Dolbier HW Solutions 516 - 610 AMINES(c N...

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( c ) N , N -Dimethylbenzylamine is a tertiary amine. Its preparation from benzaldehyde requires dimethylamine, a secondary amine. ( d ) The preparation of N -butylpiperidine by reductive amination is described in the text in Section 22.11. An analogous procedure is used to prepare N -benzylpiperidine. 22.13 ( b ) First identify the available hydrogens. Elimination must involve a proton from the carbon atom adjacent to the one that bears the nitrogen. It is a proton from one of the methyl groups, rather than one from the more sterically hindered methylene, that is lost on elimination. ( c ) The base may abstract a proton from either of two carbons. Deprotonation of the methyl carbon yields ethylene. Deprotonation of the methylene carbon yields 1-butene. 1-Butene H 2 C CHCH 2 CH 3 N -Ethyl- N , N -dimethylbutylammonium hydroxide heat ( H 2 O) N , N -Dimethylethylamine
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