intermediate and hence follow an addition–elimination pathway. Piperidine acts as a nucleophileand substitutes for bromine on the same carbon atom from which bromine is lost.When the strong base sodium piperidide is used, reaction occurs by the elimination–additionpathway via a“naphthalyne”intermediate. Only one mode of elimination is possible from 1-bromo-naphthalene.This intermediate can yield both A and B in the addition stage.Two modes of elimination are possible from 2-bromonaphthalene:
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