Chapter Four
MULTIPLE CHOICE QUESTIONS
Topic: Nomenclature
Section: 4.2
Difficulty Level: Easy
1.
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
Ans: E
Topic: General
Section: 4.2
Difficulty Level: Easy
2.
A)
B)
C)
D)
E)
How many constitutional isomers are possible for the formula C6H14?
2
3
4
5
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
173
Topic: General
Section: 4.2 and 4.3
Difficulty Level: Medium
4.
A)
B)
C)
D)
E)
How many alkanes of formula C7H16 possess a quaternary carbon atom?
1
2
3
4
5
Ans: C
Topic: Nomenclature
Section: 4.3B
Difficulty Level: Easy
5.
A)
B)
C)
D)
E)
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
Ans: C
is:
Topic: Nomenclature
Section: 4.3B
Difficulty Level: Medium
6.
A)
B)
C)
D)
E)
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
Ans: D
is:
174
Topic: Nomenclature
Section: 4.3B
Difficulty Level: Medium
7. A correct IUPAC name for the following compound is:
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
Ans: E
Topic: Nomenclature
Section: 4.3C
Difficulty Level: Easy
8.
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
Ans: B
Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium
CH3CHCH2
9.
A)
B)
C)
D)
E)
An IUPAC name for the group
Isopentyl
Isoamyl
sec-Butylmethyl
2-Methylbutyl
2-Ethylpropyl
Ans: D
CH2CH3 is:
175
Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium
10.
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
Ans: C
Topic: Nomenclature
Section: 4.3C
Difficulty Level: Medium
11. Isopentyl is the common name for which alkyl group?
A) CH3CH2CH2CH
CH3
B) CH3CH2CHCH2
CH3
C) CH3CHCH2CH2
CH3
CH
CH
D)
3
2CH
CH2CH3
E)
CH3
CH3CCH2
CH3
Ans: C
176
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)
B)
C)
D)
E)
3-Isobutyl-2-methylheptane
3-sec-Butyl-2-methyloctane
5-Isobutyl-6-methylheptane
2-Ethyl-3-isopropyloctane
4-Isopropyl-3-methylnonane
Ans: E
Topic: Nomenclature
Section: 4.3B/C
Difficulty Level: Medium
14.
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
Ans: D
is:
177
Topic: Nomenclature
Section: 4.3B/C
Difficulty Level: Medium
15. 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
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?
Br
A)
B)
C)
D)
E)
Isobutyl bromide
tert-Butyl bromide
Butyl bromide
sec-Butyl bromide
Bromo-sec-butane
Ans: A
178
Topic: Nomenclature
Section: 4.3E
Difficulty Level: Medium
18.
A)
B)
C)
D)
E)
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
Ans: C
Topic: Nomenclature
Section: 4.3F
Difficulty Level: Easy
19. What is the correct IUPAC name for the following compound?
HO
A)
B)
C)
D)
E)
3-Hydroxymethylheptane
3-Hydroxymethylhexane
3-Methyloxyheptane
2-Ethyl-1-hexanol
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?
