Ch_322b_20.13

Ch_322b_20.13 - Reactions of Amines: Amides and...

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Reactions of Amines: Amides and Sulfonamides Primary and secondary amines react readily with acyl and sulfonyl chlorides : Similarly, Tertiary amines do not give stable products. RNH 2 : + R'CCl O (-HCl) RNH CR' acyl chloride amide RNH 2 + ArSCl sulfonyl chloride (-HCl) RNH SAr N-substituted sulfonamide O O O O O RR'NH + R'CCl (-HCl) RR'N CR' acyl chloride amide RR'NH + ArSCl sulfonyl chloride (-HCl) RR'N SAr N,N-disubstituted sulfonamide O O O O O O
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Carboxamides (amides derived from carboxylic acids) hydrolyze under either acid or base conditions. NHC O = benzanilide (N-phenyl benzamide) HCl H 2 O, heat HO - H 2 O, heat NH 3 + + COOH NH 2 + CO 2 - Sulfonamides hydrolyze much more slowly than carboxamides. Hydrolysis does occur under acid conditions. Under basic conditions, the rapid formation of an anion (derived from the acidic H on nitrogen) inhibits nucleophilic attack and hydrolysis. RN O - resists hydrolysis
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Ch_322b_20.13 - Reactions of Amines: Amides and...

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