The decreasing order of acidic strengths of t | vedclass

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Question

(D) The acidic strength of a compound depends on the stability of its conjugate base formed after the removal of a proton $(H^+)$.$(x)$ Cyclopentadien

Vedclass · Accepted Answer

$z > x > y$

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(D) The acidic strength of a compound depends on the stability of its conjugate base formed after the removal of a proton $(H^+)$.$(x)$ Cyclopentadiene: Upon losing a proton,it forms a cyclopentadienyl anion,which is aromatic ($6 \pi$ electrons,Huckel's rule).$(y)$ Cycloheptatriene: Upon losing a proton,it forms a cycloheptatrienyl anion,which is anti-aromatic ($8 \pi$ electrons,unstable).$(z)$ $5-$cyanocyclopentadiene: Upon losing a proton,it forms a cyclopentadienyl anion substituted with a $-CN$ group. The $-CN$ group is a strong electron-withdrawing group ($-I$ and $-M$ effect),which further stabilizes the already aromatic anion through resonance and inductive effects.Comparing the stabilities of the conjugate bases:$1$. The anion of $(z)$ is the most stable due to the $-CN$ group.$2$. The anion of $(x)$ is aromatic and stable.$3$. The anion of $(y)$ is anti-aromatic and highly unstable.Therefore,the order of acidic strength is $z > x > y$.

The decreasing order of acidic strengths of the following compounds is:

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