Ans. Carboxylic Hydrogen in Glycolic Acid Reaction

  • Thread starter Thread starter Char. Limit
  • Start date Start date
Click For Summary

Discussion Overview

The discussion centers around the acidity of hydrogen atoms in Glycolic Acid, specifically which hydrogen—carboxylic or hydroxyl—would be removed first in an acid-base reaction. The context is primarily homework-related, focusing on chemical properties and reactions.

Discussion Character

  • Homework-related, Technical explanation

Main Points Raised

  • One participant suggests that the carboxylic hydrogen is likely to be removed first in an acid-base reaction, expressing uncertainty about this conclusion.
  • Another participant confirms the initial assertion that the carboxylic hydrogen is indeed the one that will be removed first.
  • A further explanation is provided regarding the acidity of the carboxylic hydrogen, noting that the resulting carboxylate group benefits from resonance stabilization, unlike the hydroxyl group formed from deprotonating the alcohol.

Areas of Agreement / Disagreement

There appears to be agreement among participants that the carboxylic hydrogen is more acidic and will be removed first, although the initial uncertainty expressed by the first participant indicates that some level of doubt remains.

Contextual Notes

The discussion does not address potential limitations or assumptions regarding the definitions of acidity or the specific conditions under which the reactions occur.

Char. Limit
Gold Member
Messages
1,222
Reaction score
23

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?
 
Physics news on Phys.org
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.
 

Similar threads

  • · Replies 4 ·
Replies
4
Views
2K
  • · Replies 28 ·
Replies
28
Views
6K
Replies
3
Views
3K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 8 ·
Replies
8
Views
3K
  • · Replies 4 ·
Replies
4
Views
16K
  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 2 ·
Replies
2
Views
5K