The mechanism for the formation of phenol from bromobenzene and sodium hydroxide is to be drawn. It is to be explained what percentage of the product contains the deuterium atom when the deuterium-labeled bromobenzene undergoes the same reaction. Concept introduction: In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. These reactions proceed by a nucleophilic addition-elimination mechanism or by an elimination-nucleophilic addition mechanism. A halobenzene can undergo nucleophilic substitution reaction via an elimination-nucleophilic addition mechanism under basic condition. These reactions proceed through benzyne intermediate formation. Since the benzyne intermediate is highly unstable, it undergoes a nucleophilic addition reaction with a nucleophile. Therefore, such reactions require extreme conditions like high temperature, a very strong base, or sometimes both. Deuterium (D) is an isotope of hydrogen, so the chemical properties of deuterium are similar to hydrogen.

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Chapter 23, Problem 23.26P

Interpretation Introduction

Interpretation:

The mechanism for the formation of phenol from bromobenzene and sodium hydroxide is to be drawn. It is to be explained what percentage of the product contains the deuterium atom when the deuterium-labeled bromobenzene undergoes the same reaction.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. These reactions proceed by a nucleophilic addition-elimination mechanism or by an elimination-nucleophilic addition mechanism. A halobenzene can undergo nucleophilic substitution reaction via an elimination-nucleophilic addition mechanism under basic condition. These reactions proceed through benzyne intermediate formation. Since the benzyne intermediate is highly unstable, it undergoes a nucleophilic addition reaction with a nucleophile. Therefore, such reactions require extreme conditions like high temperature, a very strong base, or sometimes both. Deuterium (D) is an isotope of hydrogen, so the chemical properties of deuterium are similar to hydrogen.

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