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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

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$1,3-$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.

$I. -OH$	$II. -CN$
$III. -CO_2H$	$IV. -OCH_3$
$V. -NHCOCH_3$	$VI. -CHO$

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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$V. -NHCOCH_3$ $VI. -CHO$

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