Chapter 9 - Benzene and Its Derivatives
Multiple Choice
Section: 9.1 and 9.2
Difficulty Level: Medium
1. How many Kekule structures are possible for benzene, naphthalene, and anthracene ?
I
II
a)
b)
c)
d)
III
I: 3, II: 4, III: 4
I: 2, II:3, III: 4
I: 2, II: 4, III: 4
I: 3, II: 3, III: 4
Section: 9.2
Difficulty Level: Medium
2. Which structures are aromatic?
O
O
N
O
III
IV
CH2
I
a)
b)
c)
d)
II
II, III
III, IV
I, III
II, IV
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Chapter 9 - Benzene and Its Derivatives
Section: 9.2
Difficulty Level: Hard
3. How many -orbital electrons are in the following molecule?
NH
N
O
N
N
NH2
N
N
N
N
H
N
N
O
imidazole
a)
b)
c)
d)
adenine
caffeine
imidazole: 5, adenine: 10, caffeine: 5
imidazole: 6, adenine: 9, caffeine: 6
imidazole: 6, adenine: 10, caffeine: 6
imidazole; 4, adenine, 9, caffeine, 5
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Chapter 9 - Benzene and Its Derivatives
Section: 9.3
Difficulty Level: Easy
4. Which structures have the correct IUPAC names?
Cl
Br
Br
ortho-bromotoluene
para-bromo-meta-chlorotoluene
I
II
NO2
O
Cl
meta-chloroaniline
para-ethylanisole
IV
III
a)
b)
c)
d)
I, II
III, IV
I, IV
II, III
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Chapter 9 - Benzene and Its Derivatives
Section: 9.3
Difficulty Level: Easy
5. Which of the named compounds have correct structures?
Br
O
OH
Cl
Br
meta-chlorotoluene
bromomethyltoluene
I
para-bromophenol
II
III
O
NH2
NO2
Cl
Cl
Cl
ortho-nitroanisole
2,4,6-trichloroaniline
IV
V
a)
b)
c)
d)
I, II, IV
I, III, IV
I, IV, V
II, III, V
Section: 9.2 and 9.3
Difficulty Level: Easy
6. How many mono-bromobenzenes are possible?
a)
b)
c)
d)
1
2
3
4
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Chapter 9 - Benzene and Its Derivatives
Section: 9.2 and 9.3
Difficulty Level: Medium
7. How many bromo-naphthalenes are possible?
a)
b)
c)
d)
1
2
3
4
Section: 9.2 and 9.3
Difficulty Level: Medium
8. How many mono-bromoanthracenes are possible?
a)
b)
c)
d)
1
2
3
4
Section: 9.6
Difficulty Level: Medium
9. Which is the electrophile in the nitration of benzene?
O
HO N
O
O N O
O
I
O N
N O
O
II
III
a) I
b) II
c) III
d) IV
173
IV
Chapter 9 - Benzene and Its Derivatives
Section: 9.6
Difficulty Level: Medium
10. Arrange the compounds in order of decreasing reactivity towards the aromatic nitration reaction?
HN
O
O
O S O
OH
OH
O
I
II
a)
b)
c)
d)
III
IV
I > III > IV > II
III > II > I > IV
II > I > III > IV
IV > II > III > I
Section: 9.6
Difficulty Level: Medium
11. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first).
O
O
NH
I
NH2
II
O
N
O
HN
III
IV
a) III < I < IV < II
b) I < III < II < IV
c) II < I < IV < III
d) IV < II < I < III
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Chapter 9 - Benzene and Its Derivatives
Section: 9.6
Difficulty Level: Medium
12. Which electrophiles are formed – at different stages of the reaction, by the reaction of phenol and
acetone in the presence of phosphoric acid (a strong mineral acid)?
OH
CH3
H3PO3
O
+
HO
CH3
C
CH3
OH
CH3
CH3
HO
HO
C
C
CH3
OH
CH3
II
I
H
O
HO
C
O
CH3
III
a)
b)
c)
d)
IV
I and IV
II and III
III and IV
II and IV
Section: 9.6
Difficulty Level: Medium
13. Which is the electrophile in the following reaction?
H3PO4
+
I
II
CH3
III
IV
a) I
b) II
c) III
d) IV
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Chapter 9 - Benzene and Its Derivatives
Section: 9.6
Difficulty Level: Hard
14. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first).
I
Cl
OH
II
III
O
IV
a) III, II, I, IV
b) IV, II, I, III
c) III, I, II, IV
d) I, II, III, IV
Section: 9.6
Difficulty Level: Hard
15. Which are the major reaction products of the following reaction, which is carried out in an inert
solvent?
