November 30, 2022, 06:20:51 AM
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Topic: Is ethanol a good leaving group?  (Read 850 times)

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Offline sj3107

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Is ethanol a good leaving group?
« on: January 30, 2020, 07:26:29 AM »
If you generate +OHEt in a reaction mechanism, can you kick it out? Is it a good enough leaving group? I always thought alcohols were poor leaving groups and I can't find much online about ethanol specifically

Offline Babcock_Hall

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Re: Is ethanol a good leaving group?
« Reply #1 on: January 30, 2020, 09:45:49 AM »
It is important to differentiate between (negatively charged) ethoxide versus (neutral) ethanol as leaving groups, and you seem to be focused on the latter.  Do you know the pKa values of the conjugate acids of these two species?  Do you know the relationship between pKa and leaving group?
EDT
With this information the answer becomes straightforward.
« Last Edit: January 30, 2020, 10:19:30 AM by Babcock_Hall »

Offline rolnor

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Re: Is ethanol a good leaving group?
« Reply #2 on: January 30, 2020, 10:01:09 AM »
One example of this is cleavege of ethyl-ethers with HBr i guess.

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