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Many kinds of enols are known. [1] Keto–enol tautomerism refers to a chemical equilibrium between a "keto" form (a carbonyl, named for the common ketone case) and an enol. The interconversion of the two forms involves the transfer of an alpha hydrogen atom and the reorganisation of bonding electrons. The keto and enol forms are tautomers of ...
The shortened term ynol typically refers to alkynols with the hydroxyl group affixed to one of the two carbon atoms composing the triple bond (C≡C−OH), the triple-bond analogues to enols. [1] Ynols can tautomerize to ketenes. The deprotonated anions of ynols are known as ynolates, the triple-bond analogues to enolates.
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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]
The ferric chloride test is used to determine the presence of phenols in a given sample or compound (for instance natural phenols in a plant extract). Enols , hydroxamic acids , oximes, and sulfinic acids give positive results as well. [ 1 ]
They are the sulfur analogs of enols (hence the thio-prefix). Alkenes with a thiol group on both atoms of the double bond are called enedithiols. Deprotonated anions of thioenols are called thioenolates. These structures exhibit tautomerism to give thioketones or thioaldehydes, analogous to keto–enol tautomerism of carbonyl structures. [1]
Acetoacetic acid displays keto-enol tautomerisation, with the enol form being partially stabilised by extended conjugation and intramolecular H-bonding. The equilibrium is strongly solvent depended; with the keto form dominating in polar solvents (98% in water) and the enol form accounting for 25-49% of material in non-polar solvents. [9]
This is due to its ability to form an enolate (C=C−O −) in basic solution, or an enol (C=C−OH) in acidic solution. An example of alpha halogenation is the mono-bromination of acetone ((CH 3) 2 C=O), carried out under either acidic or basic conditions, to give bromoacetone: Acidic (in acetic acid):