11.6 : Autoxidation of Ethers to Peroxides and Hydroperoxides
Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
If concentrated or heated, these peroxides may explode. Hence, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly to prevent such explosions. Autoxidation of ethers proceeds by a free-radical chain reaction consisting of a series of steps—initiation, propagation, and termination in repetitive cycles. Each of these steps forms intermediate products called chain carriers that regenerate in each step. Such a reaction will continue as long as the chain carriers persist. Hydroperoxides and peroxides can be detected by shaking ether samples with an acidified aqueous 10% solution of potassium iodide, thereby liberating iodine which gives the yellow color to the solution.
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11.6 : Autoxidation of Ethers to Peroxides and Hydroperoxides
Ethers, Epoxides, Sulfides
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11.1 : Structure and Nomenclature of Ethers
Ethers, Epoxides, Sulfides
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11.2 : Physical Properties of Ethers
Ethers, Epoxides, Sulfides
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11.3 : Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers, Epoxides, Sulfides
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11.4 : Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers, Epoxides, Sulfides
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11.5 : Ethers to Alkyl Halides: Acidic Cleavage
Ethers, Epoxides, Sulfides
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11.7 : Crown Ethers
Ethers, Epoxides, Sulfides
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11.8 : Structure and Nomenclature of Epoxides
Ethers, Epoxides, Sulfides
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11.9 : Preparation of Epoxides
Ethers, Epoxides, Sulfides
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11.10 : Sharpless Epoxidation
Ethers, Epoxides, Sulfides
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11.11 : Acid-Catalyzed Ring-Opening of Epoxides
Ethers, Epoxides, Sulfides
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11.12 : Base-Catalyzed Ring-Opening of Epoxides
Ethers, Epoxides, Sulfides
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11.13 : Structure and Nomenclature of Thiols and Sulfides
Ethers, Epoxides, Sulfides
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11.14 : Preparation and Reactions of Thiols
Ethers, Epoxides, Sulfides
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11.15 : Preparation and Reactions of Sulfides
Ethers, Epoxides, Sulfides
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