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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

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Loss of Carboxy Group as CO₂: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...

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

Nitrosation of Enols

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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Light-driven Enzymatic Decarboxylation

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Published on: May 22, 2016

Electrochemically driven desaturation of carbonyl compounds.

Samer Gnaim¹, Yusuke Takahira¹, Henrik R Wilke¹

¹Department of Chemistry, Scripps Research, La Jolla, CA, USA.

Nature Chemistry

|March 24, 2021

Summary

This study introduces a sustainable electrochemical method for carbonyl desaturation, using electrons as the primary reagent. This novel approach offers a scalable and versatile alternative to traditional metal-catalyzed or stoichiometric methods for organic oxidation.

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Published on: June 20, 2014

Area of Science:

Organic Chemistry
Electrochemistry
Sustainable Synthesis

Background:

Carbonyl desaturation is a key organic oxidation reaction.
Existing methods often rely on transition metals (Pd, Cu) or stoichiometric reagents (I, Br, Se, S).
These traditional methods can lack sustainability and efficiency.

Purpose of the Study:

To develop a novel, sustainable electrochemical method for carbonyl desaturation.
To provide an operationally simple and scalable alternative to existing techniques.
To demonstrate the broad applicability of the new method across various carbonyl derivatives.

Main Methods:

Utilizing electrons as the primary reagent for oxidation.
Employing enol silanes and phosphates as starting materials.
Electrochemical driving force for the desaturation reaction.

Main Results:

Achieved efficient carbonyl desaturation using electrochemistry.
Demonstrated a broad scope of reaction across diverse carbonyl compounds.
Successfully scaled the reaction from 1 to 100 grams.
Method can be predictably implemented using NMR shift data.

Conclusions:

The developed electrochemical desaturation is a sustainable and operationally simple pathway.
This method offers a unique and versatile alternative to state-of-the-art techniques.
Mechanistic studies suggest a radical-based reaction pathway.