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18.25 : Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ringeven in the absence of anα hydrogen.

o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in several physiological systems to catalyzebiological reactions. For example, cellular respiration utilizes ubiquinones or coenzyme Q as electron mediators for reducing molecular oxygen to water. The most important functional group in vitamin K2, which is involved in blood clotting, is a quinone.Quinones are also present inmenadione, which is a synthetic supplement for vitamin K2.

Tags
OxidationPhenolsQuinonesRedox ReactionsElectron TransferBiological ReactionsCellular RespirationUbiquinonesCoenzyme QVitamin K2Menadione

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18.25 : Oxidation of Phenols to Quinones

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18.1 : NMR Spectroscopy of Benzene Derivatives

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18.2 : Reactions at the Benzylic Position: Oxidation and Reduction

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18.3 : Reactions at the Benzylic Position: Halogenation

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18.4 : Electrophilic Aromatic Substitution: Overview

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18.5 : Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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18.6 : Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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18.7 : Electrophilic Aromatic Substitution: Nitration of Benzene

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18.8 : Electrophilic Aromatic Substitution: Sulfonation of Benzene

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18.9 : Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

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18.10 : Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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18.11 : Limitations of Friedel–Crafts Reactions

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18.12 : Directing Effect of Substituents: ortho–para-Directing Groups

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18.13 : Directing Effect of Substituents: meta-Directing Groups

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18.14 : ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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