
C
D
D
A
A
D
A
C
A
D
E
A
D
A
A
D
C
C
C
B
E
C
D
E
B
E
E
C
D
C
B
E
A
E
B

Rtt/Fel

Frga
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81

Svar
D
B
A
D
A
A
A
C
C
C
A
E
D
D
B
D
B
A
C
D
E
B
A
B
A
B
C
E
D
A
A
E
A
A
D
C
E
C
A
B
C

108

Rtt/Fel

Chapter 4

Svar
92.
93.
94.
95.
96:

Part 4 Nomenklatur, konformation forts.:

5-bromo-6-cyclopentyl-2-hexanol
3-(2-bromobutyl)cyclopentanol
trans-1-bromo-2-fluorocyclohexane
3-ethyl-6,7-dimethyl-2-octanol
Br

97:

98:

CH3
H
H

99:

H
H
CH3

H
H

CH2CH3

CH3
H

CH2CH3

109