19. Reactions of Aromatics: EAS and Beyond

Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.

b. methyl orange

Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.

Show how you would convert aniline to the following compounds.

(c) 1,3,5-trimethylbenzene

Show how you would convert aniline to the following compounds.

(g) phenol

Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?

Conversion of t-butylbenzene to a phenol results in two products when the reaction occurs through the benzyne mechanism. Devise a sequence involving a diazonium ion in which only one phenol product is produced.

Synthesize the dye shown starting with aniline and naphthol using reactions from Chapters 23 and 24. [Hint. Start by identifying how each substituent might be installed and then plan the order of their introduction.]