19. Reactions of Aromatics: EAS and Beyond

Provide the structure of the product formed from the reaction of 1-bromo-2,4,6- trinitrobenzene with one equivalent of sodium methoxide. 

Provide the major organic product for the following reaction.

Provide the major organic product for the following reaction.

Which of the following compounds is most likely to undergo nucleophilic aromatic substitution via the addition-elimination pathway? 

Propose mechanisms and show the expected products of the following reactions.

(a) 2,4-dinitrochlorobenzene + sodium methoxide (NaOCH₃)

(b) 2,4-dimethylchlorobenzene + sodium hydroxide, 350 °C

Propose mechanisms and show the expected products of the following reactions.

(c) p-nitrobromobenzene + methylamine (CH₃–NH₂)

(d) 2,4-dinitrochlorobenzene + excess hydrazine (H₂N–NH₂)

Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene were to react with hydroxide ion. Why doesn't the reaction occur?

Show how the substituents containing the azo group (N=N) can facilitate both electrophilic and nucleophilic aromatic substitution.

(a)