When an amine is protonated, the resulting ammonium ion is not electrophilic: However, when an imine is

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When an amine is protonated, the resulting ammonium ion is not electrophilic:

R H CI: Н- 'R An amine An ammonium ion


However, when an imine is protonated, the resulting iminium ion is highly electrophilic:

N. CI: R. :Cl: An imine An iminium ion


Explain this difference in reactivity between an ammonium ion and an iminium ion.

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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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