Solution Found!
Nucleophilic aromatic substitution provides one of the
Chapter 11, Problem 24P(choose chapter or problem)
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.