I've shown the reaction for an alkyne starting material but it also works for alkenes to give alcohols rather than ketones.
So why did I end up doing an oxy-mercuration? Well as it turns out we needed to get hold of a serious quantity of acetoxymethyl vinyl ketone and a quick search resulted in the following result:
Now these Scandos did a thorough job and wrote a fairly detailed experimental procedure:
A few small additions to the experimental procedure would be:
1) During the acetylation the reaction is indeed somewhat exothermic and unintentionally I proceeded to boil the crap out of it (boils at ~150 oC) for about 5 minutes.
2) If reactions go jet black and shite starts precipitating from them this should be included in the experimental procedure. This is exactly what happens when you start adding the alkyne to the mercury cocktail. At this stage I was convinced that I had fried my alkyne but apparently black crap means that the reactions is working smoothly! This is what it looks like after the addition of a small amount of the alkyne:3) Removing "part of the acetic acid" should be changed to: "remove most of the acetic acid". Otherwise, you'll end up doing nothing but adding sodium bicarbonate and filtering bucket loads of sodium acetate off for an entire day (just like I did!).
Anyway, to finish this oxy-mercuration business the chemistry works very well but man I was working my ass off for two days to get it all done. There's quite a few time consuming steps in this prep such as the adjusting of the pH to 8 followed by removal of endless quantities of sodium acetate not to mention a vacuum distillation at the very end. D!