In electrophilic nitration of anisole, which nitrated product is major?

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Multiple Choice

In electrophilic nitration of anisole, which nitrated product is major?

The methoxy group on anisole donates electron density to the ring by resonance, making the ring highly activated for electrophilic aromatic substitution and directing attack to the ortho and para positions. When the nitronium ion adds, the sigma complex is more stable at these activated positions, with the para position being less hindered than the ortho position. This combination of strong activation and lower steric hindrance makes the para substitution pathway the most favorable, so para-nitroanisole is the major product. The ortho product forms to a lesser extent because of steric interactions in the transition state, while meta substitution is not favored by the directing effect of the methoxy group.

The methoxy group on anisole donates electron density to the ring by resonance, making the ring highly activated for electrophilic aromatic substitution and directing attack to the ortho and para positions. When the nitronium ion adds, the sigma complex is more stable at these activated positions, with the para position being less hindered than the ortho position. This combination of strong activation and lower steric hindrance makes the para substitution pathway the most favorable, so para-nitroanisole is the major product. The ortho product forms to a lesser extent because of steric interactions in the transition state, while meta substitution is not favored by the directing effect of the methoxy group.

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