Rank the following compounds from greatest tendency to least tendency to undergo nucleophilic aromatic substitution:
chlorobenzene 
1-chloro-2,4-dinitrobenzene 
p-chloronitrobenzene

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

(b)

Show how you would accomplish the following syntheses.

(c) benzene → p-methoxybenzaldehyde

Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.

Propose a mechanism for each of the following reactions:

b.

In the context of nucleophilic aromatic substitution, why is the ${\mathrm{NO}}_2$ group considered a meta director when it comes to electrophilic aromatic substitution reactions?

Which of the following statements about nucleophilic aromatic substitution is true?

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