Dual Studies on a Hydrogen–Deuterium Exchange of Resorcinol and the Subsequent Kinetic Isotope Effect

[Image: see text] An efficient laboratory experiment has been developed for undergraduate students to conduct hydrogen–deuterium (H–D) exchange of resorcinol by electrophilic aromatic substitution using D(2)O and a catalytic amount of H(2)SO(4). The resulting labeled product is characterized by (1)H NMR. Students also visualize a significant kinetic isotope effect (k(H)/k(D) ≈ 3 to 4) by adding iodine tincture to solutions of unlabeled resorcinol and the H–D exchange product. This method is highly adaptable to fit a target audience and has been successfully implemented in a pedagogical capacity with second-year introductory organic chemistry students as part of their laboratory curriculum. It was also adapted for students at the advanced high school level.