HO3S
Br2
FeBr3
solvent
HO3S
HO3S
Br
Br
(II)
(I)
HO3S
HO3S
Br
(III)
(IV)
Br
a)
b)
c)
d)
I and II
II and III
III and IV
II and IV
176
Chapter 9 - Benzene and Its Derivatives
16. Which are the major reaction products of the following reaction, which is carried out in an inert
solvent? (HINT: add the lone pairs to the line-angle formula first.)
O
O
Cl
NO2
AlCl3
solvent
O
O
O
NO2
NO2
O
I
II
O
O
NO2
NO2
O
III
O
IV
a) I and II
b) III and IV
c) I and IV
d) II and III
Section: 9.4, 9.5, 9.6
Difficulty Level: Hard
17. Which are the final reaction products (2), which are formed by the following sequence of reactions.?
(HINT: assume an excess of K2Cr2O7 in step 2)
177
Chapter 9 - Benzene and Its Derivatives
O
Cl
AlCl3
K2Cr2O7
H2SO4
solvent
O
COOH
COOH
I
II
COOH
COOH
COOH
O
III
a)
b)
c)
d)
IV
I and II
II and III
II and IV
I and IV
178
Chapter 9 - Benzene and Its Derivatives
Section: 9.7
Difficulty Level: Medium
18. What is the major contributing structure to the cation intermediate of the bromination of anisole?
O
H
O
Br
H
I
O
Br
H
II
O
Br
III
H
Br
IV
a) I
b) II
c) III
d) IV
Section: 9.4, 9.5, 9.7
Difficulty Level: Hard
19. Which is the major product of the following reactions?
a)
b)
c)
d)
CH3Cl
Cl2
K2Cr2O7
FeCl3
FeCl3
H2SO4
para-chlorobenzoic acid
meta-chlorobenzoic acid
a mixture of para- and meta-chlorobenzoic acid
a mixture of ortho- and para-chlorobenzoic acid
Section: 9.5 and 9.7
Difficulty Level: Hard
20. Which is the major product of the following reaction?
HNO3
H2SO4
a)
b)
c)
d)
Cl2
FeCl3
1-chloro-4-nitrobenzene
1-chloro-3-nitrobenzene
1-chloro-2-nitrobenzene
a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene
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Chapter 9 - Benzene and Its Derivatives
Section: 9.5 and 9.7
Difficulty Level: Hard
21. Which is one possible product from the following consecutive reactions?
CH2
Br
HNO3
Br2
H2SO4
FeBr3
Br
NO2
CH2
CH2
I
II
NO2
NO2
Br
CH2
NO2
Br
CH2
IV
III
a)
b)
c)
d)
I
II
III
IV
180
Chapter 9 - Benzene and Its Derivatives
Section: 9.6 and 9.7
Difficulty Level: Medium
22. Which is the best reaction sequence for preparing the following compound from benzene? (HINT:
consider only the reaction product from electrophilic addition in the ortho position).
O
OH
NO2
AlCl3
K2Cr2O7
HNO3
CH3Cl
H2SO4
H2SO4
HNO3
AlCl3
K2Cr2O7
H2SO4
CH3Cl
H2SO4
AlCl3
HNO3
CH3Cl
H2SO4
AlCl3
HNO3
K2Cr2O7
CH3Cl
H2SO4
H2SO4
I
II
III
IV
a)
b)
c)
d)
I
II
III
IV
181
Chapter 9 - Benzene and Its Derivatives
Section: 9.6 and 9.7
Difficulty Level: Medium
23. Which is the best reaction sequence for preparing the following compound from benzene?
O
OH
NO2
AlCl3
K2Cr2O7
HNO3
CH3Cl
H2SO4
H2SO4
HNO3
AlCl3
K2Cr2O7
H2SO4
CH3Cl
H2SO4
AlCl3
HNO3
CH3Cl
H2SO4
AlCl3
HNO3
K2Cr2O7
CH3Cl
H2SO4
H2SO4
I
II
III
IV
a)
b)
c)
d)
I
II
III
IV
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Chapter 9 - Benzene and Its Derivatives
Section: 9.6 and 9.7
Difficulty Level: Medium
24. Which is the major product of the following reaction?
O
AlCl3
Cl
O
O
I
II
O
III
a)
b)
c)
d)
O
IV O
I
II
III
IV
183
Chapter 9 - Benzene and Its Derivatives
Section: 9.6 and 9.7
Difficulty Level: Medium
25. Which is the product in the following reaction?
H3PO4
+
H2PO3
I
a)
a)
b)
c)
II
IV
III
I
II
III
IV
Section: 9.8
Difficulty Level: Easy
26. Arrange the compounds in order of increasing acidity (least first).
OH
OH
OH
OH
NO2
I
a)
b)
c)
d)
