Simple O-Chem question

  • #1
Char. Limit
Gold Member
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14

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?
 

Answers and Replies

  • #2
Borek
Mentor
28,600
3,078
Yes.
 
  • #3
Char. Limit
Gold Member
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14
All right, thanks. Now I can finish this chem homework.
 
  • #4
Ygggdrasil
Science Advisor
Insights Author
Gold Member
3,198
3,211
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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