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19.11 Inductive Effects for Aromatic Acids

  • Page ID
    28373
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    Electron-withdrawing groups

    The conjugate base of benzoic acid is stabilized by electron-withdrawing groups (EWG). This makes the acid more acidic by delocalizing the charge of the carboxylate ion.

    Smith Ch 19 EWG.png

     

    Electron-withdrawing groups deactivate the benzene ring to electrophilic attack and make benzoic acids more acidic.

    Electron-donating groups

    The conjugate base of benzoic acid is destabilized by electron-donating groups (EDG). This makes the acid less acidic by pushing more electron density toward the negative charge in the carboxylate.

    Smith Ch 19 EDG.png

    Electron-donating groups activate the benzene ring to electrophilic attack and make benzoic acids less acidic.

    Several examples of electron donating groups.

    Contributors 

    • Layne Morsch (University of Illinois Springfield)

    This page titled 19.11 Inductive Effects for Aromatic Acids is shared under a not declared license and was authored, remixed, and/or curated by Layne Morsch.

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