Order C-I, C-Br, C-Cl, & C-F Bonds by Length

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Discussion Overview

The discussion revolves around the ordering of carbon-halogen bonds (C-I, C-Br, C-Cl, C-F) by bond length. Participants explore various factors that may influence bond length, including electronegativity and atomic radii, while seeking a method to determine the order without resorting to molecular orbital diagrams.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant suggests that electronegativity could determine bond length, proposing that the shortest bond would be with the most electronegative halogen (fluorine).
  • Another participant questions whether atomic radii might be sufficient to predict bond lengths, arguing that the carbon-halogen bonds are similar enough to allow for simpler assumptions.
  • It is noted that both atomic radii and electronegativity follow a similar pattern, with one participant expressing uncertainty about the reasons behind trends in atomic size across periods.
  • One participant expresses skepticism about relying solely on electronegativity, citing a lack of examples where electronegativity is the only variable affecting bond length.
  • Another participant agrees that while atomic size is a factor, it may not be conceptually sufficient to determine bond lengths, emphasizing the role of electronegativity and electron affinity in the context of carbon's interactions with halogens.
  • Concerns are raised about the potential for misinformation due to a lapse in recent chemistry knowledge.

Areas of Agreement / Disagreement

Participants express differing views on the adequacy of electronegativity and atomic size as predictors of bond length, indicating that multiple competing perspectives remain without a clear consensus.

Contextual Notes

Participants acknowledge limitations in their understanding and recall of chemistry concepts, which may affect the accuracy of their claims. The discussion does not resolve the complexities of the factors influencing bond length.

henry3369
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Arrange these bonds in order of increasing bond length.
C-I, C-Br, C-Cl, C-F

Is there a way to figure this out without drawing molecular orbital diagrams and determining the bond order?
 
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its been a while since chemistry, but won't electronegativity do it , shortest being carbon with the most electronegative (flourine)?
 
What about radii of the atoms involved? Aren't they enough to predict the outcome? These are all very similar bonds, carbon-halogen, no need for any more advanced approach when you can safely solve the problem assuming "all other factors are being equal".
 
The radii and the electronegativity follow the same pattern in this case, one is because of the other but its amazing how much you forget in a year (i can't remember off hand why size decreases as number increases across a row, I am sure with a little thinking I'd get it)

but if either of s are right both of us are right in the context of your question and I'm pretty sure we are
 
I am not convinced following electronegativity is a good idea. I can't think of good examples of molecules where the electronegativity is the only thing changing (or at least where all other changes are negligible) which is an important condition for such comparisons.
 
you may be right, as I said its been a year and I can't get into my chemistry brain right now, but I'm sure electronegativity goes down with increasing radius so our answers would be the same in this context.

personally I feel just looking at the size of the atoms isn't conceptually enough, it happens to work here but the haogens sharing with carbon in the first place cause it wants those electrons bad and carbon doesn't want to give them up.
how bad the halogen wants them would be its electronegativity and changes with the halogen choosen
how much carbon wants to keep them would be its electron affinity, and is constant

sooo, how hard there pulled together should be to some degree a function of electronegativity right? like I said its been a minute and my brains in physics world atm. so any misinformation is possible and accidental
 
Jediknight said:
I feel just looking at the size of the atoms isn't conceptually enough

In general it is not, but this is a very specific question.
 

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