Chapter 9 Benzene and Its Derivatives

100

Multiple Choice

1. Which structures have the correct IUPAC names? (Sec. 9.4)

a) I, II
b) III, IV
c) I, IV
d) II, III

























CH
3
Br
CH
3
Cl
Br
NO
2
Cl
OCH
3
CH
2
CH
3
I. 2-bromotoluene II. para methyl, meta chloro
bromobenzene
III. meta chloroaniline
IV. para ethylanisole
Chapter 9 Benzene and Its Derivatives
101



2. Which of the named compounds have correct structures? (Sec. 9.4)
CH
3
Cl
CH
2
CH
2
Br
O OH
Br
OCH
3
NO
2
NH
2
Cl Cl
Cl
I. meta chlorotoluene
II. bromomethyltoluene III. para bromophenol
IV. ortho nitroanisole
V. 2,4,6-trichloroaniline


a) I, II, IV
b) I, III, IV
c) I, IV, V
d) II, III, V

3. How many Kekule structures are possible for naphthalene? (Sec. 9.2, 9.3)

a) 3
b) 4
c) 5
d) 6

4. How many -orbital electrons are in the following molecule? (Sec. 9.3)
a) 4
b) 6
c) 8
d) 10
N
N
H
Chapter 9 Benzene and Its Derivatives
102


5. Which structures are aromatic? (Sec. 9.3)


a) II, III
b) III, IV
c) I, III
d) II, IV

6. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)


a) I, II, III, IV
b) III, II, IV, I
c) I, IV, III, II
d) II, III, IV, I

7. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)

OH
OH
O
OH
OCH
3
I II III
IV


a) I, II, III, IV
b) III, I, II, IV
c) IV, II, I, III
d) IV, II, III, I




O
CH
2
N O
O
I II III IV
IV III II I
OH
NO
2
NO
2
OH
NO
2
OH
Cl
OH
Chapter 9 Benzene and Its Derivatives
103

8. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9, 2.4)


a) I, II, III, IV
b) III, IV, II, I
c) I, II, IV, III
d) II, I, III, IV

9. How can phenol be distinguished from cyclohexanol? (Sec. 9.9, 8.3)

a) solubility in water
b) solubility in hydrochloric acid solution
c) solubility in sodium bicarbonate solution
d) solubility in sodium hydroxide solution

10. How many mono-bromoanthracenes are possible? (Sec. 9.2, 9.3)

a) 1
b) 2
c) 3
d) 4

11. Which contributing resonance structure is the most important for the bromination of anisole? (Sec. 9.8)



12. Which is the electrophile in the nitration of benzene? (Sec. 9.7)









OCH
3
H Br
OCH
3
Br H
OCH
3
Br H
OCH
3
Br H
a)
b) c)
d)
HNO
3
NO
2
NO
3 NO
a) b) c) d)
IV III II I
CH
3
COH
O
H
2
CO
3
OH OH
Chapter 9 Benzene and Its Derivatives
104

13. Which compound reacts most readily in the nitration reaction? (Sec. 9.7)



14. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first). (Sec. 9.7)


a) II, I, IV, III
b) I, III, IV, II
c) III, I, IV, II
d) IV, III, II, I



15. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first). (Sec. 9.7)
CH
3
Cl OH
O
I II III
IV


a) III, II, I, IV
b) IV, II, I, III
c) III, I, II, IV
d) I, II, III, IV




CH
3
HNCCH
3
O
CH
3
OCH
3
CH
3
COH
O
CH
3
SO
3
H
a) b)
c)
d)
CNHCH
3
O
NH
2
NO
2
HNCCH
3
O
I II III IV
Chapter 9 Benzene and Its Derivatives
105

16. Which is the major product of the following reaction? (Sec. 9.6)


17. Which is the major product of the following reaction? (Sec. 9.6, 9.8)


OCH
3
NO
2
H
3
CCCl
O
AlCl
3
OCH
2
CCH
3
O
NO
2
OCH
3
NO
2
H
3
CC
O
OCH
3
NO
2
CCH
3
O
OCH
3
NO
2
CCH
3
O
a)
b) c)
d)
d)
c)
b) a)
CH
2
HC
O
Br
CH
2
HC
O
Br
CH
2
HC
O
Br
CH
2
HC
O
Br
FeBr
3
Br
2
CH
2
HC
O
Chapter 9 Benzene and Its Derivatives
106

18. Which is the major product of the following series of reactions? (Sec. 9.5, 9.8)

19. Which is the best reaction sequence for preparing the following compound from benzene?
(Sec. 9.6, 9.8)







CH
3
AlCl
3
H
3
CCCl
O
K
2
Cr
2
O
7
H
2
SO
4
COH
O
COH
O
CCH
3
O
COH
O
CCH
3
O
CCH
3
O
OCH
3
COH
O
a) b) c)
d)
COH
O
NO
2
AlCl
3
CH
3
Cl
K
2
Cr
2
O
7
H
2
SO
4
HNO
3
H
2
SO
4
HNO
3
H
2
SO
4
K
2
Cr
2
O
7
H
2
SO
4
AlCl
3
CH
3
Cl
AlCl
3
CH
3
Cl
HNO
3
H
2
SO
4
K
2
Cr
2
O
7
H
2
SO
4
AlCl
3
H
3
CCl
O
HNO
3
H
2
SO
4
a)
b)
c)
d)
Chapter 9 Benzene and Its Derivatives
107


