Dolbier HW Solutions 463

Dolbier HW - 557 CARBOXYLIC ACID DERIVATIVES NUCLEOPHILIC ACYL SUBSTITUTION(x Nitriles are hydrolyzed to carboxylic acids in acidic media

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( x ) Nitriles are hydrolyzed to carboxylic acids in acidic media. ( y ) Nitriles are hydrolyzed in aqueous base to salts of carboxylic acids. ( z ) Grignard reagents react with nitriles to yield ketones after addition of aqueous acid. ( aa ) Amides undergo the Hofmann rearrangement on reaction with bromine and base. A methyl carbamate is the product isolated when the reaction is carried out in methanol. ( bb ) Saponi f cation of the carbamate in part ( aa ) gives the corresponding amine. 20.28 ( a ) Acetyl chloride is prepared by reaction of acetic acid with thionyl chloride. The f rst task then is to prepare acetic acid by oxidation of ethanol. ( b ) Acetic acid and acetyl chloride, available from part ( a ), can be combined to form acetic anhydride.
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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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