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You are watching: Why is oh a bad leaving group

OH is a strong base which renders it an excellent nucleophile. Why then is it an excellent leaving group?

Also, why are bad nucleophiles great leaving groups? What are the criteria a great leaving group have to fulfill?


I can’t fairly follow you because hydroxide is among the lousiest leaving teams well-known to chemisattempt that are still taken into consideration potential leaving groups (mostly by students, that is).

Keep in mind that nucleophilicity and also basicity are unassociated as are nucleophilicity and also leaving team capability. Here are 2 examples:

hydroxide is a pretty good nucleophile, a really solid base and also a lousy leaving group.

iodide is a pretty excellent nucleophile, a really weak base and also a very good leaving group.


Good leaving groups are groups that are stabilized in the reactivity medium. In general, the conjugate base for a solid acid is an excellent leaving group, and also indeed, you deserve to use the same rationale for why somepoint is the conjugate base of a solid acid to why it"s a great leaving group.

This, of course, refutes your insurance claim that hydroxide is a great leaving group since it is not the conjugate base of a strong acid.

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Nucleophicility is a much harder idea to quantify in regards to what is important, and also I think it"s finest if I not attempt a lengthy answer right here.


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