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Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Primary Kinetic Isotope Effect in the Hypochlorite Oxidation of 1-Phenylethanol in the Physical Chemistry Laboratory

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Chem. Educ. 2017, 94, 9, 1338-1342
    Laboratory Experiment

    Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Primary Kinetic Isotope Effect in the Hypochlorite Oxidation of 1-Phenylethanol in the Physical Chemistry Laboratory
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    Department of Chemistry and Physics, Indiana State University, Terre Haute, Indiana 47809, United States
    *E-mail: [email protected]
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    Journal of Chemical Education

    Cite this: J. Chem. Educ. 2017, 94, 9, 1338–1342
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    https://doi.org/10.1021/acs.jchemed.6b00950
    Published June 23, 2017
    Copyright © 2017 The American Chemical Society and Division of Chemical Education, Inc.
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    Abstract

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    A kinetic isotope effect (KIE) experiment is described for the physical chemistry laboratory. Students conduct a hypochlorite (household bleach) oxidation of an equimolar mixture of 1-phenylethanol and 1-deuterio-1-phenylethanol to acetophenone. The reaction occurs in a biphasic reaction mixture and follows first-order kinetics with respect to either isotopomer of 1-phenylethanol. Reaction progress is measured by gas chromatography–mass spectrometry (GC–MS). Alternatively, the experiment could be conducted with each isotopomer serially and followed by GC alone. The reaction rate constant for the disappearance of 1-phenylethanol, kH, ranges from 3 × 10–4 to 2 × 10–3 s–1, while kD, for 1-deuterio-1-phenylethanol, ranges from 9 × 10–5 to 5 × 10–4 s–1. The observed KIE, the ratio kH/kD, is remarkably robust, ranging between 2.3 and 3.6, with a mean of 2.9 and standard deviation of 0.4 over three years of student data. The robustness of the observed KIE stems from using competing reactions. The experiment can be completed in about 3 h; GC–MS data is conveniently acquired overnight using an autosampler. The experiment, as presented here, can stand alone, but is well-suited to cross-course collaboration between the organic and physical chemistry laboratories. The preceding companion paper describes the synthesis of 1-phenylethanol and 1-deuterio-1-phenylethanol using borohydride or borodeuteride reduction of acetophenone as an experiment for the organic laboratory.

    Copyright © 2017 The American Chemical Society and Division of Chemical Education, Inc.

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    Cited By

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    This article is cited by 7 publications.

    1. Fritz Deufel, Manuel van Gemmeren. Deuteration of Arenes via Pd-Catalyzed C–H Activation: A Lesson in Nondirected C–H Activation, Isotopic Labeling, and NMR Characterization. Journal of Chemical Education 2024, 101 (8) , 3410-3417. https://doi.org/10.1021/acs.jchemed.4c00270
    2. Sarah E. Shaner, Kari L. Stone. Determination of Stretching Frequencies by Isotopic Substitution Using Infrared Spectroscopy: An Upper-Level Undergraduate Experiment for an In-Person or Online Laboratory. Journal of Chemical Education 2023, 100 (6) , 2347-2352. https://doi.org/10.1021/acs.jchemed.2c00905
    3. Julius Pavlov, Ramu Errabelli, Sihang Xu, Zhaoyu Zheng, David Douce, Steve Bajic, Athula B. Attygalle. Real-Time Monitoring of Reactions by Headspace Sampling under Ambient Mass Spectrometric Conditions. Journal of Chemical Education 2023, 100 (6) , 2207-2214. https://doi.org/10.1021/acs.jchemed.2c01150
    4. Sherri C. Young. Incorporating Interlab Collaborations into the Organic Chemistry Teaching Laboratories. Journal of Chemical Education 2021, 98 (9) , 2848-2860. https://doi.org/10.1021/acs.jchemed.0c01350
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    6. Richard A. Kjonaas, Richard W. Fitch, and Robert J. Noll . Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Isotopic Labeling with Sodium Borodeuteride in the Introductory Organic Chemistry Laboratory. Journal of Chemical Education 2017, 94 (9) , 1334-1337. https://doi.org/10.1021/acs.jchemed.6b00949
    7. Yuhan Lin, Chaoyuan Deng, Lei Wu, Yuchao Zhang, Chuncheng Chen, Wanghong Ma, Jincai Zhao. Quantitative isotope measurements in heterogeneous photocatalysis and electrocatalysis. Energy & Environmental Science 2020, 13 (9) , 2602-2617. https://doi.org/10.1039/D0EE01790F
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    Journal of Chemical Education

    Cite this: J. Chem. Educ. 2017, 94, 9, 1338–1342
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jchemed.6b00950
    Published June 23, 2017
    Copyright © 2017 The American Chemical Society and Division of Chemical Education, Inc.
    Request reuse permissions

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