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

• Autores: Richard Giles, Iris Kim, Weyjuin Eric Chao, Jennifer Moore, Kyung Woon Jung
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 91, Nº 8, 2014, págs. 1220-1223
• Idioma: inglés
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• Resumen

  • 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 by 1 H 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.