Ochem reaction

[BMEEngineer]

I don't understand why this reagent replaces the hydrogen of NH2 instead of adding to benzene ortho and para.

Thanks!

http://imgur.com/HsEEtdL

 

[IsaacYankem]

Acyl substitution. The Cl is a good leaving group, and the N will replace it on the alpha position. The product is stable as it is conjugated, and the N-C bond will have some double bond character due to resonance. Chad has a great breakdown of this in his videos, OC topic 4.

 

[BMEEngineer]

Thank you! I must have not paid enough attention in that video. I will re-watch!

 

[IsaacYankem]

I found myself rewatching parts of Chad a lot after Destroyer kicked my ass the first time. It's great to go back to Chad after something in Destroyer or elsewhere hangs you up. I must have watched the damn video about Claisen Condensation/Malonic Esters about 4x