Calzone Synthesis

During the second day of chemistry Collaborations Workshops & Community of Scholars (cCWCS) participants performed an aldol condensation between a substituted benzaldehyde and a substituted acetophenone. This experiment was recently published in JCE in an article entitled “Synthesis and Hydrogenation of Disubstituted Chalcones. A Guided-Inquiry Organic Chemistry Project.” We used a least 7 different combinations of the two reactants. The experiment proceeds quite smoothly and in good yield – my partner and I had a 64% yield after recrystallization. The product was shown to be of high purity by melting point, IR, GC-MS and NMR.  However, the fact that different reactant combinations are used does introduce the possibility that yields will vary and/or different optimal reaction conditions will be required. Obviously, it also costs more to buy several bottles of differently substituted benzaldehydes rather than large bottle of benzaldehyde. The use of different reactants does set up the second part of the synthesis to be richer (read more complex). We performed the experiment in pairs, whereas, it could very well be done by individual students. As far as I know, aldol condensations are usually not covered until late in the second semester in most organic chemistry schedules. I have always thought it optimal to introduce reactions in orgo lab about the same time they are covered in the lecture. More creativity in lab may require a less-than-concurrent introduction of reactions in lab and lecture.


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