ORGANIC CHEMISTRY HELP!!!?

  • Thread starter Thread starter chick*from*the*moon
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chick*from*the*moon

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prontonation of a carboxilic acid....

i know that usually sp^3 hybridized molecules are much stronger than an sp^2 hybridized molecule. ..........based on this theory, protonation of a carboxilic acid functional group, which contains both a carbonyl oxygen and a hydroxyl oxygen, should occur at the hydroxyl oxygen.........however that is not the case....why does protonation occur preferentially at the carbonyl oxygen (sp^2) than the hydroxyl oxygen (sp^3)
 
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