Ether and Epoxide Reactions

This organic chemistry video tutorial provides a basic introduction into the reactions of ethers and epoxides. It discusses the williamson ether synthesis reaction as well as the production of ethers using the alkoxymercuration demercuration reaction. The full version of this video contains example problems of acid catalyzed cleavage of ethers in addition to acid catalyzed and base catalyzed cleavage of epoxides. In addition, it discusses the synthesis of epoxides from alkenes using a peroxyacid such as MCPBA and by means of the halohydrin formation reaction.
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[@TheOrganicChemistryTutor]

Direct Link to The Full 29 Minute Video on Patreon: bit.ly/3BbhijN

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We're about to go over ethers and epoxides in my class, so this is so helpful. Thank you!

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There we no epoxides in this video, but otherwise loved it! Thank you.

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More like “no info on epoxides unless you pay” 🙄 this video was a waste of time

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The title of the video is too confusing - considering the fact that epoxides don't even get mentioned! Please correct the title!

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Do you have an example many example of tangent circle and secant circle

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Can you make a video on epoxide ring opening?

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[@galaxywolf3192]

Why doesn’t 4:30 example leave you with an alkene? Chloride is a decent leaving group.

[@iconicguy5717]

yes you're right but it will be a minor product due to the tertbutyl oxide being bulky. As it is bulky, its tendency to attack as a nucleophile will be less.

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4:50 why doesn't the tert-butoxide act as a base and eliminate the chlorine to form an alkene?

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Because steric hinderances on bulky bases cause them to act as bases instead of nucleophiles

[@michaelspltwrng]

Jay’ crisp sorry i should’ve been clearer but i meant why can it not take a hydrogen from the carbon and form an alkene, kicking off the Cl (E2 elimination)

[@yourlocalscribe948]

@@michaelspltwrng well elimination and substitution are often competing pathways. I think for this one there is probably a *minor* elimination product, how minor it is idrc to check but you could figure it out by checking bond dissociation energy etc. I think the intermolecular substitution is just favorable in terms of enthalpy. You wouldnt be wrong if you said there was some amount of elimination

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@@michaelspltwrng also remember substitution is highly highly favored under primary substrates

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You didnt draw 1 epoxide

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Not first

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1st comment