Aromatic Ring Rxns

Question 1

Ar with Deact and LG (strong Nuc ->)

Answer 1

Replace LG with strong nuc
(Meisenheimer complex moved lp)
(Deact and LG ortho or para)
(Nuc attack, resonance, loss of LG)

Question 2

Ar with Activating or Deactivating Group (Li, K, or Na (2equiv) -> NH3 and ROH)

Answer 2

Removes 1 pi bond from AR
(EDG = sp2)
(EWG = sp3)
(Mech uses radicals)

Question 3

Conj pi system with O (strong nuc -> quench)

Answer 3

Nuc attacks O pi bond and O gains electrons. Bounces back and forth between Nuc attack and loss of LG
(If R2CuLI, Nuc attacks end of C=C and other electrons move accordingly)

Question 4

Ar with LG (strong nuc in xs -> quench)

Answer 4

Replaces LG with strong nuc
(Uses a Hydrogen ortho to LG to make lp)
(Benzyne Formation)