Questions on Polycyclic Aromatic Hydrocarbons

1. Complete the following equations:

CrO3/ CH3COOH

C2H5COClAlCl3

C6H5NO2

Na/ C2H5OH

HNO3

H2SO4

Na/ C2H5OH

H2SO4

Br2/ CCl4

acidic KMnO4

HNO3

H2SO4

CrO3/ CH3COOH

Br2/ CCl4

K2Cr2O7/ H2SO4

Br2/ CCl4

Na/ C2H5OH

Naphthalenea) +Naphthaleneb) +

Naphthalenec) +

1-Methoxynaphthalened)

e) +Anthracene

1-Acetonaphthalenef)

Phenanthreneg)

low temp.

Naphthaleneh) +

2-Methylnaphthalenei)

2-Ethylnaphthalenej) +

1-Naphthalene sulfonic acidk)

l) +Anthracene

m) Anthracenelow temp.

Phenanthrenen) +

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