Which of the following compounds is hydrolyzed most slowly in aqueous ?
A
(ethyl acetate)
B
(phenyl acetate)
C
(methyl acetate)
D
(hydroxyethyl acetate)
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1
Identify the type of reaction involved: hydrolysis of esters in aqueous NaOH is a base-catalyzed ester hydrolysis (saponification), where the ester bond is cleaved to form a carboxylate salt and an alcohol.
Analyze the structure of each ester, focusing on the nature of the alkoxy (–OR) group attached to the carbonyl carbon, since this influences the rate of hydrolysis.
Recall that the rate of base hydrolysis depends on the leaving group ability of the alkoxide formed; better leaving groups facilitate faster hydrolysis.
Consider the resonance and electronic effects: phenyl esters (like phenyl acetate) have an alkoxy group that is a phenolate ion upon leaving, which is resonance stabilized and thus a poorer leaving group compared to alkoxide ions from alkyl esters.
Conclude that phenyl acetate hydrolyzes more slowly because the phenolate ion is less reactive as a leaving group, making the ester bond cleavage slower compared to alkyl esters such as ethyl, methyl, or hydroxyethyl acetate.