How many resonance structures does aniline have after the first step of electrophilic aromatic substitution?

Electrophilic aromatic substitution involves a process in an atom that is attached to an aromatic system is replaced by a electrophile. Electrophile is an electron pair acceptor. In the first step of electrophilic aromatic substitution of aniline, aniline has 3 resonance structures.

Explanation:

Aniline undergo a two step electrophilic aromatic substitution. The first step yields both ortho and para groups while the last yield a meta group.

In the first step, the amino group of aniline are strong activating group and ortho/para directing by resonance. This amino groups donates their unshared electrons to the pi-system creating a negative charge on the ortho and para positions. These positions are most reactive towards an electron-poor electrophile.

In the second step, the electrophilic aromatic substitution on aniline proceeds quite slowly to give an unexpected high yield of meta product.

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