Dolbier HW Solutions 428

Dolbier HW Solutions 428 - 522 CARBOXYLIC ACIDS (c)...

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( c ) Examining the target molecule reveals that it contains two more carbon atoms than the indi- cated starting material, suggesting use of ethylene oxide in a two-carbon chain-extension process. This suggests the following sequence of steps: ( d ) This synthesis requires extending a carbon chain by two carbon atoms. One way to form dicarboxylic acids is by hydrolysis of dinitriles. This suggests the following sequence of steps: ( e ) The desired alcohol cannot be prepared directly from the nitrile. It is available, however, by lithium aluminum hydride reduction of the carboxylic acid obtained by hydrolysis of the nitrile. heat H 2 O, H 1 2. H 2 O 1. LiAlH 4 3-Phenylbutanenitrile CH 3 CHCH 2 CN C 6 H 5 3-Phenyl-1-butanol CH 3 CHCH 2 CH 2 OH C 6 H 5 3-Phenylbutanoic acid CH 3 CHCH 2 COH C 6 H 5 O 1. LiAlH 4 2. H 2 O HO 2 C(CH 2 )
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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