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Chapter 18: Q32P (page 904)

What product is formed from the reaction of p-methylphenol with benzenediazonium chloride?

Short Answer

Expert verified

The electrophile arene diazonium chloride is large such that the substitution happens at the less sterically hindered position, that is, the para position. If a substituent is already present in the para position, the substitution will happen at the ortho position.

Step by step solution

01

Reaction with arene diazonium chloride

The electrophile arene diazonium chloride is large such that the substitution happens at the less sterically hindered position, that is, the para position. If a substituent is already present in the para position, the substitution will happen at the ortho position.

02

Reaction of p-methylphenol with benzene diazonium chloride

Both the hydroxyl and methyl groups in the above structure are ortho-para directing. Out of the methyl and hydroxyl groups, the hydroxyl group is dominant. As a result, the ortho product is formed as the methyl group occupies the para position of the hydroxyl group.

The product of the reaction is as follows.

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Most popular questions from this chapter

How many electrophilic aromatic substitution products are obtained from chlorination of

  1. o-xylene?
  2. p-xylene?
  3. m-xylene?

a. Ketoprofen, like ibuprofen, is an anti-inflammatory analgesic. How can ketoprofen be synthesised from the given starting material?

Ketoprofen

b. ketoprofen and ibuprofen both have a propanoic acid substituent. Explain why the identical subunits are synthesised in different ways.

Show how the following compounds can be synthesized from benzene:

a. N,N,N-trimethylanilinium iodide

b. 2-methyl-4-nitrophenol

c. p-benzylchlorobenzene

d. benzyl methyl ether

e. p-nitroaniline

f. m-bromoiodobenzene

g. p-dideuteriobenzene

h. p-nitro-N-methylaniline

i. 1-bromo-3-nitrobenzene

Propose a mechanism for each of the following reactions:

a.

b.

Using resonance contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.
See all solutions

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