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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap202

Cyclopentanone is treated with Mg-Hg and water to give X. X is warmed with dilute to give Y, which is reduced with (then ) to give Z. Z is

  1. Abicyclopentyl-1-ol
  2. Bspiro[4.5]decan-6-ol
  3. Ccyclodecan-1-ol
  4. D2-cyclopentylcyclopentan-1-ol

Answer: B

Bimolecular reduction gives 1,1'-bi(cyclopentyl)-1,1'-diol (X). Pinacol rearrangement with ring expansion gives spiro[4.5]decan-6-one (Y), the six-membered ring containing the C=O. reduces the ketone to the secondary alcohol spiro[4.5]decan-6-ol (Z).
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