Dolbier HW Solutions 466

Dolbier HW Solutions 466 - 560 CARBOXYLIC ACID DERIVATIVES:...

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( c ) Benzoic acid, benzoyl chloride, and benzoic anhydride have been prepared in parts ( a ) and ( b ) of this problem. Any of them could be converted to benzyl benzoate on reaction with benzyl alcohol. Thus the synthesis of benzyl benzoate requires the preparation of benzyl alcohol from toluene. This is effected by a nucleophilic substitution reaction of benzyl bromide, in turn pre- pared by halogenation of toluene. Alternatively, recall that primary alcohols may be obtained by reduction of the corresponding carboxylic acid. Then ( d ) Benzamide is prepared by reaction of ammonia with either benzoyl chloride from part ( a ) or benzoic anhydride from part ( b ). ( e ) Benzonitrile may be prepared by dehydration of benzamide. ( f ) Benzyl cyanide is the product of nucleophilic substitution by cyanide ion on benzyl bromide or benzyl chloride. The benzyl halides are prepared by free-radical halogenation of the toluene
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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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