Question on Ethers?

[tuuursh]

I just took the AAMC FL 9 and one of the questions about ethers is starting to puzzle me. The answer stated that ethers cannot hydrogen bond with water, but my review book and from being a TA for orgo & bio chem, i do know they do have hydrogen bonding capabilities, but i know they're not as strong as the hydrogen bonding capabilities of alcohols.

Can someone clarify this for me? I don't want to make this same mistake again

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[mohad]

I haven't taken the test yet, but I know there is a distinction between hydrogen bond donor and hydrogen bond acceptor, which I always got wrong before. Ethers are hydrogen bond acceptors because the oxygen has 2 lone pair groups to accept hydrogen bonds from water. However, ethers themselves can not donate hydrogen bonds since they lack H-O/N/F. Maybe that will clear up the answer for you. Sorry i can't offer you much else without taking the test or reading the asnwer. Anyone else have a better explanation?

 

[rockyDoctora]

Ethers can only hydrogen bond when other molecules with H-O/N/F are present. If it's pure ether, there are no hydrogen bonds to form. Hope this helps!

 

[mohad]

Wait, so let me see if I have this straight: Ethers can't h-bond with one another, but they can h-bond to an extent with water, correct?

 

[tuuursh]

Ethers can only hydrogen bond when other molecules with H-O/N/F are present. If it's pure ether, there are no hydrogen bonds to form. Hope this helps!

Thank you guys - the answer key said that ethers cannot hydrogen bond with water.
I believe the question was comparing an ether to an alcohol, and the question went along the lines of what kind of bonding can the alcohol partake in that the ether in water cannot?
I don't want to give too much specifics, I'm not sure what we're allowed to do but the question asked to compare the ROH compound and the R-O-R compound in water