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Posted

I'm obviously missing something, but I've been studying polymers and monomers recently, and the dissasociation of a carboxylic acid in water(carbon, double oxygen bond...and a hydroxide) produces hydrogen ions, and when bonded to an alcohol it condensates and produces water as a by-product. Why does the bonding of the hydroxide in carboxylic acid, behave like an acid ?

 

I'm sure I'm gonna kick myself when I get the answer.

Posted

If you draw out the molecule it gets pretty obvious.

 

Take just your normal carboxylic acid, the carbonyl and hydroxy, and you have this:

 

O=C-OH, with carbon bonded to something else, which I can't show here because the people who program these things hate scientists.

 

Between those 2 oxygens that carbon is in the middle of a tug of war match between 2 oxygens (made even greater by the double bond). It's this tug of war, along with electronegativities and ionization energies, that will rip the electron from the hydrogen of the hydroxy group.

 

I hope that makes sense, I've literally been up 4 minutes.

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