# Predicting product of amine elimination

From section 'Nitrogen Containing Compounds'

I spent quite a lot of time here but could not figure out the answer. It's not mentioned in my school text book either. The solution given in my book is:

I'd like to know:

1. Is the answer provided (c) correct?

2. How do I know that heating that compound in the presence of a base results in the formation of that product? We've got plenty of cases in our textbook (Tollen's Test, Fehling's Test and the aldol reaction, to name a few) where we heat organic compounds in the presence of a base, but none of them go by what happened in this question.

• Which book is it by the way? – Kartik Sep 5 '16 at 11:44

As for the mechanism, it is all there in your second picture. Indeed, that $\ce{OH-}$ would readily snatch a proton from an ammonium cation $\ce{NH4+}$, only there is no ammonium, it is a substituted ammonium, and we don't have any H linked directly to N. So we go for the next best thing and grab a proton from some carbon in $\beta$ position, simultaneously with the formation of a double bond.