Discussion
What is the major product of the following reaction?
[benzene ring with CH3, and OH para to it] + Br2 \(\xrightarrow{\mathrm{FeBr_{3}}}\) ?
Answer: C
The major product is the ring with OH, Br ortho to OH and CH3 para to OH (2-bromo-4-methylphenol).
The reactant is p-cresol (4-methylphenol). Both OH and CH3 are ortho/para directors, but OH is by far the stronger activator. Its para position is already taken by CH3, so bromine enters ortho to OH.
The other structures do not fit: bromination of the ring with FeBr3 does not attack the O-H bond (OBr) or the methyl group (CH2Br, which needs light and a radical route); the product cannot lose its CH3 group; and replacing OH with Br is not an electrophilic substitution.
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