Question: Piperidine, the amine reactant in parts (b) and (c) of the preceding problem, reacts with 1-bromonaphthalene on heating at 230C to give a single product,

Piperidine, the amine reactant in parts (b) and (c) of the preceding problem, reacts with 1-bromonaphthalene on heating at 230°C to give a single product, compound A (C15H17N), as a noncrystallizable liquid. The same reaction using 2-bromonaphthalene yielded an isomeric product, compound B, a solid melting at 50–53°C. Mixtures of A and B were formed when either 1- or 2-bromonaphthalene was allowed to react with sodium piperidide in piperidine. Suggest reasonable structures for compounds A and B and offer an explanation for their formation under each set of reaction conditions.

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