Which of the following monoalkylbenzenes undergo nitration in HNO₃/H₂SO₄ to yield a product mixture with the highest ratio?

Question

Quizplus · Accepted Answer

Toluene is the most reactive towards nitration because it has a methyl group (-CH3) which is electron-donating and increases the electron density on the ring, making it more susceptible to attack by nitronium ion (NO2+). Ethylbenzene and propylbenzene have larger alkyl groups which are less electron-donating than the methyl group in toluene, making them less reactive towards nitration. Isopropylbenzene and tert-butylbenzene have bulky substituents which hinder the approach of nitronium ion to the ring, making them even less reactive towards nitration. Therefore, toluene undergoes nitration to yield a product mixture with the highest meta/para ratio.

Which of the Following Monoalkylbenzenes Undergo Nitration in HNO3/H2SO4 to Yield

Which of the Following Monoalkylbenzenes Undergo Nitration in HNO₃/H₂SO₄ to Yield