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Lactol
Functional group >C(OH)O– on a cyclic compound
Functional group >C(OH)O– on a cyclic compound
In organic chemistry, a lactol is a functional group which is the cyclic equivalent of a hemiacetal () or a hemiketal (). The compound is formed by the intramolecular, nucleophilic addition of a hydroxyl group () to the carbonyl group () of an aldehyde () or a ketone ().
A lactol is often found as an equilibrium mixture with the corresponding hydroxyaldehyde. The equilibrium can favor either direction depending on ring size and other conformational effects. :[[File:lactol equilibrium.png|300px|left]]
The lactol functional group is prevalent in nature as component of aldose sugars.
Chemical reactivity
Lactols can participate in a variety of chemical reactions including:
- Oxidation to form lactones
- Reaction with alcohols to form acetals
- The reaction of sugars with alcohols or other nucleophiles leads to the formation of glycosides
- Reduction (deoxygenation) to form cyclic ethers
References
References
- IUPAC Gold Book [http://goldbook.iupac.org/L03438.html lactols]
- Lundt, Inge. (2001). "Oxidation, reduction and deoxygenation of carbohydrates". Glycoscience.
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