Imine / Enamine Formation

[fataliz]

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Hi, i'm getting 2 conflicting information from texts on whether this is a nucleophilic addition or substitution.

Kaplan : Substitution
EK : Addition

Seems like its a substitution to me since the oxygen leaves. comments?

 

[Cawolf]

It's not substitution, those are Sn1, SN2, EAS, etc.

This is the case of nucleophilic addition (amine to carbonyl) followed by elimination (or condensation if you prefer).