Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

Question

Quizplus · Accepted Answer

To determine the relative acidity of the highlighted hydrogens in the five compounds, we need to consider the stability of the corresponding conjugate bases. The more stable the conjugate base, the more acidic the proton. Generally, conjugate bases are stabilized by resonance and induction effects of electron-withdrawing groups.

I) The highlighted hydrogen is next to a carbonyl group, which can stabilize the negative charge on the conjugate base through resonance. However, there is no other electron-withdrawing group to provide additional stabilization.

II) The highlighted hydrogen is next to an aromatic ring, which can also stabilize the negative charge through resonance. Moreover, the sulfonic acid group is a strong electron-withdrawing group that can provide additional stabilization through induction.

III) The highlighted hydrogen is next to a tertiary amine, which is a weak electron-withdrawing group compared to the carbonyl and sulfonic acid groups. Therefore, the conjugate base is less stable.

IV) The highlighted hydrogen is next to two carbonyl groups, which can provide significant stabilization through resonance, making it a relatively strong acid.

V) The highlighted hydrogen is next to a hydroxyl group, which has a minor effect on conjugate base stability.

Based on these considerations, the decreasing order of acidity for the highlighted hydrogens is: IV > I > III > II > V

Among the given choices, only option C lists the compounds in the correct order of decreasing acidity.

Considering Only the Highlighted Hydrogens,list the Following Compounds in Order