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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 : Espectroscopía de RMN de derivados del benceno

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18.2 : Reacciones en la posición bencílica: oxidación y reducción

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18.3 : Reacciones en la posición bencílica: halogenación

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18.4 : Sustitución aromática electrofílica: descripción general

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18.5 : Sustitución aromática electrofílica: cloración y bromación del benceno

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18.6 : Sustitución aromática electrofílica: fluoración y yodación del benceno

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18.7 : Sustitución aromática electrofílica: nitración del benceno

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18.8 : Sustitución aromática electrofílica: sulfonación del benceno

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18.9 : Sustitución aromática electrofílica: Friedel-Crafts alquilación de benceno

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18.10 : Sustitución aromática electrofílica: acilación de benceno de Friedel-Crafts

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18.11 : Limitaciones de las reacciones de Friedel-Crafts

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18.12 : Efecto Directivo de los Sustituyentes: Grupos Orto-Para-Directores

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18.13 : Efecto Directivo de los Sustituyentes: Grupos Meta-Directores

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18.14 : Activadores orto-para-direccionamientos: –CH3, –OH, –⁠NH2, –OCH3

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