Photon336
  • Photon336
The question is: What is the product of the reaction of 2-Hexene with CHCl3 in the presence of potassium tert-butoxide? I chose B: I thought Potassium tert-but oxide is more likely to act as a base. I thought that it pulls the proton off of CHCl3, because the chlorine groups could hold the stabilize the negative charge, and then CHCl3 adds to the double bond. But this idea is wrong..
Chemistry
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SOLVED
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chestercat
  • chestercat
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Photon336
  • Photon336
In case it can't be seen
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Rushwr
  • Rushwr
I have no Idea but is it the A?
taramgrant0543664
  • taramgrant0543664
I'm thinking it is B as well but I'm not 100% sure but I know it's not A because that would be the reaction of Cl2 instead of CHCl3

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Photon336
  • Photon336
@taramgrant0543664 That's exactly what i thought
Photon336
  • Photon336
but for whatever reason it's wrong
taramgrant0543664
  • taramgrant0543664
Do you know which one is right?
aaronq
  • aaronq
im pretty sure its D
taramgrant0543664
  • taramgrant0543664
D was my next thought but I can't picture how that reaction would go
Photon336
  • Photon336
This is what I thought of at first
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Photon336
  • Photon336
@aaronq @taramgrant0543664 D is correct
Photon336
  • Photon336
but I can't see how it would go..
aaronq
  • aaronq
its similar to that, CHCl3 gets deprotonated by t-butoxide, then the carbanion attacks the double bond and pushes the electrons to carbon 3, then that carbanion attacks intramolecualry
JoannaBlackwelder
  • JoannaBlackwelder
Photon336
  • Photon336
oooh...
JoannaBlackwelder
  • JoannaBlackwelder
Reacting with CHCl3 and a base makes a cyclo.
Photon336
  • Photon336
@aaronq okay I see it now, the carbanion attacks the other carbon and removes the chlorine and then creates the cyclic structure.
Photon336
  • Photon336
@JoannaBlackwelder to me I always have in my mind that three ring structures are unstable especially if they have large groups attached to them
JoannaBlackwelder
  • JoannaBlackwelder
Yeah, true
Photon336
  • Photon336
especially with those chlorines that's why i didn't consider that one at first

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