Solution Found!
When an amine is protonated, the resulting ammonium ion is
Chapter 6, Problem 6.53(choose chapter or problem)
When an amine is protonated, the resulting ammonium ion is not electrophilic: An amine An ammonium ion R N R R H R N R R H Cl Cl @ ! + However, when an imine is protonated, the resulting iminium ion is highly electrophilic: An imine An iminium ion N R R R N R H R R Cl H Cl @ ! + Explain this difference in reactivity between an ammonium ion and an iminium ion.
Questions & Answers
QUESTION:
When an amine is protonated, the resulting ammonium ion is not electrophilic: An amine An ammonium ion R N R R H R N R R H Cl Cl @ ! + However, when an imine is protonated, the resulting iminium ion is highly electrophilic: An imine An iminium ion N R R R N R H R R Cl H Cl @ ! + Explain this difference in reactivity between an ammonium ion and an iminium ion.
ANSWER:Step 1 of 2
An ammonium ion is positively charged, it is not electrophilic. This is because electrophiles must have an empty orbital that can be attacked by a nucleophile. Since nitrogen has four valence orbitals and is bound to four atoms, all of its valence orbitals are occupied, and it cannot be attacked by a nucleophile.
