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NEETChemistryAldehydes and Ketones

An unknown organic compound X having the molecular formula C ₃ H ₆ O gives a yellow precipitate when treated with I ₂ and NaOH . Compound X reacts with HCN to give an intermediate Y, which upon strong heating with concentrated H ₂ SO ₄ yields compound Z. Identify the IUPAC name of compound Z.

Options

  1. ABut-2-enoic acid
  2. B2-Hydroxy-2-methylpropanoic acid
  3. C2-Methylprop-2-enoic acid
  4. DPropan-2-ol

Correct answer

C. 2-Methylprop-2-enoic acid

Step-by-step solution

The compound X ( C ₃ H ₆ O ) gives a positive iodoform test (yellow precipitate with I ₂ and NaOH ), which indicates the presence of a methyl ketone group. Thus, X is propanone (acetone), CH ₃ COCH ₃ . Propanone reacts with HCN via nucleophilic addition to form the intermediate Y, acetone cyanohydrin ( CH ₃ C ( OH )( CN ) CH ₃ ). Upon strong heating with concentrated H ₂ SO ₄ , the cyanohydrin undergoes hydrolysis of the - CN group to a - COOH group, accompanied by the dehydration of the - OH group to form a double

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