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COMEDK2024ChemistryAlcohols Phenols and EthersActual

The major product ' X ' of the following reaction is

Options

  1. A3, 4-dimethylpent-1-ene
  2. B3-methylpent-2-ene
  3. C3, 3-dimethylpent-1-ene
  4. D2, 3-dimethylpent-2-ene

Correct answer

D. 2, 3-dimethylpent-2-ene

Step-by-step solution

The reaction is an acid-catalyzed dehydration of a secondary alcohol, 3,3-dimethylpentan-2-ol. The mechanism proceeds via the formation of a carbocation intermediate. Protonation of the hydroxyl group by H₂SO₄ to form a good leaving group, -OH₂⁺ . Loss of water molecule to form a secondary carbocation at the C2 position: CH₃-CH⁺-C(CH₃)₂-CH₂-CH₃ . The secondary carbocation undergoes a 1,2-methyl shift to form a more stable tertiary carbocation: CH₃-CH(CH₃)-C⁺(CH₃)-CH₂-CH₃ . Elimination of a proton from the adjacent

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