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anonymous

  • one year ago

List in order of most acidic to least acidic: \(CHF_2CH_2CH_2CO_2H\) \(CH_3CF_2CH_2CO_2H\) \(CH_3CH_2CF_2CO_2H\) \(CH_3CH_2CH_2CO_2H\)

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  1. anonymous
    • one year ago
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    Acidity is the measure of the tendency of acidic H to go in to the solution. C. is the most acidic, as two florine atoms are very electro negative, and pull on them the e- form the C, which after that pulls e- from COOH. |dw:1438626295009:dw| |dw:1438626474232:dw|

  2. anonymous
    • one year ago
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    For the other, you need to consider the distance of COOH from F atoms. C. B. A. D.

  3. nincompoop
    • one year ago
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    look for the size of the atom and the kind of atom that is most electronegative, look for the shape of the molecule and various partial charges

  4. nincompoop
    • one year ago
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    giving you the answer won't help you but providing you some of the tools to identify, you'll be able to solve this kind of problem yourself

  5. nincompoop
    • one year ago
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    a quick review helps look for David Klein's Organic Chemistry as a second language it is discussed in acid-base chapter

  6. anonymous
    • one year ago
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    Right, I had assumed the inductive affect would just entirely pull the electrons away so I think @Bozhena helped because it looks like it's more like every other one is sort of either helping or hindering the acidity.

  7. nincompoop
    • one year ago
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    induction is just one of the key things to look for when looking for acidity

  8. nincompoop
    • one year ago
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    orbitals count too

  9. anonymous
    • one year ago
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    So can I label it through like this to reason out if it will help or hinder it? |dw:1438627078381:dw| Since this places a partial positive on the oxygen, this will allow the Hydrogen to leave and of course the carboxylic acid is resonance stabilized.

  10. nincompoop
    • one year ago
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    |dw:1438627430132:dw|

  11. nincompoop
    • one year ago
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    oxygen is more electronegative than hydrogen and carbon so it shouldn't be partial + charge

  12. nincompoop
    • one year ago
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    |dw:1438627525767:dw|

  13. anonymous
    • one year ago
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    I was considering it based on it being kind of an alternant structure, see: http://chemistry.umeche.maine.edu/CHY556/Alternant.html But I agree, oxygen is not strictly positive, only partially more positive than it would have been normally. I'm starting from those two extremely electronegative fluorines as being partially negative, leaving some deficit of electrons at the carbon boned to those two. Since this carbon is quite positive, then the next over will be partly negative as a sorta wavelike effect that travels down the molecule weaker and weaker of an effect as it gets away from the Fluorines. Similarly this is kind of like the explanation for why halobenzenes are ortho-para directors and rarely add to the meta positions, so I'm sorta taking this kinda perspective but trying to place everything together relatively well.

  14. nincompoop
    • one year ago
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    true

  15. anonymous
    • one year ago
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    I guess what I'm saying is I'm overcomplicating it and it's been a while since I did this stuff so I gotta like rememorize a handful of pKas and stuff haha.

  16. nincompoop
    • one year ago
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    ya memorizing pKa is a pain

  17. anonymous
    • one year ago
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    Yeah don't tell anyone I only want to do chemistry and not be distracted by math. Ok so here's what I don't get: If Fluorine is so electronegative then won't it pull the electron density away from the carboxylic acid, therefore destabilizing the resonance structure meaning losing hydrogen is actually less favorable in this example @Bozhena

  18. nincompoop
    • one year ago
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    correct

  19. nincompoop
    • one year ago
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    here is what I think, the F's are quite far and not big enough to have that huge effect maybe I am dreaming haha I just woke up

  20. nincompoop
    • one year ago
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    I see why you put + in oxygen

  21. nincompoop
    • one year ago
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    their difference in electronegativity is very little 3.0 vs 3.5

  22. anonymous
    • one year ago
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    Yeah I have some stuff messed up in my brain, but then again this reminds me of that weird rule for stabilities of alkenes when it comes to the disubstituted ones I think. Actually I don't even remember what the exception was exactly, but something weird.

  23. anonymous
    • one year ago
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    Do either of you know what I'm talking about? (sorry on a side tangent here haha) Like something to do with cis/trans or EZ in their reactivities perhaps? not sure... I guess I just better grab my book since I can kinda remember what the page looked like.

  24. nincompoop
    • one year ago
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    it is time to crack our books open or perhaps ask king abb0t he knows this stuff like a pimp keeping track of H's

  25. Photon336
    • one year ago
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    @nincompoop klien... that's a really good book, I wish he were my prof for o-chem

  26. anonymous
    • one year ago
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    \(\color{blue}{\text{Originally Posted by}}\) @nincompoop their difference in electronegativity is very little 3.0 vs 3.5 \(\color{blue}{\text{End of Quote}}\) What did you mean by this, where did you find this and what are you referring to?

  27. nincompoop
    • one year ago
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    that would mean you need to be in John Hopkins University in Maryland, USA

  28. nincompoop
    • one year ago
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    I think it is in Maryland

  29. nincompoop
    • one year ago
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    ya he makes most of his money breaking down and doing simple reviews for orgo

  30. nincompoop
    • one year ago
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    on the right side

  31. nincompoop
    • one year ago
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    maybe I am thinking about something else hahaha

  32. Rushwr
    • one year ago
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    I agree @Bozhena

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