Cl
NO2
NO2
II
III
IV
I, II, III, IV
III, II, IV, I
I, IV, III, II
II, III, IV, I
184
Chapter 9 - Benzene and Its Derivatives
Section: 9.8
Difficulty Level: Medium
27. Arrange the compounds in order of increasing acidity (least first).
OH
OH
O
OH
O
NO2
I
a)
b)
c)
d)
II
III
I, II, III, IV
III, IV, II, I
I, II, IV, III
II, I, III, IV
Section: 9.8
Difficulty Level: Medium
28. How can phenol be distinguished from cyclohexanol?
a)
b)
c)
d)
solubility in water
solubility in aqueous hydrochloric acid solution
solubility in aqueous sodium bicarbonate solution
solubility in aqueous sodium hydroxide solution
185
OH
IV
Chapter 9 - Benzene and Its Derivatives
Section: 9.9
Difficulty Level: Hard
29. Arrange the compounds in order of increasing acidity (least first).
O
OH
OH
I
II
d)
b)
c)
d)
OH
III
HO
IV
I, II, III, IV
II, IV, I, III
III, II, IV, I
II, III, I, IV
186
Chapter 9 - Benzene and Its Derivatives
187
Chapter 9 - Benzene and Its Derivatives
Fill in the Blank Questions
Section: 9.4
Difficulty Level: Hard
1. The major product of the following reaction is,
K2Cr2O7
H2SO4
Section: 9.6
Difficulty Level: Medium
2. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
Br
H
Br
Br
H
+
Section: 9.5 and 9.7
Difficulty Level: Medium
3. The major products of the following reaction are?
OH
H3PO4
188
H+
Chapter 9 - Benzene and Its Derivatives
Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
4. The reagent that completes the following reaction is
CH3
CH3
NO2
Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
5. The reagents that complete the following reactions are
SO3H
Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
6. Your choice of starting material and reagent that complete the following reaction are?
SO3H
Cl
189
Chapter 9 - Benzene and Its Derivatives
Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
7. Your choice of starting material, intermediate and reagents that complete the following reaction are?
Cl
O
Section: 9.5 and 9.7
Difficulty Level: Medium
8. The major product of the following reaction is
O
Cl
+
AlCl3
Section: 9.8
Difficulty Level: Medium
9. The major products of the following reaction are
OH
OH
NaOH
+
H2O
190
Chapter 9 - Benzene and Its Derivatives
Section: 9.8
Difficulty Level: Medium
10. The major products of the following reaction are
OH
O
OH
NaHCO3
+
H2O
True-False Questions
Section: 9.1
Difficulty Level: Easy
1. The name of the following structure is 2,4-diethylnitrobenzene.
NO2
Section: 9.1
Difficulty Level: Easy
2. The name of the following structure is 3,5-dibromobenzoic acid.
O
Br
OH
Br
191
Chapter 9 - Benzene and Its Derivatives
Section: 9.2
Difficulty Level: Easy
3. The following compound is aromatic.
Section: 9.2
Difficulty Level: Medium
4. The following compound is aromatic
Section: 9.4
Difficulty Level: Medium
5. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone.
Section: 9.4, 9.5, 9.7
Difficulty Level: Hard
6. The following reaction scheme will synthesize the product shown.
OH
O
CH3CH2Cl
AlCl3
K2Cr2O7
Br2
H2SO4
FeBr3
Br
192
Chapter 9 - Benzene and Its Derivatives
Section: 9.5 and 9.7
Difficulty Level: Medium
7. The following reaction scheme will synthesize the product shown.
SO3H
SO3
CH3CH2Cl
H2SO4
AlCl3
Section: 9.6
Difficulty Level: Medium
8. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution.
OH
CH3
>
SO3 H
>
>
Section: 9.6
Difficulty Level: Medium
9. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution.
Cl
O
NO2
>
>
>
193
Chapter 9 - Benzene and Its Derivatives
Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
10. The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene.
Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
11. The product of the reaction of methyl benzoate and chlorine/AlCl 3 is methyl 3-chlorobenzoate.
194
Chapter 9 - Benzene and Its Derivatives
Answers
Multiple Choice
1. b
2. c
3. c
4. c
5. c
6. a
7. b
8. c
9. b
10. c
11. a
12. a
13. b
14. b
15. c
16. c
17. c
18. d
19. d
20. b
21. c
22. d
23. a
24. d
25. a
26. a
27. c
28. d
29. b
Fill in the Blank Questions
1.
O
OH
195
Chapter 9 - Benzene and Its Derivatives
2.
Br
H
Br
Br
H
3.
4. HNO3, H2SO4
5.
Cl
SO3, H2SO4
AlCl3
6.
Cl
SO3 , H2SO4
7.
O
Cl
AlCl3
O
Cl2 , FeCl3
196
Chapter 9 - Benzene and Its Derivatives
8.
O
+
O
9.
O
OH
+
10.
O
O Na
OH
+
True-False Questions
1. T
2. T
3. F
4. T
5. F
6. F
7. T
8. T
9. F
10. F
11. T
197