20. Which is the major product of the following reaction? (Sec. 9.6, 9.8)


21. Which is the electrophile in the final reaction step for the following reaction? (Sec. 9.7)


22. Which is the major product of the following reaction? (Sec. 9.6, 9.8)

a) 1-chloro-4-nitrobenzene
b) 1-chloro-3-nitrobenzene
c) 1-chloro-2-nitrobenzene
d) a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene


CCH
2
CH
2
CCl
O O
AlCl
3
O
O
O
O
a)
b)
c)
d)
OH H
3
CCCH
3
O
C
CH
3
CH
3
HO OH
H
3
PO
4
+
HO CCH
3
CH
3
C
CH
3
HO OH
HO C
O
H
3
CCCH
3
OH
a) b)
c) d)
HNO
3
H
2
SO
4
Cl
2
FeCl
3
Chapter 9 Benzene and Its Derivatives
108


23. Which is the major product of the following reactions? (Sec. 9.6, 9.8)




24. Which is the major product of the following reactions? (Sec. 9.5, 9.6, 9.8)



a) para chlorobenzoic acid
b) meta chlorobenzoic acid
c) a mixture of para and meta chlorobenzoic acid
d) a mixture of ortho and para chlorobenzoic acid


25. Which is the electrophile in the following reaction? (Sec. 9.7)


CH
2
HNO
3
H
2
SO
4
Br
2
FeBr
3
CH
2
Br NO
2
CH
2
Br
NO
2
CH
2
Br NO
2
CH
2
Br
NO
2
a) b)
c)
d)
Cl
2
FeCl
3
CH
3
Cl
FeCl
3
K
2
Cr
2
O
7
H
2
SO
4
+
H
3
PO
4
HPO
3
a)
b) c)
d)
Chapter 9 Benzene and Its Derivatives
109


Fill in the Blank

1. The major product of the following reaction is,

OH
H
3
PO
4
(Sec. 9.6, 9.8)

2. The major product of the following reaction is,

K
2
Cr
2
O
7
H
2
SO
4
(Sec. 9.5)

3. The major product of the following reaction is,

Br O
Cl
AlCl
3
(Sec. 9.6, 9.8)

4. The major products of the following reaction are,

OH OH
NaOH
H
2
O
+
(Sec. 9.9)










Chapter 9 Benzene and Its Derivatives
110

5. The major products of the following reaction are,

O OH
OH
+
NaHCO
3
H
2
O
(Sec. 9.9)

6. The reagent that completes the following reaction is,

CH
3
CH
3
NO
2
(Sec. 9.6, 9.8)

7. The reagents that complete the following reactions are,

SO
3
H
(Sec. 9.6, 9.8)

8. The starting material and reagent that complete the following reaction are,

SO
3
H
Cl
(Sec. 9.6, 9.8)









Chapter 9 Benzene and Its Derivatives
111

9. The reagents and mid-reaction product that complete the following scheme are,

Cl
O

(Sec. 9.6, 9.8)

10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,

Br
+
C
+
Br
H
H
Br
(Sec. 9.7)

True-False

1. The name of the following structure is 2,4-diethylnitrobenzene. (Sec. 9.4)

NO
2


2. The name of the following structure is 3,5-dibromobenzoic acid. (Sec. 9.4)

O OH
Br Br


3. The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene.
(Sec. 9.6, 9.8)

4. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone. (Sec. 9.5)

5. The product of the reaction of benzoic acid and chlorine/AlCl
3
is m-chlorobenzoic acid. (Sec. 9.6, 9.8)

Chapter 9 Benzene and Its Derivatives
112



6. The following compound is aromatic. (Sec. 9.3)



7. The following reaction scheme will synthesize the product shown. (Sec. 9.5, 9.6, 9.8)

Br
O OH
CH
3
CH
2
Cl
AlCl
3
K
2
Cr
2
O
7
H
2
SO
4
Br
2
FeBr
3


8. The following reaction scheme will synthesize the product shown. (Sec. 9.6, 9.8)

SO
3
H
CH
3
CH
2
Cl
AlCl
3
H
2
SO
4
SO
3


9. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution. (Sec. 9.7)

OH CH
3
SO
3
H
> > >


10. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution. (Sec. 9.7)

Cl NO
2
O
> > >



Chapter 9 Benzene and Its Derivatives
113


Answers

Multiple Choice

1. c
2. c
3. a
4. b
5. c
6. a
7. c
8. a
9. d
10. c
11. d
12. b
13. b
14. c
15. b
16. b
17. c
18. b
19. d
20. d
21. a
22. b
23. c
24. d
25. b

Fill in the Blank

1.


2.
OH O




Chapter 9 Benzene and Its Derivatives
114


3.
Br
O


4.
O
OH
+


5.
O O
OH
+


6. HNO
3
, H
2
SO
4


7.
Cl
AlCl
3
SO
3
, H
2
SO
4


8.
Cl
SO
3
, H
2
SO
4










Chapter 9 Benzene and Its Derivatives
115


9.
Cl
O
O
AlCl
3
Cl
2
, FeCl
3


10.
Br
+
C
+
Br
H
H
Br


True-False

1. T
2. T
3. F
4. F
5. T
6. F
7. F
8. T
9. T
10. F