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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3034

Heating 3,3-dimethylbutan-2-ol with concentrated gives mainly (Saytzeff product after carbocation rearrangement):

  1. Ahex-2-ene
  2. B3,3-dimethylbut-1-ene
  3. C2,3-dimethylbut-2-ene
  4. D2,3-dimethylbut-1-ene

Answer: C

Protonation and loss of water give the secondary 3,3-dimethylbutan-2-yl cation. A 1,2-methyl shift gives the tertiary 2,3-dimethylbutan-2-yl cation. Loss of a proton from the more substituted side gives the tetrasubstituted 2,3-dimethylbut-2-ene as the major product.
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