Which of the following two-step reaction sequences will yield 2-chloro-4-nitroanisole as the major product starting from anisole?

Step-by-step solution

To synthesize 2-chloro-4-nitroanisole as the major product, we must consider the directing effects of the intermediate formed after the first step. If chlorination is performed first: Anisole reacts with Cl ₂ / FeCl ₃ to give 4-chloroanisole as the major product (due to less steric hindrance at the para position). Subsequent nitration of 4-chloroanisole is controlled by the strongly activating - OCH ₃ group, which directs the incoming NO ₂^+ to its ortho position, yielding 4-chloro-2-nitroanisole. This is not the d