An amine of unknown structure contains one nitrogen and nine carbon atoms, as well as at least one six-membered ring. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence (1. CH3I, 2. Ag20, H20, 3. Heat) give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine. Justify your answer.

An amine of unknown structure contains one nitrogen and nine carbon atoms, as well as at least one six-membered ring. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence (1. CH3I, 2. Ag20, H20, 3. Heat) give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine. Justify your answer.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.39P

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