are ethers soluble in water?

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hoyas19

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kaplan says ethers are slightly soluble but the 3rd test on top score said they aren't at all so i got the question wrong. i know they're barely soluble but which would you choose on the actual DAT?

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I would go with them not being at all soluble. That is unless there is a choice that says "barely soluble".
 
kaplan says ethers are slightly soluble but the 3rd test on top score said they aren't at all so i got the question wrong. i know they're barely soluble but which would you choose on the actual DAT?


Destroyer says it is soluble since it is polar. Oh well i will go with destroyer.
 
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Not all ethers are symmetric though...so slight polarity does exist.

Fo sho.
I guess if they start looking more and more like alcohols in that the Oxygen is completely on one side and lots of carbons on the other side.
 
i think im still a little confused. i looked at a previous post about this and they said that THF is totally soluble whereas diethyl ether is only slightly soluble so i guess it depends on what the question asks.

also, i was almost positive that ethers don't hydrogen bond but im not sure anymore..do they or does that too depend on what ether it is? thanks!
 
i think im still a little confused. i looked at a previous post about this and they said that THF is totally soluble whereas diethyl ether is only slightly soluble so i guess it depends on what the question asks.

also, i was almost positive that ethers don't hydrogen bond but im not sure anymore..do they or does that too depend on what ether it is? thanks!
Ethers can't hydrogen bond because there is no Hydrogen on the Oxygen. Ethers are different from alcohols and carbox acids.
 
Ethers can hydrogen bond with water but not with themselves because there is no F-H, N-H, or O-H. So, I think it would be slightly soluble, not sure though.
 
Ethers can hydrogen bond with water but not with themselves because there is no F-H, N-H, or O-H. So, I think it would be slightly soluble, not sure though.

That is true, but Oxygen on the ether has no hydrogens on it so it can put hydrogens out there for other oxygens to hydrogen bond to.
If you can mix ether with water then you deserve the Nobel. :D
 
That is true, but Oxygen on the ether has no hydrogens on it so it can put hydrogens out there for other oxygens to hydrogen bond to.
If you can mix ether with water then you deserve the Nobel. :D

Haha, yeah now that I think about extraction with the ether and aqueous layer, the fact that ether is insoluble in water makes more sense
 
im with water88. the lack of a hydrogen on the ether's oxygen doesnt keep it from reacting in hydrogen bonding, it just isnt a two way relationship. ethers are soluble in water but not miscible. the bent shape at the oxygen causes a slightly polar region to build up where the two lone pairs of electrons are and a positive charge where the alkyl groups are. the slightly polar portion allows some level of solvation between water molecules. to my understand, dimethyl ether is miscible in water while other ethers are soluble on some level.

ps - remember that DAT questions arent supposed to be absolute, theyre supposed to say "most of the time" instead of never, etc. So if an answer has never as an option for such a subjective question, its probably wrong.
 
im with water88. the lack of a hydrogen on the ether's oxygen doesnt keep it from reacting in hydrogen bonding, it just isnt a two way relationship. ethers are soluble in water but not miscible. the bent shape at the oxygen causes a slightly polar region to build up where the two lone pairs of electrons are and a positive charge where the alkyl groups are. the slightly polar portion allows some level of solvation between water molecules. to my understand, dimethyl ether is miscible in water while other ethers are soluble on some level.

ps - remember that DAT questions arent supposed to be absolute, theyre supposed to say "most of the time" instead of never, etc. So if an answer has never as an option for such a subjective question, its probably wrong.

Incorrect - This is directly from Wiki:

By contrast, substances are said to be immiscible if in any proportion, they do not form a solution. For example, diethyl ether is fairly soluble in water, but these two solvents are not miscible since they are not soluble in all proportions.

I really don't think the DAT will ask if ethers are either soluble or insoluble. (at least I hope not). They are partially soluble but it is very small.
 
If you guys have destroyer, please look at question 79 gchem. It says that "Water is polar, and will mix (miscible) with other polar molecules such as ether and alcohol. Water will not mix with other non-polar substances such as CBR4, benzene, C5H12,etc."

I originally answer the question that ether not soluble but i was wrong. The answer says that ether are soluble
 
Come on...I will agree it is slightly soluble, but barely that. It is NOT soluble. I don't care what Destroyer says...it's still not soluble. I am taking about the most common ether, diethyl ether.
 
We need one definite answer people!

And I made it of behalf of SDN. It is not soluble in water. I consulted with my associate. Octanol has hydrogen bonding similarly to ether but is not soluble due to its size.
 
First, apparently I'm getting the Nobel Prize because I mixed THF (an ether) and water today........ But the only reason 79 in destroyer says ethers are soluble is because it is a cyclic ether, Tetrahydrofuran and it makes the O bend with the electrons on the outside making it polar and mix with water.

And ethers with small carbon chains like dimethylether are miscible in water but larger carbon chained ethers are completely imiscible in water.

I would look at the question if it were on the DAT and try to figure it out but the answer is going to be that ethers are not soluble in water 90% of the time a question is asked about them.
 
First, apparently I'm getting the Nobel Prize because I mixed THF (an ether) and water today........ But the only reason 79 in destroyer says ethers are soluble is because it is a cyclic ether, Tetrahydrofuran and it makes the O bend with the electrons on the outside making it polar and mix with water.

And ethers with small carbon chains like dimethylether are miscible in water but larger carbon chained ethers are completely imiscible in water.

I would look at the question if it were on the DAT and try to figure it out but the answer is going to be that ethers are not soluble in water 90% of the time a question is asked about them.

Ouch...I said ether though, not "an ether." And we both know diethyl ether is commonly referred to as ether for short. Anyway, If you get a polarized type of ether it will be soluble, but we are just talking about the average there, like the most common type: ether (diethyl ether).
 
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