Integration of Computational and Preparative Techniques To Demonstrate Physical Organic Concepts in Synthetic Organic Chemistry: An Example Using Diels-Alder Reactions

Preparative experiments in organic chemistry rarely invoke physical organic principles explicitly, even at the intermediate level where these principles are taught. Computational exercises often address such topics as molecular orbital theory and reaction energetics, but may not allow students to make the conceptual leap from computer to flask. The experiment described, based on endo–exo selectivity of Diels–Alder reactions, bridges this gap by integrating computational and preparative experiments.