Both pyridine and pyrrole are nitrogen- containing aromatic heterocyclic compounds (see below). When treated with HCI, pyridine forms a hydrochloride salt, whereas pyrrole is unreactive. Provide an explanation for this observed difference in reactivity. Pyridine (pK, 8.77) = Ĥ Pyrrole (pK, 17.8) = Select one: O A. The pyrrole nitrogen is a strongly deactivating group. B. Pyrrole has a large bond angle strain, preventing it from reacting. O C. Reaction of pyrrole with HCl forms an unstable nitrogenous anion.

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
Chapter23: Amines
Section: Chapter Questions
Problem 23.72P
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Question 16
Both pyridine and pyrrole are nitrogen-
containing aromatic heterocyclic compounds
(see below). When treated with HCI, pyridine
forms a hydrochloride salt, whereas pyrrole is
unreactive. Provide an explanation for this
observed difference in reactivity.
Pyridine (pK8.77)
Select one:
Pyrrole (pK 17.8)
=
A. The pyrrole nitrogen is a strongly
deactivating group.
B. Pyrrole has a large bond angle strain,
preventing it from reacting.
O C. Reaction of pyrrole with HCl forms an
unstable nitrogenous anion.
Transcribed Image Text:Both pyridine and pyrrole are nitrogen- containing aromatic heterocyclic compounds (see below). When treated with HCI, pyridine forms a hydrochloride salt, whereas pyrrole is unreactive. Provide an explanation for this observed difference in reactivity. Pyridine (pK8.77) Select one: Pyrrole (pK 17.8) = A. The pyrrole nitrogen is a strongly deactivating group. B. Pyrrole has a large bond angle strain, preventing it from reacting. O C. Reaction of pyrrole with HCl forms an unstable nitrogenous anion.
Pyridine (pK8.77)
Select one:
Pyrrole (pK 17.8)
A. The pyrrole nitrogen is a strongly
deactivating group.
B. Pyrrole has a large bond angle strain,
preventing it from reacting.
C. Reaction of pyrrole with HCl forms an
unstable nitrogenous anion.
O D. Pyrrole is sterically hindered; pyridine
is not.
O E. Protonation of pyrrole destroys a
stable aromatic ring, while protonation
of pyridine does not disrupt its
aromaticity.
OF. pyrdine is planar while pyrrole is not.
Transcribed Image Text:Pyridine (pK8.77) Select one: Pyrrole (pK 17.8) A. The pyrrole nitrogen is a strongly deactivating group. B. Pyrrole has a large bond angle strain, preventing it from reacting. C. Reaction of pyrrole with HCl forms an unstable nitrogenous anion. O D. Pyrrole is sterically hindered; pyridine is not. O E. Protonation of pyrrole destroys a stable aromatic ring, while protonation of pyridine does not disrupt its aromaticity. OF. pyrdine is planar while pyrrole is not.
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