WEEKS 12 – 14
Introduction
The purpose of the first weeks experiment is to synthesize a di-substituted chalcone. This reaction was done by performing a green synthesis where an aldehyde was mixed with a ketone synthesizing one of six possible chalcones. For the second and third weeks of the experiment, catalytic hydrogenation was to be performed on the chalcone synthesized in the first week. Various spectroscopic techniques were performed to determine which of the chalcone’s functional groups had been reduced after the catalytic hydrogenation.
Methods and Results The first week’s experiments involved a synthesis of a di-substituted chalcone by combining an aldehyde and a ketone. Initially we were supposed to make chalcone number 4, which involved combining 4-chlorobenzaldehyde with 4-methylacetophenone. Unfortunately the reaction did not work out too well which caused our group to switch over to chalcone number 3, which involved combining 4-fluroacetophenone with 4-methylbenzaldehyde. The aldehyde and ketone were combined with NaOH in a reaction flask then heated and stirred for 30 minutes resulting in the di-substituted chalcone. A sample of the chalcone was used for NMR data. The second week’s experiments involved the hydrogenation of the di-substituted chalcone synthesized in the first week of the experiment. Hydrogenation was performed by combining the di-substituted chalcone with ammonium formate and palladium attached to carbon in a round bottom flask. The reaction mixture was then refluxed for 20 minutes. The mixture was filtered through a filter syringe and then extracted with a separatory funnel (after this step a TLC was performed on the starting and the product after the extraction). The product was then filtered again using a PTFE filter with a syringe again, resulting in the final hydrogenated chalcone. Samples of the hydrogenated chalcone were used for NMR and GC-MS data. The third week of the experiment involved analyzing the data acquired from the previous two weeks. This analysis was done to determine which products resulted from the
