Question

Draw the mechanism for the base-catalyzed tautomerization of butanal to it's enol form?

Draw the mechanism for the base-catalyzed tautomerization of butanal to it's enol form?

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Answer #1

When an aldehyde have at least one hydrogen atom on the carbon atom adjacent to the carbonyl group, called the alpha (?) carbon, this hydrogen can transfer to the oxygen atom of the carbonyl group. The double bond then migrates to the ?-carbon. As a consequence, a carbonyl compound with an ?-hydrogen can exist in two isomeric forms, called tautomers. In the keto form, the hydrogen is bonded to the ?-carbon, while in the enol form it is bonded to the carbonyl oxygen with the migration of the double bond.

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