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On the 3rd diagram (from left), the one with net charge = -1 ,

Why did it lose the H to OH- from the CH2CO2H from the neutral form ?

I was told that while moving to the right , the OH- will take H+ electrons meaning it should take H+ from NH3 .. ?

Is there any reason why they took the H from CH2CO2H ?

Any help would be appreciated!

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1 Answer 1

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The -CO₂H groups are carboxylic acid groups, better represented as -COOH. These, being acidic, have a lower pKₐ than the -NH₃⁺ group and so as the pH increases these -COOH groups lose their protons first.

The pKₐ values for the three are shown below the arrows: as you can see the α carboxylic acid is more acidic than that in the side chain, but they are both much more acidic than the protonated amino group.

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