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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc090

A hydrocarbon X () liberates hydrogen with sodium, gives a ketone on Hg(II)-catalysed hydration and gives 2-methylbutane on complete hydrogenation. X is

  1. Apent-1-yne
  2. Bpent-2-yne
  3. C2-methylbuta-1,3-diene
  4. D3-methylbut-1-yne

Answer: D

Hydrogen evolution with sodium means a terminal alkyne, and hydration to a ketone fits . Hydrogenation to 2-methylbutane fixes the branched skeleton, so X is , which hydrates to 3-methylbutan-2-one. Pent-1-yne would give pentane, pent-2-yne is not terminal, and isoprene has no acidic hydrogen and gives no ketone.
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