Chemistry Reference
In-Depth Information
10.11
There are several possible approaches. First, the alcohol must be converted to a
halide. The halide can then be converted to the corresponding Grignard reagent,
which can react with carbon dioxide to provide the carboxylic acid.
PBr
3
CH
3
CH
2
CH
2
OH
CH
3
CH
2
CH
2
Br
Mg, ether
1.
CO
2
CH
3
CH
2
CH
2
CO H
CH
3
CH
2
CH
2
MgBr
2
+
2.
H O
3
Conversion of the halide to a nitrile followed by hydrolysis would also provide the
carboxylic acid. This reaction is introduced in the next section (10.7d), so do not be
concerned if it did not occur to you when initially working this problem.
+
NaCN
H O
3
CH
3
CH
2
CH
2
Br
CH
3
CH
2
CH
2
CN
CH
3
CH
2
CH
2
CO H
2
heat
10.12
It is not possible to conduct S
N
2 displacements at
sp
2
-hybridized (aryl, vinyl) carbon
atoms. The conversion can be accomplished via the Grignard reagent:
Mg
1.
CO
2
Br
MgBr
CO
2
+
ether
2.
H O
3
10.13
Mg, ether
1.
CO
2
CH
Br
CH MgBr
2
2
+
2.
H O
3
CH C
2
H
+
NaCN
H O, H
2
CH
Br
CH CN
2
2
heat
CH C
2
H
10.14
a.
methyl methanoate
b.
cyclopropyl propanoate
