Explain why pyrrole (pKa∼17) is a much stronger acid than ammonia (pKa=36). There are schemes of two reversible reactions. In the first reaction, the reactant is a five-membered ring, where a segment with four vertices is followed by an N atom (clockwise). There is a double bond between the first and the second and between the third and the fourth vertices. An H atom is attached to the N atom. The reactant gives a five-membered ring, where a segment with four vertices is followed by N, and H plus. There is a double bond between the first and the second and between the third and the fourth vertices of the ring. The N atom is negatively charged. The pKa value of the reactant is approximately equal to 17. In the second reaction, NH3 produces one equivalent of NH2 minus and one equivalent of H plus. The pKa value is equal to 36. Check all that apply. Check all that apply. Stabilizing the base decreases the acidity of its conjugate acid. Stabilizing the base increases the acidity of its conjugate acid. When pyrrole loses a proton, the electrons left behind remain on nitrogen. Electron delocalization stabilizes the anion and makes it heavier to form. Electron delocalization stabilizes the anion and makes it easier to form. 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.
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Explain why pyrrole (pKa∼17) is a much stronger acid than ammonia (pKa=36). There are schemes of two...
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