Structure Determination of Naphthalene

Structure Determination of Naphthalene

Structure Determination of Naphthalene

Structure of naphthalene was established by the following facts, evidences and synthesis of it-
1. Elemental analysis and molecular weight determination shows that the molecular formula of naphthalene is C10H8.
2. Dipole moment of naphthalene is zero which indicated that naphthalene is symmetrical.
3. Oxidation of naphthalene with Vanadium pentoxide at 470°C yields phthalic anhydride which indicates the presence of benzene ring with two ortho side chains in the molecule.
structure determination of naphthalene
4. Nitration of naphthalene produce nitronaphthalene which oxidize to 3-nitrophthalic acid and reduced to aminonaphthalene which on oxidation gives only phthalic acid.
The nitro group stabilizes the benzene ring to which it is attached and the other ring is oxidized. On the other hand, the amino group makes the benzene ring to which it is attached mire susceptible to oxidation.
structure determination of naphthalene
All these results clearly indicates that the naphthalene consists of two fused benzene ring.
Structure of Naphthalene
The above structure was confirmed by the various synthesis of naphthalene.

Haworth Synthesis of Naphthalene

Synthesis of Naphthalene by Haworth Process

Synthesis of Naphthalene from 4-Phenyl 3-butenoic acid

Synthesis of Naphthalene

Synthesis of Naphthelene

Reactions of of Naphthalene