Question

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

Short answer

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

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.

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.