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(D) The reactivity of a compound toward an aqueous solution of sodium carbonate $(Na_2CO_3)$ depends on its acidity. Compounds that are sufficiently a

Vedclass · Accepted Answer

$1,3-$Cyclopentadiene

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(D) The reactivity of a compound toward an aqueous solution of sodium carbonate $(Na_2CO_3)$ depends on its acidity. Compounds that are sufficiently acidic to donate a proton to the carbonate ion $(CO_3^{2-})$ or bicarbonate ion $(HCO_3^-)$ will react. In this case,we evaluate the acidity of the hydrocarbons by looking at the stability of their conjugate bases (the corresponding carbanions formed after deprotonation). $(a)$ Cyclopropene: Forms an antiaromatic $(4\pi e^-)$ carbanion,which is highly unstable. $(b)$ Cyclobutene: Forms an antiaromatic $(4\pi e^-)$ carbanion,which is highly unstable. $(c)$ $1,3-$Cyclohexadiene: Forms a homoaromatic carbanion,which is unstable due to the lack of continuous delocalization. $(d)$ $1,3-$Cyclopentadiene: Upon losing a proton,it forms the cyclopentadienyl anion,which is aromatic $(6\pi e^-)$ and highly stable. Because the conjugate base of $1,3-$cyclopentadiene is aromatic and exceptionally stable,$1$,$3$-cyclopentadiene is the most acidic among the given options and thus the most reactive toward an aqueous solution of sodium carbonate.

Which of the following compounds is most reactive to an aqueous solution of sodium carbonate $?$ (The structures correspond to cyclic hydrocarbons with varying degrees of unsaturation).

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