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Topic: can ether form H-bonds with water  (Read 13561 times)

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Offline hkalfighter

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can ether form H-bonds with water
« on: April 17, 2006, 12:57:52 PM »
ether is used to extract organic layer in solvent extraction because it's immiscible with water . However , can ether form H-bond with water with it's O on ROR coz there are 2 lone pair e- ? if it can , why is it immiscible with water ?
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Offline Albert

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Re: can ether form H-bonds with water
« Reply #1 on: April 17, 2006, 01:15:12 PM »
No, they don't. You can foresee it looking at their boiling points.
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Offline hkalfighter

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Re: can ether form H-bonds with water
« Reply #2 on: April 17, 2006, 01:48:19 PM »
why don't they form ? they have an O with lone pair e- which should attract the bared H on H2O
How about aldehyde and ketone , there are H-bonds with H2O . what s the difference between ether and aldehyde , ketone ?
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Offline Albert

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Re: can ether form H-bonds with water
« Reply #3 on: April 17, 2006, 03:13:31 PM »
Ethers can be only H-bond acceptor. In fact, small ethers, such as dimethyl ether, are soluble in water. For what concerns the others, their oxygen atoms are less accessible for hydrogen bonding to water molecules: that's why ethers are unsoluble in water.
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Offline Donaldson Tan

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Re: can ether form H-bonds with water
« Reply #4 on: April 17, 2006, 03:23:14 PM »
the key word is accessibility
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Offline hkalfighter

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Re: can ether form H-bonds with water
« Reply #5 on: April 17, 2006, 03:38:56 PM »
accessibility ?? does it mean bared H can't get access to the O on ether due to the steric hinderance of large alkyl group attached to it ?
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Offline Albert

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Re: can ether form H-bonds with water
« Reply #6 on: April 17, 2006, 04:07:19 PM »
Yes, indeed.
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Offline hkalfighter

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Re: can ether form H-bonds with water
« Reply #7 on: April 18, 2006, 02:38:54 AM »
how about aldehyde and ketone ?
they don't form H-bond with each other but with H2O , am i right ?
and how about RF , i thought there's H-bond with H2O too , am i right ?
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Offline hkalfighter

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Re: can ether form H-bonds with water
« Reply #8 on: April 18, 2006, 08:23:03 AM »
why does Aldehyde or ketone form H-bond with water or i have made it wrong ?
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Offline AWK

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Re: can ether form H-bonds with water
« Reply #9 on: April 19, 2006, 02:01:19 AM »
Ethyl ether is slightly soluble in water. There is no doubt that these molecules form hydrogen bonds.
I searched CSD database and found at least 4 examples with HB water-ethyl ether with distance of 265 to 300 pm between donor and acceptor.
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Offline Mitch

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Re: can ether form H-bonds with water
« Reply #10 on: April 19, 2006, 02:17:24 AM »
Okay sounds good to me. :)
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