Details below. Acidity order "?"

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1 Answer
Mar 1, 2018

Your first question is cut off. I won't answer that because I don't know all of the information.

Regarding your second question: Consider #P#,

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What happens when we deprotonate the carbon adjacent to the nitro functional group? The negative charge is delocalized via resonance.

Consider #Q#,

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When we deprotonate the methyl group, the negative charge can be delocalized to two oxygen atoms via resonance.

Consider #R#,

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When we deprotonate the central carbon, the negative charge is delocalized among the three phenyl substituents via resonance.

Consider #S#,

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When we deprotonate the carbon allylic to the carbonyl oxygen, its negative charge would delocalize to the oxygen via resonance.

Recall: more electronegative atoms will make for a more stable negative charge. In assessing acidity, we want to determine which of these potential acids has the most stable base.

From the preceding reasoning I would determine,

#P > Q > S > R#, or #"c".#

I don't really agree that the sulfone proton is more acidic than the carbonyl proton, but they're pretty close so I could see why one would argue the other way.