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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Which of the following intermediates is not formed during the iodoform reaction of acetone?

Options

  1. ACH ₃ COCHI ₂
  2. BCH ₃ COCH ₂ I
  3. CCH ₃ COCI ₃
  4. DICH ₂ COCH ₂ I

Correct answer

D. ICH ₂ COCH ₂ I

Step-by-step solution

The iodoform reaction of acetone involves the base-catalyzed halogenation of the alpha-carbon. The introduction of an iodine atom increases the acidity of the remaining alpha-hydrogens on the same carbon atom due to its electron-withdrawing inductive effect. As a result, successive halogenations occur more rapidly at the already halogenated carbon rather than at the unhalogenated methyl group. The sequence of intermediates formed is CH ₃ COCH ₂ I , followed by CH ₃ COCHI ₂ , and then CH ₃ COCI ₃ . Halogenation does

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