Two methods convert an alkyl halide into a carboxylic acid having one more carbon atom. (1] R-X + "CN R-CN R,COOH COOH (Section 22.18) + X- new C-C bond [1] CO2 RCOOH (Section 20.14) [2] H3O [2] R-X + Mg R-MgX Depending on the structure of the alkyl halide, one or both of these methods may be employed. For each alkyl halide, write out a stepwise sequence that converts it to a carboxylic acid with one more carbon atom. If both methods work, draw both routes. If one method cannot be used, state why it can't. Br a. CH,CI b. c. (CH3)3CCI d. HOCH,CH,CH,CH,Br

Introduction to General, Organic and Biochemistry
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Chapter16: Amines
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Two methods convert an alkyl halide into a carboxylic acid having one more carbon atom.
(1]
R-X
+
"CN
R-CN
R,COOH
COOH (Section 22.18)
+ X-
new C-C bond
[1] CO2 RCOOH (Section 20.14)
[2] H3O
[2] R-X
+ Mg
R-MgX
Depending on the structure of the alkyl halide, one or both of these methods may be employed. For each alkyl halide, write out
a stepwise sequence that converts it to a carboxylic acid with one more carbon atom. If both methods work, draw both routes.
If one method cannot be used, state why it can't.
Br
a. CH,CI
b.
c. (CH3)3CCI
d. HOCH,CH,CH,CH,Br
Transcribed Image Text:Two methods convert an alkyl halide into a carboxylic acid having one more carbon atom. (1] R-X + "CN R-CN R,COOH COOH (Section 22.18) + X- new C-C bond [1] CO2 RCOOH (Section 20.14) [2] H3O [2] R-X + Mg R-MgX Depending on the structure of the alkyl halide, one or both of these methods may be employed. For each alkyl halide, write out a stepwise sequence that converts it to a carboxylic acid with one more carbon atom. If both methods work, draw both routes. If one method cannot be used, state why it can't. Br a. CH,CI b. c. (CH3)3CCI d. HOCH,CH,CH,CH,Br
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