Question

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

Answer 1

Here's what I get.

Explanation:

The aldol condensation involves attack of an enolate ion on a carbonyl compound to form a β-hydroxycarbonyl adduct (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 the reaction of 4-methylbenzaldehyde with cyclohexanone will form
(`2E,6E`)-4-methyl-2,6-bis(4-methylbenzylidene)cyclohexanone.

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