Topic: Is ethanol a good leaving group? (Read 1485 times)

sj3107 · « **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

Babcock_Hall · « **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 pK_a values of the conjugate acids of these two species? Do you know the relationship between pK_a and leaving group?
EDT
With this information the answer becomes straightforward.

rolnor · « **Reply #2 on:** January 30, 2020, 10:01:09 AM »

One example of this is cleavege of ethyl-ethers with HBr i guess.

Topic: Is ethanol a good leaving group? (Read 1485 times)

sj3107

Is ethanol a good leaving group?

Babcock_Hall

Re: Is ethanol a good leaving group?

rolnor

Re: Is ethanol a good leaving group?

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