Perkin Condensation: Mechanism and Applications

Table of Contents

Perkin Condensation, examples, mechanisms, and applications in organic chemistry have been discussed here:

Perkin Condensation Reaction Definition

Perkin condensation reaction is the condensation reaction of an aromatic aldehyde and an aliphatic acid anhydride containing at least two α-hydrogen atoms in the presence of a sodium or potassium salt of the corresponding acid to form, α, β-unsaturated acid. Generally, such type of reaction is only applicable to aromatic aldehyde, and should be noted that only the anhydride’s α-hydrogen atoms are involved in the condensation.

Some of the examples of perkin reactions are:

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Perkin Condensation Mechanism

The aldol condensation of an aromatic aldehyde and an acid anhydride produces an α, β-unsaturated aromatic acid in the Perkin reaction. Here, the base abstracts the α-hydrogen atom and leads to the formation of the carbanion intermediate. The carbanion now attacks carbonyl carbon i.e. aldehyde by nucleophilic addition leading to the formation of α, β-unsaturated acid.

The perkin condensation mechanism takes place by multiple steps as:

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Applications of Perkin Condensation

1. Conversion of Furfural into Furylacrylic acid (65-70% yield)

Furylacrylic acid, furfural, perkin condensation reaction

2. Formation of Coumaric acid from salicylaldehyde, which on dehydration yields Coumarin.

perkin condensation reaction mechanism, coumarin, coumaric acid

3. Synthesis of phytoestrogenic stilbene resveratrol

Perkin Condensation Video

FAQs/MCQs

What is perkin reaction?

Perkin reaction is a condensation reaction that involves the reaction of an aromatic aldehyde and an aliphatic acid anhydride containing at least two α-hydrogen atoms in the presence of a sodium or potassium salt of the corresponding acid to form, α, β-unsaturated acid.

References

  • Morrison, R. T., & Boyd, R. N., Organic chemistry, Allyn and Bacon, Inc. 1987.
  • March, J., Advanced Organic Chemistry, Wiley Eastern Limited, 1986.
  • Skyes, P., A Guide Book to Mechanism in Organic Chemistry, Second edition, Orient Longman Ltd., 1988.

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