Reacting (2R)-2-pentanol with HBr leads to the formation of equal amounts of (2R)-2-bromopentane and (2S)-2-bromopentane. Draw a stepwise mechanism for the reaction that is consistent with this observation.

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Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.