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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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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.
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Oxidation of Alcohols02:37

Oxidation of Alcohols

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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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 ring even in the absence of an α 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...
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One- or Two-Electron Water Oxidation, Hydroxyl Radical, or H2O2 Evolution.

Samira Siahrostami1, Guo-Ling Li2,3, Venkatasubramanian Viswanathan4

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Developing catalysts for water disinfection via electrochemical oxidation is key. This study reveals how catalyst properties control selectivity for producing hydroxyl radicals, hydrogen peroxide, or oxygen.

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Area of Science:

  • Electrochemistry
  • Catalysis
  • Water treatment

Background:

  • Electrochemical water oxidation is promising for disinfection and hydrogen peroxide production.
  • A key challenge is preventing the four-electron pathway that produces oxygen.

Purpose of the Study:

  • To understand catalyst properties governing selectivity in water oxidation.
  • To identify pathways for hydroxyl radical and hydrogen peroxide generation.

Main Methods:

  • Developing a thermochemical model for catalyst selectivity.
  • Analyzing one-, two-, and four-electron transfer processes.

Main Results:

  • Catalyst properties dictate the selectivity towards hydroxyl radicals, hydrogen peroxide, or oxygen.
  • A thermochemical picture explains the control over reaction pathways.

Conclusions:

  • Understanding catalyst thermochemistry is crucial for designing selective electrocatalysts.
  • This work provides a framework for developing efficient water disinfection and H2O2 production technologies.