Reaction of epoxides with nucleophiles under basic conditions

by James

Description: When epoxides are treated with negatively charged nucleophiles, they will add to the least substituted position of the epoxide in an SN2 reaction.
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{ 5 comments… read them below or add one }

Anjala Wijayanthi

Thanks a lot . I was wondering how this reaction takes place.


Rajarshi Banerjee

In the second stage of the mechanism its should be H-OH2


Alexander Peltekoff

Think you could add a page on the opening of epoxides with a Nu to form a Polymer? My text doesn’t show the full mechanism and I would find it really helpful.


Prokhor Sobko

All examples shown at the acidic conditions. However, the title stated that basic conditions. Is it a mistake or I am missed something?



The nucleophile to open the epoxide is basic (in step 1). This results in a negatively charged oxygen. The purpose of acid workup (step 2) is to protonate the oxygen to give neutral OH.


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