title: Dual Studies on a Hydrogen-Deuterium Exchange of Resorcinol and the Subsequent Kinetic Isotope Effect.
abstract: An efficient laboratory experiment has been developed for undergraduate students to conduct hydrogen-deuterium (H-D) exchange of resorcinol by electrophilic aromatic substitution using D2O and a catalytic amount of H2SO4. The resulting labeled product is characterized by1H NMR. Students also visualize a significant kinetic isotope effect (kH/kD≈ 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.
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Richard
authors.initials: R
authors.lastname: Giles
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Iris
authors.initials: I
authors.lastname: Kim
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Weyjuin Eric
authors.initials: WE
authors.lastname: Chao
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Moore
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Kyung Woon
authors.initials: KW
authors.lastname: Jung
keywords: Brønsted-Lowry Acids/Bases; Electrophilic Substitution; First-Year Undergraduate/General; Hands-On Learning/Manipulatives; Isotopes; Kinetics; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate