Return of The SN2

by James

The concepts and reactions you learn in Org 1 don’t suddenly go away in Org 2. You’ll see a lot of the things you learned last semester thrown back to you in slightly different circumstances. Take everyone’s favorite reaction from Org 1, nucleophilic substitution (bimolecular) – aka, the SN2.

One of the most important reactions of alcohols is the Williamson ether synthesis, where an alcohol is treated with base, and then an alkyl halide. This should hopefully not look new to you – it’s just an SN2 reaction. Now – let’s say you wanted to make the ether below (tert-butyl methyl ether). What would be the best way to do it?  Well there’s two different SN2 reactions that could work.

 

Which one is going to give you the desired product, and which one isn’t going to work?

Hint: remember that the “big barrier” to the SN2 is steric hindrance.

Thanks for reading! James

P.S. More on the Williamson Ether synthesis in the Reaction Guide, here