Problem

Nucleophilic aromatic substitution provides one of the common methods for making phenols...

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

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