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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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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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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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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Oxidative Cleavage of Alkenes: Ozonolysis01:46

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxidation and Reduction of Organic Molecules01:19

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Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
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Interfacial Oxidative Oligomerization of Catechol.

Marcelo I Guzman1, Elizabeth A Pillar-Little1, Alexis J Eugene1

  • 1Department of Chemistry, University of Kentucky, Lexington, Kentucky40506, United States.

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|October 17, 2022
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Summary
This summary is machine-generated.

Ozone reacts with catechol films, forming hydroxyl radicals and semiquinone intermediates. This process leads to the oligomerization of polyphenols, contributing to brown organic carbon in aerosols.

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Area of Science:

  • Atmospheric Chemistry
  • Surface Science
  • Organic Chemistry

Background:

  • Catechol oxidation by ozone is a key process in atmospheric chemistry.
  • Understanding the formation of brown organic carbon from polyphenol oligomerization is crucial.

Purpose of the Study:

  • To investigate the surface alterations and chemical composition changes during catechol oxidation by ozone.
  • To elucidate the reaction mechanism and kinetics under varying relative humidity.

Main Methods:

  • Fourier transform infrared micro-spectroscopy
  • Atomic force microscopy
  • Electrospray ionization mass spectrometry
  • Liquid chromatography with UV-visible and mass spectrometry detection

Main Results:

  • Ozone exposure alters catechol aromatic surfaces, forming heavier polyhydroxylated products.
  • Reaction rates, half-lives, and reactive uptake coefficients were determined using a Langmuir-Hinshelwood mechanism.
  • Relative humidity significantly influences the heterogeneous oxidation process.

Conclusions:

  • The study provides physical insights into the heterogeneous oxidation of catechol films.
  • Oligomerization of polyphenols at interfaces contributes to brown organic carbon formation in atmospheric aerosols.
  • The findings enhance understanding of atmospheric aerosol composition and evolution.