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Part of a question I did involved comparing the acidity of NH4+ vs. HF. I reasoned that:
NH4+ -----> yields a conjugate base: NH3
HF-------> yields a conjugate base: F-
Based on the fact that F- has a charge, whereas NH3 does not, I thought that F- would be considered a stronger, more reactive base. The negative charge would destabilize the base, making it more reactive. Thus, HF would be a weaker acid than NH4+. However, this was incorrect. What is wrong with this reasoning?
The correct reasoning would have been to look at the electronegativity difference between N and F. Since Fluorine is more electronegative, the bond between H and F is more polar, and thus more likely to break, making HF more acidic.
NH4+ -----> yields a conjugate base: NH3
HF-------> yields a conjugate base: F-
Based on the fact that F- has a charge, whereas NH3 does not, I thought that F- would be considered a stronger, more reactive base. The negative charge would destabilize the base, making it more reactive. Thus, HF would be a weaker acid than NH4+. However, this was incorrect. What is wrong with this reasoning?
The correct reasoning would have been to look at the electronegativity difference between N and F. Since Fluorine is more electronegative, the bond between H and F is more polar, and thus more likely to break, making HF more acidic.