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Chapter 18 625
Copyright © 2017 Pearson Education, Inc.
61.
Three ways to synthesize anisole from benzene are shown below.
1.
OCH
3
NH
2
NO
2
N
N
+
Cl
−
HNO
3
H
2
SO
4
H
2
, Pd/C
HCl
NaNO
2
0
°
C
CH
3
OH HCl,
2.
OH
OCH
3
HNO
3
H
2
SO
4
H
2
, Pd/C
HCl
NaNO
2
0
°
C
1. NaH
2. CH
3
I
NH
2
NO
2
N
N
+
Cl
−
H
2
O
Cu O
2
Cu
(
NO
3
)
2
or
H
3
O
+
3.
Cl
−
OCH
3
O
2
N
Cl
O
2
N
Cl
+
OCH
3
H
2
N
OCH
3
N
N
OCH
3
Cl
2
FeCl
3
HNO
3
H
2
SO
4
CH
3
O
−
H
2
, Pd/C
HCl
NaNO
2
0
°
C
H
3
PO
2
62.
The compound with the methoxy substituent is the more reactive because it forms the more stable
carbocation intermediate. The carbocation intermediate is stabilized by resonance electron donation.
CH
3
O
CH CH
3
+