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JEE Advanced levelSingle correct optionDifficulty 3 of 3co100

Cyclohexanone (1 mol) is treated with benzaldehyde (2 mol) and NaOH in ethanol until both condensations and dehydration are complete. The product is

  1. A2-benzylidenecyclohexan-1-one
  2. B2,6-dibenzylcyclohexan-1-one
  3. C2,6-dibenzylidenecyclohexan-1-one
  4. D2,2-dibenzylcyclohexan-1-one

Answer: C

Cyclohexanone has alpha-hydrogens on both C2 and C6, and benzaldehyde has none. Each alpha carbon condenses with one benzaldehyde and loses to give an exocyclic C=C. Two are lost in total, and the product is 2,6-dibenzylidenecyclohexan-1-one.
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