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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 Preview

    (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 ...

    Solution Summary

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