1) Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B b) Explain why compound A is more acidic than C, the conjugate acid of pyridine. H H C2 : N- H H +N -H Pyrrole pKa=0.4 pKa=5.3 -H

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter4: Acids And Bases
Section: Chapter Questions
Problem 4.30P: Will acetylene react with sodium hydride according to the following equation to form a salt and...
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3.
a) Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B
b) Explain why compound A is more acidic than C, the conjugate acid of pyridine.
H
H
C2
+N
-H
Pyrrole
pKa=0.4
pKa=5.3
A
B
C
.H
Transcribed Image Text:3. a) Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B b) Explain why compound A is more acidic than C, the conjugate acid of pyridine. H H C2 +N -H Pyrrole pKa=0.4 pKa=5.3 A B C .H
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