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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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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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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.
Peroxisomes01:24

Peroxisomes

Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
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Oxidation of Alcohols

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.
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...

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Membraneless Hydrogen Peroxide Fuel Cells as a Promising Clean Energy Source
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Does more MnSOD mean more hydrogen peroxide?

Lee Ann MacMillan-Crow1, John P Crow

  • 1University of Arkansas for Medical Sciences, Department of Pharmacology and Toxicology Little Rock, AR 72205, USA. lmcrow@uams.edu

Anti-Cancer Agents in Medicinal Chemistry
|February 5, 2011
PubMed
Summary
This summary is machine-generated.

Increased manganese superoxide dismutase (MnSOD) may not always raise hydrogen peroxide levels. MnSOD can use hydrogen peroxide to create toxic peroxynitrite, especially with nitric oxide present.

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Use of Electron Paramagnetic Resonance in Biological Samples at Ambient Temperature and 77 K
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Use of Electron Paramagnetic Resonance in Biological Samples at Ambient Temperature and 77 K

Published on: January 11, 2019

Area of Science:

  • Biochemistry
  • Enzymology
  • Oxidative Stress

Background:

  • Superoxide dismutases (SODs) are key antioxidant enzymes.
  • SODs convert superoxide radicals to hydrogen peroxide and oxygen.
  • Hydrogen peroxide is further detoxified by other antioxidant enzymes.

Purpose of the Study:

  • To address the misconception that elevated manganese superoxide dismutase (MnSOD) increases hydrogen peroxide levels.
  • To explore reasons behind this confusion and offer potential resolutions.
  • To present data on MnSOD's interaction with nitric oxide and hydrogen peroxide.

Main Methods:

  • Enzyme activity assays.
  • Oxidant production measurements.
  • Biochemical analysis of reactive oxygen species.

Main Results:

  • Demonstrated MnSOD's capacity to consume hydrogen peroxide under specific conditions.
  • Showcased MnSOD's role in producing superoxide and peroxynitrite in the presence of nitric oxide.
  • Provided evidence contradicting the simple correlation between increased MnSOD and increased hydrogen peroxide.

Conclusions:

  • The relationship between MnSOD levels and hydrogen peroxide is complex.
  • MnSOD can paradoxically contribute to oxidative stress by generating peroxynitrite.
  • Understanding MnSOD's interactions is crucial for antioxidant research.