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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sj3107 on January 30, 2020, 07:26:29 AM

Title: Is ethanol a good leaving group?
Post by: 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

Title: Re: Is ethanol a good leaving group?
Post by: Babcock_Hall 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.

Title: Re: Is ethanol a good leaving group?
Post by: rolnor on January 30, 2020, 10:01:09 AM

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