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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...

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.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

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...

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:

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Related Experiment Video

Updated: Nov 5, 2025

Visualizing Methane-Cycling Microbial Dynamics in Coastal Wetlands

Visualizing Methane-Cycling Microbial Dynamics in Coastal Wetlands

Published on: January 31, 2025

Methane Oxidation to Methanol in Water.

Simon J Freakley¹, Nikolaos Dimitratos², David J Willock³

¹Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.

Accounts of Chemical Research

|May 19, 2021

Summary

Researchers developed novel catalysts for selective methane oxidation to methanol, a crucial step for fuel production. New colloidal AuPd nanoparticles show high efficiency using molecular oxygen, overcoming previous limitations.

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Methane Hydrate Crystallization on Sessile Water Droplets

Methane Hydrate Crystallization on Sessile Water Droplets

Published on: May 26, 2021

Area of Science:

Catalytic Chemistry
Green Chemistry
Materials Science

Background:

Methane is an abundant carbon source, but its transportation and flaring are costly.
Selective oxidation of methane to methanol is challenging due to high energy barriers and overoxidation.
Current methods like steam reforming are energy-intensive.

Purpose of the Study:

To develop low-temperature selective oxidation of methane to methanol using molecular oxygen.
To create efficient and selective catalysts for methane conversion.
To gain insights into biomimetic catalytic processes.

Main Methods:

Development of Fe-Cu-ZSM-5 materials for methane oxidation using H2O2.
Investigation of colloidal AuPd nanoparticles for methane oxidation using O2.
Optimization to minimize H2O2 decomposition and maximize methanol yield.

Main Results:

Fe-Cu-ZSM-5 catalysts demonstrated high activity and selectivity for methane to methanol at 50 °C.
Colloidal AuPd nanoparticles significantly improved methanol production efficiency (4 orders of magnitude).
Achieved 91% selectivity for molecular oxygen incorporation into methanol.

Conclusions:

Novel catalytic approaches offer efficient pathways for selective methane oxidation to methanol.
Colloidal AuPd nanoparticles represent a promising catalyst for utilizing molecular oxygen.
These findings provide valuable insights for future methane conversion strategies.