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JEE Main levelSingle correct optionDifficulty 2 of 3o2015

3,3-Dimethylbut-1-ene is heated with dilute aqueous . The major alcohol is

  1. A2,3-dimethylbutan-2-ol
  2. B2,2-dimethylbutan-1-ol
  3. C3,3-dimethylbutan-1-ol
  4. D3,3-dimethylbutan-2-ol

Answer: A

Protonation gives the secondary cation . A 1,2-methyl shift gives the tertiary cation , which is trapped by water. The major alcohol is 2,3-dimethylbutan-2-ol, not the unrearranged 3,3-dimethylbutan-2-ol.
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