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Related Concept Videos

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

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...
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

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 Alcohols02:37

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:
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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.

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Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Biomimetic flavin-catalyzed aldehyde oxidation.

Alexander T Murray1, Pascal Matton, Nathan W G Fairhurst

  • 1Department of Chemistry, University of Bath , Bath BA2 7AY, United Kingdom, and GlaxoSmithKline , Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom.

Organic Letters
|July 13, 2012
PubMed
Summary
This summary is machine-generated.

A novel biomimetic flavin catalyst efficiently oxidizes aldehydes to carboxylic acids using hydrogen peroxide. This green chemistry approach avoids harsh solvents, offering a sustainable and simple synthetic method.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Aldehyde oxidation is crucial for synthesizing carboxylic acids.
  • Traditional methods often involve harsh reagents and solvents.
  • Developing sustainable oxidation protocols is an ongoing challenge.

Purpose of the Study:

  • To develop a green and efficient method for oxidizing aldehydes to carboxylic acids.
  • To utilize a biomimetic flavin catalyst for this transformation.
  • To employ hydrogen peroxide as a sustainable oxidant.

Main Methods:

  • Employing a biomimetic bridged flavin catalyst.
  • Utilizing 35% aqueous hydrogen peroxide as the oxidant.
  • Performing the oxidation reaction under simple operational conditions.

Main Results:

  • Successful oxidation of alkyl and aryl aldehydes to their corresponding carboxylic acids.
  • The reaction proceeds efficiently with minimal byproducts.
  • The protocol obviates the need for chlorinated solvents.

Conclusions:

  • The biomimetic flavin catalyst provides a green and sustainable route for aldehyde oxidation.
  • This method offers an operationally simple and environmentally friendly alternative.
  • The catalyst demonstrates potential for broader applications in sustainable synthesis.