Welcome to ChemZipper !!!: Although both in benzylic carbanion and cyclopentadienyl anion 6 electrons are spread, but benzylic carbanion is more stable. Why?

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Although both in benzylic carbanion and cyclopentadienyl anion 6 electrons are spread, but benzylic carbanion is more stable. Why?

The answer of this question lies in the fact that in benzylic carbanions 6 electrons  are delocalized  over six carbon atoms while in cyclopentadienyl anion 6 electrons are delocalized over 5 carbon atoms , so the dispersal is more in former. We know that greater the dispersal, more is the stability, hence Benzylic carbanion is more stable than cyclopentadienyl anion.

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