The 1950 Nobel Prize in Chemistry was awarded to Otto Diels and Kurt Alder who were the first to document a reaction between a diene and a dienophile. Over fifty years later the Diels-Alder reaction continues to be one of the topics studied in the undergraduate organic chemistry curriculum. These reactions are particularly useful for students to learn because they demonstrate a simple method of multiple carbon-carbon bond formation. We have developed an undergraduate laboratory designed to feature a Diels-Alder/retro-Diels-Alder reaction between 1, 3-cyclohexadiene and either Dimethyl or Diethyl acetylenedicarboxylate (DMAD or DEAD, respectively) through microwave irradiation to form an intermediate compound that partially decomposes to an aromatically stabilized product. This procedure will expose students to conducting reactions using alternative heat sources such as microwaves as well as teach them how to perform essential lab techniques; Column Chromatography, Thin-layer Chromatography, and Rotary Evaporation. Students will also be instructed on how to interpret data from Nuclear Magnetic Resonance (NMR) and Gas Chromatography-Mass Spectroscopy (GC-MS) for product analysis purposes. A typical undergraduate class was able to isolate the desired product and obtain yields that ranged from 7.41 to 66.67% with an average of 27.23% when DMAD was used and yields that ranged from 10.03 to 55.17% with an average of 32.00% when DEAD was used. These data show that undergraduate students are capable of performing the designed reaction. In conclusion, the laboratory will teach students a variety of skills that are crucial for any proficient chemist to understand.

Diels-Alder/retro-Diels-Alder synthesis via microwave irradiation

247th National Meeting (2014)

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