Reactions of Anthracene

Nitration of Anthracene

It is very difficult to nitrate anthracene without oxidation. Anthracene may be nitrated using acetic anhydride at 15-20°C to give 9-nitroanthracene and 9,10-dinitroanthracene.

Sulphonation of Anthracene

Anthracene undergoes sulphonation with concentration sulphuric acid to yield anthracene sulphonic acid. At low temperature 1-anthracene sulphonic acid is the major product where as at high temperature 2-anthracene sulphonic acid is the major product.

Chlorination of Anthracene

Anthracene reacts with chlorine in the presence of CCl₄ at room temperature to give 9,10-dichloro 9,10-dihydroanthracene. On heating this 9,10-dichloro 9,10-dihydroanthracene loses a molecule of HCl by 1,4-elimination to form 9-chloroanthracene. 9-chloroanthracene may also be prepared by heating anthracene at 100° C.
The best method for the preparation of 9-chloro or bromo anthracene from anthracene is to heat anthracene with the corresponding cupric halide in CCl₄ solution.

Friedel-Craft Acylation of Anthracene

Anthracene udergoes Friedel Craft acylation with acetyl chloride in the presence of anhydrous AlCl₃ in benzene or ethylene dichloride to form 9-acetylanthracene while in nitrobenzene, 1-acetylanthracene is formed.

Chloromethylation of Anthracene

Anthracene reacts with formaldehyde and HCl in the presence of ZnCl₂ to form 9-chloromethylanthracene.

Addition of Sodium to Anthracene

Anthracene reacts with metallic sodium in liquid ammonia gives 9,10-disodiumanthracene which on treatment with hot alkyl halide gives 9,10-dialkylanthracene.

Addition of Oxygen to Anthracene

Anthracene adds a molecule of oxygen in the presence of light to form a colorless 9,10-peroxide.

Dieles-Alder Reaction
Addition of Maleic Anhydride to Anthracene

Anthracene adds maleic anhydride to form 9,10-endo-anthracene maleic anhydride.

Reduction of Anthracene

Anthracene undergoes reduction with Na/EtOH gives 9,10-dihydroanthracene.
Catalytic reduction using Ni at 200-250°C first gives 9,10-dihydroanthracene, and on further reduction gives 1,2,3,4-tetrahydroanthracene, 1,2,3,4,5,6,7,8-octahydroanthracene and finally 1,2,3,4,5,6,7,8,9,10-decahydroanthracene..

Oxidation of Anthracene

Anthracene oxidized to 9,10-anthraquinone with oxygen and V₂O₅ or Nitric acid or Dichromate in sulphuric acid.

Synthesis of Anthracene

Synthesis of Anthracene

Structure Determination of Anthracene

Polynuclear Aromatic Hydrocarbons MCQs