MolSynapsequestion bank
MolSynapse / Question bank / Alcohols, Phenols and Ethers / Pinacol-pinacolone and related rearrangements
JEE Main levelSingle correct optionDifficulty 2 of 3ap188

2-Methylpropane-1,2-diol, , is warmed with dilute and rearranges. The carbonyl product is

  1. Abutan-2-one
  2. Bbutanal
  3. C2-methylprop-2-en-1-ol
  4. D2-methylpropanal

Answer: D

The tertiary OH is lost preferentially to give . A hydride shifts from the carbon to the cationic carbon, leaving , which gives , 2-methylpropanal.
Practice Alcohols, Phenols and Ethers More on Pinacol-pinacolone and related rearrangements

More questions on Pinacol-pinacolone and related rearrangements