Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Which of the following intermediates is not formed during the iodoform reaction of acetone?
Options
- ACH ₃ COCHI ₂
- BCH ₃ COCH ₂ I
- CCH ₃ COCI ₃
- 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