JEE Advanced · ChemistryHard

Consider the reaction of with excess . Which of the following statements regarding the formation of is correct?

  1. A.The reaction involves the oxidation of the hydroxyl group to a carbonyl group.
  2. B.The reaction proceeds through the formation of a stable cyclic phenylhydrazone intermediate.
  3. C.The configuration at , , and is lost during the formation of the .
  4. D.The reaction is specific to and does not occur with .
Show correct answer & step-by-step solution

Correct answer: AThe reaction involves the oxidation of the hydroxyl group to a carbonyl group.

Solution

  1. The reaction of with three equivalents of produces .
  2. The first equivalent forms a at the position.
  3. The second equivalent acts as an oxidizing agent, converting the hydroxyl group into a carbonyl group via an rearrangement.
  4. The third equivalent forms a second at the position.
  5. Hence the answer is (A).

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