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Dolbier HW Solutions 536 - 630 AMINES g Acetanilide is an...

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( g ) Acetanilide is an amide and can be hydrolyzed when heated with aqueous acid. Under acidic conditions 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 with p -toluenesulfonyl chloride converts them to p -toluenesulfonate esters. p -Toluenesulfonate is an excellent leaving group in nucleophilic substitution reactions. Dimethylamine is the nucleophile. ( d ) Amines are suf fi ciently nucleophilic to react with epoxides. Attack occurs at the less substi- tuted carbon of the epoxide. CHCH 2 NHCH(CH 3 ) 2 OH CH 3 O OCH 3 1-(2,5-Dimethoxyphenyl)-2- (isopropylamino)ethanol (67%) CH CH 2 O CH 3 O OCH 3 2-(2,5-Dimethoxyphenyl)oxirane H 2 NCH(CH 3 ) 2 Isopropylamine
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