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|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.
carbonyl has a propensity to reform, resulting in expulsion of chlorine.
|dw:1437884048544:dw| chlorine attacks carbonyl, C=O resulting in loss of SOCL2 , H+ picked up by Cl-
|dw:1437884409597:dw| Now we've generated a great electrophile
Both oxygen and chlorine are withdrawing e density form the carbon making it a good site for a nucleophile to attack.
\[EtMgBr\] 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.
|dw:1437885106270:dw| carbonyl is most likely going to reform, expelling the chlorine, giving us a ketone.
it's probably going to react again with the carbonyl C=O electrophilic center, since we technically have a carbanion
|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
|dw:1437885449736:dw| we get a tertiary alcohol
This problem was taken from Organic Chemistry as a second language (Second semester topics) Klien for those of you interested.
Little messy but looks good. Good descriptions on how you did it though!
thanks a lot tara haha.. used that draw tool a little new to it.
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!!
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
The o-chem forum is practically dead haha. I think I will close this one out.
Normally is and ok