I was looking to make the lesser known ether Ethyl Isopropyl Ether. I am looking for this because it has a higher boiling point than Diethyl Ether.
I was hoping to make it with the Williamson ether synthesis if this is possible.
This may not work, but if it does, I think the reaction would go like this: C2H5Br + C3H8OH =NaOH=> C3H8OC2H5 + H2O + NaBr
I have a question about this.
Does Ethyl Isopropyl Ether form peroxides? If so, do I try to prevent this by the same methods as I would with Diethyl Ether?macckone - 31-12-2013 at 07:42
Yes, it forms peroxides.
More so than ethyl ether but not as bad as isopropyl ether.
Keep in mind you may get some degree of disproportionation
so the BP might not be as stable as ethyl ether or isopropyl ether.12thealchemist - 1-1-2014 at 02:49
Are you sure that you've got the Williamson synthesis right? I thought it was an alkoxide + halogenoalkane -> ether + salt. Correct me if am wrong,
but the NaOH could hydrolyse the ethyl bromide, as a side reaction. However, it would be good if your method did work. It would make ether synthesis
much easier, since alkoxides require elemental alkali metals, which are expensive and hard to get hold of.
Also, how about this?: http://www.scienceforums.net/topic/31282-can-someone-critiqu...Aconite - 3-1-2014 at 20:53
- This is unlikely to work without very high temperatures (too high for ethyl bromide to remain as a liquid unless under pressure)... and even then,
doubtful. The equilibrium lies almost completely towards the alcohol and hydroxide. Typically alkoxides are prepared as salts by dissolving a reactive
metal (sodium, potassium, lithium) into the anhydrous alcohol.
- The ether would form peroxides on standing in air.Random - 3-1-2014 at 23:46
Could aluminum or magnesium alkoxide be used?Organikum - 4-1-2014 at 10:26
Thanks, it works now. So is aluminum alkoxide a strong enough base? Alkali metal alkoxides are probably much stronger and maybe it's meant for them.
Aluminum alkoxides are much cheaper fir a home chemist.DraconicAcid - 4-1-2014 at 16:36
You don't want your alkoxide to act as a base; you want it to act as a nucleophile. I would hazard a guess that the aluminum alkoxide would be a
poorer nucleophile than the the potassium or sodium alkoxide, since there'd be more covalent character to the metal-oxygen bond. I don't know if this
would stop your reaction from happening.UnintentionalChaos - 4-1-2014 at 16:43
Aluminum is an inappropriate metal choice here. It's oxide is amphoteric and it's halides are powerfully lewis acidic. Aluminum halides will react
with alkali alkoxides to form aluminum alkoxides, which is the opposite of what you want happening. Magnesium might work but probably not as well as
an alkali alkoxide.Random - 4-1-2014 at 17:13
Yeah, so magnesium is my best bet then. I might try it once I find a way to make alkyl chlorides with easily obtained stuff.
