Organic Chemistry 2 · Substituent effects and directing
Classify a nitro group
Conditions: Electrophilic aromatic substitution (e.g. nitration or bromination) of the monosubstituted benzene shown.
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The question
How does the nitro (–NO2) group on the benzene ring shown affect electrophilic aromatic substitution?
Reveal the answer and explanation
Answer and explanation
Not this one Activating, ortho/para director
The nitro nitrogen has no lone pair to donate; it carries a positive formal charge and withdraws electrons.
Not this one Weakly deactivating, ortho/para director
Halogens are weak deactivators that direct ortho/para; nitro is a strong deactivator with no donor lone pair.
Correct answer Deactivating, meta director
Correct: the nitro group withdraws electrons by induction and resonance, slowing EAS strongly; ortho/para attack would put positive charge next to the N⁺, so meta wins.
Not this one Activating, meta director
No group both speeds EAS and directs meta.
Worked solution
Nitrobenzene nitrates about 10⁷ times more slowly than benzene and gives mainly the meta product, because the ortho and para σ-complexes place a positive charge on the carbon bonded to the positively charged nitrogen.
What you'll practice
Classify the nitro (–NO2) substituent by its effect on EAS rate and orientation.
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