OH
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
Ans: E
179
Topic: Nomenclature
Section: 4.3F
Difficulty Level: Easy
21. What is the correct IUPAC name for the following compound?
OH
F
A)
B)
C)
D)
E)
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
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 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
Ans: C
Topic: Nomenclature
Section: 4.3B/E/F
Difficulty Level: Medium
23. A correct IUPAC name for the following compound is:
OH
A)
B)
C)
D)
E)
Ans:
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
D
180
Topic: Nomenclature
Section: 4.3F and 4.4
Difficulty Level: Hard
24. The correct IUPAC name for the following compound is:
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
Ans: B
181
Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium
25. The most stable conformation of 3-bromo-2-methylpentane, viewed through the
C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back):
H
H
CH3
Br
CH3
H
Br
H
CH3
CH2CH3
H
H3C
CH3
I
H
H
CH3
CH(CH3)2
II
III
CH3
Br
CH3
CH2CH3
H
A)
B)
C)
D)
E)
Br
H
Br
H
CH3
CH3
H
CH2CH3
IV
V
I
II
III
IV
V
Ans: E
182
Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium
26. The least stable conformation of 3-bromo-2-methylpentane, viewed through the
C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back):
CH3
Br
H
CH3
H
H
H
CH(CH3)2
CH3
Br
H
Br
CH2CH3
I
CH2CH3
CH3
H
H
CH3
II
III
H
Br
CH(CH3)2
H
CH3
H
Br
H
IV
A)
B)
C)
D)
E)
CH3
CH(CH3)2
H
H
V
I
II
III
IV
V
Ans: C
183
Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium
27. The most stable conformation of 2,3-dimethylpentane, viewed through the
C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back):
CH3
CH3
CH3
H
H
CH3
H
CH2CH3
CH3
CH2CH3
H
H
H3C
I
CH3
H
H
CH(CH3)2
II
III
CH3
H
CH3
CH3
H3CH2C
A)
B)
C)
D)
E)
H
H
H
H3C
H
CH3
CH3
CH(CH3)2
IV
V
I
II
III
IV
V
Ans: D
184
Topic: Conformational Analysis
Section: 4.4A
Difficulty Level: Medium
28. The least stable conformation of 2,3-dimethylpentane, viewed through the
C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back):
CH3
CH3
H
H
CH3
H
CH2CH3
CH3
CH2CH3
H
H
H3C
I
CH3
H
CH2CH3
CH3
H
H3C
II
III
CH3
H
H
H3C
H3C
CH2CH3
CH3
H
CH3
CH(CH3)2
IV
A)
B)
C)
D)
E)
H
H3C
V
I
II
III
IV
V
Ans: D
185
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
29. Which of the following is bicyclo[3.2.2]nonane?
I
II
IV
A)
B)
C)
D)
E)
III
V
I
II
III
IV
V
Ans: C
186
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
30. Which compound is a bicycloheptane?
I
II
IV
A)
B)
C)
D)
E)
III
V
I
II
III
IV
V
Ans: D
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
31. Which is the correct name for the compound shown below?
A)
B)
C)
D)
E)
Bicyclo[2.2.0]hexane
Bicyclo[2.2.0]butane
Bicyclo[2.2.2]hexane
Bicyclo[2.2.1]hexane
Disquarane
Ans: A
187
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
32. What is the name of this compound?
A)
B)
C)
D)
E)
Bicyclo[2.2.2]octane
Bicyclo[3.2.1]octane
Bicyclo[4.1.1]octane
Bicyclo[4.2.0]octane
Bicyclo[3.3.0]octane
Ans: D
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
I
II
IV
33.
A)
B)
C)
D)
E)
III
V
Which of the above is bicyclo[3.3.1]nonane?
I
II
III
IV
V
Ans: D
188
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
I
II
IV
34.
A)
B)
C)
D)
E)
III
V
Which of the above is bicyclo[5.2.0]nonane?
I
II
III
IV
V
Ans: E
189
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
I
35.
A)
B)
C)
D)
E)
II
III
IV
V
Which of the above is bicyclo[4.3.0]nonane?
I
II
III
IV
V
Ans: A
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Easy
36. Which of the following structures represents bicyclo[3.2.1]octane?
I
II
IV
A)
B)
C)
D)
E)
III
V
I
II
III
IV
V
Ans: E
190
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard
37. A correct name for the following compound is:
A)
B)
C)
D)
E)
2-Methylbicyclo[4.3.0]nonane
1-Methylbicyclo[4.3.1]nonane
7-Methylbicyclo[4.3.0]nonane
2-Methylbicyclo[4.3.1]nonane
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?
