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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.
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 more favored. The acid-catalyzed conversion of an enol to the keto form proceeds by proton transfer from O to carbon.
Many carbonyl compounds exhibit keto–enol tautomerism. This effect is especially pronounced in 1,3-dicarbonyl compounds that can form hydrogen-bonded enols. The equilibrium constant is dependent upon the solvent polarity, with the cis -enol form predominating at low polarity and the diketo form predominating at high polarity.
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.
The tautomerization can also be catalyzed via photochemical process. These findings suggest that the keto–enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere. [5] [6]
Keto is short for ketogenic diet, which is a low carbohydrate, moderate protein, and high fat program. The goal of a keto diet is to be in a metabolic state known as “ketosis,” through the ...
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