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14.9: Organometallic Compounds from Organohalogen Compounds

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    One of the more important reactions of organohalogen compounds is the formation of organometallic compounds by replacement of the halogen by a metal atom. Carbon is positive in carbon-halogen bonds and becomes negative in carbon-metal bonds, and therefore carbon is considered to be reduced in formation of an organometallic compound (Section 11-1):

    Roberts and Caserio Screenshot 14-8-1.png

    This transformation is of value because it makes an electrophilic carbon into a nucleophilic carbon. Organometallic compounds are a convenient source of nucleophilic carbon. A typical example of their utility is the way the achieve addition of nucleophilic carbon to carbonyl groups with formation of carbon-carbon bonds:

    Roberts and Caserio Screenshot 14-8-2.png

    In this chapter we will restrict our discussion of organometallic compounds to the alkyl and aryl compounds of magnesium and lithium, and the sodium and potassium salts of 1-alkynes. These substances normally are derived directly or indirectly from organohalogen compounds and are used very widely in organic synthesis. Organometallic compounds of transition metals and of boron are discussed in Chapters 11 and 31.

    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 14.9: Organometallic Compounds from Organohalogen Compounds 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.