Cl
A)
B)
C)
D)
E)
1-Chlorobicyclo[4.1.1]octane
2-Chlorobicyclo[4.1.0]octane
2-Chlorobicyclo[4.1.1]octane
2-Chlorobicyclo[4.1.1]heptane
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:
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
Ans: A
191
Topic: Nomenclature
Section: 4.4B
Difficulty Level: Hard
40. A correct name for the following compound is:
Br
A)
B)
C)
D)
E)
4-bromo-3,8-dimethylbicyclo[5.2.2]nonane
3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane
4-bromo-3,8-dimethylbicyclo[5.2.1]decane
7-bromo-2,6-dimethylbicyclo[5.2.0]nonane
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:
Br
A)
B)
C)
D)
E)
Ans:
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
4-bromo-6-isopropyl-3,6-dimethyl-1-hexene
C
192
Topic: Nomenclature
Section: 4.5
Difficulty Level: Hard
42. What is the correct IUPAC name for the following compound?
HO
A)
B)
C)
D)
E)
trans-3-Hydroxymethyl-2-heptene
trans-2-(1-methylethyl)-4-hexen-1-ol
trans-5-(1-methylethyl)-2-hexen-6-ol
cis-5-isopropyl-2,6-hexenol
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)
B)
C)
D)
E)
3-Methyl-4-hexyne
4-Methyl-2-hexyne
2-Ethyl-3-pentyne
4-Ethyl-2-pentyne
3-Methyl-2-hexyne
Ans: B
Topic: Nomenclature
Section: 4.6
Difficulty Level: Easy
44.
A)
B)
C)
D)
E)
The IUPAC name for diisobutylacetylene is
2,7-Dimethyl-4-octene
2,7-Dimethyl-4-octyne
3,6-Dimethyl-4-octyne
2,5-Diethyl-3-hexyne
2,2,5,5-Tetramethyl-3-hexyne
Ans: B
193
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy
45. The least stable conformation of butane is:
H
H3C
H
H3C
H
H
H
H
CH3
CH3
H
H
H
I
H
H3C
H
H
II
III
H
A)
B)
C)
D)
E)
CH3
CH3
H
CH3
H
H
CH3
H
H
H
IV
V
I
II
III
IV
V
Ans: B
194
CH3
H
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy
46. The most stable conformation of butane is:
H
H3C
H
H3C
H
H
H
H
CH3
CH3
H
H
H
I
H
H3C
H
H
II
III
H
A)
B)
C)
D)
E)
CH3
CH3
H
CH3
H
H
CH3
H
H
H
IV
V
I
II
III
IV
V
Ans: C
195
CH3
H
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy
47. The least stable conformation of butane is:
H
H3C
H
H3C
H
H
H
H
CH3
CH3
H
H
H
I
H
H3C
H
H
II
III
H
A)
B)
C)
D)
E)
CH3
CH3
H
CH3
H
H
CH3
H
H
H
IV
V
I
II
III
IV
V
Ans: B
196
CH3
H
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Easy
48. The most stable conformation of 1,2-dibromoethane is:
H
Br
H
Br
H
H
H
H
Br
Br
H
H
H
I
H
Br
H
H
II
III
H
A)
B)
C)
D)
E)
Br
Br
H
Br
H
H
Br
H
H
H
IV
V
Br
H
I
II
III
IV
V
Ans: C
197
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?
