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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.8K
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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Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
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Radical Formation: Elimination00:51

Radical Formation: Elimination

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Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
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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.
6.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Transient hydroperoxyalkyl intermediates (•QOOH) in isopentane oxidation. II. Isomer-resolved unimolecular dynamics.

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Watching a hydroperoxyalkyl radical (•QOOH) dissociate.

Anne S Hansen1, Trisha Bhagde1, Kevin B Moore2

  • 1Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA.

Science (New York, N.Y.)
|August 6, 2021
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Summary

Researchers directly observed a hydroperoxyalkyl radical (•QOOH) intermediate during volatile organic compound oxidation. Its decay pathway, enhanced by heavy-atom tunneling, provides crucial data for atmospheric and combustion chemistry models.

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Area of Science:

  • Chemical Kinetics
  • Atmospheric Chemistry
  • Combustion Chemistry

Background:

  • Hydroperoxyalkyl radicals (•QOOH) are key transient intermediates in the oxidation of volatile organic compounds (VOCs).
  • Understanding their unimolecular decay is crucial for accurate atmospheric and combustion models.

Purpose of the Study:

  • To directly observe and characterize the hydroperoxyalkyl radical (•QOOH) intermediate.
  • To measure its energy-dependent unimolecular decay rates and compare them with theoretical predictions.
  • To investigate the role of heavy-atom tunneling in the dissociation process.

Main Methods:

  • Direct observation of the •QOOH radical using its infrared fingerprint.
  • Time-domain measurements of unimolecular dissociation rates over a range of energies.
  • Theoretical calculations using state-of-the-art electronic structure methods.
  • Master equation modeling to predict pressure-dependent thermal dissociation rates.

Main Results:

  • Direct observation of the •QOOH radical and its infrared spectrum.
  • Experimental unimolecular decay rates align with theoretical predictions.
  • Significant enhancement of unimolecular decay due to heavy-atom tunneling (O-O bond elongation and C-C-O angle contraction).
  • Master equation modeling successfully predicted pressure-dependent rates, incorporating tunneling effects.

Conclusions:

  • The study provides direct experimental evidence and characterization of the •QOOH intermediate.
  • Heavy-atom tunneling plays a significant role in the unimolecular decay of •QOOH radicals.
  • The findings offer crucial, a priori predicted kinetic data for improving global atmospheric and combustion chemistry models.