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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.
The hydrogenation process takes place on the...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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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.
7.7K
Catalysis02:50

Catalysis

26.9K
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 Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
1.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Related Experiment Video

Updated: Jul 1, 2025

Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics
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Intramolecular Catalytic Hydrogen Atom Transfer (CHAT).

Rubik Asatryan1, Jason Hudzik1, Mark Swihart1

  • 1Department of Chemical and Biological Engineering, and Center for Hybrid Rocket Exascale Simulation Technology (CHREST), University at Buffalo, The State University of New York, Buffalo, New York 14260, United States.

The Journal of Physical Chemistry. A
|March 7, 2024
PubMed
Summary

We introduce intramolecular catalytic transfer of hydrogen atoms (CHAT), a novel mechanism where a molecule

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Chemical Kinetics

Background:

  • Intramolecular catalysis (IntraCat) involves a molecule catalyzing its own reaction, often with external aid.
  • Previous work systematized intermolecular catalysis, particularly dihydrogen catalysis.
  • Understanding intramolecular hydrogen transfer is crucial for various chemical processes.

Purpose of the Study:

  • To introduce and define a general, first-principles-based intramolecular catalytic transfer of hydrogen atoms (CHAT) mechanism.
  • To demonstrate the broad applicability of CHAT in catalyzing various organic transformations.
  • To investigate the kinetic impact of CHAT on combustion processes.

Main Methods:

  • First-principles calculations to elucidate the CHAT mechanism and potential energy surfaces.
  • Analysis of characteristic examples including tautomerization, cyclization, and H-migration.
  • Detailed kinetic analysis of pentane-2,4-ketohydroperoxide isomerization and decomposition.

Main Results:

  • CHAT strictly occurs within a single molecule, involving a catalytic moiety that is regenerated.
  • CHAT significantly reduces activation barriers for reactions like keto-enol tautomerization, amino-imino tautomerization, and cyclization.
  • CHAT pathways are competitive in combustion, as shown by kinetic analysis of 2,4-KHP, and offer alternatives to known mechanisms.

Conclusions:

  • CHAT represents a general and previously underappreciated class of intramolecular catalysis.
  • This mechanism can accelerate reactions in diverse fields, including atmospheric chemistry and biochemistry.
  • CHAT pathways play a significant role in chemical transformations, impacting areas from combustion to biological processes.