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Related Concept Videos

Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...
Radical Formation: Elimination00:51

Radical Formation: Elimination

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 with respect to...
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Related Experiment Video

Updated: May 26, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Fragmentation of β-hydroxy hydroperoxides.

Xiaodong Gu1, Wujuan Zhang, Robert G Salomon

  • 1Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.

The Journal of Organic Chemistry
|December 30, 2011
PubMed
Summary

Vitamins E and C break down a specific hydroperoxide, creating aldehydes. This process, especially with iron, may cause oxidative injury by damaging proteins and DNA.

Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Oxidative Stress Research

Background:

  • Singlet oxygenation of cyclohepta-1,4-diene yields a hydroperoxy endoperoxide.
  • Base-catalyzed disproportionation of this endoperoxide produces a β-hydroxy hydroperoxide.

Purpose of the Study:

  • To investigate the fragmentation of β-hydroxy hydroperoxide induced by vitamins E and C.
  • To explore the role of redox-active metal ions, like iron, in this fragmentation process.
  • To understand the potential contribution of this chemistry to oxidative injury.

Main Methods:

  • Singlet oxygenation of cyclohepta-1,4-diene.
  • Base-catalyzed disproportionation.
  • Fragmentation assays involving vitamins E and C, and metal ions.

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Laser-free Hydroxyl Radical Protein Footprinting to Perform Higher Order Structural Analysis of Proteins

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Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting
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Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting

Published on: October 17, 2011

Related Experiment Videos

Last Updated: May 26, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Laser-free Hydroxyl Radical Protein Footprinting to Perform Higher Order Structural Analysis of Proteins
09:59

Laser-free Hydroxyl Radical Protein Footprinting to Perform Higher Order Structural Analysis of Proteins

Published on: June 4, 2021

Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting
13:41

Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting

Published on: October 17, 2011

Main Results:

  • β-hydroxy hydroperoxide was synthesized.
  • Vitamins E and C induced fragmentation of β-hydroxy hydroperoxide, generating aldehydes.
  • Redox-active metal ions, particularly iron, enhanced aldehyde generation.
  • This aldehyde formation pathway may mimic oxidative cleavage of polyunsaturated fatty acyls.

Conclusions:

  • The fragmentation of β-hydroxy hydroperoxide by vitamins E and C, especially with iron, generates aldehydes.
  • This chemical pathway could contribute to the formation of reactive aldehydes implicated in oxidative injury.
  • The findings provide insights into mechanisms of oxidative damage to proteins and DNA.