Abstract
The hydrocarbons naphthalene, anthracene, and phenanthrene represent the simplest examples of a series of polynuclear hydrocarbons in which benzene rings are condensed or fused so that neighbouring rings share a pair of adjacent carbon atoms. Electrophilic substitution in naphthalene proceeds more readily than in the case of benzene. With naphthalene, the charged intermediates involved retain a considerable degree of resonance stabilization because of the presence of the intact benzene system, whereas during substitutions in benzene, the formation of the charged intermediate results in the resonance stabilization being largely destroyed. The activation energy for substitution in naphthalene must, therefore, be less than in the case of benzene with the result that substitution requires milder reaction conditions. Naphthalene also undergoes addition reactions more readily than benzene. It is reduced by sodium and amyl alcohol to tetra-hydronaphthalene, whereas benzene is unattacked by the reagent. The product tetralin is also obtained by the partial catalytic hydrogenation of naphthalene.
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