MolSynapsequestion bank
MolSynapse / Question bank / Reduction, Oxidation and Hydrolysis in Organic Chemistry / Periodic acid and lead tetraacetate cleavage
NEET levelSingle correct optionDifficulty 1 of 3ro077

The cleavage of a vicinal diol by proceeds through

  1. Aa free carbocation
  2. Ban open-chain radical chain
  3. Ca cyclic periodate ester
  4. Da carbanion

Answer: C

The two OH groups on adjacent carbons form a five-membered cyclic periodate ester with iodine. This intermediate breaks down by a concerted electron shift that cleaves the C-C bond. No free ion is involved.
Practice Reduction, Oxidation and Hydrolysis in Organic Chemistry More on Periodic acid and lead tetraacetate cleavage
Previous questionNext question

More questions on Periodic acid and lead tetraacetate cleavage