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In organic chemistry, a lactol is a functional group which is the cyclic equivalent of a hemiacetal (−CH(OH)O−) or a hemiketal (>C(OH)O−). The compound is formed by the intramolecular , nucleophilic addition of a hydroxyl group ( −OH ) to the carbonyl group ( C=O ) of an aldehyde ( −CH=O ) or a ketone ( >C=O ).
This also allows for a classic use of Fétizon's reagent to form lactones from a primary diol. By oxidizing one of the alcohols to an aldehyde, the second alcohol equilibrates with the aldehyde to form a lactol which is reacted quickly with more Fétizon's reagent to trap the cyclic intermediate as a lactone. [8]
Right: a lactol of fructose, a cyclic hemiketal. Hemiacetals commonly exist in nature as aldoses such as glucose , and hemiketals commonly exist in nature as ketoses such as fructose . The favorability of the formation of a strain-free six-membered ring and the electrophilicity of an aldehyde combine to strongly favor the acetal form.
2-Carboxybenzaldehyde is a chemical compound.It consists of a benzene ring, with an aldehyde and a carboxylic acid as substituents that are ortho to each other. The compound exhibits ring–chain tautomerism: the two substituents can react with each other to form 3-hydroxyphthalide, a cyclic lactol.
Lactones are usually named according to the precursor acid molecule (aceto = 2 carbon atoms, propio = 3, butyro = 4, valero = 5, capro = 6, etc.), with a -lactone suffix and a Greek letter prefix that specifies the number of carbon atoms in the heterocycle — that is, the distance between the relevant -OH and the -COOH groups along said backbone.
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Lactams can be formed from cyclisation of amino acids via the coupling between an amine and a carboxylic acid within the same molecule. Lactamization is most efficient in this way if the product is a γ-lactam.
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