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 300oC. Sodium 2-naphthoxide is formed which on treatment with dilute sulphuric acid yields 2-naphthol.
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