In the nitration of toluene, besides the major para product, which other nitro product is formed in smaller amounts?

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Multiple Choice

In the nitration of toluene, besides the major para product, which other nitro product is formed in smaller amounts?

Methyl on toluene activates the ring for electrophilic substitution and directs new substituents to the ortho and para positions. In nitration, the nitronium ion adds mainly at the para position because it gives a resonance-stabilized intermediate with less steric clash, making para-nitrotoluene the major product. A smaller amount forms at the ortho position since that site is also activated by the methyl group, though steric hindrance slightly lowers its yield. The meta position is not favored by a methyl director, so meta-nitrotoluene is not produced in significant amounts. Therefore, the nitro product formed in smaller amounts is ortho-nitrotoluene.

Methyl on toluene activates the ring for electrophilic substitution and directs new substituents to the ortho and para positions. In nitration, the nitronium ion adds mainly at the para position because it gives a resonance-stabilized intermediate with less steric clash, making para-nitrotoluene the major product. A smaller amount forms at the ortho position since that site is also activated by the methyl group, though steric hindrance slightly lowers its yield. The meta position is not favored by a methyl director, so meta-nitrotoluene is not produced in significant amounts. Therefore, the nitro product formed in smaller amounts is ortho-nitrotoluene.

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