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The base-catalyzed reaction of an aldehyde (having no

Chapter 16, Problem 58P

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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.)

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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)

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