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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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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

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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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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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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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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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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.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics
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Bifunctional versus Defect-Mediated Effects in Electrocatalytic Methanol Oxidation.

Albert K Engstfeld1,2, Jens Klein1, Sylvain Brimaud3

  • 1Institute of Surface Chemistry and Catalysis, Ulm University, Albert-Einstein-Allee 47, 89081, Ulm, Germany.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|February 26, 2021
PubMed
Summary

Ruthenium and platinum catalysts are key for direct methanol oxidation fuel cells. This study finds pure platinum defect sites, not bifunctional Pt-Ru sites, are unexpectedly crucial for methanol oxidation catalysis.

Keywords:
bifunctional mechanismelectrocatalysismethanol oxidationplatinumruthenium

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Catalysis

Background:

  • Platinum (Pt) and ruthenium (Ru) are prominent anode catalysts for direct methanol oxidation fuel cells (DMFCs).
  • Their high performance is traditionally explained by bifunctional catalysis: Ru provides oxygen species, and Pt oxidizes intermediates like carbon monoxide (CO).

Purpose of the Study:

  • To investigate the catalytic activity of well-defined Pt-modified Ru(0001) single crystal electrodes for methanol oxidation.
  • To challenge the established bifunctional mechanism by examining varying Pt contents and configurations.

Main Methods:

  • Fabrication of single crystal electrodes with controlled Pt modification on Ru(0001).
  • Electrochemical characterization of methanol oxidation reaction (MOR) on electrodes with diverse Pt loadings and surface arrangements.

Main Results:

  • Pt-modified Ru(0001) electrodes showed unexpected inactivity for methanol oxidation.
  • This contradicts predictions based on the bifunctional catalysis model.
  • Pure Pt defect sites were identified as potentially more critical than bifunctional PtRu sites.

Conclusions:

  • The traditional bifunctional mechanism may not fully explain methanol oxidation catalysis on Pt-Ru systems.
  • Defect sites on pure Pt surfaces appear to play a more significant role than previously assumed.
  • Rethinking catalyst design for DMFCs is necessary, focusing on specific defect site functionalities.