The formation of an enamine is a useful chemical transformation, serving as a platform for other reactions such as alkylation, acylation, or halogenation. This framework can provide multi-week exploration into synthetic transformations for the undergraduate organic chemistry instructional laboratory courses (UOCLCs). Herein, we describe a multi-outcome experiment (MOE) for the UOCLCs, in which one unknown secondary amine (either pyrrolidine, piperidine, or morpholine) is reacted with cyclopentanone to form the enamine. Students are provided with a palette of potential unknown secondary amines and deduce the identity of the unknown alkyl halide using the benchtop NMR spectrum they obtain from their synthesized product. This MOE provides each student group with the opportunity to complete the same experimental procedure as their peers; however, different observations and results are obtained based on the unknown secondary amine used. The MOE leads to more individualized reports and student ownership of their laboratory experience.

A multi-outcome experiment for the preparation of enamines in the undergraduate organic chemistry teaching laboratories

255th National Meeting (2018)

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