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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx013

3-Methylbut-1-ene is treated with in the absence of peroxide. The major product is

  1. A2-bromo-3-methylbutane
  2. B1-bromo-2-methylbutane
  3. C1-bromo-3-methylbutane
  4. D2-bromo-2-methylbutane

Answer: D

Protonation gives the secondary cation (Markovnikov). A 1,2-hydride shift converts it to the more stable tertiary cation , which captures to give 2-bromo-2-methylbutane as the major product. 2-Bromo-3-methylbutane is the minor unrearranged product.
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