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Identifying Acidic Compounds

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** Please see the attached file for the complete problem description **

For the attached pairs of compounds, predict which is the stronger acid and briefly explain why (acidic proton marked in bold type).

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Solution Summary

In this solution we predict which compound is stronger, for a series of pairs, and explain why.

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(a) Protonated pyrrole is the stronger acid as the positive charge on the N in pyrrole is not delocalized in any of the resonance structures. In fact, there is a loss of aromatic stabilization when the pyrrole N is protonated--2 electrons are contributed by pyrrole to the ring to attain the 6 pi electron configuration necessary for aromatic stabilization.

In case of pyridine, the lone pair of N is orthogonal to the pi system of the ring and you do not lose aromatic stabilization on protonating the ...

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