H
Br
H
Br
H
H
H
H
Br
Br
H
H
H
I
H
Br
H
Br
H
Br
H
Br
H
H
IV
I and II only
II, III, and V only
I, III, and IV only
All but one above
All the above
Ans: D
H
H
III
H
A)
B)
C)
D)
E)
Br
II
H
Br
H
V
198
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
50. The most stable conformation of 3-bromo-2-methylpentane, viewed through the
C-3—C-4 bond (i.e., C-3 in the front, C-4 in the back):
CH3
Br
H
H
Br
H
H
CH3
CH(CH3)2
H
H
H
CH(CH3)2
I
H
H
CH3
CH(CH3)2
II
III
H
Br
CH3
CH(CH3)2
H
A)
B)
C)
D)
E)
Br
H
Br
H
CH3
CH3
H
CH2CH3
IV
V
I
II
III
IV
V
Ans: A
199
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
51. The most stable conformation of 2,3-dibromobutane, viewed through the C-2—C-3
bond :
CH3
Br
H
Br
H
H
H
H
Br
Br
H3C
H3C
CH3
I
H3C
Br
CH3
H
II
III
Br
A)
B)
C)
D)
E)
Br
Br
H3C
H
H
Br
H3C
H
H3C
H
Br
CH3
IV
V
I
II
III
IV
V
Ans: C
200
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
52. Which conformation(s) show(s) the bromines in a gauche orientation for 2,3dibromobutane, viewed through the C-2—C-3 bond?
CH3
Br
H
Br
H
H
H
H
Br
Br
H3C
H3C
CH3
I
H3C
Br
CH3
H
II
III
Br
A)
B)
C)
D)
E)
Br
Br
H3C
H
H
Br
H3C
H
H3C
H
Br
CH3
IV
V
I and II only
III and IV only
I and V only
II only
None of the above
Ans: C
201
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
53. The least stable conformation of 3-bromo-2-methylpentane, viewed through the
C-3—C-4 bond (i.e., C-3 in the front, C-4 in the back):
CH3
Br
H
CH3
H
H
H
CH(CH3)2
CH3
Br
H
Br
CH2CH3
I
CH2CH3
CH3
H
H
CH3
II
III
H
Br
CH(CH3)2
H
CH3
H
Br
H
IV
A)
B)
C)
D)
E)
CH3
CH(CH3)2
H
H
V
I
II
III
IV
V
Ans: E
202
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
Relative energy
54. Consider the graph below, which is a plot of the relative energies of the various
conformations of hexane, viewed through the C-2—C-3 bond. The conformations
corresponding to the 60o and 300o are:
0o
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
Ans: B
203
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Medium
Relative energy
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-2—C-3 bond. The
conformations corresponding to the 120o and 240o are:
0o
A)
B)
C)
D)
E)
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
Ans: A
204
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
56. Which staggered Newman projection(s), looking down the C-2—C-3 bond (C-2 in front
and C-3 in back), illustrates the following boxed compound?
OH
CH3
CH3
CH=CH2
H3C
H
HO
H
H3C
HO
H
H3C
H
H
CH=CH2
II
III
CH3
H
HO
A)
B)
C)
D)
E)
OH
CH=CH2
CH3
I
H
CH3
CH3
H
CH3
H
H
OH
CH=CH2
CH=CH2
IV
V
I, II and V
II and V
III and IV
V only
None of the above
Ans: B
205
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
57. Which staggered Newman projection(s), looking down the C-2—C-3 bond (C-2 in front
and C-3 in back), illustrates the following boxed compound?
Cl
H
CH2CH3
Cl
H3C
H
CH3
Cl
H
H
H3C
H
Cl
CH3
H
CH2CH3
CH3
I
II
H3C
III
H
CH2CH3
Cl
H
H
H
H
H
H
CH(CH3)CHClCH3
CH3
IV
A)
B)
C)
D)
E)
CH3
CH2CH3
V
I, II and III
II and V
I and II
V only
None of the above
Ans: E
206
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
58. Which staggered Newman projection(s), looking down the C-3—C-4 bond (C-3 in front
and C-4 in back), illustrate(s) the following boxed compound?
OH
HO
CH2CH(CH3)2
H
HO
CH3
H3C
H
CH2CH3
I
H
H
HO
H
CH2CH3
H
CH2CH(CH3)2
II
H3CH2C
III
CH2CH(CH3)2
OH
HO
CH3
H3C
H
H
H
H
CH2CH(CH3)2
CH2CH3
IV
A)
B)
C)
D)
E)
CH2CH3
CH3
CH2CH(CH3)2
V
I, II and III
II and V
I and II
III only
None of the above
Ans: D
207
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
59. Which staggered Newman projection(s), looking down the C-2—C-3 bond (C-2 in front
and C-3 in back), illustrate(s) the following boxed compound?
