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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro274

The alcohol shown is oxidised with PCC or with Jones reagent, and the product is then treated with and in methanol. Select ALL correct statements.

  1. APCC gives the conjugated enone.
  2. BJones reagent also gives the conjugated enone, with the C=C bond left intact.
  3. CJones reagent cleaves the ring to give a dicarboxylic acid.
  4. DThe / step converts the enone back into the starting alcohol (as a racemate).

Answer: A, B, D

The compound is cyclohex-2-en-1-ol, a secondary allylic alcohol. Both PCC and Jones reagent oxidise it to cyclohex-2-en-1-one with the double bond unaffected (statements 1 and 2 true); ring cleavage does not occur under these conditions. Luche reduction (/) performs 1,2-reduction of the enone to the allylic alcohol, formed as a racemate (true).
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