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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap073

Which of the following alcohols give 2-methylbut-2-ene as the major alkene on heating with conc. at 443 K?

  1. Apentan-1-ol
  2. B3-methylbutan-2-ol
  3. C2,2-dimethylpropan-1-ol
  4. D2-methylbutan-2-ol

Answer: B, C, D

2-Methylbutan-2-ol gives the tertiary cation directly. 3-Methylbutan-2-ol gives it after a 1,2-hydride shift, and neopentyl alcohol gives it after a 1,2-methyl shift. All three therefore yield 2-methylbut-2-ene (Saytzeff product). Pentan-1-ol has an unbranched skeleton and gives pentenes, not a branched alkene.
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