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JEE Main levelSingle correct optionDifficulty 2 of 3ro252

The compound shown is a cis vicinal diol. It is treated with excess periodic acid. Which structure is the organic product (one molecule of product per molecule of reactant)?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The compound is cis-cyclopentane-1,2-diol. The cis diol forms a cyclic periodate ester and the C1-C2 bond breaks; since both carbons are in one ring, the ring opens to the dialdehyde pentanedial (glutaraldehyde). Aldehydes survive , so the diacid is not formed, and nothing remains to give a hydroxy-aldehyde or ketone.
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