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Dolbier HW Solutions 462 - 556 CARBOXYLIC ACID DERIVATIVES...

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( r ) In acid solution amides yield carboxylic acids and ammonium salts. ( s ) The starting material is a cyclic imide. Both its amide bonds are cleaved by nucleophilic attack by hydroxide ion. ( t ) In acid the imide undergoes cleavage to give a dicarboxylic acid and the conjugate acid of methylamine. ( u ) Acetanilide is hydrolyzed in acid to acetic acid and the conjugate acid of aniline. ( v ) This is another example of amide hydrolysis. ( w ) One way to prepare nitriles is by dehydration of amides. H 2 O Cyclopentanecarboxamide O CNH 2 Cyclopentyl cyanide C N P 4 O 10 Water H 2 O Sulfuric acid H 2 SO 4 N -Methylbenzamide O C 6 H 5 CNHCH 3 Benzoic acid O C 6 H 5 COH Methylammonium hydrogen sulfate CH
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