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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

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...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Catalysis

Catalysis

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.

Acid-Catalyzed Hydration of Alkenes

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Related Experiment Video

Updated: Aug 10, 2025

Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics

Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics

Published on: April 12, 2019

Cation Effects on Interfacial Water Structure and Hydrogen Peroxide Reduction on Pt(111).

Valentín Briega-Martos¹, Francisco J Sarabia¹, Víctor Climent¹

¹Instituto de Electroquímica, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.

ACS Measurement Science Au

|February 14, 2023

Summary

The cation in aqueous electrolytes significantly alters interfacial water structure and electrocatalytic activity on platinum surfaces. This effect is linked to changes in water adlayer structure and charge accumulation.

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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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Published on: April 12, 2019

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

Area of Science:

Electrochemistry
Surface Science
Physical Chemistry

Background:

The structure of water at electrode-electrolyte interfaces is crucial for electrochemical reactions.
Alkali metal cations in electrolytes can influence interfacial properties.
Understanding these influences is key to designing efficient electrocatalysts.

Purpose of the Study:

To investigate the effect of different alkali metal cations (Li+, Na+, Cs+) on the Pt(111) electrode-electrolyte interface.
To study the impact of interfacial water structure on the hydrogen peroxide reduction reaction.
To correlate interfacial water structure with electrocatalytic activity.

Main Methods:

Cyclic voltammetry to probe interfacial properties and reaction kinetics.
Laser-induced temperature jump experiments to analyze interfacial water dynamics.
Electrochemical measurements under varying electrolyte compositions.

Main Results:

The potential of maximum entropy (pme) varies with alkali metal cation, following the order Li+ < Na+ < Cs+.
The hydrogen peroxide reduction reaction is inhibited at low potentials due to negative charge buildup.
The potential of inhibition (Einhibition) correlates with the pme trend, indicating cation-dependent interfacial effects.

Conclusions:

Electrolyte cation nature profoundly affects interfacial water structure at the Pt(111) electrode.
Interfacial water adlayer structure plays a significant role in electrocatalytic reaction activity.
Modulating interfacial water structure via cation choice offers a pathway to control electrocatalysis.