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Chapter 18 639
Copyright © 2017 Pearson Education, Inc.
90.
The signal at 7.1–7.3 ppm that integrates to 5 protons indicates a monosubstituted benzene ring. The
doublet at 1.3 ppm that integrates to 6 protons and the septet at 2.9 ppm that integrates to 1 proton indicate
an isopropyl group. Therefore, compound
A
is isopropylbenzene.
91.
a.
tert
-BuO
−
CH
3
CH
3
CHCH
3
CH
3
CCH
3
Br
CH
3
Cl
AlCl
3
CH
3
CHCH
3
Cl
AlCl
3
CH
3
C CH
2
−
Br
Br
Br
Br
2
FeBr
3
H
2
SO
4
OCH
3
HNO
3
NO
2
NO
2
Br
2
FeBr
3
Br
NO
2
Br
CH
3
O
CH
3
C CH
2
CH
3
CH
3
CH
Br
PdL
2
HO
−
3
B(OR)
2
CH
3
Cl
AlCl
3
Br
2
FeBr
3
CH
or
3
C CH
2
Br
2
h
b.
c.
C
CH(CH
3
)
2
O
CH
2
CH(CH
3
)
2
(CH
3
)
2
CHCCl
O
AlCl
3
1.
2. H
2
O
CH
2
CH(CH
3
)
2
C
CH
3
O
CH
2
CH(CH
3
)
2
C
CH
3
O
SO
3
H
1. CH
3
CCl,
O
AlCl
3
2. H
2
O
H
2
SO
4
or
H
2
NNH
2
HO ,
H
2
, Pd/C