R-OH + SOCl2 stereochemistry

[Dasypus]

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Does anyone know if we should try to figure out / memorize the stereochemistry of reacting an alcohol with SOCl2? The AAMC list seems to be silent on the matter: it says to know "reactions with SOCl2 and PBr3." But what should we know about them? Is there an assumed solvent/workup here?

 

[dmf2682]

Does anyone know if we should try to figure out / memorize the stereochemistry of reacting an alcohol with SOCl2? The AAMC list seems to be silent on the matter: it says to know "reactions with SOCl2 and PBr3." But what should we know about them? Is there an assumed solvent/workup here?

I believe socl2 reacts with an sn2 mechanism, so make sure you account for the backside attack.

 

[Dasypus]

Okay, that'd definitely true in the presence of pyridine, which is what TPRH has it with. But 😕 The Wiki tells me that it's not really SN2, but rather its own weird thing, SNi (http://en.wikipedia.org/wiki/SNi_reaction), and that the stereochemistry is sometimes inverted and sometimes retained, depending on solvent and workup. Which is what inspired my question in the first place. I'm so confused! 😕

 

[MedPR]

The outline says SOCl2 and PBr3 specifically? Wow.

 

[milski]

The outline says SOCl2 and PBr3 specifically? Wow.

Yes. Under important reactions for oxygen containing compounds. I guess it is important. 😱

 

[dmf2682]

Okay, that'd definitely true in the presence of pyridine, which is what TPRH has it with. But 😕 The Wiki tells me that it's not really SN2, but rather its own weird thing, SNi (http://en.wikipedia.org/wiki/SNi_reaction), and that the stereochemistry is sometimes inverted and sometimes retained, depending on solvent and workup. Which is what inspired my question in the first place. I'm so confused! 😕

Oh yeah. Sometimes my prof says that it's just like xx reaction but slightly different, but for our orgo class we can treat it as such. That's my plan for the mcat.