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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4129

Each alcohol below is heated with conc. under E1-type conditions that allow 1,2-shifts. For which are 2-methylbut-2-ene the major alkene?

  1. A2-methylbutan-2-ol
  2. B3-methylbutan-2-ol
  3. C2,2-dimethylpropan-1-ol
  4. Dbutan-2-ol

Answer: A, B, C

All of the first three give the tertiary cation directly, by hydride shift, or by methyl shift, so Saytzeff loss of H gives 2-methylbut-2-ene. Butan-2-ol has only four carbons and gives but-2-ene.
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