Molecular Orbitals Q3

Heterocyclic amines are a very important type of amino group. One use of them includes being the base of DNA. The most important property however is their basicity due to nitrogen.
Pyrrole undergoes electrophilic substitution at position 2 because:

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Reveal Answer »

A.

Attack at position 2 gives three resonance structures greatly adding to stability of the molecule (positive charge on nitrogen, then position 3, and then position 5). Position 3 only has two resonance structures.

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