Explain why pyrrole (p K a?17) is a much stronger acid than ammonia (p K a=36).

Question

Explain why pyrrole (pKa?17) is a much stronger acid than ammonia (pKa=36).

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() When pyrrole loses a proton, the electrons left behind remain on nitrogen.

() Stabilizing the base increases the acidity of its conjugate acid.

() Electron delocalization stabilizes the anion and makes it heavier to form.

() When pyrrole loses a proton, the electrons left behind can be delocalized onto the four ring carbons.

() When ammonia loses a proton, the electrons left behind remain on nitrogen.

() When ammonia loses a proton, the electrons left behind remain on another atom.

() Stabilizing the base decreases the acidity of its conjugate acid.

() Electron delocalization stabilizes the anion and makes it easier to form.

Explanation / Answer

Stabilizing the base increases the acidity of its conjugate acid.

When pyrrole loses a proton the electrons left behind can be delocalized onto the four ring carbons.

When ammonia loses a proton, the electrons left behind remain on nitrogen.

Electron delocalization stabilizes the anion and makes it easier to form.

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