A natural product laboratory experiment that provides two alternative safe and effective methods to introduce undergraduate organic chemistry students to the palladium catalyzed hydrogenation reaction is described. Students can hydrogenate curcumin (1  ) to tetrahydrocurucmin (2 ) either by refluxing it in methanol with 10% Pd/C and a transfer hydrogenation chemical, such as cyclohexene, or by using a hydrogenation flow reactor, an H-cube, a type of instrument that is quickly becoming an industry standard. Students develop proficiency in chromatography and spectroscopy by performing thin-layer chromatographic analysis on curcumin and tetrahydrocurcumin, performing a silica gel column the crude reaction product material, and acquiring a proton NMR spectrum of the product.  Voluntary identical pre- and post-lab quantitative tests, as well as a voluntary post-lab qualitative test, were used to assess the experiment's effectiveness in improving student understanding of NMR. These tests on combined laboratory classes numbering over one hundred students demonstrated a statistically significant improvement in student understanding of NMR.

Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that also enhances student understanding of NMR spectroscopy

248th National Meeting (2014)

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