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Related Concept Videos

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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Oxidation of Phenols to Quinones01:17

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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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Polyprotic Acids

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Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
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Electron Transport Chain: Complex III and IV01:43

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During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
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Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

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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.
The removal of an electron from a molecule, results in a...
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Oxidation-Reduction Reactions03:11

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Oxidation–Reduction Reactions
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Related Experiment Video

Updated: Dec 13, 2025

A Rapid and Specific Microplate Assay for the Determination of Intra- and Extracellular Ascorbate in Cultured Cells
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Ascorbic acid: The chemistry underlying its antioxidant properties.

David Njus1, Patrick M Kelley1, Yi-Jung Tu2

  • 1Department of Biological Sciences, Wayne State University, Detroit, MI, 48202, USA.

Free Radical Biology & Medicine
|August 2, 2020
PubMed
Summary
This summary is machine-generated.

Ascorbic acid (vitamin C) is an unusual antioxidant. Its radical form, monodehydroascorbate, preferentially reacts with other radicals, avoiding an energetically unfavorable tricarbonyl structure.

Keywords:
AntioxidantAscorbic acidDehydroascorbateDisproportionationMonodehydroascorbateSuperoxide

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Area of Science:

  • Biochemistry
  • Oxidative Stress

Background:

  • Ascorbic acid (vitamin C) functions as a potent antioxidant.
  • Its unique single-electron donation mechanism forms the monodehydroascorbate radical.

Purpose of the Study:

  • To clarify the oxidation products of ascorbic acid.
  • To correct misconceptions regarding dehydroascorbate formation.

Main Methods:

  • Review of established chemical principles.
  • Analysis of kinetic considerations in ascorbic acid oxidation.

Main Results:

  • Monodehydroascorbate preferentially reacts with radicals.
  • Formation of a tricarbonyl structure (pseudodehydroascorbate) is energetically unfavorable.
  • Dehydroascorbate possesses a bicyclic hemiketal structure, not the tricarbonyl form.

Conclusions:

  • The commonly cited tricarbonyl oxidation product of ascorbic acid is likely incorrect.
  • Misconceptions about dehydroascorbate obscure the chemical basis of vitamin C's antioxidant activity.