Tutorial 2- Advanced Aromatic Chemistry

1. Which of the following compounds are aromatic?

2. Draw the resonance structures for the carbocation intermediates in the bromination reaction of naphthalene and explain why naphthalene undergoes electrophilic attack at C1 and not at C2.

3. 4-chloropyridine reacts with dimethylamine to give 4-dimethylaminopyridine. Suggest a mechanism for this reaction.

4. p-Bromotoluene reacts with potassium amide and ammonia to give a mixture of m- and p-methylaniline. Explain using equations.

5. The CHO group is an activating group to the benzene ring for an aromatic nucleophilic substitution reaction whereas the OCH3 group activates the ring. Using curved arrows draw all the resonance structures to explain why these two groups can act as activating and deactivating groups to the benzene ring.

6. Complete the following reactions :

7. Nitrobenzene reacts with KOH to produce o-nitrophenol. Write the mechanism for this reaction showing all the intermediate anionic resonance structures.

8. Draw all the resonance structures of the carbanion produced when m- chloronitrobenzene reacts with the hydroxide ion. Explain why this reaction

cannot take place.

9. Show the products for these reactions: