Section 17-12 showed how nucleophilic aromatic substitution can give aryl amines if ther...

Section 17-12 showed how nucleophilic aromatic substitution can give aryl amines if there is a strong electron-withdrawing group ortho or para to the site of substitution. Consider the following example.

(a) Propose a mechanism for this reaction.

(b) We usually think of fluoride ion as a poor leaving group. Explain why this reaction readily displaces fluoride as the leaving group.

(c) Explain why this reaction stops with the desired product, rather than reacting with another dinitrofluorobenzene.