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Chapter 18 623
Copyright © 2017 Pearson Education, Inc.
55.
a.
anisole
7
ethylbenzene
7
benzene
7
chlorobenzene
7
nitrobenzene
b.
2,4-dinitrophenol
7
1-methyl-2,4-dinitrobenzene
7
1-chloro-2,4-dinitrobenzene
c.
p-
cresol
7
p
-xylene
7
toluene
7
benzene
d.
phenol
7
propylbenzene
7
benzene
7
benzoic acid
e.
p
-chloromethylbenzene
7
p
-methylnitrobenzene
7
2-chloro-1-methyl-4-nitrobenzene > 1-methyl-
2,4-dinitrobenzene
f.
fluorobenzene
7
chlorobenzene
7
bromobenzene
7
iodobenzene
56.
a.
Two products are obtained. Less of the product on the right is obtained because of steric hindrance.
FeCl
3
Cl
2
CH
3
CH
3
CH
3
CH
3
Cl
CH
3
CH
3
+
Cl
b.
One product is obtained. (Notice that the four positions are equivalent.)
FeCl
3
Cl
2
CH
3
CH
3
Cl
CH
3
CH
3
c.
Two products can be obtained, but little, if any, of one of the products is obtained because of
steric hindrance.
FeCl
3
Cl
2
CH
3
CH
3
CH
3
CH
3
+
CH
3
Cl
CH
3
Cl
major
minor
57.
a.
O
C
O
CH
3
O
2
N
+
O
C
O
CH
3
NO
2
b.
CH
3
D
c.
OCH
3
O
−
O
O
+
OCH
3
O
O
O
−