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22.10: Oxidation Reactions

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    The reagents usually employed for the oxidation of alkenes (e.g., \(\ce{CrO_3}\), \(\ce{KMnO_4}\), \(\ce{H_2O_2}\), \(\ce{OsO_4}\)) normally do not attack benzene. At high temperatures, benzene can be oxidized to cis-butenedioic (maleic) anhydride by air with a vanadium pentoxide catalyst. Naphthalene can be similarly oxidized to 1,2-benzenedioic (phthalic) anhydride:

    Roberts and Caserio Screenshot 22-10-1.png

    Both anhydrides are prepared in this manner on a large scale for use in the production of ester polymers (Section 29-5A). Phthalic anhydride also is prepared by the oxidation of 1,2-dimethylbenzene:

    Roberts and Caserio Screenshot 22-10-2.png

    Phthalic anhydride is used to make anthraquinone and to make esters of phthalic acid, which are used widely to plasticize polymers.

    Ozonization of aromatic hydrocarbons is possible. Benzene itself gives ethanedial (glyoxal):

    Roberts and Caserio Screenshot 22-10-3.png

    The double-bond character of the 9,10 bond in phenanthrene is particularly evident in ozonization. This bond is attacked preferentially, which leads to the formation of a dialdehyde when the ozonide is reduced with iodide ion:

    Roberts and Caserio Screenshot 22-10-4.png

    Contributors and Attributions

    John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."

    This page titled 22.10: Oxidation Reactions is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by John D. Roberts and Marjorie C. Caserio.