sp3 or sp2 pyrrole??

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cc609

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10+ Year Member
I know that pyrrole is aromatic and Chad's video explained how the Nitrogen on the pyrrole is NOT sp3 (thus it is aromatic along with other qualifications) but on the achiever a question asked
"Select only heterocyclic compounds where the unshared electron pair of nitrogen occupies an sp2 orbital in the plane of the ring" and pyrrole was not included, meaning it's not sp2..? I may be understanding the question wrong, is it not asking if it is sp2? If it's not sp3 or sp2 what is it then?
 
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The unshared electron pair on nitrogen of pyrrole is not in an SP hybridized orbital. The 3 sp2 orbitals are used in bonding for pyrrole (2 to carbons, one to hydrogen).

That's what makes pyrrole aromatic. It has 2 pi bonds and an electron pair (therefore 6 electrons, and according to the 4n+2 rule, is thus aromatic).
 
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