(c)The amino group of arylamines is nucleophilic and undergoes acylation on reaction withchloroacetyl chloride.Chloroacetyl chloride is a difunctional compound—it is both an acyl chloride and an alkylchloride. Acyl chlorides react with nucleophiles faster than do alkyl chlorides, so that acyla-tion of the amine nitrogen occurs rather than alkylation.(d)The fnal step in the synthesis of lidocaine is displacement of the chloride by diethylaminefrom 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 thehydrogen chloride formed.(e)For use as an anesthetic, lidocaine is made available as its hydrochloride salt. Of the twonitrogens 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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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.