Levulinic Acid Promoted Cyclization Cascade. A Holistic Research-Based Approach to an Undergraduate Organic Spectroscopy Laboratory

In this Article, we describe a straightforward organic synthesis of three unexpected polycyclic compounds followed by an attempt at a guided inquiry approach to help students with their spectroscopy analyses (IR, NMR, and mass spectra) to identify their reaction products. In these experiments, third-year undergraduate students investigated trends in multiple sets of spectroscopic data and attempted to correlate them with specific structural properties. The effectiveness of this learning strategy was evaluated in different assessment setups, students' collaboration environments, and a different level of information accessibility. A summary of the lessons learned at attempting such a guided inquiry approach will be shared in order to improve future organic spectroscopy assignments.