Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Lanthanide17 on April 25, 2016, 11:44:58 AM
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Okay, so I've been reading on organic acids and bases and I've been a bit confused about some stuff. Most inorganic acids are easy to understand as they dissociate to produce OH- and H+ ions. However, my problem is with organic acids and ammonia/amines. According to what I've read, carboxylic acids are acidic because they dissolve in water to produce H+ ions, making them proton donors, hence acids. Ammonia on the other hand is basic because it accepts H+ ions in solution, making it a proton acceptor and hence a base.
1)My first question is, how is it possible for water molecules to break up the strong covalent O-H bond in carboxylic acids. Is it because it is polar? And if so, why doesn't the same thing happen with the N-H bond in the case of Ammonia.
2)If Nitrogen can be basic by donating a lone pair to H+ ions why can't the Oxygen in the O-H bond in carboxylic acids do the same?
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2)If Nitrogen can be basic by donating a lone pair to H+ ions why can't the Oxygen in the O-H bond in carboxylic acids do the same?
It does the same, and H3O+ is formed.
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It might be worth pointing out that carboxylic acids are weak acids and that ammonia is a weak base. In other words, dissociation is far from complete. When a carboxylic acid does dissociate, what intermolecular forces come into play to stabilize the carboxylate ion?