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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3260

The ketone shown is treated with LDA in THF at C and then with acetaldehyde at low temperature; the mixture is quenched with aqueous at low temperature. Which structure shown is the major aldol product?

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

Answer: D

The ketone shown is cyclopentyl methyl ketone. LDA at C gives the kinetic enolate at the CH group, which adds to acetaldehyde to give the beta-hydroxy ketone -cyclopentyl (3-hydroxy-1-cyclopentylbutan-1-one). The tertiary-site aldol would need the thermodynamic enolate, the enone requires heating or acid or base for dehydration, and a diol would need a reducing agent.
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