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Dolbier HW Solutions 650 - 744 LIPIDS 26.22(a There are no...

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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 fi 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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