Stability of extended enolates

I'd expect an extended enolate to be more stable than a normal enolate, when both can form, but my textbook suggests otherwise.


What is the stability of an extended enolate compared with a normal enolate? For example, following an enolate alkylation of the molecule depicted below, which product ($\alpha$- or $\gamma$-alkylated) will form? 



> 
> [![enter image description here](https://i.stack.imgur.com/JpO81.png)](https://i.stack.imgur.com/JpO81.png)
> 
> 
> 


