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Oxidation of Alcohols

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
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Radical Autoxidation

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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.

Oxidation and Reduction of Organic Molecules

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

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Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

Radical Oxidation of Allylic and Benzylic Alcohols

Radical Oxidation of Allylic and Benzylic Alcohols

Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...

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Updated: Jul 2, 2026

Preparation of Biomass-based Mesoporous Carbon with Higher Nitrogen-/Oxygen-chelating Adsorption for Cu(II) Through Microwave Pre-Pyrolysis

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Oxidation using activated carbon and molecular oxygen system.

Masahiko Hayashi¹

¹Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe 657-8501, Japan. mhayashi@kobe-u.ac.jp

Chemical Record (New York, N.Y.)

|August 30, 2008

Summary

This study introduces an activated carbon-molecular oxygen system for efficient oxidation and carbonylation of benzylic alcohols. This method also facilitates the synthesis of diverse heteroaromatic and aromatic compounds via oxidative aromatization.

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Area of Science:

Organic Chemistry
Catalysis
Green Chemistry

Background:

Benzylic and allylic alcohols are important synthetic intermediates.
Efficient oxidation and carbonylation methods are crucial in organic synthesis.
Developing sustainable catalytic systems is a key goal in modern chemistry.

Purpose of the Study:

To explore the utility of an activated carbon-molecular oxygen system.
To achieve direct oxidation and carbonylation at the benzylic position.
To synthesize a variety of heteroaromatic and aromatic compounds.

Main Methods:

Utilizing an activated carbon supported catalyst.
Employing molecular oxygen as the oxidant.
Performing reactions under optimized conditions for oxidation, carbonylation, and oxidative aromatization.

Main Results:

The activated carbon-molecular oxygen system effectively oxidizes benzylic and allylic alcohols.
Direct carbonylation at the benzylic position is achieved.
A diverse range of heteroaromatic and aromatic compounds were synthesized, including pyridines, pyrazoles, benzoxazoles, benzimidazoles, benzothiazoles, imidazoles, indoles, pyrimidinones, and anthracenes.

Conclusions:

The activated carbon-molecular oxygen system is a versatile and effective tool for benzylic functionalization.
This catalytic system offers a green and efficient approach for synthesizing complex aromatic and heteroaromatic structures.
The method holds promise for broader applications in organic synthesis and materials science.