In base-catalyzed halogenation of acetone, how do you explain why the second (and third) halogenation occurs on the same carbon but not on the carbon in the other methyl group?

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter14: Aldehydes And Ketones
Section: Chapter Questions
Problem 14.55E: The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically...
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In base-catalyzed halogenation of acetone, how do you explain why the second (and third) halogenation occurs on the same carbon but not on the carbon in the other methyl group?

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