Tutorial 2- Advanced Aromatic Chemistry

1. Which of the following compounds are aromatic?

+
CH2

+
N

H
N
NH
O

N
H

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.
Br

1
2

Br2

3. 4-chloropyridine reacts with dimethylamine to give 4-dimethylaminopyridine.

Suggest a mechanism for this reaction.
Cl

N(CH3)2
HN(CH3)2

+ HCl
N

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 :

(i)

PhLi

(ii)

O-

Haba

O
NO2
(iii)

NO2

NH3, EtOH
100oC

Cl
(iv)

(CH3)2 NH
180oC
NO2

NaNH2,100oC

(v)

________________________________

(vi)

KOH, 320 C
________________________________

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 mchloronitrobenzene reacts with the hydroxide ion. Explain why this reaction
cannot take place.
9. Show the products for these reactions:
CH3

Na N (CH3)2

(i)

(CH3)2NH

Br
CH3
(ii)

Br
Na N (CH3)2
(CH3)2NH

Br

(iii)

(CH3)3CO(CH3)3COH

CH2CH3
(iv)
NaNH2
NH3 (l)

Br