hydroxymethylgrupper

The hydroxymethyl group, also known as the hydroxymethyl substituent, is a functional group in organic chemistry with the formula -CH2OH. It consists of a methylene carbon attached to a hydroxyl group and to the rest of the molecule; the carbon is sp3-hybridized and bears two hydrogens, one hydroxyl, and one bond to the parent structure.

In naming, the group is treated as a substituent that can be described as hydroxymethyl-, for example hydroxymethylbenzene corresponds to benzyl alcohol (Ph-CH2OH). Common simple instances include benzyl alcohol and compounds where the group terminates a carbon chain. The group also appears prominently in carbohydrates; many sugars contain a terminal CH2OH group, which remains outside the ring form and can influence solubility and reactivity. Glycerol is another example, having two end hydroxymethyl groups (HO-CH2- and -CH2-OH) on a three-carbon backbone.

Reactivity and transformations of the hydroxymethyl group follow typical alcohol chemistry. The -OH can undergo oxidation to formyl (-CHO) and then carboxyl (-COOH) groups under appropriate conditions. It can participate in ether formation, acetal or acylation reactions, and can be converted into chloromethyl, bromomethyl, or other derivatives for further functionalization. Protection strategies in synthesis often involve converting the alcohol into ethers or esters to prevent undesired reactions at that site.

Overall, the hydroxymethyl group is a common and versatile functional group that imparts alcohol character and reactive sites at terminal positions in a wide range of organic and biochemical molecules.