carboxyl group

carboxyl group (kärbŏkˈsĭl) [key], in chemistry, functional group that consists of a carbon atom joined to an oxygen atom by a double bond and to a hydroxyl group, OH, by a single bond. Carboxylic acids are compounds whose molecules contain a carboxyl group that is joined to a hydrogen atom, an alkyl group, or an aryl group by a single bond to its carbon atom. Dicarboxylic acids, compounds that contain two carboxyl groups, are important in a number of industrial processes. The four main types of reactions of carboxylic acids are chiefly due to either the weak acidity of the hydroxyl hydrogen or to the difference in electronegativity between carbon and oxygen. One type involves cleavage of the hydroxyl oxygen-hydrogen bond, e.g., reaction with an alcohol to form an ester or reaction with an alkali to form a water-soluble salt. A second type involves addition of an electron-rich species to the electron-deficient carbon atom of the carboxyl group. A third type is characterized by the joining of a carbon atom directly to the carboxyl group. A fourth type involves the loss of carbon dioxide (decarboxylation). The second and third types are similar to reactions of the carbonyl group; the carboxyl group may be thought of as a carbonyl group joined to a hydroxyl group.

The Columbia Electronic Encyclopedia, 6th ed. Copyright © 2012, Columbia University Press. All rights reserved.

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