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17.8: 1,2-Dicarbonyl Compounds

  • Page ID
    22282
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    Some typical and important members of this class have structures as follows:

    Roberts and Caserio Screenshot 17-7-1.png

    Most of the 1,2-dicarbonyl compounds are yellow. Ethanedial is unusual in being yellow in the liquid state, but green in the vapor state. It has very reactive aldehyde groups and is employed in the manufacture of plastics and as a component of embalming fluids to harden proteins by linking together their amino groups through imine formation:

    Roberts and Caserio Screenshot 17-7-2.png

    Ethanedial undergoes an internal Cannizzaro reaction with alkali to give hydroxyethanoic (glycolic) acid:

    Roberts and Caserio Screenshot 17-7-3.png

    An analogous reaction occurs with diphenylethanedione, which results in carbon-skeleton rearrangement. This is one of the few carbon-skeleton rearrangements brought about by basic reagents, and is known as the "benzilic acid rearrangement".

    Roberts and Caserio Screenshot 17-7-4.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."


    17.8: 1,2-Dicarbonyl Compounds is shared under a not declared license and was authored, remixed, and/or curated by John D. Roberts and Marjorie C. Caserio.