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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...

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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...

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Updated: Jun 11, 2025

Hydrogen Production and Utilization in a Membrane Reactor

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

Electricity-driven organic hydrogenation using water as the hydrogen source.

Bidyut Kumar Kundu¹, Yujie Sun¹

¹Department of Chemistry, University of Cincinnati Cincinnati Ohio 45221 USA yujie.sun@uc.edu.

Chemical Science

|October 7, 2024

Summary

Water can now be used as a sustainable hydrogen source for organic hydrogenation, replacing hazardous molecular hydrogen (H2) gas. This electrocatalytic method operates safely under ambient conditions, offering a greener alternative for the chemical industry.

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Area of Science:

Green Chemistry and Sustainable Catalysis
Organic Synthesis and Reaction Mechanisms
Electrocatalysis and Energy Conversion

Background:

Traditional hydrogenation relies on molecular hydrogen (H2) gas, often requiring high temperatures and pressures, posing operational challenges.
Alternative hydrogen sources like inorganic hydrides and organic acids are frequently too expensive for large-scale industrial applications.
The chemical industry seeks safer, more cost-effective, and environmentally friendly hydrogenation methods.

Purpose of the Study:

To explore the potential of using water as a sustainable hydrogen source for organic hydrogenation reactions.
To introduce and discuss electrocatalytic systems, particularly heterogeneous electrocatalysts, that enable water-based hydrogenation.
To highlight the advantages of water as a hydrogen source over conventional methods in terms of safety, cost, and sustainability.

Main Methods:

Review and discussion of conventional hydrogen sources (H2, hydrides, organic acids) and their limitations.
Introduction of electrocatalytic systems utilizing water as the sole hydrogen source.
Focus on heterogeneous electrocatalysts for efficient water-based hydrogenation.

Main Results:

Demonstration of successful organic hydrogenation transformations using water as the hydrogen source.
Electrocatalytic systems operating under ambient conditions with electricity as the driving force were presented.
Highlighting the feasibility of achieving hydrogenation with water, overcoming drawbacks of traditional methods.

Conclusions:

Transitioning to water as a hydrogen source for organic hydrogenation is a significant step towards sustainable chemistry.
Electrocatalytic hydrogenation using water offers a safer, greener, and potentially more economical alternative.
Optimization of these systems can reduce industry reliance on hazardous and expensive hydrogen sources, promoting eco-friendly processes.