Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 22, Problem 22.52P
Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In a Friedel-Crafts acylation reaction, an aromatic carbon atom forms a bond to an acyl carbon. In intramolecular FC acylation reactions, the electrophile and the nucleophile are present within the same molecule and usually result in the formation of a five or six-membered ring. The carbonyl carbon of the aldehyde is electrophilic while the benzene ring serves as the nucleophile. The concentration of the positive charge on the carbonyl carbon atom in the aldehyde is increased by the use of a strong acid such as HBr. Being a strong acid, it will protonate the oxygen atom of the carbonyl group. This will activate the carbonyl carbon towards the nucleophilic attack. This forms a six-membered ring. The role of heating the product of this reaction with acetic acid is to promote the elimination reaction that results in the formation of a carbon-carbon double bond.

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Chapter 22 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

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