🌸 Quick Gist: Benzene, the popular aromatic compound, prefers substitution over addition reactions due to its stable aromatic ring. One of its many reactions is nitration, where our star nitronium ion (NO2+) plays a key role!

🌟 Fun Fact: Think of benzene like the well-defended castle from medieval times. Its walls (the aromatic ring) are sturdy and resist invaders, but sometimes, it’s willing to make trades at the gate (substitution)!

• Mixing nitric acid (HNO3) with sulfuric acid (H₂SO₄) at 50°C leads to
  • HNO₃ + H₂SO₄ ⇌ H₂NO₃+ + HSO₄−
  • H₂NO₃+ ⇌ NO₂+ + H₂O
• The more nitronium ions, the faster the nitration!

🍎 Real-World Application: Imagine nitronium ions as apples at a store. On their own, there aren’t many apples (NO₂+ ions). But when you mix apple trees (nitric and sulfuric acids), you get tons of apples!

• Nitronium ion gets cozy with the benzene ring, thanks to the ring's electron-rich environment.
• Benzene donates two electrons to the nitronium ion, forming a new C-N bond.
  • This step breaks benzene's aromaticity, signified by a dashed circle.
  • It’s a big step, so it determines the speed of the whole reaction.
• Water, being a good Samaritan, donates a proton, bringing back benzene's aromaticity.
  • Result? Nitrobenzene!

🍿 Real-World Example: Imagine benzene as a popcorn kernel. The nitronium ion is heat. Initially, when the popcorn pops (benzene loses aromaticity), it's a big deal! But eventually, it settles down to become a tasty popcorn (nitrobenzene) with the help of butter (water)!

• Start the curly arrow from the benzene's electron-rich ring and end at the electrophile's positive charge.
• Draw the carbocation with a dashed circle and a + charge.
• Draw another curly arrow from the C-H bond to the benzene ring cation.
• Water's lone electron pair should direct towards the outgoing hydrogen ion.
• Finish with the substituted benzene and the departing hydrogen or hydronium ion.