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HCl is a stronger acid because the bond between H and Cl is weaker than the bond between H and F (this is because Cl has a greater atomic radius). HClO is a stronger acid than HBrO because the resulting anion of HClO is more stable as a result of Cl having a greater electron withdrawing power than Br.
In this case, you are looking at the HF bond length vs the HCL bong length. Since Florine is more elctronegative than Cl, it will have a stronger pull on the H make it harder to donate the H. The longer the bond, the easier it is to remove the H. It follows one of three rules in the book for stronger acids
Because there is no O present, think of it as simple terms. H attached to an F that is small in radius is going to have a short bond, But CLs radius is bigger so longer bond, more easily broke, more acidic.
This comparison is different because in your first comparison, you are comparing bond lengths, but in your second comparison, you are comparing the electronegativity. The reason why we compare electronegativity in your latter comparison is because H is attached to O in both molecules; thus, comparing the bond lengths won't do you anything. You need to look at the electronegativity, or dipole, in order to determine how stable the anion will be after the hydrogen proton is donated.
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