2. There are two methods to convert an alkyl halide into a carboxylic acid containing one additional carbon atom: R-X R-X NaCN CH3CI Mg R-CN Br R-MgX H3O+ 1) CO₂ 2) H3O+ Depending on the structure of the alkyl halide, one or both of these methods may be used. For each alkyl halide shown, write out a stepwise mechanism that converts it to a carboxylic acid. If both methods work, draw both routes. If one method cannot be used, state why it cannot. (CH3)3CCI R OH HO R OH Br

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...
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2. There are two methods to convert an alkyl halide into a carboxylic acid containing one
additional carbon atom:
R-X
R-X
NaCN
CH3CI
Mg
R-CN
Br
R-MgX
H3O+
1) CO₂
2) H3O+
(CH3)3CCI
i
Depending on the structure of the alkyl halide, one or both of these methods may be used. For
each alkyl halide shown, write out a stepwise mechanism that converts it to a carboxylic acid. If
both methods work, draw both routes. If one method cannot be used, state why it cannot.
HO
R
OH
AiOH
R
OH
Br
Transcribed Image Text:2. There are two methods to convert an alkyl halide into a carboxylic acid containing one additional carbon atom: R-X R-X NaCN CH3CI Mg R-CN Br R-MgX H3O+ 1) CO₂ 2) H3O+ (CH3)3CCI i Depending on the structure of the alkyl halide, one or both of these methods may be used. For each alkyl halide shown, write out a stepwise mechanism that converts it to a carboxylic acid. If both methods work, draw both routes. If one method cannot be used, state why it cannot. HO R OH AiOH R OH Br
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