How do I know which proton is more acidic?

[crimsonn]

Homework Statement

So this was a little acid-base reaction that ended up showing up on my quiz. I'm just not sure how to pick out the hydrogen in the group that is the most acidic. I wrote it as being the hydrogen that was attached to the carbon with the double bond. Could anyone explain why that is wrong? And give general guide lines to follow?

Homework Equations

My reasoning for the hydrogen attached to the carbon with the double bond was because it was sp2 hybridized which generally makes protons more acidic?

I'm not sure, my logic is probably flawed, so if someone could correct it that would be much appreciated!

 

[Nino MMP]

The Attempt at a Solution The general rule of thumb for determining which hydrogen in a group is the most acidic is to look at the electron withdrawing groups (EWGs). EWGs decrease the electron density around the hydrogen, making it more acidic. In this case, the double bond between the two carbons is an EWG. Therefore, the hydrogen that is attached to the carbon with the double bond would be the most acidic of the three.