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624 Chapter 18
Copyright © 2017 Pearson Education, Inc.
d.
Br
N
+
Br
N
e.
CH
2
CH
2
CH
2
OH
f.
CF
3
Cl
58.
NO
2
COOH
a.
d.
COOH
OH
OCH
3
c.
Cl
h.
Cl
CH
3
g.
NO
2
Cl
minor
CH
3
Br
minor
f.
minor
OH
b.
OCCH
3
O
CH
3
OC
O
e.
CCH
3
O
59.
1.
C
Cl
O
CH
3
+
C
O
CH
3
1. AlCl
3
2. H
2
O
2.
CH
3
C
Cl
O
+
C
O
CH
3
1. AlCl
3
2. H
2
O
60.
Because the 2
p
orbital of oxygen overlaps the 2
p
orbital of carbon better than does the 3
p
orbital of sulfur,
oxygen is better than sulfur at donating electrons by resonance. Therefore, the benzene ring of anisole is
more activated toward electrophilic aromatic substitution than is the benzene ring of thioanisole.