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JEE MainChemistryAldehydes and Ketones

Propanenitrile is reacted with methylmagnesium bromide in dry ether, followed by acidic hydrolysis, to yield compound X . Compound X is then warmed with iodine and aqueous sodium hydroxide, producing a yellow precipitate and a soluble sodium salt. The aqueous layer is separated and acidified to give compound Y . The IUPAC name of compound Y is:

Options

  1. AEthanoic acid
  2. BPropanoic acid
  3. CButanoic acid
  4. DButan-2-ol

Correct answer

B. Propanoic acid

Step-by-step solution

Propanenitrile ( CH ₃ CH ₂ CN ) reacts with methylmagnesium bromide ( CH ₃ MgBr ) to form an imine intermediate, which upon acidic hydrolysis yields butan-2-one ( CH ₃ CH ₂ COCH ₃ ). This is compound X . Butan-2-one contains a methyl ketone group ( -COCH ₃ ) and thus gives a positive iodoform test when warmed with I ₂ and aqueous NaOH . The reaction involves the oxidative cleavage of the methyl group to form iodoform ( CHI ₃ ), which is the yellow precipitate, and the sodium salt of a carboxylic acid with one less

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