relative acid strength question

[athockey7]

---

Members do not see this ad.

so if you have a compound like FCH3CH2OH vs CLCH3CH2OH, the one with the F is the better acid because F is more electron withdrawing allowing the H to be released more easily.


BUT --- HCL is a better acid than HF because F is too electronegative it holds the H

So is it fair to say when an atom is bonded directly to an H, the MORE electronegative it is the WORSE acid... whereas if it is not directly bonded to the H then the MORE electronegative it is the BETTER acid it is?

not sure doee

 

[NA19]

Somewhat. Just thing about it logically. In HF, if F is electron-withdrawing, then it becomes very negative. Meaning it is good at attracting the very positive H. So the H will not fall off and the compound will not be acidic.

In alkyl halides, the F is bonded to a C. So it is withdrawing electrons from the C. This makes the C increasingly positive. And makes the C less able to hold onto H since positive C and positive H are not attracted (positives don't attract positives). So H will easily fall off and the compound will be acidic.

So, yes, your shortcut in a way is right. But try to actually think about what's happening.