Dolbier HW Solutions 650

Dolbier HW Solutions 650 - 744 LIPIDS 26.22 (a) There are...

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26.22 ( a ) There are no direct methods for the reduction of a carboxylic acid to an alkane. A number of indirect methods that may be used, however, involve f rst converting the carboxylic acid to an alkyl bromide via the corresponding alcohol. Once the alkyl bromide is in hand, it may be converted to an alkane by conversion to a Grignard reagent followed by addition of water. Other routes are also possible. For example, E2 elimination from 1-bromooctadecane followed by hydrogenation of the resulting alkene will also yield octadecane. ( b ) Retrosynthetic analysis reveals that the 18-carbon chain of the starting material must be attached to a benzene ring. The desired sequence may be carried out by a Friedel Crafts acylation, followed by Clemmensen or Wolff Kishner reduction of the ketone. ( c ) First examine the structure of the target molecule 3-ethylicosane.
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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