When an electrophile attacks aniline at the ortho position, how many reasonable resonance structures — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

In standard ortho/para attack on a substituted benzene, 3 resonance structures distribute the positive charge around the ring carbons. For aniline, the lone pair on the nitrogen can form an extra $\pi$ -bond with the adjacent positively charged ring carbon, yielding a 4th, highly stable resonance structure where every atom (except hydrogen) has a complete octet.