Textbook Question
The chemical shifts of the C-2 hydrogen in the spectra of pyrrole, pyridine, and pyrrolidine are 2.82 ppm, 6.42 ppm, and 8.50 ppm. Match each heterocycle with its chemical shift.
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Bruice 8th Edition
Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds
Problem 37
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The chemical shifts of the C-2 hydrogen in the spectra of pyrrole, pyridine, and pyrrolidine are 2.82 ppm, 6.42 ppm, and 8.50 ppm. Match each heterocycle with its chemical shift.
Propose a mechanism for the following reactions:
a.
b. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?
What is the major product of the following reactions?
a.
Explain why pyrrole (pKa ~ 17) is a much stronger acid than ammonia (pKa = 36).
Propose a mechanism for the following reactions:
b.