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Chapter 18 649
Copyright © 2017 Pearson Education, Inc.
103.
a.
O
CH
3
O
CH
2
Br
O
CH
2
C N
O
CHC N
O
CHCOH
CH
3
O
Br
2
h
−
C N
HCl, H
2
O
CH
3
1. LDA/THF
2. CH
3
Br
b.
The substituent in ibuprofen is placed on the ring by a Friedel–Crafts acylation reaction. A Friedel–
Crafts reaction cannot be done in the synthesis of ketoprofen, because the benzene rings are deactivated
and deactivated rings cannot undergo Friedel–Crafts reactions.
104.
N CH
3
H
NO
2
NH
2
N CH
3
CH
3
H
N
C
CH
3
O
C
HO
O
H
NH
3
C
HO
O
+
NH
3
+
N
H
+
H
2
SO
4
HNO
3
NH
3
C
−
O
O
+
Pd/C
H
2
CH
3
CCl
O
AlCl
3
CH
3
Cl
HCl
H
2
O
(CH
3
CH
2
)
2
NHCH
2
CH
2
OH
1. SOCl
2
HCl
+
HO
−
C
O
C
O
+
O
O
C
NH
2
N
O
O
C
2.
H
2
CrO
4
adjust pH to 6