Question

Orgo II Tutorial: SnAR mechanism

Answer 1

\({\bf{Overview:}}\) adding to a benzene ring is possible however we must have electron-withdrawing groups in the ortho/para positions

Answer 2

\({\bf{the~Mechanism:}}\)

first the -OH attacks the carbon containing the leaving group, pushing the double bound electrons around the ring (slow step)

Answer 3

the next step is the exit of the leaving group Cl



if desired, an -OH group can be added to remove the hydrogen on the attached OH group to make water

Answer 4

\({\bf{Meisenheimer~Intermediate:}}\) benzene carbanion that can be stabilized by EWG on the ortho/para positions (gives the eletrons a way to escape the ring)

Answer 5

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.