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Epoxidation with Possibilities: Discovering Stereochemistry in Organic Chemistry via Coupling Constants

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Chem. Educ. 2017, 94, 5, 640-643
    Laboratory Experiment

    Epoxidation with Possibilities: Discovering Stereochemistry in Organic Chemistry via Coupling Constants
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    Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, Illinois 61920, United States
    *E-mail: [email protected]
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    Journal of Chemical Education

    Cite this: J. Chem. Educ. 2017, 94, 5, 640–643
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    https://doi.org/10.1021/acs.jchemed.6b00587
    Published March 31, 2017
    Copyright © 2017 The American Chemical Society and Division of Chemical Education, Inc.
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    Abstract

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    A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an “unknown” stereoisomer of 3-hexen-1-ol, and use 1H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereochemistry of their starting alkene.

    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 4 publications.

    1. Erwann Grenet, Pierre-Yves Géant, Xavier J. Salom-Roig. Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine. Organic Letters 2021, 23 (21) , 8539-8542. https://doi.org/10.1021/acs.orglett.1c03237
    2. Matthew C. O’Reilly, Stacey A. Stoffregen, Karl P. Peterson, Mitchell P. Maddox III, Cordell Schrank. Discovery-Based Bromination of Alcohols: An Organic Chemistry Experiment Supporting Spectroscopic Analysis and Mechanistic Reasoning. Journal of Chemical Education 2021, 98 (10) , 3326-3332. https://doi.org/10.1021/acs.jchemed.1c00544
    3. Ronald Soong, Brent G. Pautler, Arvin Moser, Amy Jenne, Daniel H. Lysak, Antonio Adamo, Andre J. Simpson. CASE (Computer-Assisted Structure Elucidation) Study for an Undergraduate Organic Chemistry Class. Journal of Chemical Education 2020, 97 (3) , 855-860. https://doi.org/10.1021/acs.jchemed.9b00498
    4. Sangwook Kang, Jaeho Han, Sung Chul Jang, Joon Soo An, Ilnam Kang, Yun Kwon, Sang-Jip Nam, Sang Hee Shim, Jang-Cheon Cho, Sang Kook Lee, Dong-Chan Oh. Epoxinnamide: An Epoxy Cinnamoyl-Containing Nonribosomal Peptide from an Intertidal Mudflat-Derived Streptomyces sp.. Marine Drugs 2022, 20 (7) , 455. https://doi.org/10.3390/md20070455
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    Journal of Chemical Education

    Cite this: J. Chem. Educ. 2017, 94, 5, 640–643
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jchemed.6b00587
    Published March 31, 2017
    Copyright © 2017 The American Chemical Society and Division of Chemical Education, Inc.
    Request reuse permissions

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