Arndt Eistert Reaction- Mechanism and Salient Features — Chem Content
2 min readOct 24, 2021
In this reaction, the length of carbon chain in carboxylic acids is increased by insertion of a methylene (CH2) group.
This conversion includes the following steps:
Treatment of acid with thionyl chloride converts it into acid chloride which then reacts with diazomethane to form diazoketone.
In the next step, diazoketone on heating with Ag2O in aqueous medium evolves N2 and undergo rearrangement to ketene.
In the final step, hydrolysis of ketene gives an acid which is one higher analogue of the acid taken as substrate.
Mechanism:
Once the thionyl chloride has converted acid into acid chloride, diazomethane attacks as a nucleophile on it’s carbonyl carbon to form an intermediate(i).
Removal of HCl from that intermediate form………
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