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550 Chapter 16
Copyright © 2017 Pearson Education, Inc.
91.
O
N N
CH
2
+
CH
2
O
+
O
+
N
2
−
N N
+
−
92.
The compound that gives the
1
H NMR
spectrum is 2-phenyl-2-butanol.
CCH
2
CH
3
OH
CH
3
Therefore, the compound that reacts with methylmagnesium bromide is 1-phenyl-1-propanone.
CCH
2
CH
3
OH
CH
3
CCH
2
CH
3
O
1. CH
3
MgBr
2. HCl
93.
a.
CH
3
CHCH
2
COCH
3
OH
O
imidazole
CH
3
CHCH
2
COCH
3
OSi(CH
3
)
3
O
1. CH
3
MgBr
2. HCl
excess
CH
3
CHCH
2
CCH
3
OH
OH
CH
3
(CH
3
)
3
Si(CH
3
)
2
Cl
b.
1. HCl
Cl
OH
Cl
OSi(CH
3
)
3
Mg
Et
2
O
MgCl
OSi(CH
3
)
3
COO
–
OSi(CH
3
)
3
COOH
OH
CO
2
imidazole
(CH
3
)
3
Si(CH
3
)
2
Cl
2. (CH
3
CH
2
CH
2
CH
2
)
4
NF
c.
C
CH
3
Br
O
HCl
HOCH
2
CH
2
OH
Br
1. Li
2. CuLi
3.
H
2
O HCl
C
CH
3
CH
2
CH
2
OH
O
O
O
CH
3
O
CH
2
CH
2
O
O
O
CH
3
−