NH3 abstract H from COOH

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NH3 + RCOOH --> NH4+ COOR-

I'm confuse sometimes if sometimes a lewis base will go ahead and abstract a proton from a hydroxyl proton of an an alcohol or a carboxylic proton.

Does anybody know if there are some kind of trend that will predict if it does abstract a proton?
thanks for the help

 

[Danny289]

^sorry, but not really undertanding your question, in your equetion there is simple base and acid reaction. base gains "H" and acid looses "H".

 

[yankees27th]

If something is more acidic (higher Ka, lower pKa) it gives off its protons more easily. In a situation like the equation you gave, the less acidic (more basic) one will have take the proton, even if it is very acidic compared to most other things.