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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2243

The alkene shown is treated first with and the major bromide so formed is heated with alcoholic (Zaitsev elimination). Which alkene is the major final product?

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

Answer: A

The alkene is 3,3-dimethylbut-1-ene. Methyl shift in the cation gives 2-bromo-2,3-dimethylbutane as the major bromide. Dehydrohalogenation with alcoholic follows Zaitsev's rule and gives the more substituted, tetrasubstituted alkene, 2,3-dimethylbut-2-ene.
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