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Arndt−Ester synthesis

Arndt-Ester synthesis

This method is used to convert lower carboxylic acid into higher carboxylic acid.

RCO2H →  RCOCl  Arndt−Ester synthesis RCONH2 Arndt−Ester synthesis  RCH2CO2H

Arndt-Ester synthesis Mechanism

Nucleophilic attack of diazomethane on the carbonyl carbon of the acid chloride gives an intermediate (i) which eliminates a molecule of HCl to give diazoketone (ii) Diazoketone then splits off a molecule of nitrogen to form a carbene (iii) which rearranges to ketene. The highly reative ketene readily reacts with the nuclephile present (H2O) to form the next higher acid.

Arndt−Ester synthesis
Arndt−Ester synthesis

For more detail about the example and questions of Arndt ester synthesis read the complite theory of carboxylic acid chapter 

Examples of Arndt−Ester synthesis 

Arndt−Ester synthesis

List of Name Reaction of Organic Chemistry consist of detail Reaction Mechanism of all name reactions of organic chemistry.

 

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