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JEE Main 2017 · Chemistry · Alcohols, Phenols, Ethers and Haloalkanes · easy

The major product when 3-methylbutan-2-ol is treated with concentrated HBr is

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The major product when 3-methylbutan-2-ol is treated with concentrated HBr is
  1. A. 1-bromo-2-methylbutane
  2. B. 1-bromo-3-methylbutane
  3. C. 2-bromo-3-methylbutane
  4. D. 2-bromo-2-methylbutane
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Answer: (D) 2-bromo-2-methylbutane

The secondary alcohol is protonated and loses water giving the secondary carbocation (CH3)2CH−C+H−CH3\mathrm{(CH_3)_2CH{-}C^+H{-}CH_3}. A 1,2-hydride shift moves the cation to the adjacent tertiary carbon, (CH3)2C+−CH2CH3\mathrm{(CH_3)_2C^+{-}CH_2CH_3}, which is more stable. Attack by Br−\mathrm{Br^-} gives 2-bromo-2-methylbutane as the major product, and 2-bromo-3-methylbutane (direct substitution) is minor.
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