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Dolbier HW Solutions 570 - 664 ARYL HALIDES intermediate...

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intermediate and hence follow an addition elimination pathway. Piperidine acts as a nucleophile and 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 addition pathway 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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