Acidic Hydrogens in Aspartame: Which Ones Are Most Acidic and Why?

[ahhppull]

Homework Statement

http://en.wikipedia.org/wiki/File:Aspart…

What are the 2 most acidic hydrogens in this molecule?and why?

Homework Equations

The Attempt at a Solution

I narrowed it to:

1) the H on the carbon wedge connected to NH
2) the H on the carboxylic acid COOH
3) the H on the NH

 

[Borek]

http://en.wikipedia.org/wiki/File:Aspartame.svg

 

[Highway]

Acidic hydrogens are going to be attached to atoms that can stabilize a charge the best through resonance, so draw some diagrams, and look at electronegativity, comparing them...