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The base-catalyzed reaction of an aldehyde (having no
Chapter 16, Problem 58P(choose chapter or problem)
The base-catalyzed reaction of an aldehyde (having no hydrogens) with an anhydride is called the Perkin condensation. Propose a mechanism for the following example of the Perkin condensation. (Sodium acetate serves as the base.)
Questions & Answers
QUESTION:
The base-catalyzed reaction of an aldehyde (having no hydrogens) with an anhydride is called the Perkin condensation. Propose a mechanism for the following example of the Perkin condensation. (Sodium acetate serves as the base.)
ANSWER:
Solution:
Here we have to propose a mechanism for the given perkin condensation reaction.
Step 1
Perkin condensation reaction:-
The Perkin reaction is used to convert an aromatic aldehyde and an anhydride to an α,β-unsaturated carboxylic acid using sodium acetate, a base, and an acid. The regiochemistry of the reaction, the relative position of the carboxylic acid and aromatic ring in the final product, can be either E or Z. The mechanism goes through numerous steps including several additions and eliminations reaction.
(aromatic aldehyde) (anhydride) (,unsaturated carboxylic acid)