Question about Imidazole
Imidazole is a weak acid, and thus reacts with strong bases to form the corresponding anion. Show this reaction, and draw resonance structures that account for the stability of conjugate base.
Suggest a mechanism for the dehydration involved in the last step in the synthesis of benzimidazole.
Imidazole, acting as a nucleophile, catalyzes the hydrolysis of phenyl 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.