19. Reactions of Aromatics: EAS and Beyond

In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?

a. Explain why the following reaction leads to the products shown:

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.

(d) aniline

Propose a mechanism for the synthesis of methyl orange.

Show how you would convert aniline to the following compounds.

(a) fluorobenzene

(b) chlorobenzene

Predict the products of the following reactions:

(c)

Show how you would convert aniline to the following compounds.

(d) bromobenzene

(e) iodobenzene

Show how you would convert aniline to the following compounds.

(f) benzonitrile

Predict the products of the following reactions.

(a)