Imidazole forms part of the structure of the amino acid histidine and can act as both an

Chapter 2, Problem 2.18

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Imidazole forms part of the structure of the amino acid histidine and can act as both an acid and a base. O C O N N H H3N + H H H N N HH Imidazole Histidine (a) Look at the electrostatic potential map of imidazole, and identify the most acidic hydrogen atom and the most basic nitrogen atom. (b) Draw structures for the resonance forms of the products that result when imidazole is protonated by an acid and deprotonated by a base.

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