Chemistry Homework Solutions
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#43443

Imidazole, acting as a nucleophile

Imidazole, acting as a nucleophile, catalyzes the hydrolysis of phenol acetate by attack on the carbonyl carbon atom of the ester. The imidazole displaces the phenoxide anion and forms acetyl imidazole. In turn, the acetyl imidazole is quite unstable in water and hydrolyzes to form acetic acid, and regenerates the imidazole molecule. Write a suitable mechanism outlining these steps. (Please show work)

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