Question

Which of the following carboxylic acid derivatives has the fastest rate of hydrolysis – the anhydride or the amide? Explain.

Answer 1

Answer – The carboxylic acid derivatives has the fastest rate of hydrolysis for the anhydride than amide, since there is anhydride reacts with water faster than amide. The anhydride easily reacts with water and without heat, but amide needed heating and strong acid. We know for the nucleophilic substitution reaction we must to break the carbonyl C and leaving group bond and there is formation of new bond between the carbonyl C and nucleophile. When we react the amide with water then there is bond between carbonyl C and nitrogen in the amine is not easily break and it need more energy, so we need to heat, but in the anhydride there is leaving group is acetate, which is more stable and easily removed, so anhydride has faster hydrolysis than amide.