Epoxidation of Alkenes

[@VictortheOrganicChemistryTutor]

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[@andreitanasa2068]

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[@mecha37000fighter]

I don't understand why the oxygen would attack the alkene carbon, isn't the C=C pi bond electron rich/nucleophilic. Based on other alkene reactions I would guess the C=C pi bond would do a nucleophilic attack on the hydrogen of the peroxy acid? What exactly am I missing?

[@VictortheOrganicChemistryTutor]

Peroxides, including peroxy acids, are actually quite electrophilic. Think about how an alkene reacts with, say, halogens. Halogens have a ton of electrons as well, and yet, they are very electrophilic! Having an O-O bond makes peroxides, similarly to halogens, very electrophilic. Why is that the case? Well, that's a topic for a whole different discussion... We teach the intro organic chemistry in a very simplistic, I dare say primitive or superficial level. We don't touch the molecular orbital energies, the specifics of the HOMO-LUMO interactions, and the orbital geometries when talking about any of those reactions. So, yeah, some of those reactions will seem like they are contradicting the "basic" idea of nucleophilicity and electrophilicity we see in other examples, but in reality they don't.

[@mecha37000fighter]

Thank you very much for the response, this has been bugging me even after this college semester has ended! 😁 I'll go look up some of those concepts you mentioned, it might be too advanced for me to handle at the moment but at the very least I'll get a better sense of the lessons to come. Thank you once again for the prompt reply, I really appreciate the expertise 😎👍

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