As described in “A Word About . . . Water Treatment and the Chemistry of Enols/Enolates,” carbonyl compounds can become halogenated by treatment with a base and a halogen source, such as Cl2. As shown on page 279, base-catalyzed chlorination of acetone leads to 1,1,1-trichloroacetone. For acetone, provide a mechanism that rationalizes the formation of 1,1,1-trichloroacetone vs. chlorination on both sides of the carbonyl group.
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