HOOCCH2COCH2CH2CH3

3-Oxohexanoic acid, with the structural formula HOOC-CH2-CO-CH2-CH2-CH3, is a small aliphatic beta-keto acid. Its IUPAC name is 3-oxohexanoic acid, and its molecular formula is C6H10O3. The molecule features a carboxylic acid group at one end and a ketone functional group at the beta position relative to that carboxyl group.

Structure and naming

- Carboxyl group: HOOC- at one terminus, giving it acidic character typical of carboxylic acids.

- Ketone: a carbonyl group located on the third carbon (1- carboxyl carbon, 2- CH2, 3- CO), classifying the compound as a beta-keto acid.

- Carbon skeleton: a six-carbon chain consistent with the name hexanoic acid.

Chemical properties

- As a beta-keto acid, it exhibits the characteristic tendency to undergo decarboxylation upon heating, yielding a corresponding ketone.

- The carboxylic acid group provides typical acidity and potential for salt formation, while the ketone increases reactivity at the adjacent carbon.

Reactivity and applications

- Decarboxylation: heating 3-oxohexanoic acid generally produces 2-pentanone (pentan-2-one) as a common degradation product.

- Use: such beta-keto acids are mainly encountered as intermediates in organic synthesis and in discussions of beta-keto acid chemistry; they are not common as standalone reagents or widely used commercial chemicals.

See also

- Beta-keto acids

- 2-Pentanone

- Carboxylic acids and ketones in organic synthesis