Nicotine is a dibasic alkaloid. A pKa value of 8 is associated with the aliphatic nitrogen in the 5-membered saturated ring, and a pka of 3 is associated with the heterocyclic nitrogen contained within the aromatic 6-membered ring. Nitrogen containing aromatic heterocycles are typically much less basic than are aliphatic or alicyclic amines. Which of the following forms of nicotine is predicted to be most abundant in water solution at pH 6? A. N CH3 B. H÷N¬ CH3 C. H N CH3 D. N* H -N-H CH3

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
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.63P
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Nicotine is a dibasic alkaloid. A pKa value of 8 is associated with the
aliphatic nitrogen
in the 5-membered saturated ring, and a pk of 3 is associated with the heterocyclic
nitrogen contained within the aromatic 6-membered ring. Nitrogen containing aromatic
heterocycles are typically much less basic than are aliphatic or alicyclic amines. Which
of the following forms of nicotine is predicted to be most abundant in water solution at
pH 6?
C.
D.
B.
A.
N
N
-N=H
OR DA ER DE
CH3
CH3
CH3
CH3
`N+
H
Transcribed Image Text:Nicotine is a dibasic alkaloid. A pKa value of 8 is associated with the aliphatic nitrogen in the 5-membered saturated ring, and a pk of 3 is associated with the heterocyclic nitrogen contained within the aromatic 6-membered ring. Nitrogen containing aromatic heterocycles are typically much less basic than are aliphatic or alicyclic amines. Which of the following forms of nicotine is predicted to be most abundant in water solution at pH 6? C. D. B. A. N N -N=H OR DA ER DE CH3 CH3 CH3 CH3 `N+ H
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