Resumen de Computational Investigations for Undergraduate Organic Chemistry:: Predicting the Mechanism of the Ritter Reaction
In an effort to engage students more deeply in their laboratory work and provide them with valuable learning experiences in the applications and limitations of computational chemistry as a research tool, students are instructed to carry out a computational pre-lab exercise. Before carrying out a laboratory experiment that investigates the mechanism for the formation of N-t-butylbenzamide, students construct and obtain heats of formation for reactants, products, postulated reaction intermediates, and one transition state structure for each proposed mechanism. This is designed as a companion to an open-ended laboratory experiment that hones skills learned early in most traditional organic chemistry courses. The incorporation of a preliminary computational exercise enables students to move beyond guessing what the outcome of the reaction will be. It challenges them to test what they believe they "know" about such fundamental concepts as stability of carbocations, or the significance and utility of thermodynamic data relative to kinetic data. On the basis of their computations and their own experimental data, students then verify or dispute their hypothesis, finally arriving at a defensible and logical conclusion about the course of the reaction mechanism. The manner of implementation of the exercise and typical computational data are described.
