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Chapter 18: Q 59. (page 724)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The mechanism for the given reaction is following:

Step by step solution

01

Nucleophilic aromatic substitution reaction

The aromatic nucleophilic substitution reaction takes place by the elimination-addition mechanism. In this mechanism, the substitution can take place on the carbon attached to the leaving group as well as the adjacent carbon atom.

This results in the formation of two possible products because of the formation of the benzyne intermediate.

02

The stepwise mechanism for the given reaction

The given reaction proceeds by the abstraction of a proton by the base in the first step and results in the formation of the benzyne intermediate as shown below:

In the next step, the intramolecular ring closure takes place and results in the formation of the following product:

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Most popular questions from this chapter


Question: Draw a stepwise, detailed mechanism for the following intramolecular reaction.

Label each compound as more or less reactive than benzene in electrophilic aromatic substitution.

The 1 H NMR spectrum of phenol (\({C_6}{H_5}OH\)) shows three absorptions in the aromatic region: 6.70 (2 ortho H’s), 7.14 (2 meta H’s), and 6.80 (1 para H) ppm. Explain why the ortho and para absorptions occur at lower chemical shift than the meta absorption.

Which halides are unreactive in a Friedel–Crafts alkylation reaction?

Question: Draw a stepwise mechanism for the following reaction.
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