I’m trying to understand why nitration of nitrobenzene is so much slower than that of benzene. I know the nitro group is a strong electron-withdrawing group, so it deactivates the aromatic ring. But then how does electrophilic substitution still happen?
Also, if nitro pulls electrons away through both inductive and resonance effects, wouldn’t that make the carbocation intermediate even more unstable? Then how does it still direct incoming electrophiles to the meta position?
I’ve seen the resonance structures but they’re not clicking. Why is the meta product more stable when the nitro group seems to destabilize the ring overall?
If anyone can explain this in terms of resonance and electron density without jumping too quickly to memorized rules, I’d really appreciate it.