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c.
9.18
CH
O
+
CH
N
+O
H 2
H 2
N
9.19
a.
b.
c.
d.
9.20
a.
Follow eq. 9.33:
O
OH
1. LiAlH 4
C
CH 3
C
CH 3
2.
H 2
O
H
b.
Follow eq. 9.33:
O
OH
1. LiAlH 4
CH 3 CH 2 CH 2 CH 2
C
H
CH 3 CH 2 CH 2 CH 2
C
H
2.
H 2
O
H
9.21
A metal hydride will reduce the C=O bond but not the aromatic ring.
O
HO
H
NaBH
CH 3
4
CH 3
HO
9.22
Follow eq. 9.39 as a guide, replacing R with H:
O + 2 Ag(NH 3 +
3 HO -
HCO -
H 2
C
)
+
+ 2 Ag
+
4
3
+
2
H 2
O
9.23 Remove an α -hydrogen and place it on the oxygen; make the carbon-oxygen bond
single, and make the bond between the α -carbon and what was the carbonyl carbon
double.
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