Day Two: To Design an Experiment

Today was the perfect reminder that this research project is much more concerned about the process than the product.  I love being part of a collaborative group that is happy to progress at an even but not hurried pace.  It gives us the opportunity to focus on preparation, what we're attempting to accomplish, and how the work can be divided to simultaneously challenge us, highlight our strong points, and complete our tasks in an efficient manner.

As I mentioned yesterday, we did learn to operate the IR and NMR instruments today.  We will certainly practice more in the future, but it was helpful to get an overview of these instruments' functions and review how to read the spectra that they produce.  These spectra will be essential in determining whether or not our reactions proceed as we expect.

Since a big component of our project deals with monomers that we aren't even sure will polymerize, Dr. Bass suggested that we carry out a practice reaction with materials that we have and that have been evaluated in the literature before we attempt to synthesize our target compounds.  This process will also familiarize us with the procedures on a general level.  As it turns out, preparation methods aren't necessarily right on-hand, and some research and modifications are needed before beginning the process.

The first procedure that we modified was the oxidation of cyclohexanol to cyclohexanone:

The process was relatively simple, as we had a method outlined for this process (1) and simply wanted to scale down from 16 mL of starting material (cyclohexanol) to 10 mL.  The only concern that we've encountered thus far has to do with the apparatus.  The article calls for a three-necked 500-mL round-bottomed flask with an addition funnel, a West condenser, and a thermometer inserted in the three necks.  However, it may be simpler for us to use materials already accessible in the student organic chemistry laboratory - namely, a 250-mL round-bottomed flask, a distillation head, and alternating uses of the addition funnel and thermometer at the top portion of the distillation head.  We will find out what Dr. Bass suggests when we return on Monday.

Our next step involved searching for methods describing the Baeyer-Villiger oxidation of cyclohexanone to caprolactone and general Grignard reactions of cyclohexene oxide:

We found a method for the Baeyer-Villiger oxidation in Synthetic Communications via the SciFinder database (2).  The reaction with cyclohexanone is expected to proceed over the course of thirty minutes with 100% yield.  The Grignard procedure will be detailed in later posts.

So far, it has been a thoroughly enjoyable process, and we look forward to beginning our first series of reactions next Monday morning!



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References:

1. Mohrig, Jerry R., Christina Noring Hammond, Paul F. Schatz, and Terence C. Morrill.  "Green Chemistry: Oxidation of Cyclohexanol Using Sodium Hypochlorite."  Modern Projects and Experiments in Organic Chemistry: Miniscale and Williamson Microscale.  2nd ed.  W.H. Freeman and Company, 2002.  107-14.  Print.
2. Alam, M. Mujahid, Ravi Varala, and Srinivas R. Adapa.  "Bi(OTf)3-Catalyzed Baeyer-Villiger Oxidation of Carbonyl Compounds with m-CPBA."  Synthetic Communications 33.17 (2003): 3035-3040.  http://web.ebscohost.com/ehost/pdfviewer/pdfviewer?sid=c39ae472-aa6e-4a8c-b2fc-1c33e5172b38%40sessionmgr104&vid=2&hid=119.

Images courtesy of Google and SciFinder.