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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 : 벤젠 유도체의 NMR 분광법

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18.2 : 벤질산 위치에서의 반응: 산화 및 환원

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18.3 : 벤질산 위치에서의 반응 : 할로겐화

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18.4 : 친전자성 방향족 대체: 개요

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18.5 : 친전자성 방향족 치환: 벤젠의 염소화 및 브롬화

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18.6 : 친전자성 방향족 치환: 벤젠의 불소화 및 요오드화

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18.7 : 친전자성 방향족 치환: 벤젠의 질화

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18.8 : 친전자성 방향족 치환: 벤젠의 설폰화

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18.9 : 친전자성 방향족 치환: Friedel–Crafts 벤젠의 알킬화

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18.10 : 친전자성 방향족 치환: Friedel–Crafts 벤젠의 아실화

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18.11 : Friedel-Crafts 반응의 한계

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18.12 : 치환의 지시 효과: ortho-para-directing groups

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18.13 : 치환의 지시 효과: 메타 지시 그룹

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18.14 : 직교-파라-디렉팅 활성제: -CH3, -OH, -⁠NH2, -OCH3

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