(g)Acetanilide is an amide and can be hydrolyzed when heated with aqueous acid. Under acidicconditions the aniline that is formed exists in its protonated form as the anilinium cation.(h)Amides are hydrolyzed in base.22.34(a)The reaction illustrates the preparation of a secondary amine by reductive amination.(b)Amides are reduced to amines by lithium aluminum hydride.(c)Treatment of alcohols withp-toluenesulfonyl chloride converts them top-toluenesulfonateesters.p-Toluenesulfonate is an excellent leaving group in nucleophilic substitution reactions.Dimethylamine is the nucleophile.(d)Amines are sufficiently nucleophilic to react with epoxides. Attack occurs at the less substi-tuted carbon of the epoxide.CHCH2NHCH(CH3)2OHCH3OOCH31-(2,5-Dimethoxyphenyl)-2-(isopropylamino)ethanol (67%)CHCH2OCH3OOCH32-(2,5-Dimethoxyphenyl)oxiraneH2NCH(CH3)2Isopropylamine
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