Photon336
  • Photon336
O-chem problem
Chemistry
chestercat
  • chestercat
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Photon336
  • Photon336
Attached here
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Photon336
  • Photon336
|dw:1437883637405:dw| Lone pair electrons on the oxygen attack the sulfur atom in SOCL2 creating a tetrahedral intermediate that collapses and results in the release of a chloride ion as a leaving group. Good leaving group (LG) = Something that's good at holding negative charge.
Photon336
  • Photon336
carbonyl has a propensity to reform, resulting in expulsion of chlorine.

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Photon336
  • Photon336
|dw:1437884048544:dw| chlorine attacks carbonyl, C=O resulting in loss of SOCL2 , H+ picked up by Cl-
Photon336
  • Photon336
|dw:1437884277920:dw|
Photon336
  • Photon336
|dw:1437884409597:dw| Now we've generated a great electrophile
Photon336
  • Photon336
Both oxygen and chlorine are withdrawing e density form the carbon making it a good site for a nucleophile to attack.
Photon336
  • Photon336
\[EtMgBr\] now we have our gringard reagent which is more like |dw:1437884957349:dw| Mg doesn't really want to form that bond with the carbon, though it does b/c it would rather lose electrons, that's why the bromine carries a partial negative while the magnesium a partial positive charge. so we really kind of have a carbanion in this system. I think of it as a complex, and this attacks our carbonyl, (C=O) acyl chloride that was just created.
Photon336
  • Photon336
|dw:1437885106270:dw| carbonyl is most likely going to reform, expelling the chlorine, giving us a ketone.
Photon336
  • Photon336
it's probably going to react again with the carbonyl C=O electrophilic center, since we technically have a carbanion
Photon336
  • Photon336
|dw:1437885322551:dw| The water is to do the work up and finish off the reaction, note we have an alkoxide ion, an oxygen with a negative charge. we need to get rid of that to form our alcohol
Photon336
  • Photon336
|dw:1437885449736:dw| we get a tertiary alcohol
Photon336
  • Photon336
This problem was taken from Organic Chemistry as a second language (Second semester topics) Klien for those of you interested.
taramgrant0543664
  • taramgrant0543664
Little messy but looks good. Good descriptions on how you did it though!
Photon336
  • Photon336
thanks a lot tara haha.. used that draw tool a little new to it.
taramgrant0543664
  • taramgrant0543664
Ya it's a little hard to use, I've used it helping people with math and it was tricky. Keep using it and it'll get easier!!
Photon336
  • Photon336
@Taramgrant0543664 yeah, I don't go on the math from that much, but I don't think chemistry is as popular though.. especially with O chem.
taramgrant0543664
  • taramgrant0543664
Chem is definitely not as popular which kind of sucks since it's a great thing to study! And o chem is definitely not my favourite part of chem I do like the experiments from this section of chemistry though
Photon336
  • Photon336
The o-chem forum is practically dead haha. I think I will close this one out.
taramgrant0543664
  • taramgrant0543664
Normally is and ok

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