The Claisen Condensation of diethyl succinate has documented use as an instructional tool for undergraduate organic chemistry. Although the literature results and various databases describe a keto product, our work replicating the Claisen Condensation in various conditions reproducibly results in the enol tautomer exclusively. While exploring the tautomeric equilibrium, we discovered several interesting features of this reaction system which make it suitable for a course-based undergraduate research experience (CURE). Our work focuses on characterizing this reaction and others under various conditions (e.g., solvent, temperature, work-up, time). Our goals with this work are to fully characterize the tautomeric equilibrium, incorporate the reaction and subsequent product characterization into a set of undergraduate experiments for an Introduction to Research course. Overall, the project provides students experience in hazard assessment, data organization, method development, organic structure determination, and communicating accurate results.

“Novel” tautomeric equilibrium for use in a course-based undergraduate research experience

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