TUTORIAL 3

CHAPTER 3
Benzene and aromaticity
3.1 Sources and names of aromatic compounds
3.2 Structure and stability of benzene
3.3 Aromatic ions
3.4 Aromatic heterocycles Pyridine and pyrrole
3.5 Reaction of aromatic compounds

1. Synthesize p!bromobenzoic acic from benzene.

2. "#plain $hy the reactions $ill not form the %i&en product. 'hen desi%n a synthesis of A from
benzene.
S(
3
)

S(
3
)
*(*)
3
*l
3. +ra$ the product ,s-.
,i-
*,*)
3
-
3
)
3
*
(ii)
(

,iii-
CH3COCl
Cl2
AlCl3 FeCl3
A
KMnO4
NH2NH2
-
OH,
Br2
hv
(iv)
)
3
*
(

4. +ra$ a step$ise mechanism/

*l
*)
3
+
5. Synthesis 0 from benzene
(
1. 2hen benzene reacts $ith 1!chloro!2/2!dimethylpropane in the presence of aluminium
chloride/ the ma3or product is 2!methyl!2!phenylbutane/ not 2/2!dimethyl!1!phenylpropane.
"#plain this result. +ra$ the detailed mechanism.
Zn(Hg)
HCl,
AlCl3
HCl
B
+
4. Startin% $ith acetanilide/ outline a synthesis of o!nitroanaline.
)5
(
5)
2
5(
2
6. Startin% $ith toluene/ outline a synthesis of
a. 1!bromo!2!trichloromethylbenzene
b. 1!bromo!3!trichloromethylbenzene
c. 1!bromo!4!trichloromethylbenzene
7. Suppose you need to synthesize m!chloroethylbenzene from benzene.
*l
8ou could be%in by chlorination benzene then follo$ $ith a 9riedel!*rafts al:ylation usin%
chloroethane and Al*l3/ or &ice &ersa.
5either method $ill %i&e the desired product.
2hy $ill neither %i&e the desired product;
'here is a 3!step method that $ill $or: if the step are done in the ri%ht order. 2hat is this method;
?
?