Question

Select the reason why two molecules of benzaldehyde cannot react via the aldol condensation.

Answer 1

Benzaldehyde or C6H5CHO would not undergo the aldol condensation because it does not contain an alpha-hydrogen in its structure. Aldol condensation is a type of reaction that happens between an enolate and an aldehyde or ketone leading to a alkene that has a planar structure. The lack of an alpha-hydrogen would not allow for it to undergo such process since it cannot enolize. Benzaldehyde undergoes a nucleophilic reaction known as Claisen-Schmidt condensation. It has somehow same mechanism of the aldol reaction however, the nucleophilic attack on the carbonyl happens even without the alpha-hydrogen but with an enolate that is from a ketone.