Aldehydes and Ketones - What Is Keto–Enol Tautomerism?

3 important questions on Aldehydes and Ketones - What Is Keto–Enol Tautomerism?

Why does the equilibrium of the keto-enol tautomerism lie far to the side of the keto for most simple ketones and aldehydes?

Because the carbon-oxygen double bond is stronger than the carbon-carbon double bond.

How can the racemization of (R or S)-3-Phenyl-2-bunanone be explained?

Due to the formation of an achiral enol tautomer in the presence of an acid generates the chiral R and S keto form in equal probability.

What are the steps in acid-catalyzed α-Halogenation?

1. Keto-enol tautomerism.
2. Reaction between a nucleophile and an electrophile.
3. Removal of a proton.

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