Cl
Br
H
CH2CH2CH3
Br
H
H
H
Cl
CH3
Br
Cl
H
Cl
Br
H
CH2CH2CH3
CH3
I
II
III
H
H
Br
H
Cl
CH2CH2CH3
CH2CH2CH3
Cl
H3C
CH3
Br
H
IV
A)
B)
C)
D)
E)
CH3
CH2CH2CH3
V
I only
II and V
I and II
III only
None of the above
Ans: A
208
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
Relative energy
60. The graph below is a plot of the relative energies of the various conformations of:
0o
A)
B)
C)
D)
E)
60o 120o 180o 240o 300o 360o
Angle of rotation
Ethane
Propane
Chloroethane
1-Chloropropane (C1-C2 rotation)
Butane (C1-C2 rotation)
Ans: D
209
Topic: Conformational Analysis
Section: 4.8A
Difficulty Level: Hard
Relative energy
61. The graph below is a plot of the relative energies of the various conformations of:
0o
A)
B)
C)
D)
E)
60o 120o 180o 240o 300o 360o
Angle of rotation
2-chloropropane
1,3-dichloropropane
2-methylpropane
Butane (C1-C2 rotation)
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:
H
H
OH
H
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.
Ans: C
210
Topic: Ring Strain
Section: 4.10
Difficulty Level: Easy
63.
A)
B)
C)
D)
E)
Which cycloalkane has the greatest ring strain?
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Cycloheptane
Ans: A
Topic: Ring Strain
Section: 4.10
Difficulty Level: Easy
64.
A)
B)
C)
D)
E)
Which cycloalkane has the least ring strain?
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Cycloheptane
Ans: D
Topic: Ring Strain
Section: 4.11
Difficulty Level: Easy
65.
A)
B)
C)
D)
E)
Which is the most stable conformation of cyclohexane?
Chair
Twist
Boat
One-half chair
Staggered
Ans: A
211
Topic: Conformational Analysis
Section: 4.11
Difficulty Level: Easy
66.
A)
B)
C)
D)
E)
The least stable conformation of cyclohexane is the:
boat.
twist boat.
chair.
half-chair.
twist chair.
Ans: D
Topic: Conformational Analysis
Section: 4.12
Difficulty Level: Medium
67.
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.
Ans: D
Topic: Nomenclature
Section: 4.13
Difficulty Level: Easy
68. Select the systematic name for
A)
B)
C)
D)
E)
Cl
H
H
Cl
cis-1,3-Dichlorocyclopentane
trans-1,4-Dichlorocyclopentane
cis-1,2-Dichlorocyclopentane
trans-1,3-Dichlorocyclopentane
1,1-Dichlorocyclopentane
Ans: D
212
Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium
Br
H
H
Br
Br
H
H
Br
H
I
69.
A)
B)
C)
D)
E)
Br
Br
H
II
III
trans-1,2-Dibromocyclohexane is represented by structure(s):
I
II
III
II and III
I and II
Ans: D
Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium
Br
H
H
Br
Br
H
H
I
70.
A)
B)
C)
D)
E)
Br
Br
H
Br
H
II
III
cis-1,2-Dibromocyclohexane is represented by structure(s):
I
II
III
II and III
I and II
Ans: A
213
Topic: Nomenclature
Section: 4.13
Difficulty Level: Medium
71. cis-1,3-Dibromocyclohexane is represented by structure(s):
Br
H
Br
H
H
Br
Br
H
I
A)
B)
C)
D)
E)
H
H
Br
Br
II
III
I
II
III
II and III
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?
