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614 Chapter 18
Copyright © 2017 Pearson Education, Inc.
39.
a.
The more nitro substituents ortho and para to the halogen, the faster the rate of nucleophilic aromatic
substitution.
1-chloro-2,4-dinitrobenzene
7
p
-chloronitrobenzene
7
chlorobenzene
b.
The fewer nitro substituents attached to the benzene ring, the faster the rate of electrophilic aromatic
substitution.
chlorobenzene
7
p
-chloronitrobenzene
7
1-chloro-2,4-dinitrobenzene
40.
a.
Br
2
FeBr
3
HNO
3
H
2
SO
4
HO
−
Br
NO
2
Br
NO
2
OH
b.
Br
2
FeBr
3
HNO
3
H
2
SO
4
NH
3
Br
Br
NH
3
NO
2
NO
2
HO
−
NH
2
NO
2
+
c.
Br
2
FeBr
3
HNO
3
H
2
SO
4
CH
3
O
Br
Br
OCH
3
NO
2
−
NO
2
OCH
3
NaNO
2
NH
2
HCl
0
°
C
OCH
3
CuBr
OCH
3
Br
H
2
, Pd/C
N
N
+
Cl
−
d.
This synthesis would be carried out exactly as in
c
(above) except for the second to last step which
would be:
OCH
3
H
3
PO
2
OCH
3
N
N
+
Cl
−