Are ethers miscible in water?

[failedmagician]

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Destroyer says yes. Top score says no. Which is it?

 

[failedmagician]

http://forums.studentdoctor.net/showthread.php?t=552729

and

http://forums.studentdoctor.net/arch.../t-422599.html


Still Do not really know. 😕

 

[nze82]

It's a bit complicated in case of ethers. Ethers have lone pair of electrons on their oxygen, which allows them to establish hydrogen bonding with water molecules. Therefore, as long as these lone pairs are sufficiently exposed, ethers are water soluble. This exposure is maximum in case of cyclic ethers, and minimal in case of aliphatic (non-cyclic ethers). Therefore, cyclic ethers tend to be water soluble; whereas, aliphatic ethers are either not soluble at all or have minimal solubility (Aliphatic ethers with up to 3-4 carbons are water soluble to some extent).
So, really, the solubility of ethers in water depends on the kind of the ether that we're interested in.

 

[failedmagician]

It's a bit complicated in case of ethers. Ethers have lone pair of electrons on their oxygen, which allows them to establish hydrogen bonding with water molecules. Therefore, as long as these lone pairs are sufficiently exposed, ethers are water soluble. This exposure is maximum in case of cyclic ethers, and minimal in case of aliphatic (non-cyclic ethers). Therefore, cyclic ethers tend to be water soluble; whereas, aliphatic ethers are either not soluble at all or have minimal solubility (Aliphatic ethers with up to 3-4 carbons are water soluble to some extent).
So, really, the solubility of ethers in water depends on the kind of the ether that we're interested in.

Makes complete sense thank you again. That's what I was thinking based on those old threads. But I did not want to assume. Thank you again for your explanation.

 

[doc toothache]

Dimethylether has a solubility of 32.8 g/100ml while diethylether has a solubility of 6.9g/100ml. Oxirane and tetrahydrofuran are miscible with water while furan is insoluble in water. Maybe Destroyer had those compounds in mind when claiming solubility of ethers.

 

[dentalmon]

I think it is..

 

[navneetdh]

i used the MCAT o-chem book by kaplan and in there it said Ethers are aprotic solvents. So i would say they are not miscible in water since they wont be able to make H-bonds.

and on similiar note they said alcohols are protic solvents and therefore they should be able to make H-bonds and dissolve in water easily, which everyone knew they do.

 

[dfymarine]

i used the MCAT o-chem book by kaplan and in there it said Ethers are aprotic solvents. So i would say they are not miscible in water since they wont be able to make H-bonds.

and on similiar note they said alcohols are protic solvents and therefore they should be able to make H-bonds and dissolve in water easily, which everyone knew they do.

ethers can make hydrogen bond in water, it has lone pairs!

aprotic solvents simply mean that the solvent does not have hydrogen for solvation.

 

[nze82]

ethers can make hydrogen bond in water, it has lone pairs!
Where did you come up with that?!!
Ethers DO NOT form hydrogen bonds. It takes more than just having lone pairs of electrons for a compound to establish hydrogen bonds?
aprotic solvents simply mean that the solvent does not have hydrogen for solvation.

🙂

 

[joonkimdds]

I think it's 50% miscible.

 

[sixkiller]

🙂

I think what the person meant is that ether can act as a H-bond acceptor...not that ethers can hydrogen bond amongst themselves.

 

[navneetdh]

yeah i thought "Hydrogen bonds form on the FON" so yeah Ethers wont make hydrogen bonds. lone pair of electrons shouldnt make a diff.

and the aprotic solvents explanation i got from the kaplan MCAT book. I didnt find any typos mistakes etc in it for any topic and looked definitely reliable so I am sticking to what they said.

 

[printer21]

i thought polar solvents dissolve in polar and non polar in nonpolar? Thus.. if the ether is polar, then it dissolves, if not, then it doesn't dissolve...