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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3053

Select the reaction(s) that proceed with a 1,2-shift (hydride or methyl) of an intermediate carbocation to give the major product.

  1. A2,2-dimethylpropan-1-ol with concentrated HBr
  2. Bpropene with HBr (no peroxide)
  3. C3-methylbutan-2-ol with concentrated HBr
  4. D3,3-dimethylbut-1-ene with HCl

Answer: A, C, D

3,3-Dimethylbut-1-ene gives a methyl shift and neopentyl alcohol gives a methyl shift. 3-Methylbutan-2-ol gives a hydride shift to the tertiary cation, so 2-bromo-2-methylbutane forms. Propene gives the isopropyl cation directly with nothing more stable available.
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