Question

Which is the most suitable reagent for the following conversion ?

• A. Tollen’s reagent
• B. Benzoyl peroxide
• C. I₂ and NaOH solution with subsequent acidification
• D. Sn and NaOH solution

Answer 1

The Correct Option is C

The given reaction involves the conversion of an α,β-unsaturated carbonyl compound (CH₃CH=CHCOCH₃) into a β-hydroxy ketone (CH₃CH=CHCOOH) through an aldol-like reaction. This type of conversion is a typical reaction of an enone with iodine in an alkaline medium, followed by acidification. This is known as the iodoform test or iodine in alkaline solution, which results in the formation of a β-hydroxy ketone and the release of iodine in the process.

The mechanism involves the formation of an enolate ion under the basic conditions provided by NaOH, which then reacts with I₂ to form the desired product.

The correct answer is (C) : I₂ and NaOH solution with subsequent acidification.