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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap031

2,2-Dimethylpropan-1-ol (neopentyl alcohol) is heated with conc. . The major product is

  1. A1-bromo-2,2-dimethylpropane
  2. B2-bromo-2-methylbutane
  3. C2-bromo-3-methylbutane
  4. D1-bromo-2-methylbutane

Answer: B

The primary cation from protonated neopentyl alcohol cannot form easily; a methyl shift occurs with ionisation, giving the tertiary cation . Bromide capture gives 2-bromo-2-methylbutane.
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