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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4109

3,3-Dimethylbutan-2-ol is heated with conc. . Select all correct statements.

  1. ALoss of water from the protonated alcohol gives a secondary carbocation.
  2. BA 1,2-methyl shift converts it to a more stable tertiary carbocation.
  3. CThe major alkene is 2,3-dimethylbut-2-ene.
  4. D2,3-Dimethylbut-1-ene is the major alkene, as there are more hydrogens available on the methyl groups.

Answer: A, B, C

Protonation and loss of water give the secondary 3,3-dimethylbut-2-yl cation. A methyl group migrates from C-3 to C-2, giving the tertiary 2,3-dimethylbut-2-yl cation. Loss of a proton from C-3 gives the tetrasubstituted alkene 2,3-dimethylbut-2-ene (Saytzeff), so the fourth statement is false.
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