CH3
H
H
H
CH3
H3C
H
CH3
H
H3C
I
H
II
III
H
H
CH3
H3C
H
IV
A)
B)
C)
D)
E)
CH3
H3C
H
CH3
V
I
II
III
IV
V
Ans: B
214
Topic: Conformational Analysis
Section: 4.13
Difficulty Level: Medium
73.
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
Ans: A
Topic: Nomenclature
Section: 4.5, 4.13
Difficulty Level: Easy
74. Select the structure for cis-3-methyl-6-vinylcyclohexene.
I
II
IV
A)
B)
C)
D)
E)
III
V
I
II
III
IV
V
Ans: B
215
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
216
Topic: Conformational Analysis
Section: 4.11, 4.12, and 4.13
Difficulty Level: Medium
78.
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
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
217
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-4methylcyclohexane?
CH3
Br
Br
Br
CH3
CH3
I
II
III
CH3
Br
H3C
Br
IV
A)
B)
C)
D)
E)
V
I
II
III
IV
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?
OH
HO
Cl
Br
F
CH3
I
II
CH3
III
CH2CH3
HO
CH2CH3
IV
A)
B)
C)
D)
E)
V
I
II
III
IV
V
Ans: E
218
Topic: Cis-Trans Isomers
Section: 4.12 and 4.13
Difficulty Level: Easy
82. Which of the following can be described as cis isomers?
Br
HO
Cl
Br
F
CH3
I
II
III
CH3
CH3
HO
CH2CH3
IV
A)
B)
C)
D)
E)
V
I
II, V
III, IV
I, III and IV
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?
Br
HO
Cl
Br
F
CH3
I
II
CH3
III
CH3
HO
CH2CH3
IV
A)
B)
C)
D)
E)
V
I
II, V
III, IV
I, III and IV
None of the above are trans isomers.
Ans: C
219
Topic: Ring Strain
Section: 4.14
Difficulty Level: Medium
84. Which of these C10H18 isomers is predicted to be the most stable?
I
A)
B)
C)
D)
E)
II
III
H
H
H
H
IV
V
I
II
III
IV
V
Ans: E
Topic: Alkane Synthesis
Section: 4.16
Difficulty Level: Easy
85.
A)
B)
C)
D)
E)
Select the reagents necessary to convert cyclopentene into cyclopentane.
H2 and Ni
H2O
Heat
Zn, H3O+
Light
Ans: A
220
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.
A)
B)
C)
D)
E)
Catalytic hydrogenation of which of the following will yield 2-methylpentane?
2-methyl-1-pentene
2-methyl-2-pentene
4-methyl-2-pentene
4-methyl-1-pentene
All of the above
Ans: E
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
88.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with (trans, trans)-hepta-3,5-dien-1-yne?
1
2
3
4
5
Ans: D
2
221
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
89.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with 3-cyclobutylpropan-1-ol?
1
2
3
4
None of the above
Ans: E
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
90.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with 5-chlorocyclohex-3-en-1-ol?
1
2
3
4
None of the above
Ans: A
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
91.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with cylohexa-2,5-diene-1,4-diol?
1
2
3
4
None of the above
Ans: B
2
222
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
92.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with 3-vinylcyclo-2-penten-1-ol?
0
1
2
3
4
Ans: C
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
93.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with trans-1,2-dimethylcyclohexane?
0
1
2
3
4
Ans: A
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.16A
Difficulty Level: Medium
94.
A)
B)
C)
D)
E)
How many moles of hydrogen (H2) will react with cis-2,3,3-trimethylhepta-1,5-diene?
0
1
2
3
4
Ans: C
2
223
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
B) cis-1,2-dimethylcyclohexane
C) trans-3,4-dimethylhexane
D) trans-1,2-dimethylhexane
E) None of the above
Ans: A
2
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
B) 2,3,3-trimethylhept-1-ene
C) 5,5,6-trimethylheptane
D) 2-isopropyl-2-methylhexane
E) None of the above
Ans: E
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium
97.
