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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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.
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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
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A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
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The electronic factor in alkane oxidation catalysis.

Maik Eichelbaum1, Michael Hävecker, Christian Heine

  • 1Department of Inorganic Chemistry, Fritz-Haber-Institut der Max-Planck-Gesellschaft, Faradayweg 4-6, 14195 Berlin (Germany); BasCat, UniCat BASF JointLab, TU Berlin, Marchstrasse 6, 10587 Berlin (Germany). me@fhi-berlin.mpg.de.

Angewandte Chemie (International Ed. in English)
|January 30, 2015
PubMed
Summary
This summary is machine-generated.

Semiconductor physics concepts explain heterogeneous oxidation catalysts. A dynamic surface potential barrier, influenced by gas phase, differentiates selective catalysts from unselective ones.

Keywords:
heterogeneous catalysisn-butaneselective oxidationsemiconductors

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Area of Science:

  • Heterogeneous catalysis
  • Semiconductor physics
  • Surface science

Background:

  • Understanding the fundamental working principles of heterogeneous oxidation catalysts is crucial for designing efficient catalytic systems.
  • Distinguishing between selective and unselective reaction pathways remains a key challenge in catalysis research.

Purpose of the Study:

  • To investigate the applicability of semiconductor physics concepts to heterogeneous oxidation catalysts.
  • To determine if these concepts can differentiate between selective and unselective catalytic pathways.

Main Methods:

  • Near-ambient-pressure X-ray photoelectron spectroscopy (NAP-XPS) was employed.
  • The study focused on the oxidation of n-butane to maleic anhydride.
  • Catalysts examined included vanadyl pyrophosphate (highly selective) and MoVTeNbO(x) M1 phase (moderately selective), alongside V2O5 (total oxidation).

Main Results:

  • Catalysts exhibited semiconducting behavior with dynamic charge transfer between bulk and surface.
  • Work function, electron affinity, and surface potential barrier were dependent on the gas phase for selective catalysts.
  • Total oxidation catalyst V2O5 showed minimal gas phase influence on semiconducting properties and no dynamic surface potential barrier.

Conclusions:

  • Heterogeneous oxidation catalysts can be described using semiconductor physics principles.
  • A dynamic surface potential barrier acts as a descriptor for selective oxidation catalysts.
  • This finding offers a new perspective for catalyst design and performance prediction.