ABSTRACT In many cases, computational geometry optimizations of carbanions containing potential leaving groups are observed to be nonstationary points on the potential energy surface. Instead of optimization leading to an energy minimized stationary point, spontaneous loss of the leaving group may lead to formation of an entirely new compound. Over several years, groups of students taking the Advanced Organic Chemistry course at Berry College have been tasked with investigating instances in which such compound transformations have occurred within the context of a course‐based undergraduate research experience (CURE). The spontaneous formation of propellanes, hetero‐substituted propellanes, anti‐Bredt bridgehead alkenes, and propargyl‐substituted cyclooctynes has been studied. The computational results have been compared with known experimental results. Our conclusion is that computational geometry optimizations do an excellent job at reproducing and predicting known experimental results. Such computations are recommended to help experimental chemists select the most promising synthetic targets when many possible options exist.
Gary W. Breton (Fri,) studied this question.