Explain this difference in reactivity between an ammonium ion and an iminium ion. O The ammonium ion is a stronger acid, making it less electrophilic. The iminium ion has a resonance structure with an empty p orbital on the carbon atom, making it electrophilic. O The pi bond in the iminium ion is electron-rich, making it more electrophilic. The iminium ion is resonance-stabilized, making it more reactive.

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 4.33P: Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label...
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An amine
R.
However, when an imine is protonated, the resulting iminium ion is highly electrophilic:
R
An ammonium ion
An imine
R.
R
R
An iminium ion
Explain this difference in reactivity between an ammonium ion and an iminium ion.
O The ammonium ion is a stronger acid, making it less electrophilic.
• The iminium ion has a resonance structure with an empty p orbital on the carbon atom, making it electrophilic.
The pi bond in the iminium ion is electron-rich, making it more electrophilic..
O The iminium ion is resonance-stabilized, making it more reactive.
Transcribed Image Text:An amine R. However, when an imine is protonated, the resulting iminium ion is highly electrophilic: R An ammonium ion An imine R. R R An iminium ion Explain this difference in reactivity between an ammonium ion and an iminium ion. O The ammonium ion is a stronger acid, making it less electrophilic. • The iminium ion has a resonance structure with an empty p orbital on the carbon atom, making it electrophilic. The pi bond in the iminium ion is electron-rich, making it more electrophilic.. O The iminium ion is resonance-stabilized, making it more reactive.
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