Thaekross
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Is it possible to have an organolithium compound with a hydroxyl group?
http://s27.postimg.org/fqa9opc73/image.png
Are either of these compounds possible?
If so, how would one go about it?
I was asked the other day and it got me thinking: My theory was that chloromethanol or 2-chloroethanol and Lithium metal could be used, but I wondered
if the metal would react to form something with a Li atom at either end (i.e. Alkoxyl-organolithium).
Okay, so think of it like this: It's the part of existence that makes different things happen. I guess you could call it the first thing other than
nothing.
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gdflp
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No, those compounds are not possible. In the initial reaction which you propose, the lithium metal would preferentially deprotonate the alcohol,
rather than reacting with the halogen as you want. If any lithium did react with the halogen, the lithium superbase formed would immediately
deprotonate a nearby unreacted alcohol.
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Thaekross
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Thank you, very useful information 
Okay, so think of it like this: It's the part of existence that makes different things happen. I guess you could call it the first thing other than
nothing.
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fluorescence
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The second molecule can be made but not protonated.
If you think of a ring opening of an oxirane.
It's called Lithium 2-Lithioethoxide
http://pubs.acs.org/doi/abs/10.1021/jo00292a029
If you just read the first lines in the introduction they mention Oxirane there and how
it's converted into something that should if I'm not mistaking a bit like your molecule.
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