Question

Explain why cyclopentadiene (pKa 16) is many orders of magnitude more acidic than cyclopentane (pKa > 50). (Hint: Draw the structural formula for the anion formed by removing one of the protons on the −CH2− group, and then apply the Hückel criteria for aromaticity.)

Explain why cyclopentadiene (PK, 16) is many orders of magnitude more acidic than cyclopentane (pka > 50). (Hint: Draw the structural formula for the anion formed by removing one of the protons on the -CH2- group, and then apply the Hückel criteria for aromaticity.) Cyclopentadiene Cyclopentane Cyclopentadiene is much more acidic than cyclopentane because the conjugate base of cyclopentadiene, the cyclopentadienyl anion, is not aromatic and thus less stable than the aromatic conjugate base of cyclopentane. O the conjugate base of cyclopentadiene, the cyclopentadienyl anion, is not aromatic and thus more stable than the aromatic conjugate base of cyclopentane. the conjugate base of cyclopentadiene, the cyclopentadienyl anion, is aromatic and thus more stable than the conjugate base of cyclopentane. the conjugate base of cyclopentadiene, the cyclopentadienyl anion, is aromatic and thus less stable than the conjugate base of cyclopentane.

Answer 1

Non Avomahe AYoma ic Cun +e) Nom- ATomaie nan Anfonna H c The coyugate bade ot ayelopenta diene, he Cyclo pen tadienyl anin, is avomalie and thus mare shable than the conjugate bade o ycbpantane