Chemistry Reference
In-Depth Information
h.
i.
O
O
O
O
NH
3
(excess)
Cl
C
(
CH
2
)
4
C
Cl
H N
C
(
CH
2
)
4
C
NH
2
2
+2NH
4
C
+-
10.56
a.
See eq.10.33.
O
O
CH
3
CH
2
CH
2
C
OH
+ PCl
5
CH
3
CH
2
CH
2
C
Cl
+ HCl
+ POCl
3
b.
See eq. 10.32.
CH
3
CH
2
(
)
6
CO
2
H
+ SOCl
2
CH
3
CH
2
(
)
6
COCl
+ HCl
+ SO
2
c.
See eq. 10.8.
CH
3
CO
2
H
KMnO
4
heat
CH
3
CO
2
H
d.
See eq. 10.41.
O
CO
-
O
heat
4
+
NH
C
NH
+
H O
2
2
e.
See eq. 10.43.
O
LiAlH
4
CH
3
(
CH
2
)
5
C
NH
2
CH
3
(
CH
2
)
5
CH
2
NH
2
f.
See eq. 10.28.
1.
LiAlH
4
CO
2
CH
2
CH
3
CH
2
OH
+ CH
3
CH
2
OH
+
2. H O
3
10.57
Ketones are more reactive toward nucleophiles than esters. Reduction therefore
occurs at the ketone carbonyl group, to give
CH
3
CH(OH)CH
2
CH
2
CO
2
CH
3
10.58
The method combines the formation of a cyanohydrin (Sec. 9.10) with the hydrolysis
of a cyanide to an acid (Sec. 10.7d).
OH
OH
+
HCN
H O
3
CH
O
C
CN
C
CO H
2
heat
H
H
