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.)
Step 1 of 3
Here we have to propose a mechanism for the given perkin condensation reaction.
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)
The 1st involves formation of the nucleophile (-CH2-CO-OCOCH3) from acetic anhydride.
Textbook: Organic Chemistry
Author: L.G. Wade Jr
The full step-by-step solution to problem: 58P from chapter: 22 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. The answer to “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.)” is broken down into a number of easy to follow steps, and 34 words. Since the solution to 58P from 22 chapter was answered, more than 263 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: base, perkin, condensation, having, called. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by and is associated to the ISBN: 9780321768414.