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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2054

Which of the following compounds liberate hydrogen on treatment with sodium metal?

  1. Abut-1-yne
  2. Bbut-2-yne
  3. Cethanol
  4. Dphenol

Answer: A, C, D

Sodium reduces any sufficiently acidic X-H bond to H2. But-1-yne (terminal sp C-H, pKa about 25), ethanol (15.9) and phenol (10.0) all react to give the sodium salt. But-2-yne has no acidic sp C-H bond, and its sp3 C-H bonds are far too weak as acids, so there is no reaction.
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