A Laboratory Experiment for Illustrating the Kinetic Isotope Effect

Pauline Lebrun, Alice Kirk, Andrew McStay, Arno Manfred Kraft

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Abstract

This paper describes the study of the kinetic isotope effect for the reaction between cyclohexanone and iodine under acidic conditions that has been adapted for an advanced level undergraduate organic chemistry laboratory class. The kinetics of the reaction of iodine with cyclohexanone can be readily followed with a UV-Vis spectrophotometer or even a home-built colorimeter. The results are compared with the reaction of iodine with cyclohexanone-d4, a deuterated analog which students prepare by a simple and cheap deuteration. The
deuterated cyclohexanone reacts more slowly than the non-deuterated cyclohexanone by a factor of 3.5 ± 1.2, which confirms that a C-H bond is broken in the rate-determining step and illustrates a primary kinetic isotope
effect.
Original languageEnglish
Pages (from-to)169-173
JournalChemical Educator
Volume23
Publication statusPublished - 14 Aug 2018

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