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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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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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Initiation Chemistries in Hydrocarbon (Aut)Oxidation.

Lakshmanan Sandhiya1, Hendrik Zipse2

  • 1Ludwig-Maximilians-Universität München, Department of Chemistry, Butenandtstrasse 5-13, 81377 München (Germany), Fax: (+49) 89-2180-77738.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 17, 2015
PubMed
Summary

Benzyl hydroperoxide is a key intermediate in toluene autoxidation. Its O-O bond cleavage is endothermic, but a bimolecular reaction offers a favorable initiation pathway for radical generation.

Keywords:
hydrocarbonsoxidationradical reactionstheoretical calculationsthermochemistry

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Area of Science:

  • Chemical kinetics
  • Reaction mechanisms
  • Thermochemistry

Background:

  • Toluene autoxidation yields benzyl hydroperoxide, benzyl alcohol, benzaldehyde, and benzoic acid.
  • Understanding radical-generating reactions is crucial for controlling oxidation processes.

Purpose of the Study:

  • To compare thermochemical profiles of radical-generating reactions in toluene autoxidation.
  • To identify the most favorable initiation pathway for these reactions.

Main Methods:

  • Computational chemistry calculations (CBS-QB3, G4, G3B3) were used to estimate the heat of formation of benzyl hydroperoxide.
  • Reaction enthalpies and free energies were calculated for various initiation processes.

Main Results:

  • Homolytic O-O bond cleavage of benzyl hydroperoxide is strongly endothermic and unlikely to initiate reactions.
  • A bimolecular reaction of benzyl hydroperoxide is the most thermodynamically favorable initiation process.
  • This bimolecular pathway is more favorable than unimolecular dissociation of common radical initiators.

Conclusions:

  • Benzyl hydroperoxide is a key intermediate, but not a primary radical initiator via O-O bond cleavage.
  • A bimolecular reaction involving benzyl hydroperoxide provides a more efficient initiation mechanism for toluene autoxidation radical processes.