Reactions of Naphthalene

Nitration of Naphthalene

Naphthalene reacts with conc. nitric acid and sulphuric acid at 60° C gives 1-nitronaphthalene.


On further nitration gives 1,8-dinitronaphthalene and 1,5-dinitronaphthalene.

Sulphonation of Naphthalene

Naphthalene undergoes sulphonation with concentrated sulphuric acid at two different temperature. At 60° C, it gives 1-nephtalenesulphonic acid while at 165° C, it gives 2-nephtalenesulphonic acid.

Chlorination of Naphthalene

Naphthalene reacts with chlorine in presence of carbon tetrachloride gives 1-chloronaphthalene.

Friedel-Craft Alkylation of Naphthalene

Naphthalene undergoes Friedel-Craft alkylation with alkyl halide in the presence of lewis acid gives 2-alkylnaphthalene.

Friedel-Craft Acylation of Naphthalene

Naphthalene undergoes Friedel-Craft acylation with acid halide and Lewis acid in CS₂ and in nitrobenzene. In CS₂, it gives 1-Acetylnaphthalene while in nitrobenzene, it gives 2-Acetylnaphthalene.

Chloromethylation of Naphthalene

Naphthalene reacts with formaldehyde and HCl in the presence of ZnCl₂ to form 1-chloromethylnaphthalene.

Addition of Sodium to Naphthalene

Naphthalene adds on sodium to give 1,4-disodiumnaphthalene which on treatment with carbondioxide yield the disodium salt of 1,4-dihydronaphthalene-1,4-dicarboxylic acid.

Ozonolysis of Naphthalene

Ozonolysis of naphthalene gives phthaldehyde. Naphthalene gives diozonide when ozone add which on hydrolysis gives phthaldehyde.

Reduction of Naphthalene

Naphthalene undergoes reduction with Na/EtOH gives 1,4-dialin (1,4-dihydronaphthalene), with Na/ isopentanol gives tetralin (1,2,3,4-tetrahydronaphthalene) and on catalytic reduction, it completely reduced to decalin or decahydronaphthalene.

Oxidation of Naphthalene

Naphthalene oxidized to 1,4-naphaquinone with CrO₃ in AcOH and to phthalic anhydride with oxygen and V₂O₅ at 470°C.

Naphthalene on oxidation with alkaline KMnO₄ gives phthalonic acid and then phthalic acid.

Naphthalene to β-Naphthol

2-naphthol or β-naphthol is obtained by fusing sodium 2-naphthalenesulphonate with NaOH at 300^oC. Sodium 2-naphthoxide is formed which on treatment with dilute sulphuric acid yields 2-naphthol.

Structure Determination of Naphthalene

Synthesis of Naphthelene