Chapter Eighteen
1.
Toluene is the common name for:
A)
hydroxybenzene
B)
aminobenzene
C)
methylbenzene
D)
ethylbenzene
E)
methoxybenzene
Ans:
C
2.
Anisole is the common name for:
A)
hydroxybenzene
B)
aminobenzene
C)
methylbenzene
D)
ethylbenzene
E)
methoxybenzene
3.
Phenol is the common name for:
A)
hydroxybenzene
B)
aminobenzene
C)
methylbenzene
D)
ethylbenzene
E)
methoxybenzene
Ans:
A
4.
o-xylene is the common name for:
A)
hydroxybenzene
B)
aminobenzene
C)
1,2-dimethylbenzene
D)
ethylbenzene
E)
1,3-dimethylbenzene
5.
What is the IUPAC name for the following compound?
OH
Br
A)
5-bromophenol
B)
3-bromophenol
C)
5-bromoaniline
D)
3-bromoaniline
E)
1-bromophenol
Ans:
B
6.
Which of the following is another name for 4-chlorobenzaldehyde?
A)
o-chlorobenzaldehyde
B)
m- chlorobenzaldehyde
C)
p-chlorobenzaldehyde
D)
styrene
E)
1-chlorobenzaldehyde
Ans:
C
Ans:
C
7.
What is the IUPAC name for the following compound?
NH2
Br
NO2
A)
5-bromo-4-nitroaniline
B)
5-bromo-p-nitroaniline
C)
1-bromo-2-nitroaniline
D)
3-bromo-4-nitroaniline
E)
p-nitro-m-bromoaniline
8.
What is the correct structure for 4-amino-2-chlorophenol?
NH2
Cl
OH
NO2
Cl
OH
NH2
Cl
CH
O
NO2
Cl
OCH3
OH
Cl
NH2
I II III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
Ans:
D
9.
What is the correct order of the names for the following compound?
III III
A)
I-naphthalene; II-triphenyl; III-biphenyl
B)
I-naphthalene; II-phenanthrene; III-biphenyl
C)
I-biphenyl; II-anthracene; III-naphthalene
D)
I-naphthalene; II-anthracene; III-biphenyl
E)
I-biphenyl; II- phenanthrene; III-naphthalene
10.
What is the IUPAC name for the following compound?
NH2
Cl
Cl
A)
3,4-dichloroaniline
B)
2,4-dichloroaniline
C)
2,5-dichloroaniline
D)
3,6-dichloroaniline
E)
2,6-dichloroaniline
Ans:
C
Ans:
C
11.
What is the IUPAC name for the following compound?
OH
A)
4-butylphenol
B)
1-sec-butylphenol
C)
4-propylphenol
D)
4-sec-butylphenol
E)
1-isobutylphenol
12.
What is the IUPAC name for the following compound?
NO2
COH
O
A)
6-ethyl-3-nitrobenzoic acid
B)
1-ethyl-4-nitrobenzoic acid
C)
2-ethyl-5-nitrobenzoic acid
D)
2-ethyl-5-nitrobenzaldehyde
E)
4-nitro-3-carboxyethylbenzene
Ans:
C
Ans:
D
13.
What is the structure for 1,3-diphenylbutane?
14.
What is the structure for p-aminobenzoic acid (PABA)?
15.
What is the IUPAC name for the following compound?
O
F
H
Ans:
2-ethyl-4-fluoro-5-methylbenzaldehyde
16.
What is the IUPAC name for the following compound?
NO2
H3CO
Cl
17.
What is the IUPAC name for the following compound?
Ans:
Phenanthrene
18.
What is the structure of styrene?
Ans:
4-chloromethyl-2-nitroanisole
19.
What is the structure for 3-isobutyl-5-isopropylaniline?
20.
What is the structure for 4-amino-2-bromophenol?
OH
NH2
Br
OH
Br
H2N
OCH3
Br
NH2
OCH3
NH2
Br
OH
NH2
Br
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
21.
Which one of the following statement is not true for a compound to be considered as
aromatic?
A)
The compound must be cyclic and planar
B)
The compound must be monocyclic.
C)
The compound must have a conjugated system with p orbital at every vertex
D)
The compound must satisfy Hückel’s rule –must have (4n + 2) electrons.
E)
none of these
Ans:
B
22.
What is the main difference between an aromatic and antiaromatic compound?
A)
Aromatic compounds must be cyclic and planar, but not antiaromatic compounds
B)
Aromatic compounds must be monocyclic.
C)
Antiaromatic compounds must have a conjugated system with p orbital at every vertex
D)
Aromatic compounds must satisfy Hückel’s rule.
E)
none of these
Ans:
D
23.
The number of π electrons present in an antiaromatic compound:
A)
4n + 2
B)
2n + 2
C)
4n
D)
none
E)
none of these
Ans:
C
24.
The number of π electrons present in an aromatic compound:
A)
4n + 2
B)
2n + 2
C)
4n
D)
none
E)
None of these
Ans:
A
25.
Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl
anion and predict if it is aromatic.
26.
Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl
anion and predict if it is aromatic.
27.
Using a Frost circle, draw the molecular orbital energy diagram for the tropylium cation
and predict if it is aromatic.
28.
Using a Frost circle, draw the molecular orbital energy diagram for the
cyclononatetraenyl cation and predict if it is aromatic.
29.
Which one of the following compound is aromatic?
S
O
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
None of these
30.
Which one of the following compound is antiaromatic?
NN
H
H
N
N
HH
H
N
N
III
III IV
A)
I
B)
II
C)
III
D)
IV
Ans:
B
Ans:
D
31.
Which one of the following compound is nonaromatic?
N
H
N
III
III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
32.
Which one of the following compound is aromatic?
III III IV
A)
I
B)
II
C)
III
D)
IV
Ans:
C
Ans:
B
33.
Which one of the following compound is nonaromatic?
N
N
H
H
II
O
III
N
H
O
IV
B CH3
I
A)
I
B)
II
C)
III
D)
IV
34.
Which one of the following compound is aromatic?
N
N
H
H
II
O
III
N
H
O
IV
B CH3
I
A)
I
B)
II
C)
III
D)
IV
Ans:
A
Ans:
B
35.
Which one of the following compound(s) is antiaromatic?
N
N
H
H
II
O
III
N
H
O
IV
B CH3
I
A)
I
B)
II
C)
III
D)
IV
E)
III & IV
36.
Which one of the following compounds is aromatic?
B
H
I
N
H
O
IV
II III
A)
I
B)
II
C)
III
D)
IV
Ans:
A
Ans:
E
37.
Which one of the following compounds is antiaromatic?
S O N
H
B
H
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
38.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
O
hybridized.
39.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
S
Ans:
IV
40.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
41.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
O
42.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
O
43.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
N
N
H
H
44.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
N
H
O
45.
Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
N
N
H
N
46.
Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
O
O
III
47.
Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain
your choice.
N
H
OS
O
O
O
III IV
II
I
N
H
N
O
NH2