616 / 912
608 Chapter 18
Copyright © 2017 Pearson Education, Inc.
25.
a.
COOH
COOH
Cl
2
FeCl
3
COOH
COOH
Cl
COOH
COOH directs to the meta
position. The same product
will be obtained regardless
of which COOH is the
director.
Less of this compound
will be obtained because
of steric hindrance.
Cl
COOH
CH
3
CH
3
COOH
Br
FeBr
3
Br
2
COOH is a meta director, and
CH
3
is an ortho-para director, so both
direct to the same position.
COOH
c.
COOH directs to its meta
position, and Cl directs
to its ortho position,
so they both direct to the
same position on the ring.
COOH
Cl
Br
2
FeBr
3
COOH
Cl
Br
d.
OCH
3
F
OCH
3
F
NO
2
HNO
3
H
2
SO
4
A methoxy substituent is strongly activating,
and a uorine substituent is deactivating, so
the methoxy substituent will do the directing.
e.
H
2
SO
4
HNO
3
C
O H
OCH
3
OCH
3
NO
2
The aldehyde group is a meta director, and
the methoxy group is an ortho-para director,
so both direct to the same position.
C
O H
f.
H
2
SO
4
HNO
3
CH
3
CH
3
CCH
3
Less of this product will be obtained
because of steric hindrance.
CH
3
CH
3
CH
3
CCH
3
CH
3
NO
2
CH
3
CH
3
CCH
3
CH
3
NO
2
+
b.