What electrophile is generated during the nitration of benzene using a mixture of concentrated nitric acid and concentrated sulfuric acid?
Answer and explanation
Correct answer: C. Nitronium ion (NO2+)
- Step 1: H2SO4 acts as a Brønsted acid, protonating HNO3: HNO3 + 2 H2SO4 <=> H2O+-NO2 + 2 HSO4-. Step 2. Loss of water generates the strongly electrophilic nitronium ion (NO2+). Step 3. NO2+ attacks the electron-rich aromatic pi system. Answer: Nitronium ion (NO2+). Why not the others: NO+ is involved in diazotization of amines, not nitration; NO2- is a nucleophile.
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