The Aldol Condensation: Synthesis of Dibenzalacetone

Objective:
The benefit of this lab was to acquaint oneself with the fundamentals of the Aldol Condensation reaction by demonstrating the synthesis of dibenzalacetone (trans, trans-1,5-Diphenyl-1,4-pentadien-3-one) through the aldol condensation of acetone with benzaldehyde. The synthesis began by using a strong base to generate the acetone enolate ion. The ketone/enol tautomerization is an equilibrium process that produces little of the enol (ppm or less). However, any enol that formed quickly reacted with the strong base to form the enolate ion. …