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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.
General structure of 1,2-, 1,3-, and 1,4-dicarbonyls. In organic chemistry, a dicarbonyl is a molecule containing two carbonyl (C=O) groups.Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4 ...
Dibenzoylmethane (DBM) is an organic compound with the formula (C 6 H 5 C(O)) 2 CH 2.DBM is the name for a 1,3-diketone, but the compound exists primarily as one of two equivalent enol tautomers. [2]
Benzoylacetone is the organic compound with the nominal formula C 6 H 5 C(O)CH 2 C(O)CH 3. As a 1,3-dicarbonyl, it is a precursor to many heterocycles, such as pyrazoles. [1] It exists predominantly as the enol tautomer C 6 H 5 C(OH)=CHC(O)CH 3. [2] Its conjugate base (pK a =8.7) forms stable complexes with transition metals and lanthanides. [3]
The equilibrium constant tends to be high in nonpolar solvents; when K keto→enol is equal or greater than 1, the enol form is favoured. The keto form becomes more favourable in polar, hydrogen-bonding solvents, such as water. [7] The enol form is a vinylogous analogue of a carboxylic acid. [citation needed]
Dimedone is an organic compound with the formula (CH 3) 2 C(CH 2) 2 (CO) 2 (CH 2). Classified as a cyclic diketone, it is a derivative of 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used as a reagent to test for the aldehyde functional group.
Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic.
1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C 6 H 4 (CO) 2 CH 2. It is a β-diketone with indane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish [ 3 ] or even green.
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