Chapter 19, Problem 19.39P

Interpretation Introduction

Interpretation:

The reason for that the less substituted double bond the enolate is more favoured product has to be explained.

Concept introduction:

Enamine reaction:

In the six atom system of an enamine, the nitrogen is $s{p}^2$ hybridisation, so there is overlap of the $2p$ orbital of nitrogen atom with the $2p$ orbitals of the carbon-carbon double bond. This overlap allows electrons delocalization and thus stabilization of the enamine.