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QUESTION

# What is the product of the aldol condensation between cyclopentanone and 4-methylbenzaldehyde?

The product is probably (2E,5E)-2,5-bis(4-methylbenzylidene)cyclopentanone.

The aldol condensation involves attack of an enolate ion on the base of a carbonyl compound to form a β-hydroxycarbonyl compound (an aldol).

(from www.chem.ucla.edu)

The aldol can then dehydrate to form an α,β-unsaturated carbonyl compound.

The process requires an active methylene adjacent to a carbonyl group.

If there are two active methylenes, the condensation can occur on each side of the carbonyl group.

For example, benzaldehyde with acetone gives dibenzalacetone.

By analogy, I predict that 4-methylbenzaldehyde with cyclopentanone will form (2E,5E)-2,5-bis(4-methylbenzylidene)cyclopentanone.

The E,E isomer should be more stable because the steric interactions of the ortho hydrogens with the "H" atoms on the cyclopentane ring are smaller than those with the carbonyl oxygen