How do you discern Acidity when it comes to a carbon attached to an atom.

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JohnTulisa

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My answer is absolutely wrong, so now its C vs D, since they're arguing the fact that electronegativity wins during same attachment to the carbon, what is the hierarchy that I should follow? Thanks guys!
 
In this case, you should notice the factor that contributes to acidity is something called "Inductive Effect".

Obviously, Fluorine is a lot more electronegative than Sulfur and Carbon. So the answer choose that has Fluorine closest to the acidic proton has the lowest pKa.
 
Remember when ranking acids, you always want to think of the stability of the conjugate base. The conjugate base of the above choices would have S- instead of SH. Whichever conjugate base is more stable, it means the acid is stronger (stable conj. base = strong acid, unstable conj base = weak acid).

The correct answer has a Fluorine on the end because the Fluorine helps stabilize the negative charge of the conjugate base. Comparing it to choice A, you know that D is stronger because the fluorine is closer to the negative charge, so it will have a larger stabilizing effect. This is definitely something you want to become good at!
 
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