Why are more polarized bonds weaker (Acid dissociation)?

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SUMMARY

The discussion centers on the relationship between bond polarity and bond strength, specifically comparing the H-F bond to the H-I bond. It establishes that while the H-F bond is stronger than the H-I bond, the acidity of hydrofluoric acid (HF) is influenced by the high bond strength and the enthalpy of hydration of the fluoride ion. The argument that stronger bonds lead to weaker acids is challenged, emphasizing the importance of considering electron affinity and hydration enthalpy in acid dissociation. The discussion also touches on the impact of electron-donating groups on the O-H bond strength in carboxylic acids.

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  • Understanding of acid dissociation and bond enthalpies
  • Familiarity with concepts of polarity and bond strength
  • Knowledge of electron affinity and hydration enthalpy
  • Basic principles of carboxylic acids and inductive effects
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  • Research the concept of acid dissociation constants (Ka) and their relation to bond strength
  • Study the role of hydration enthalpy in acid-base chemistry
  • Explore the inductive effect in organic chemistry and its impact on acidity
  • Examine the differences in bond strength and polarity among various halogen acids
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Chemistry students, organic chemists, and researchers focusing on acid-base reactions and bond strength analysis.

yucheng
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Wikipedia says that:
The weak acidity in dilute solution is sometimes attributed to the high H—F bond strength, which combines with the high dissolution enthalpy of HF to outweigh the more negative enthalpy of hydration of the fluoride ion.
(https://en.wikipedia.org/wiki/Hydrofluoric_acid)
(the H-F bond is highly polar compared to the H-I bond)
(H-F bond is stronger than H-I bond)

It is a common argument to say that H-F bond is stronger than H-I bond on the basis of bond enthalpies:

$$\text{HX} -> \text{H(g)} + \text{X(g)}$$.

However, for dissociation of acids, we must actually consider (hence the electron affinity comes in)

$$\text{HX} -> \text{H}^+(g) + \text{X}^-(g)$$,

and then the hydration of the ions, no? Does this mean the argument given above is... inaccurate, though it works?
____________
For O-H bonds in carboxylic acids, electron donating group causes the O-H bond to be less polar hence stronger.
Carboxylic acids, https://en.wikipedia.org/wiki/Inductive_effect

Why Is polarity related to bond strength? Why are polar bonds weaker than non-polar bonds?
 
Last edited:

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