4

Basically, you are on the right track and answered the question. First, NaNH$_2$ is used as a base to deprotonate the terminal alkyne (see this Reagent Friday). Second, the generated nucleophile opens the epoxide in an S$_\mathrm{N}$2 fashion, usually adding to the lesser substituted carbon which in your case yields a quaternary alcohol after acidic workup (...


1

The reaction would theoretically occur through an SN2 mechanism because the hydroxyl (OH) group is bound to a primary carbon, and SN1 will usually only occur under tertiary (steric) conditions with a weak nucleophile. What you are trying to do is referred to as "activation of alcohols". The OH- is not a good leaving group because OH- is a stronger ...


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