In: Chemistry
Using benzene or toluene as the only aromatic organic starting material, devise a synthesis for each of the following:
a. o-chlorotoluene
b. 3-bromonitrobenzene
c. p-toluenesulfonic acid
d. 2-chloronitrobenzene
Answer.a) Synthesis of o-chlorotoluene taking benzene as starting material.
Friedal craft's alkylation of benzene,
C6 H6 + CH3 Cl
C6 H5
CH3 +HCl
Chlorination of toluene:
C6 H5 CH3 +
Cl2
o-chlorotoluene +p-chlorotoluene
b) Synthesis of 3-bromonitrobenzene using benzene
Nitration of benzene
C6 H6
+HNO3
C6
H5 NO2 +H2O
Bromination of nitrobenzene
C6 H5 NO2 +
Br2
3-bromonitrobenzene + HBr
c) p-toluenesulfonic acid
Sulfonation of toluene
C6 H5 CH3 + Conc.H2SO4
p-toluenesulfonic acid + o-toluenesulfonic acid
d) 2-Chloronitrobenzene
Chlorination of benzene:
C6 H6 +
Cl2
C6
H5 Cl + HCl
Nitration of chlorobenzene
C6 H5 Cl +
HNO3
2-chloronitrobenzene +
4-chloronitrbenzene