Why is o-fluorophenol a stronger acid than p-fluorophenol?
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Because It will produce more concentration of H+ ions when dissolved in water than the other. It depends on the partiallity in ionising.
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What you've described is a classic case of two competing factors. Having two competing factors doesn't mean that it is simultaneously more and less acidic - all it means is that one factor is more important than the other. From the pKa values it should be clear which one is more important, and you seem to have realised that too.
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