Using NMR Spectroscopy to Analyze and Compare Reaction Progress of Nucleophilic Aromatic Substitutions in Undergraduate Organic Laboratories

Abstract The chemistry of aromatic compounds is an important component of second-year organic chemistry. However, lecture courses and laboratory experiments tend to focus on electrophilic aromatic substitution, whereas nucleophilic aromatic substitution is taught as an afterthought. This article focuses on a simple, efficient, and cost-effective nucleophilic aromatic substitution between 2-chloropyridine and benzyl alcohol. In addition to showcasing the utility of this type of reaction, it also introduces students to heterocyclic compounds and demonstrates an instance of their unique reactivity compared with simple benzene derivatives. The experiment also allows students to investigate factors affecting the reaction rate by analysis of the 1H NMR spectra of the crude reaction mixtures of a variety of variable reaction conditions.