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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3262

Which of the structures shown are enolates that can be formed from the ketone shown by removing a proton with a suitable base? Select all that apply.

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

Answer: B, D

The ketone shown is 1-cyclopentylpropan-1-one with two alpha carbons: the CH of the ethyl group and the ring CH. Removal of a proton from either gives a resonance-stabilised enolate, cyclopentyl or cyclopentylidene. The structures with the carbanion on the terminal CH or at a ring carbon beta to the carbonyl are not conjugated with C=O, so they are not enolates.
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