Alkoholeiden

Alkoholeiden is a term occasionally used in Dutch-language chemistry literature to describe compounds that contain both hydroxyl groups (alcohol functionality) and an aldehyde group within the same molecule. It is not a formal, widely adopted IUPAC category; in standard nomenclature these compounds are usually referred to as hydroxyaldehydes or aldehydes bearing hydroxy substituents.

Definition and examples

Hydroxyaldehydes are multifunctional molecules in which at least one carbon bears a hydroxyl group and another carbon bears an aldehyde group. Typical examples include open-chain forms of sugars such as glyceraldehyde (HO-CH2-CHO) and erythrose (HO-CH2-CHOH-CHO). Because of the dual functionality, these compounds can participate in reactions characteristic of both alcohols and aldehydes, such as oxidation, nucleophilic addition to the carbonyl, and intramolecular cyclization.

Occurrence and significance

Hydroxyaldehydes occur naturally in carbohydrate chemistry and metabolism, often as intermediates in aldehyde-alcohol equilibria, and can be encountered in various polyols that possess terminal aldehyde groups. They serve as useful intermediates in organic synthesis for building more complex polyfunctional molecules and in studies of sugar chemistry and reactivity.

Synthesis and reactivity

Preparation commonly involves selective oxidation of primary alcohols to aldehydes under controlled conditions, or protection and sequential functional-group manipulation of polyols. Reagents such as PCC, Swern, or Dess–Martin periodinane may be employed to stop oxidation at the aldehyde stage. The aldehyde functionality enables typical carbonyl reactions (nucleophilic additions, condensations, and acetal/acetalization chemistry), while the remaining hydroxyl groups impart high polarity and potential for hydrogen bonding.

See also

Hydroxyaldehydes, aldehydes, alcohols, carbohydrate chemistry.