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Example · Example 9

Q.Write the general structure of an α\alpha-amino acid, and explain what is meant by saying it exists as a zwitterion.

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An α\alpha-amino acid's general structure is R−CH(NH2)−COOH\text{R}{-}\text{CH}(\text{NH}_2){-}\text{COOH}: a central alpha carbon bonded to an amino group (−NH2-\text{NH}_2), a carboxyl group (−COOH-\text{COOH}), a hydrogen atom, and a variable side chain R that determines the identity of the specific amino acid.

Because the acidic −COOH-\text{COOH} group and the basic −NH2-\text{NH}_2 group are both present on the same molecule (and close together, both on the alpha carbon), an internal proton transfer occurs spontaneously: the −COOH-\text{COOH} group donates its acidic proton directly to the neighbouring −NH2-\text{NH}_2 group. This converts the carboxyl group into a negatively charged carboxylate ion, −COO−-\text{COO}^-, and the amino group into a positively charged ammonium ion, −NH3+-\text{NH}_3^+ -- giving the structure R−CH(NH3+)−COO−\text{R}{-}\text{CH}(\text{NH}_3^+){-}\text{COO}^-. Although this molecule now carries both a positive and a negative charge simultaneously, the two charges cancel and the molecule as a whole is electrically neutral. A molecule carrying separated positive and negative charges like …

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