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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2039

Which of the following alkenes does NOT give 2,3-dimethylbutan-2-ol as the major product on hydration with dilute ?

  1. A2,3-dimethylbut-1-ene
  2. B2,3-dimethylbut-2-ene
  3. C3,3-dimethylbut-1-ene
  4. D4-methylpent-1-ene

Answer: D

2,3-Dimethylbut-1-ene and 2,3-dimethylbut-2-ene both protonate to the tertiary cation . 3,3-Dimethylbut-1-ene reaches it by a methyl shift. 4-Methylpent-1-ene gives a secondary cation with no stabilising 1,2-shift, so it gives 4-methylpentan-2-ol.
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