MolSynapsequestion bank
MolSynapse / Question bank / Alcohols, Phenols and Ethers / Pinacol-pinacolone and related rearrangements
JEE Main levelOne or more correct optionsDifficulty 2 of 3ap083

Which of the following statements about the pinacol rearrangement are correct?

  1. AAn alkene is formed first and is then hydrated to give the ketone.
  2. BThe hydroxyl lost as water is the one whose departure gives the more stable carbocation.
  3. CThe last step is loss of a proton from a protonated carbonyl compound.
  4. DThe migrating group moves with its bonding electron pair to the adjacent cationic carbon.

Answer: B, C, D

The first step is protonation of the more easily ionised hydroxyl, giving the more stable cation. A 1,2-shift of a group with its electron pair follows, and the resulting oxonium (protonated carbonyl) loses . No alkene intermediate is involved, so the fourth statement is wrong.
Practice Alcohols, Phenols and Ethers More on Pinacol-pinacolone and related rearrangements

More questions on Pinacol-pinacolone and related rearrangements