For this proton transfer, why does the NH3 electron pair move to the H and not the electron pair from the Br?

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 23.36P
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Hi,

For this proton transfer, why does the NH3 electron pair move to the H and not the electron pair from the Br?

Furthermore, when the substitution product bears a positive charge and also contains a proton bonded to O or N, the initial substitution
product readily loses a proton in a Brønsted-Lowry acid-base reaction, forming a neutral product.
D
Br
G
+
:NH3
excess
nucleophilic
substitution
+ Bri
H
H
H
NH3
proton
transfer
+
NH4
NH₂
Transcribed Image Text:Furthermore, when the substitution product bears a positive charge and also contains a proton bonded to O or N, the initial substitution product readily loses a proton in a Brønsted-Lowry acid-base reaction, forming a neutral product. D Br G + :NH3 excess nucleophilic substitution + Bri H H H NH3 proton transfer + NH4 NH₂
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