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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

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.

Oxidation of Alcohols

Oxidation of Alcohols

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.
The process of oxidation in a chemical reaction is observed in any of the three forms:

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps. ...

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Related Experiment Video

Updated: Jun 26, 2025

Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts

Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts

Published on: February 7, 2017

Eugenol Hydrodeoxygenation Over Mixed Mo-W Carbides.

Dahi Akmach^1,2, Chi-Cong Tran¹, Tatjana Stevanovic³

¹Department of Chemical Engineering, Laval University, Québec, Québec, G1V 0A6, Canada.

|May 10, 2024

Summary

Adding tungsten (W) to molybdenum carbide (Mo2C) catalysts enhances lignin derivative hydrodeoxygenation. This modification improves selectivity for non-oxygenated aromatics by controlling ring hydrogenation and facilitating deoxygenation.

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Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts

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Reverse Microemulsion-mediated Synthesis of Monometallic and Bimetallic Early Transition Metal Carbide and Nitride Nanoparticles

Reverse Microemulsion-mediated Synthesis of Monometallic and Bimetallic Early Transition Metal Carbide and Nitride Nanoparticles

Published on: November 27, 2015

Area of Science:

Catalysis
Materials Science
Chemical Engineering

Background:

Transition metal modification of molybdenum carbide (Mo2C) catalysts is crucial for improving hydrodeoxygenation (HDO) of lignin derivatives.
Cobalt (Co) and Nickel (Ni) are commonly used for hydrogenation, but tungsten (W) offers unique selectivity benefits.

Purpose of the Study:

To investigate the effect of tungsten (W) addition to molybdenum carbide (Mo2C) catalysts on the hydrodeoxygenation of lignin derivatives.
To understand how mixed metal carbides influence catalyst performance and selectivity.

Main Methods:

Catalyst synthesis involving the modification of Mo2C with W.
Testing catalyst performance in the hydrodeoxygenation of eugenol, a lignin derivative.
Analysis of reaction products to determine selectivity and conversion.

Main Results:

Tungsten addition to Mo2C restricted ring hydrogenation while promoting deoxygenation of oxygenated compounds.
The coexistence of Mo2C, W2C, and metallic W altered Mo2C's electronic properties, increasing active site density.
Achieved up to 83% propyl-benzene selectivity at near 100% eugenol conversion.

Conclusions:

Mixed metal carbide phases significantly impact catalyst performance in HDO.
Tungsten-modified Mo2C catalysts show promise for selective production of non-oxygenated aromatic compounds from lignin.
Findings provide insights for optimizing catalyst design for lignin depolymerization product processing.