CHM 2211 Lecture Notes - Lecture 11: Electrophilic Aromatic Directing Groups, Methyl Group, Steric Effects

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Methyl carbocation stabilization: ortho, meta, and para attacks all include a carbocation intermediate, which is stabilized by resonance, also, ortho and para attack carbocation intermediate are stabilized by an electron donating ch3 group. Same thing occurs with amine carbocation stabilization; except that ortho and para attack carbocation intermediate are not additionally stabilized by ch3. Nitro carbocation stabilization: ortho and para attack have intermediate carbocation have two adjacent positive charges, making that resonance structure the least stable. Reinforcing directing effects: the methyl group will direct the new coming atoms, the methyl will direct it to either an ortho or para position to it, the no2 will also direct the new coming atoms. It will direct them to a meta position to it: between these two influencing directions, depending on which is stronger, then the new atom will be placed in the most stable position.

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