DLS
  • DLS
Organic chemistry
Chemistry
  • Stacey Warren - Expert brainly.com
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schrodinger
  • schrodinger
I got my questions answered at brainly.com in under 10 minutes. Go to brainly.com now for free help!
DLS
  • DLS
Which carbo cation is least likely to form as as intermediate? |dw:1360852772005:dw|
shubhamsrg
  • shubhamsrg
D) maybe ?
shubhamsrg
  • shubhamsrg
A) is 3 degree and so is C)

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shubhamsrg
  • shubhamsrg
B is 2 degree, also has a double bond which adds to the stability
DLS
  • DLS
its definitely not A for sure
DLS
  • DLS
C is not 3 degree i guess
shubhamsrg
  • shubhamsrg
C is attached to 3 carbons ?
DLS
  • DLS
its bridgehead
shubhamsrg
  • shubhamsrg
hmm ? well still there are 3 carbons !
shubhamsrg
  • shubhamsrg
If i had to put a guess, I'd say D)
DLS
  • DLS
ITS C DAMMIT
shubhamsrg
  • shubhamsrg
hmm,, sorry about that then! :|
DLS
  • DLS
man I really thought u shud know all that before 2 months of JEE LOL
DLS
  • DLS
hmm okay sorry :P
shubhamsrg
  • shubhamsrg
Wish your thinking was true!
shubhamsrg
  • shubhamsrg
Well I have never seen a bridged carbocation before.
DLS
  • DLS
are u freaking kidding me ._.
shubhamsrg
  • shubhamsrg
On a bridge head a positive carbon never occurs ~Wikipedia
shubhamsrg
  • shubhamsrg
http://en.wikibooks.org/wiki/Organic_Chemistry/Introduction_to_reactions/Carbocations
DLS
  • DLS
so what :P
shubhamsrg
  • shubhamsrg
hmm, that is why it must be least likely to form! hmm, seems legit
DLS
  • DLS
wtf
shubhamsrg
  • shubhamsrg
:)
DLS
  • DLS
whaaaaaaaaaaat
DLS
  • DLS
thoda detail zara?
shubhamsrg
  • shubhamsrg
well since bridged carbocation is not formed, hence it is least likely to be formed here.
shubhamsrg
  • shubhamsrg
never formed*
DLS
  • DLS
i asked why it isnt form ._. i dont want to accept it as a fact
DLS
  • DLS
formed*
shubhamsrg
  • shubhamsrg
I don't know the fact! I just learnt it!
shubhamsrg
  • shubhamsrg
reason of the fact*
DLS
  • DLS
\m/
shubhamsrg
  • shubhamsrg
Here, you may read this, this has the reason http://www.tricity.wsu.edu/Chem540/ar00096a001.pdf
DLS
  • DLS
god i cant read that whole thing :/
shubhamsrg
  • shubhamsrg
learn as fact! thats what I just did !
shubhamsrg
  • shubhamsrg
In chem, most of times, there aren't reasons, there are rules, !
DLS
  • DLS
rehne de be :P
shubhamsrg
  • shubhamsrg
sure! :D
DLS
  • DLS
http://fc06.deviantart.net/fs70/f/2011/288/3/c/nothing_to_do_here_by_rober_raik-d4cxltj.png
shubhamsrg
  • shubhamsrg
http://narwhaler.com/img/ys/x/i-see-your-point-spear-spiderman-YsX3vo.jpg
anonymous
  • anonymous
Shuld nt the answer be D............
chmvijay
  • chmvijay
i think answer is D
DLS
  • DLS
its C
DLS
  • DLS
and its proven I guess
DLS
  • DLS
@abb0t
abb0t
  • abb0t
If (A) is benzene, then it's (D). Remember you can't form primary carbocations ever.
DLS
  • DLS
answer is C?
DLS
  • DLS
wikipedia says too..
DLS
  • DLS
but i want smt more detailed
abb0t
  • abb0t
Wikipedia says the answer is C?
DLS
  • DLS
On a bridge head a positive carbon never occurs ~Wikipedia
abb0t
  • abb0t
The + isn't on the bridge though.
DLS
  • DLS
that is why it cant resonate,the charge is localized.
DLS
  • DLS
so isnt C in a worse condition than D? it cant resonate at all but D still can
abb0t
  • abb0t
Resonance is not the same as formation of a carbocation
DLS
  • DLS
its about the stability of the carbocation
abb0t
  • abb0t
Resonance just tells you where electron behaves or forms a more stable structure
DLS
  • DLS
more resonating structures=more stable C h as 0 resonating structures
DLS
  • DLS
D has one if you see
abb0t
  • abb0t
Draw them for acetylene.
DLS
  • DLS
|dw:1360961235810:dw| not sure duh
abb0t
  • abb0t
I don't think that would work. Did you move the hydrogen?????
DLS
  • DLS
idk man
abb0t
  • abb0t
Resonance is only movement of the electron. Not protons.
DLS
  • DLS
so whatnow
abb0t
  • abb0t
Maybe @BluFoot can help right now I'm not on my comp so I can't give detailed answers right now and don't have my notes w/ me. If you're on later I will explain better if no1 else has helped you. I gtg
DLS
  • DLS
hmm okay
anonymous
  • anonymous
A is very stable because of all the resonance from the phenyl groups. B is kinda stable from the resonance of the double bond. This is called an "allylic carbocation" http://science.uvu.edu/ochem/index.php/alphabetical/a-b/allylic-carbocation/ C has no resonance, but it's tertiary at least D is definitely the least stable. Vinylic carbocations (+ on the C=C) are reaalllllllyyyy unstable. The reason is based in orbitals. C=C are sp2, but with a carbocation it becomes sp. sp orbitals are situated close to the nucleus, so the positive charge is very close to the nucleus, which is positive, so it's unstable
DLS
  • DLS
okay,thanks :D
anonymous
  • anonymous
I've never seen the structure in C btw... do you know what it's called?
DLS
  • DLS
ive been taught its bridgehead carbon (out of the plane)
anonymous
  • anonymous
Oh right, I haven't learned about those. It's still probably D but don't make my word for it since I know nothing about the bridges.
DLS
  • DLS
its C idk why....
anonymous
  • anonymous
I have no idea, sorry :/
abb0t
  • abb0t
It's a bicyclo compound.
abb0t
  • abb0t
Well, "C" would form a radical rather than a carbocation since it's an all hydrocarbon structure. That could be one argument. I'm not entirely sure about this one to be honest. But I can't help but also think the answer could be D since you don't usually ever have primary carbocations. And there's no type of resonance in structure D. If you take out the double bond, you'd have another charge and that would definitely form a very thermodynamically unstable structure. It would definitely prefer to stay.
aaronq
  • aaronq
If the answer was to be C, then, i imagine that'd it would be because the strain put on it by it's inability to undergo an sp2 conformation (180 degree angles) since it's fixed on the frame and it would make of high energy/unstable

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