CH2OHgroep

CH2OHgroep, also called hydroxymethylgroep, is a functional group in organic chemistry with the formula -CH2OH. It consists of a methylene unit (-CH2-) bonded to a hydroxyl group (-OH). When attached to the main carbon skeleton, the carbon bearing the hydroxyl is a primary alcohol carbon, making the CH2OH group a primary alcohol substituent in many compounds.

In systematic naming, the substituent is referred to as hydroxymethyl. This group is common in both aromatic and aliphatic compounds. Prominent examples include benzyl alcohol (phenylmethanol, C6H5-CH2OH) and various hydroxymethyl derivatives found in natural products and synthetic intermediates. In carbohydrates, the terminal carbon often appears as a CH2OH group (for example, glucose ends with a CH2OH moiety in its open-chain form).

Reactivity and properties: as an alcohol, the CH2OH group participates in typical alcohol chemistry. It can be oxidized to an aldehyde (-CHO) and, under stronger conditions, to a carboxyl group (-COOH). It can be reduced to a methyl group (-CH3). The hydroxyl group enables hydrogen bonding, contributing to higher boiling points and solubility in water relative to nonpolar hydrocarbons of similar size. The CH2OH group can form esters with carboxylic acids or acid chlorides, and it can participate in various condensation and protection-deprotection strategies in synthesis.

Applications and context: CH2OH is a building block in organic synthesis, used for introducing a hydroxyl-bearing methylene unit into molecules. It appears in pharmaceuticals, dyes, fragrances, and polymers, often as a functional handle for further transformations.