Day Seven: LOTS of Separations

This post is two days late, for which I apologize.  Everything that follows is written from Friday's point of view.

I never knew before this morning that so many different separations could take place to isolate an organic product.  We treated the solution that had been stirred overnight with three solids: sodium bisulfite to reduce the oxidizing agents, bleach and m-CPBA; sodium bicarbonate to neutralize the carboxylic acid formed in the reaction; and sodium chloride to extract any remaining water from the dichloromethane component of the solution.  The process involved a good number of runs through the separatory funnel and one vacuum filtration, and some of the layers looked rather interesting:

There were originally three layers in this particular separation.  The portion of the solution that resembles a cloud was in-between the organic and aqueous layers.  We believe that this center layer formed because the composition was both dichloromethane- and water-soluble, so the cloud was trying to exist in both layers at once.  By the time we performed the last separation, only two layers remained.  The organic solution was left to dry with sodium sulfate and will be characterized on Monday.



Additionally, we began to make preparations for our Grignard reaction of cyclohexene oxide, which will also take place on Monday.  We distilled "anhydrous" ether over a period of about four hours in this rather impressive apparatus:

We used a 5-L three-necked round-bottomed flask, a condensation column, a distilling head, a West condenser, a vacuum filter, and three receiving flasks, two of which were 1-L teardrop-shaped flasks.  Our apparatus also included a coiled copper tube immersed in ice to ensure that the water entering the condenser was as cold as possible.  This tube, along with the condensation column, was important to be sure that only ether and not water was distilling into the receiving flask.  We will use this more anhydrous ether to make our Grignard reagent.



Hopefully soon, I will provide on this blog the procedure used for the Baeyer-Villiger oxidation and the reference for our standard workup.  Enjoy the rest of the weekend!