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Benzoquinone, or quinone is one of the two isomers of cyclohexadienedione. It has the molecular formula C6H4O2. Orthobenzoquinone is the 1,2-dione, whereas parabenzoquinone is the 1,4-dione.
Orthobenzoquinone is the oxidized form of catechol (1,2-dihydroxybenzene), while parabenzoquinone is the oxidized form of hydroquinone. An acidic potassium iodide solution reduces a solution of benzoquinone to hydroquinone, which is oxidized back with a solution of silver nitrate.
Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). Others serve as electron acceptors in electron transport chains such as those in Photosystems I & II of photosynthesis, and aerobic respiration. A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterrent in the animal world. Quinones can be partially reduced to quinols.
Benzoquinone is used in organic chemistry as an oxidizing agent. Even stronger agents exist such as 2,3,5,6-tetrachloro-parabenzoquinone or p-chloranil and 2,3-dicyano-5,6-dichloro-parabenzoquinone or DDQ for short.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Quinone". A list of authors is available in Wikipedia.|