The aldol reaction and benzoin reaction are fundamental nucleophilic additions of the carbonyl group in the undergraduate organic chemistry laboratory. We herein describe a parallel experimental design combining the two reactions into one experiment, in which the same reactant under different reaction conditions bifurcates into aldol and benzoin products. The notable improvement to current independent practice saves time and expense at the undergraduate level. The learning objectives also encompass a range of basic synthetic techniques that enable undergraduate students to master the setup and workup procedures of organic reactions. Reagents and equipment required in the experiment are adaptable and feasible at different colleges and universities. The comparative design makes notable updates to current organic laboratory curricula, providing pedagogical value in head-to-head learning of the reaction mechanism and hands-on experience. It also advances learning to a wide range of fundamental topics in organic chemistry studies such as heterocycles and umpolung.
Han et al. (2026) studied this question.