Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mil...

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

(a) Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion, .Be careful to draw all the resonance structures of the intermediate.

(b) Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than the 3-position.