An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.

An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 78AP

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