1. Questions on Polycyclic Aromatic Hydrocarbons
1. Complete the following equations:
a) Naphthalene + CrO3/ CH3COOH
AlCl3
b) Naphthalene + C2H5COCl
C6H5NO2
c) Naphthalene + Na/ C2H5OH
HNO3
d) 1-Methoxynaphthalene
H2SO4
e) Anthracene Na/ C2H5OH
+
H2SO4
f) 1-Acetonaphthalene
Br2/ CCl4
g) Phenanthrene
low temp.
h) Naphthalene + acidic KMnO4
HNO3
i) 2-Methylnaphthalene
H2SO4
j) 2-Ethylnaphthalene + CrO3/ CH3COOH
Br2/ CCl4
k) 1-Naphthalene sulfonic acid
l) Anthracene K2Cr2O7/ H2SO4
+
Br2/ CCl4
m) Anthracene
low temp.
n) Phenanthrene
+ Na/ C2H5OH

2. 2. Explain the following:
a) Bromination of naphthalene afforded α-bromonaphthalene
and not β-bromonaphthalene.
b) Naphthalene reacts with H2SO4 at low temperature to give
1-naphthalene sulfonic acid, while, at high temp. 2- naphthalene
sulfonic acid is obtained.
c) Bromination of anthracene at high temp. resulted in 9-
bromoanthracene rather than 1-bromo or 2-bromoanthracene.
3. Starting from naphthalene, outline the synthesis of the following
compounds:
a) 1-Chloronaphthalene
b) 2-Cyanonaphthalene
c) 2-Naphthol
d) 1-Naphthol
e) 1-Naphthoic acid
f) 2-Ethylnaphthalene
4. Outline the synthesis of the following compounds:
a) 9-Phenylanthracene
b) 2-Methylanthracene
c) 2-Bromonaphthalene
d) 1-Methylnaphthalene
e) 1,4-Dimethylanthracene
f) 1,3-Dimethylphenanthrene
g) 9-Methylphenanthrene