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Differences in Acidity Between P-Cyanobenzoic Acid and M-Cyanobe

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Even through the para position is on carbon father from the carboxy group than the meta position, p-cyanobenzoic acid is more acidic than m-cyanobenzoic acid. Explain the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid.

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The solution explains the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid.

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It is very often helpful to draw the resonance structures for each molecule in these conceptual-type questions. I have drawn two resonance forms for p-cyanobenzoic acid and m-cyanobenzoic acid.

The cyano group is a powerful electron withdrawing substituent. It pulls electrons away from the pi system of the aromatic ring and onto itself. However, you will notice upon drawing all of the resonance forms that a formal positive charge can only ...

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