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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4034

But-1-ene is treated with in . The product is then heated with three equivalents of in liquid ammonia, followed by water. The final organic product is

  1. Abuta-1,3-diene
  2. Bbuta-1,2-diene
  3. Cbut-2-yne
  4. Dbut-1-yne

Answer: D

Bromine adds to give 1,2-dibromobutane. Two equivalents of amide remove two HBr by successive E2 steps to give but-1-yne. The terminal alkyne is acidic and the third equivalent converts it to sodium but-1-ynide; aqueous work-up reprotonates it to but-1-yne.
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