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Dolbier HW Solutions 541 - 635 AMINES(s Nitrosation of N...

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( s ) Nitrosation of N , N -dialkylarylamines takes place on the ring at the position para to the dialkylamino 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 molecules to escape into the gas phase. N -Methylpiperidine lacks a proton bonded to nitrogen and so cannot 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 point than 4-methylpiperidine. ( b ) The two products are diastereomeric quaternary ammonium chlorides that differ in the con- fi guration at the nitrogen atom.
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