Photon336
  • Photon336
Organic chemistry question
Chemistry
  • Stacey Warren - Expert brainly.com
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katieb
  • katieb
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Photon336
  • Photon336
A nice question about acidity
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dessyj1
  • dessyj1
I believe the answer would be C
dessyj1
  • dessyj1
I am not entirely sure, though. Esters, for sure, are more acidic than alkanes, and I choose option C over option A because I having more than one branched functional group weakens the acidity of the structure.

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dessyj1
  • dessyj1
What do you think?
Photon336
  • Photon336
|dw:1437680730609:dw| Let's look at the alkane first. like it would be so hard to pull off a Hydrogen form the end because that molecule wouldn't really be stable. well.. unless it was let's say if we used like grinard reagent. I think actually that the Ka for this molecule would be so small and, correspondingly it's pKa so high that, that proton wouldn't even be able to be pulled off. so like we obviously know that that one isn't possible so that's out.
Photon336
  • Photon336
@dessyj1 have you heard of ARIO?
Photon336
  • Photon336
for ranking compounds based on acidity we take into account ARIO so in order it would be: Atom Resonance Induction Orbitals
dessyj1
  • dessyj1
I have not heard of ARIO. My knowledge of organic chemistry only goes a far as high school.
dessyj1
  • dessyj1
Those compounds are organic compounds, right?
Photon336
  • Photon336
|dw:1437681138719:dw| You are right that the first molecule I would be acidic; but let's also look at the third compound and yes you're also right they're organic
Photon336
  • Photon336
So for ARIO we use that to rank compounds in terms of acidity so we consider first the atom were dealing with, then if there is any resonance, induction, and then orbitals. I'm not too keen on orbitals though. but the idea is that an acid does one thing A. GIVES Up a proton B. Has a negative charge a better acid is one that: can stabilize the negative charge better. a more stable negative charge = it's a better acid and it won't want to take that proton back. this can be done with the size of the atom Resonance Induction things like that.
Photon336
  • Photon336
|dw:1437681448511:dw| you'll probably learn about this later, but don't think its covered in HS as much, but there are certain protons/hydrogens that can be removed from a compound
dessyj1
  • dessyj1
So, because the di-ester will be more comfortable with losing a hydrogen, it is- in turn - more acidic?
Photon336
  • Photon336
yeah, i think that's (di ketone) if i remember correctly
Photon336
  • Photon336
i'll show you the hydrogens
Photon336
  • Photon336
|dw:1437682141969:dw| those would be the hydrogenates that would be removed most easily. you could take off the others as well. you know how mechanisms work yet or no?
Photon336
  • Photon336
say if we had a strong base or something. |dw:1437682535300:dw| it would pull off the proton from that molecule, right in the middle of those two carbonyl groups. the arrow just shows us where the electrons are going, while the R could mean any group.
Photon336
  • Photon336
|dw:1437682622691:dw| see what I did there?
Photon336
  • Photon336
Think of the oxygens as, they have a high electronegativity so the negative charge is happy there, and it's stable.
Photon336
  • Photon336
You can also move that negative charge around too, because of resonance
Photon336
  • Photon336
and resonance makes it more stable.
Photon336
  • Photon336
ok another question what if i had something like this
Photon336
  • Photon336
|dw:1437683203892:dw| These two molecules illustrate something called induction
Photon336
  • Photon336
The \[CF _{3}\] group is very electronegative so its going to pull electron density from the - charge on that oxygen once you lose the proton. and it's going to be more stable
Photon336
  • Photon336
But the catch is, for induction the longer the distance it is, it's effect doesn't really matter it goes down
Photon336
  • Photon336
so based on that which one would be more acidic ?
dessyj1
  • dessyj1
The structure with the shorter carbon chain due to induction?
dessyj1
  • dessyj1
And I was mistaken, that was not an ester.
Photon336
  • Photon336
exactly
Photon336
  • Photon336
induction, in this case is like if you have highly electronegative atoms or groups that are in close proximity to part of the molecule where your acidic proton is.
dessyj1
  • dessyj1
Ah, okay. Nice. Thank you. I learned something new. One more question. In regards to the longer carbon chained structure, it would be best to take a hydrogen from the carbon closest to the tri-bromomethane group right?
Photon336
  • Photon336
Hey can you draw that out? I'll be happy to help
dessyj1
  • dessyj1
|dw:1437686943622:dw|
Photon336
  • Photon336
good question.. |dw:1437687292922:dw| hm.. I guess you could do this like take off a negative charge from the carbon near the CF3 Group but it would be hard, I guess you would need a really strong base to do that.
Photon336
  • Photon336
if we looked at that molecule you drew there are 3 hydrogens that could possibly be pulled off.
dessyj1
  • dessyj1
By the way, I put the negative charge in place of the hydrogen I had pulled out as a example. That was the hydrogen I wanted to pull off.
Photon336
  • Photon336
oh i see, I think that's possible b/c the flourines could stabilize the negative charge. @empty hey what do you think about this?
Photon336
  • Photon336
I still think that it's possible, b/c of those fluorine groups would stabilize that - charge though
dessyj1
  • dessyj1
Ok, and if you took a hydrogen near the cooh group, the cooh group would stabilize the charge as well?
Photon336
  • Photon336
yeah, but I think that the most acidic proton would be the one on the OH group, but I think you can also take those ones off too.

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