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The base-catalyzed reaction of an aldehyde (having no

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 58P Chapter 22

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 58P

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-by-Step Solution:
Step 1 of 3

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)

Step-2

Example:

Mechanism:-

The 1st involves formation of the  nucleophile (-CH2-CO-OCOCH3) from acetic anhydride.

(Acetic...

Step 2 of 3

Chapter 22, Problem 58P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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.

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