Why are carboxylate ions more stable and more acidic than alcohols
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Why are carboxylate ions more stable and more acidic than alcohols

[From: ] [author: ] [Date: 12-04-03] [Hit: ]
they are more resistant to oxidation, since the carboxylic group is already fully oxidised.Carboxylic acids are more acidic due to the presence of the extra oxygen atom. The oxygen in the carbonyl group draws electrons away from the O-H bond, making this bond more polar than a normal O-H bond, so polar that it ionises to a small extent.......
If anybody could explain why this is it would be appreciated.

Cheers :)

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They are not necessarily more stable. However, because of the structure, they are more resistant to oxidation, since the carboxylic group is already fully oxidised.

Carboxylic acids are more acidic due to the presence of the extra oxygen atom. The oxygen in the carbonyl group draws electrons away from the O-H bond, making this bond more polar than a normal O-H bond, so polar that it ionises to a small extent. Because of this, it is easier for the hydrogen to dissociate, giving the molecule acidic properties. An alcohol does not have this activating mechanism, meaning alcohols are far less acidic.

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Draw out the structure for both the carbonate ion and the alkoxide(alcohol anion). Can you draw resonance structures for either of these molecules? Does resonance of charge lead to a more or less stable ion?

Sometimes questions answer questions, and sometimes they don't. Hopefully these will lead you to yours. Just remember to clear your head and think through it, around it, and in it, every single time you approach a problem. Otherwise you may be asking things you already can explain. : )
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