Aspartic acid, an amino acid, has the structure shown below. Which of the following best explains which proton is most acidic?
![](data:image/png;base64, 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◦ Proton V is most acidic due to the possibility of conjugate base stabilization by resonance with the adjacent C=O bond.
◦ Proton I is most acidic due to conjugate base stabilization by resonance and being further from the inductive effect of the positive nitrogen atom.
◦ Proton II is most acidic due being attached to the carbon closest to the positive nitrogen atom.
◦ Proton IV is most acidic due to conjugate base stabilization by resonance and being closer to the inductive effect of the positive nitrogen atom.
◦ Proton III is most acidic due to being attached to a positive nitrogen atom.