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Nucleophilic aromatic substitution provides one of the

Chapter 11, Problem 24P

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QUESTION:

Problem 24P

Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussed in Section 19-17.) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.

(a) p-nitrophenol

(b) 2,4,6-tribromophenol

(c) p-chlorophenol

(d) m-cresol

(e) p-n-butylphenol

Questions & Answers

QUESTION:

Problem 24P

Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussed in Section 19-17.) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.

(a) p-nitrophenol

(b) 2,4,6-tribromophenol

(c) p-chlorophenol

(d) m-cresol

(e) p-n-butylphenol

ANSWER:

Solution:

Here we will have to show the synthesis of following phenols

Step 1

(a) Synthesis of  p-nitrophenol

The synthesis of p-nitrophenol involves an addition elimination mechanism. In this reaction benzene on reaction with chlorine in presence of AlCl3 gives chlorobenzene , which on nitration (in presence of HNO3 + H2SO4) forms 4-nitrochlorobenzene ,it is on heating in presence of NaOH gives  p-nitrophenol.

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