For organic chemistry we typically look at the stability of the end product to determine if the reaction will proceed. For instance for an Sn2 reaction we would check if the product anion is more stable or less stable than the nucleophile attacking - if the product anion is more stable than the nucleophile then the reaction would proceed e.g. R3COH+F- --> R3CF+OH- is viable as OH- is more stable than F- so the reaction would occur. 1) however what I don't understand is why we don't compare the stability of the neutral species; in the example they were R3CF and R3COH. 2) this matters because in the case of polar protic solvents F- becomes more stable than OH-. So in this chemical reaction: R3COH+F- --> R3F+OH- in a polar protic solvent, shouldn't this reaction be considered viable since F- is more stable than OH-? However I thought this reaction is still not viable despite the increased stability of F-?