The reaction of cyclopentadiene with sodium metal rapidly evolves hydrogen gas and generates a highly stable carbanion intermediate. Exactly how many delocalized -electrons are present in the aromatic

Question

The reaction of cyclopentadiene with sodium metal rapidly evolves hydrogen gas and generates a highly stable carbanion intermediate. Exactly how many delocalized $\pi$ -electrons are present in the aromatic ring of this resulting cyclopentadienyl anion?

Prashant Kotian · Accepted Answer

Correct answer: 6. Cyclopentadiene loses a proton to form the cyclopentadienyl anion. The ring possesses two double bonds (4 -electrons) and one carbanionic carbon which donates its lone pair (2 electrons) into the parallel p-orbital network, creating an aromatic sextet of exactly 6 -electrons.

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