Ans. Carboxylic Hydrogen in Glycolic Acid Reaction

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In Glycolic Acid, the carboxylic hydrogen is removed first in an acid-base reaction due to its higher acidity compared to the hydroxyl hydrogen. This increased acidity is attributed to the resonance stabilization of the carboxylate group formed upon deprotonation. In contrast, the hydroxyl group does not benefit from similar resonance stabilization. The discussion confirms the initial assumption about the reactivity of the carboxylic hydrogen. Understanding these concepts is essential for completing related chemistry homework effectively.
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Homework Statement


In the compound Glycolic Acid, with the structure below:

120px-Glycolic_acid.svg.png


Which hydrogen will get removed in an acid-base reaction first?

The Attempt at a Solution



I figure that it would be the carboxylic hydrogen, rather than the alcohol hydrogen, but I can't be completely certain, and I don't like not being completely certain.

So... am I right?
 
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Yes.
 
All right, thanks. Now I can finish this chem homework.
 
The reason why the carboxylic hydrogen is more acidic than the hydroxyl hydrogen is that the carboxylate group that results when the hydrogen is removed carboxylic acid undergoes resonance stabilization. No such resonance stabilizes the hydroxide group that results from the deprotonation of the hydroxyl.
 

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