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Substitution of the Hydroxyl Hydrogen

  • Page ID
    6019
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    As with the alcohols, the phenolic hydroxyl hydrogen is rather easily replaced by other substituents. For example, phenol reacts easily with acetic anhydride to give phenyl acetate. Likewise, the phenolate anion is an effective nucleophile in SN2 reactions, as in the second example below.

    Examples:

    RXN1.jpg

    RXN2.jpg

    Contributors

    Prof. Steven Farmer (Sonoma State University)

    William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry


    Substitution of the Hydroxyl Hydrogen is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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