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The keto and enol tautomers of acetylacetone coexist in solution. The enol form has C 2v symmetry, meaning the hydrogen atom is shared equally between the two oxygen atoms. [4] In the gas phase, the equilibrium constant, K keto→enol, is 11.7, favoring the enol form.
A classic example for favoring the keto form can be seen in the equilibrium between vinyl alcohol and acetaldehyde (K = [enol]/[keto] ≈ 3 × 10 −7). In 1,3-diketones, such as acetylacetone (2,4-pentanedione), the enol form is favored. The acid-catalyzed conversion of an enol to the keto form proceeds by proton transfer from O to carbon.
Ketone bodies are water-soluble molecules or compounds that contain the ketone groups produced from fatty acids by the liver (ketogenesis). [1] [2] Ketone bodies are readily transported into tissues outside the liver, where they are converted into acetyl-CoA (acetyl-Coenzyme A) – which then enters the citric acid cycle (Krebs cycle) and is oxidized for energy.
Keto-enol tautomerism. 1 is the keto form; 2 is the enol. Ketones that have at least one alpha-hydrogen, undergo keto-enol tautomerization; the tautomer is an enol. Tautomerization is catalyzed by both acids and bases. Usually, the keto form is more stable than the enol. This equilibrium allows ketones to be prepared via the hydration of alkynes.
Some examples of tautomers Keto-enol tautomerization typically strongly favors the keto tautomer, but an important exception is the case of 1,3-diketones such as acetylacetone. [6] Tautomerization is pervasive in organic chemistry.
Ethyl acetoacetate is subject to keto-enol tautomerism. In the neat liquid at 33 °C, the enol consists of 15% of the total. [5] The enol is moderately acidic. Thus ethyl acetoacetate behaves similarly to acetylacetone: [6] CH 3 C(O)CH 2 CO 2 C 2 H 5 + NaH → CH 3 C(O)CHNaCO 2 C 2 H 5 + H 2. The resulting carbanion undergoes nucleophilic ...
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Ketogenesis pathway. The three ketone bodies (acetoacetate, acetone, and beta-hydroxy-butyrate) are marked within orange boxes. Ketogenesis is the biochemical process through which organisms produce ketone bodies by breaking down fatty acids and ketogenic amino acids.
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