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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

5.6K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Electrolysis03:00

Electrolysis

27.3K
In a galvanic cell, the electrical work is done by a redox system on its surroundings as electrons produced by the spontaneous redox reactions are transferred through an external circuit. Alternatively, an external circuit does work on a redox system by imposing a voltage sufficient to drive an otherwise nonspontaneous reaction in a process known as electrolysis. For instance, recharging a battery involves the use of an external power source to drive the spontaneous (discharge) cell reaction in...
27.3K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

3.4K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
3.4K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

11.1K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
11.1K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.1K
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.
6.1K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

3.0K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.0K

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Related Experiment Video

Updated: Sep 9, 2025

Synthesis of Platinum-nickel Nanowires and Optimization for Oxygen Reduction Performance
09:02

Synthesis of Platinum-nickel Nanowires and Optimization for Oxygen Reduction Performance

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Oxy-reductive C-N bond formation via pulsed electrolysis.

Yuxuan Zhang1, Hasan Al-Mahayni2, Pedro M Aguiar1

  • 1Department of Chemistry, Université de Montréal, Montréal, QC, Canada.

Nature Communications
|August 29, 2025
PubMed
Summary

Oxy-reductive pulsed electrocatalysis enhances C-N bond formation by enabling simultaneous partial reduction and oxidation of reactants. This novel method boosts selectivity and rates for products like urea and methylamine, outperforming static electrolysis.

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Area of Science:

  • Electrochemistry
  • Sustainable Chemistry
  • Catalysis

Background:

  • Co-electrolysis of carbon dioxide (CO2) with nitrogen species offers a sustainable pathway to C-N bond products.
  • A key challenge is promoting C-N coupling over CO2 reduction, especially with solution-based reactants like ammonia (NH3).

Purpose of the Study:

  • To introduce and validate oxy-reductive pulsed electrocatalysis for efficient C-N bond formation.
  • To overcome limitations of static electrolysis in co-electrolysis reactions.

Main Methods:

  • Developed an oxy-reductive pulsed electrocatalysis technique.
  • Utilized CO2 and NH3 as model reactants on a heterogeneous catalyst.
  • Employed operando measurements to investigate reaction mechanisms.

Main Results:

  • Achieved 3-20 fold enhancement in selectivity and formation rates for C-N products (urea, formamide, acetamide, methylamine).
  • Demonstrated parallel partial reduction and oxidation of separate reactants on the same catalyst.
  • Successfully extended the strategy to other C/N reactants and C-S coupling.

Conclusions:

  • Oxy-reductive pulsed electrocatalysis is a powerful strategy for C-N and C-S bond formation.
  • This method enhances reaction efficiency by facilitating proximal co-adsorption of activated intermediates.
  • The approach holds promise for sustainable synthesis of valuable chemicals.