Monobromination of an isomer of cresol (methylphenol) in CS ₂ yields a major product in which the newly introduced bromine atom is situated at a meta position with respect to the methyl group. Which isomer(s) of cresol exhibit this behavior?

Step-by-step solution

To determine which isomer(s) of cresol yield a product where the incoming bromine is meta to the methyl group, we evaluate the directing effects in each isomer. The - OH group is a much stronger activating group than the - CH ₃ group, so - OH dictates the position of electrophilic attack. For o -cresol (2-methylphenol): The - OH group is at position 1 and - CH ₃ is at position 2. Bromination occurs primarily at the para position with respect to - OH (position 4) due to less steric hindrance. Position 4 is meta to t