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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.3K
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...
12.3K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.5K
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...
1.5K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.9K
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.
9.9K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

5.5K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.5K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

2.6K
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...
2.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

7.7K
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...
7.7K

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Related Experiment Video

Updated: Apr 26, 2026

Quantification of Hydrogen Concentrations in Surface and Interface Layers and Bulk Materials through Depth Profiling with Nuclear Reaction Analysis
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Quantification of Hydrogen Concentrations in Surface and Interface Layers and Bulk Materials through Depth Profiling with Nuclear Reaction Analysis

Published on: March 29, 2016

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Surface hydrogenation reactions at the single-molecule level.

Satoshi Katano1, Yousoo Kim, Maki Kawai

  • 1Research Institute of Electrical Communication, Tohoku University, Sendai, 980-8577, Japan. skatano@riec.tohoku.ac.jp.

Chemical Record (New York, N.Y.)
|July 22, 2014
PubMed
Summary

Low temperature scanning tunnelling microscopy (LT-STM) enables single-molecule observation of surface reactions. Complementary techniques are crucial for interpreting these detailed surface reaction images, enhancing our understanding of heterogeneous catalysis.

Keywords:
acetonitrilehydrogenationlow temperature scanning tunnelling microscopymethyl isocyanidesingle molecule surface chemistry

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Area of Science:

  • Surface science
  • Heterogeneous catalysis
  • Chemical kinetics

Background:

  • Hydrogenation and dehydrogenation are key heterogeneous catalysis reactions.
  • Single-molecule studies offer detailed insights into surface reactions.
  • Low temperature scanning tunnelling microscopy (LT-STM) is a powerful tool for these studies.

Purpose of the Study:

  • To review single-molecule studies of surface reactions using LT-STM.
  • To illustrate the importance of complementary characterization techniques.
  • To detail specific examples of surface reactions on Pt(111).

Main Methods:

  • Low temperature scanning tunnelling microscopy (LT-STM) for single-molecule imaging.
  • Reflection absorption infrared spectroscopy (RAIS) for averaged monolayer characterization.
  • Complementary surface science techniques for detailed analysis.

Main Results:

  • LT-STM allows direct observation of surface reactions at the single-molecule level.
  • The hydrogenation of methyl isocyanide to methyl aminocarbyne on Pt(111) was studied.
  • Tip-induced dehydrogenation of acetonitrile on Pt(111) was investigated.
  • Complementary techniques are essential for accurate interpretation of LT-STM data.

Conclusions:

  • Combining LT-STM with other methods provides a comprehensive understanding of surface reactions.
  • Accurate interpretation of single-molecule surface dynamics relies on multiple characterization techniques.
  • This approach advances the study of heterogeneous catalysis on metal surfaces.