Electrophilic substitution of pyrrole, furan and thiophene

In pyrrole, the lone pair of electrons on nitrogen is part of the aromatic (six Jl-electron) ring system. The incorporation of a lone pair of electrons activates the ring, and electrophilic substitution is faster than that for 

As the lone pair is part of the aromatic sextet it is less nucleophilic/basic than aliphatic amines 

Furan is more reactive to electrophiles than benzene and hence FeBr3 is not required 

In pyrrole (C4H4NH), the lone pair of electrons on nitrogen is part of the aromatic (six Jt-electron) ring system. The incorporation of a lone pair of electrons activates the ring, and electrophilic substitution is faster than that for benzene. Substitution occurs principally at the 2-position, as attack at the 3-position produces a less stable cation intermediate (i.e. with two, rather than three, resonance structures). 

Pyrrole is much less basic than pyridine (Section 1.7.5). 

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