MolSynapsequestion bank
MolSynapse / Question bank / Alcohols, Phenols and Ethers / Pinacol-pinacolone and related rearrangements
JEE Main levelSingle correct optionDifficulty 2 of 3ap080

According to the usual JEE-level order of migratory aptitude in pinacol-type rearrangements (aryl bearing an electron-donating group phenyl alkyl, larger alkyl before methyl), which group migrates most readily?

  1. Aethyl
  2. Bphenyl
  3. C4-methoxyphenyl
  4. Dmethyl

Answer: C

Aryl groups migrate better than alkyl groups because they can bridge the two carbons through a phenonium-type transition state. An electron-donating substituent such as para-OCH stabilises that transition state further, so 4-methoxyphenyl migrates best, followed by phenyl and then the alkyl groups (ethyl before methyl).
Practice Alcohols, Phenols and Ethers More on Pinacol-pinacolone and related rearrangements

More questions on Pinacol-pinacolone and related rearrangements