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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

11.8K
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.
The hydrogenation process takes place on the...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

9.1K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal,...
9.1K
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

4.4K
Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps. ...
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Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

3.3K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
3.3K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Silver Oxide Reduction Chemistry in an Alkane Environment.

Fayez Alfayez1,2, Mikhail Agrachev3, Fabian Matter2

  • 1Department of Advanced Fibers, Empa Swiss Federal Laboratories for Materials Science and Technology, St Gallen CH-9014, Switzerland.

ACS Applied Materials & Interfaces
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Summary

The reduction of silver oxide in alkanes produces metallic silver via a surface reaction, forming fused particles. This process involves oxidation and radical species, yielding CO2 and H2O byproducts.

Keywords:
alkanehydrocarbonsmechanismpolymerreductionsilver oxide

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Surface Chemistry

Background:

  • In situ reduction of silver oxide (Ag2O) to metallic silver (Ag) is crucial for applications like conductive welding and nanoparticle generation.
  • Understanding redox mechanisms in alkane and polymer melts is essential for controlling silver particle morphology and properties.
  • Reduction in pure alkane environments presents unique challenges and poorly understood mechanisms compared to reactions with oxygen-containing organics.

Purpose of the Study:

  • To investigate the redox reaction mechanisms of silver(I) oxide reduction in a liquid alkane environment.
  • To elucidate the particulate morphology resulting from Ag2O reduction in pentadecane and compare it to polyethylene extrusion.
  • To identify reaction byproducts and understand the role of Ag2O in initiating and propagating the redox process.

Main Methods:

  • Liquid pentadecane as a model alkane for silver oxide reduction studies.
  • Comparison of redox chemistry and particle morphology with reactive melt extrusion in polyethylene.
  • Gas chromatography (GC) for byproduct analysis (CO2, H2O, alkenes, oxidized alkanes).
  • Electron paramagnetic resonance (EPR) spectroscopy to detect radical species (ROO•, HOO•).

Main Results:

  • Primary reaction byproducts identified as carbon dioxide (CO2) and water (H2O), with minor alkenes and oxidized alkanes.
  • CO2 formation detected as low as 70 °C, indicating a highly oxidative process resembling catalyzed combustion.
  • Metallic silver formed via a solid-solid surface reaction on Ag2O, resulting in fused particle morphology.
  • EPR confirmed the involvement of radical species typical of hydrocarbon oxidation.

Conclusions:

  • The reduction of Ag2O in pure alkane environments is a predominantly complete oxidation process, not a linear reduction.
  • Ag2O acts as both a radical initiator and an oxygen source, driving the oxidative decomposition of the alkane.
  • The resulting fused silver particle morphology, while seemingly suboptimal, offers a high-contact-area structure beneficial for welding applications.
  • Redox reactions in pure alkane environments are confined to the surface of the original silver oxide particles.