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The acid strength of each compound can be explained, but the acidity order is much more difficult to compare, because the two compounds are only remotely connected. It is misleading to conclude that the mere presence of a phenyl group somehow connects these molecules. The similarity of the pK$_a$s is likely a coincidence. The question needs a clear ...

1

Taken from my answer here: Comparing methane and acetylene shows a difference of $\approx 20$ $\mathrm pK_\mathrm a$ units Comparing $\mathrm p K_\mathrm a$ of phenol($10.0$) and methanol($15.5$), we see that the presence of one resonating ring only produces a 5.5 $\mathrm p K_\mathrm a$ difference. Resonance in triphenyl system is effectively only one ...

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This would be more obvious if you had a strongly electron-withdrawing group (e.g. nitro or CF3) instead of the mildly electron-donating Me. In that case it would be clear that the carbonyl para to the EWG group would have electron density drawn away from the C, increasing the polarity of the C=O bond and making it more reactive to nucleophiles. Instead we ...

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