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In organic chemistry, a hemiacetal is a functional group the general formula R 1 R 2 C(OH)OR, where R 1, R 2 is a hydrogen atom or an organic substituent. They generally result from the nucleophilic addition of an alcohol (a compound with at least one hydroxy group ) to an aldehyde ( R−CH=O ) or a ketone ( R 2 C=O ) under acidic conditions.
In contrast to variations of R, both R' groups are organic fragments. If one R' is a hydrogen, the functional group is instead a hemiacetal, while if both are H, the functional group is a ketone hydrate or aldehyde hydrate. Formation of an acetal occurs when the hydroxyl group of a hemiacetal becomes protonated and is lost as water.
Common conformations are chair (C), boat (B), skew (S), half-chair (H) or envelope (E). The ring atoms are then numbered; the anomeric, or hemiacetal, carbon is always 1. Oxygen atoms in the structure are, in general, referred to by the carbon atom they are attached to in the acyclic form, and designated O. Then:
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Hemiacetals of ketones (sometimes called hemiketals) are even less stable than those of aldehydes. However, cyclic hemiacetals and hemiacetals bearing electron withdrawing groups are stable. Electron-withdrawing groups attached to the carbonyl atom shift the equilibrium constant toward the hemiacetal.
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