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JEE Main levelSingle correct optionDifficulty 2 of 3o3032

3-Methylbutan-2-ol is heated with concentrated . The principal bromide formed is

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

Answer: C

Protonation of the hydroxyl group and loss of water give the secondary cation . A 1,2-hydride shift gives the more stable tertiary cation , which is captured by bromide to give 2-bromo-2-methylbutane.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group