[Lanthanide17]

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?
 

[AWK]

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.

[Babcock_Hall]

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?