Ketone halogenation

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In organic chemistry ketone halogenation is a special type of halogenation.

The position alpha (next) to the carbonyl group in a ketone is easily halogenated, due to the ability to form an enolate in basic or acidic solution. An example is the bromination of acetone in basic solution:

CH₃-CO-CH₃ + OH⁻ → CH₃-CO-CH₂⁻ + H₂O

CH₃-CO-CH₂⁻ + Br₂ → CH₃-CO-CH₂Br + Br⁻

Acetone bromination

This reaction has two steps, but is not a chain reaction. Multiple bromination can occur giving CH₃-CO-CHBr₂ etc.