(s)Nitrosation of N,N-dialkylarylamines takes place on the ring at the position para to thedialkylamino group.22.36(a)4-Methylpiperidine can participate in intermolecular hydrogen bonding in the liquid phase.These hydrogen bonds must be broken in order for individual 4-methylpiperidine moleculesto escape into the gas phase. N-Methylpiperidine lacks a proton bonded to nitrogen and socannot engage in intermolecular hydrogen bonding. Less energy is required to transfer a mol-ecule of N-methylpiperidine to the gaseous state, and therefore it has a lower boiling pointthan 4-methylpiperidine.(b)The two products are diastereomeric quaternary ammonium chlorides that differ in the con-figuration at the nitrogen atom.
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