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Topic: Ethers+acid  (Read 3160 times)

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Offline Rutherford

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Ethers+acid
« on: July 10, 2012, 11:35:35 AM »
Write the products for the following reaction: CH3OC2H5+H2SO4(on heating)
a)on heating
b)in cold environment

I would say that in cold environment ethyl-methyl-ether gets protonated in two steps, so at the end there are SO42- and [CH3-O(H2)-C2H5]2+, but what would happen when the mixture is heated?

Offline discodermolide

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Re: Ethers+acid
« Reply #1 on: July 10, 2012, 11:42:32 AM »
Write the products for the following reaction: CH3OC2H5+H2SO4(on heating)
a)on heating
b)in cold environment

I would say that in cold environment ethyl-methyl-ether gets protonated in two steps, so at the end there are SO42- and [CH3-O(H2)-C2H5]2+, but what would happen when the mixture is heated?

Between the ether you suggest and H2SO4 you will get no reaction even on heating. Both ether carbons are primary.

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Offline Rutherford

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Re: Ethers+acid
« Reply #2 on: July 10, 2012, 11:53:31 AM »
So only protonation will take place?

Offline discodermolide

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Re: Ethers+acid
« Reply #3 on: July 10, 2012, 11:59:53 AM »
So only protonation will take place?

Perhaps, but nothing will happen. You won't get any ether bond cleavage if that's what you are looking for.
Ethers are really quite inert compounds.

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Offline DrCMS

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Re: Ethers+acid
« Reply #4 on: July 10, 2012, 12:06:40 PM »
Go look up how you can make say diethyl ether from ethanol.

Offline Rutherford

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Re: Ethers+acid
« Reply #5 on: July 10, 2012, 12:37:08 PM »
Go look up how you can make say diethyl ether from ethanol.
I know that, do you mean it is reversible?
So only protonation will take place?

Perhaps, but nothing will happen. You won't get any ether bond cleavage if that's what you are looking for.
Ethers are really quite inert compounds.
Ok, thanks.

Offline AWK

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Re: Ethers+acid
« Reply #6 on: July 11, 2012, 03:14:15 AM »
Quote
there are SO42- and [CH3-O(H2)-C2H5]2+

Only one proton on ether in concentrated H2SO4
Sulphuric acid is strong enough (but only on the first step of dissociation) to protonate an ether. Reaction of synthesis of ether with the presence of sulphuric acid is an equilibrium reaction with formation of water. Reaction proceeds with removing of the ether.
Solvolysis of ether will be possible when removed alcohol shows much higher boiling point then parent ether.
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Offline Rutherford

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Re: Ethers+acid
« Reply #7 on: July 11, 2012, 05:13:07 AM »
Thanks, it is clear now.

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