A)
B)
C)
D)
E)
What product is formed when 3-cyclobutylpropan-1-ol is reacted with Pd/C and H2?
3-cyclobutylpropane
1-propanol
No reaction
hexane
None of the above
Ans: C
2
224
Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium
98.
A)
B)
C)
D)
E)
What product is formed when 5-chlorocyclohex-3-en-1-ol is reacted with Pd/C and H2?
5-chlorocyclohexanol
3-chlorocyclohexanol
5-chloro-3-hexanol
2-chloro-4-hexanol
None of the above
Ans: B
2
Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Medium
99.
A)
B)
C)
D)
E)
What product is formed when 3-vinylcyclo-2-penten-1-ol is reacted with Pd/C and H2?
3-vinylcyclopentanol
3-ethylcyclo-2-penten-1-ol
4-ethylcyclopentanol
3-ethylcyclopentanol
None of the above
Ans: D
2
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
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
2
225
Topic: Alkane Synthesis, Nomenclature
Section: 4.3 and 4.16A
Difficulty Level: Hard
101.
A)
B)
C)
D)
E)
What product is formed when cylohexa-2,5-diene-1,4-diol is reacted with Pd/C and H2?
hexane-1,4-diol
cyclohexa-2-ene-1,4-diol
cyclohexane-1,4-diol
hexane-1,4-diol
None of the above
Ans: C
2
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
B) 1-heptyne
C) 1-ethylpentane
D) trans-2-heptene
E) None of the above
Ans: A
2
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
226
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)
B)
C)
D)
E)
2
3
4
5
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?
O
A)
B)
C)
D)
E)
2
3
4
5
6
Ans: A
227
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?
CN
A)
B)
C)
D)
E)
OH
2
3
4
5
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)
B)
C)
D)
E)
2
3
4
5
6
Ans: C
228
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)
B)
C)
D)
E)
2
3
4
5
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?
O
N
A)
B)
C)
D)
E)
O
2
3
4
5
6
Ans: A
229
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?
O
Cl
O
A)
B)
C)
D)
E)
O
2
3
4
5
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
230
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?
OH
A)
B)
C)
D)
E)
3
4
5
6
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?
H
N
N
O
A)
B)
C)
D)
E)
3
4
5
6
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
231
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?
N
O
O
O
A)
B)
C)
D)
E)
3
4
5
6
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?
OH
O
A)
B)
C)
D)
E)
3
4
5
6
7
Ans: D
232
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?
CO2CH3
A)
B)
C)
D)
E)
2
3
4
5
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)
B)
C)
D)
E)
3
4
5
6
7
Ans: D
233
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
234
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?
O
HO
OH
OH
H
H
H
O
A)
B)
C)
D)
E)
3
4
5
6
7
Ans: E
235
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?
HO
N
O
H
HO
A)
B)
C)
D)
E)
6
7
8
9
10
Ans: D
236
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.
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
2
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.
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
2
237
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:
HO
Ans: 3-ethyl-6,7-dimethyl-2-octanol
Topic: Nomenclature
Section: 4.3
Difficulty Level: Medium
133. Give the IUPAC name corresponding to the following structure:
Br
OH
Ans: 5-bromo-6-cyclopentyl-2-hexanol
238
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:
Br
HO
Ans: 3-(2-bromobutyl)cyclopentanol
Topic: General
Section: 4.4B
Difficulty Level: Easy
138. A compound containing two fused or bridged rings is referred to as a
___________________________.
Ans: bicycloalkane
239
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-2decen-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
240
Topic: Alkane Conformations
Section: 4.8A
Difficulty Level: Easy
143. Draw the Newman projection formula for the gauche conformation of the C-2—C-3
bond in pentane.
CH3
Ans:
H
CH2CH3
H
H
H
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.
CH3
Ans:
H
CH3
H
H
CH2CH3
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:
Br
F
Ans: trans-1-bromo-2-fluorocyclohexane
241
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
Br
Ans:
242