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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

What is the major product(s) of each of the following reactions?

a. bromination of p-methylbenzoic acid

b. chlorination of o-benzenedicarboxylic acid

c. bromination of p-chlorobenzoic acid

d. nitration of p-fluoroanisole

e. nitration of p-methoxybenzaldehyde

f. nitration ofp-tert-butylmethylbenzene

List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:

a. benzene, phenol, toluene, nitrobenzene, bromobenzene

b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene

Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.

Draw the product(s) of each of the following reactions:

  1. benzoic acid + HNO3/H2SO4
  2. isopropylbenzene + Cl2 + FeCl3
  3. p-xylene + acetyl chloride + AlCl3 followed by H2O
  4. o-methylaniline + benzenediazonium chloride
  5. cyclohexyl phenyl ether + Br2
  6. phenol + H2SO4 + 螖
  7. ethylbenzene + Br2/FeBr3
  8. m-xylene + Na2Cr2O7 + HCl + 螖

Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.
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