Dolbier HW Solutions 538

Dolbier HW Solutions 538 - 632 AMINES(c The amino group of...

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( c ) The amino group of arylamines is nucleophilic and undergoes acylation on reaction with chloroacetyl chloride. Chloroacetyl chloride is a difunctional compound it is both an acyl chloride and an alkyl chloride. Acyl chlorides react with nucleophiles faster than do alkyl chlorides, so that acyla- tion of the amine nitrogen occurs rather than alkylation. ( d ) The f nal step in the synthesis of lidocaine is displacement of the chloride by diethylamine from the a -halo amide formed in part ( c ) in a nucleophilic substitution reaction. The reaction is carried out with excess diethylamine, which acts as a base to neutralize the hydrogen chloride formed. ( e ) For use as an anesthetic, lidocaine is made available as its hydrochloride salt. Of the two nitrogens in lidocaine, the amine nitrogen is more basic than the amide. ( f ) Lithium aluminum hydride reduction of amides is one of the best methods for the preparation
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