Cyclopentadiene is much more acidic than cycl | vedclass

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(D) The acidity of a compound is determined by the stability of its conjugate base. When cyclopentadiene loses a proton,it forms the cyclopentadienide

Vedclass · Accepted Answer

cyclopentadienide ion,the conjugate base of cyclopentadiene,is an aromatic species and hence has higher stability

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(D) The acidity of a compound is determined by the stability of its conjugate base. When cyclopentadiene loses a proton,it forms the cyclopentadienide ion. This ion has $6 \pi$ electrons ($4n+2$ where $n=1$),is planar,and cyclic,making it an aromatic species according to $H$ückel's rule. Due to aromaticity,the cyclopentadienide ion is exceptionally stable. In contrast,the conjugate base of cyclopentane is an aliphatic carbanion,which lacks such resonance stabilization and is unstable. Therefore,cyclopentadiene is much more acidic than cyclopentane.

Cyclopentadiene is much more acidic than cyclopentane. The reason is that

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