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JEE Main levelSingle correct optionDifficulty 2 of 3ap193

3-Methylbutan-2-ol is shaken with conc. aqueous (SN1 conditions). The major alkyl bromide is

  1. A2-bromo-3-methylbutane
  2. B1-bromo-3-methylbutane
  3. C2-bromo-2-methylbutane
  4. D1-bromo-2-methylbutane

Answer: C

The secondary cation from loss of water undergoes a 1,2-hydride shift to give the more stable tertiary cation . Bromide attacks it to give 2-bromo-2-methylbutane.
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