Consider the following molecules: (p) CH3–CH2–C(=O)–Cl (q) CH3–CH2–C(=O)–O–C(=O)–CH3 (r) CH3–CH2–C(=O)–O–CH2–CH3 (s) CH3–CH2–C(=O)–NH2 The correct order of rate of hydrolysis is :

Question

Accepted Answer

(2) p > q > r > s. The correct order of hydrolysis rates is determined by the stability of the leaving group and the electrophilicity of the carbonyl carbon. In this case, acyl chlorides (p) hydrolyze fastest due to the excellent leaving ability of Cl-, followed by esters (q and r) where the presence of alkyl groups affects the rate, and finally, amides (s) are the slowest due to the resonance stabilization of the nitrogen.

Consider the following molecules: (p) CH3–CH2–C(=O)–Cl (q) CH3–CH2–C(=O)–O–C(=O)–CH3 (r) CH3–CH2–C(=O)–O–CH2–CH3 (s) CH3–CH2–C(=O)–NH2 The correct order of rate of hydrolysis is :

Solution

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