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Multiple Choice

The product of benzoic acid nitration is:

Electrophilic aromatic substitution on benzoic acid is governed by directing effects of substituents. The carboxyl group on benzoic acid pulls electron density away from the ring through both inductive and resonance effects, making it a strong meta-director. When the nitronium electrophile attacks, the most stabilized arenium ion intermediate forms if substitution occurs at the meta position relative to the carboxyl group. This leads to the major product being meta-nitrobenzoic acid (3-nitrobenzoic acid). The ortho and para positions are less favorable because the intermediate is less stabilized (and ortho also suffers steric hindrance from the carboxyl group). So, under standard nitration conditions, the predominant product is meta-nitrobenzoic acid, with para not being the major outcome.

Electrophilic aromatic substitution on benzoic acid is governed by directing effects of substituents. The carboxyl group on benzoic acid pulls electron density away from the ring through both inductive and resonance effects, making it a strong meta-director. When the nitronium electrophile attacks, the most stabilized arenium ion intermediate forms if substitution occurs at the meta position relative to the carboxyl group. This leads to the major product being meta-nitrobenzoic acid (3-nitrobenzoic acid). The ortho and para positions are less favorable because the intermediate is less stabilized (and ortho also suffers steric hindrance from the carboxyl group). So, under standard nitration conditions, the predominant product is meta-nitrobenzoic acid, with para not being the major outcome.