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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap248

The alcohol shown is heated with concentrated and the major alkene is isolated. Which structure is the major alkene, allowing for rearrangement of the intermediate carbocation?

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

Answer: A

The alcohol is 3-methylbutan-2-ol. Loss of water gives a secondary cation, and a hydride shift from the adjacent tertiary carbon gives the more stable tertiary cation. Saytzeff elimination from this cation gives 2-methylbut-2-ene as the major product, while 3-methylbut-1-ene would be the unrearranged product.
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