The aldol condensation reaction is one of the many multi-step reactions carried out in a typical organic chemistry second-semester laboratory. During this experiment Dibenzalacetone and its derivatives were synthesized using the crossed-aldol condensation, reacting benzaldehyde and its derivatives with acetone in a basic solution, and finally purifying the product by recrystallization. These aldol products were analyzed using spectroscopic methods, specifically Nuclear Magnetic Resonance (NMR) and Gas Chromatography-Mass Spectroscopy (GC-MS). 13C-NMR, 1H-NMR, DEPT 90, DEPT 135, and 2D-NMR analysis were carried out to ensure identification of the final product in the sample. Fragments detected by the GC-MS were identified through common fragmentation patterns, such as alpha- and beta-cleavage and rearrangements. In order to collect more physical property data for these compounds, the final products were also analyzed by melting point and thin-layer chromatography.

Synthesis and analysis of derivatives of dibenzalacetone aldol products

ACS Fall 2021

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