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JEE Main levelSingle correct optionDifficulty 2 of 3hx241

The halide shown is converted to its Grignard reagent with magnesium in dry ether; heavy water () is then added. Which structure is the main organic product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

The carbon-magnesium bond is protonated (here deuterated) by D2O exactly where magnesium was bound, with no rearrangement. 2-Bromobutane gives 2-deuteriobutane, a chiral isotopologue formed as a racemate. Butane is formed if H2O is used, butan-2-ol requires oxygen, and 1-deuteriobutane would require a shift of the metal.
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