Nitration of toluene typically yields which major product?

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Multiple Choice

Nitration of toluene typically yields which major product?

Nitration on toluene proceeds via electrophilic aromatic substitution. The methyl substituent donates electron density and directs the electrophile to the ortho and para positions. Between these, the para position is less sterically hindered, so the arenium ion intermediate formed there is more stable and the reaction flows toward para-nitrotoluene as the major product. The ortho product does form but in smaller amounts due to steric hindrance near the methyl group. Metaposition is not favored because the methyl group is an ortho-para director, not a meta director. So the major product is para-nitrotoluene.

Nitration on toluene proceeds via electrophilic aromatic substitution. The methyl substituent donates electron density and directs the electrophile to the ortho and para positions. Between these, the para position is less sterically hindered, so the arenium ion intermediate formed there is more stable and the reaction flows toward para-nitrotoluene as the major product. The ortho product does form but in smaller amounts due to steric hindrance near the methyl group. Metaposition is not favored because the methyl group is an ortho-para director, not a meta director. So the major product is para-nitrotoluene.

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