Thaekross - 23-8-2015 at 17:58
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).
gdflp - 23-8-2015 at 19:10
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.
Thaekross - 23-8-2015 at 21:00
Thank you, very useful information 
fluorescence - 24-8-2015 at 04:19
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.