Pyridine is highly deactivated towards electrophilic aromatic substitution. When forced to react und — Aromatic Hydrocarbons Chemistry Question
Question
Pyridine is highly deactivated towards electrophilic aromatic substitution. When forced to react under extreme conditions, the electrophile predominantly attacks the C-3 position. Why?
Answer: A
💡 Solution & Explanation
In pyridine, attack at C-2 or C-4 places a positive charge directly on the highly electronegative nitrogen with only a sextet of electrons. C-3 attack entirely avoids this catastrophically unstable resonance contributor.
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