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Can you suggest why the Aldol's condensation between benzaldehyde and cyclopentanone proceeds more slowly than both...

Can you suggest why the Aldol's condensation between benzaldehyde and cyclopentanone proceeds more slowly than both benzaldehyde and acetone; and benzaldehyde and cyclohexanone
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Answer #1

In acetone the formation of carbanion with a trigonal pyramidal geometry is more likely to form due to free rotation of chain (after proton abstraction) than the restricted rotation ring structure in case of cyclopentanone. The carbanion is generated by base picking up an alpha-hydrogen in the first step of the aldol condensation reaction. Therefore, the formation of carbanion and enolate is more favourable with acetone and the reaction is faster than with cyclopentanone. Thus stability of carbanion is the deciding factor in rate of these two aldol reactions.

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