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Topic: Why do ethers not undergo Sn2 with hydroxide?  (Read 1723 times)

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Offline Fluorspar

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Why do ethers not undergo Sn2 with hydroxide?
« on: March 06, 2013, 10:31:49 AM »
Hi there,

All my textbooks simply say that ethers (and acetals, but that's effectively the same thing) are stable in base, but give no reasoning. Is it not possible for OH- to attack one of the carbons next to the oxygen (as it would be electrophilic), giving an alcohol and a R-O- leaving group?

Thanks
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Offline Dan

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Re: Why do ethers not undergo Sn2 with hydroxide?
« Reply #1 on: March 06, 2013, 11:43:04 AM »
Quote from: Fluorspar on March 06, 2013, 10:31:49 AM
R-O- leaving group

Therein lies the answer...
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Offline Fluorspar

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Re: Why do ethers not undergo Sn2 with hydroxide?
« Reply #2 on: March 06, 2013, 11:45:06 AM »
Not such a good leaving group, I take it...
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