Expt #2 - Oxidation of Borneol and Reduction of Camphor

Reading Assignment - Lab Manual, Expt 35. Technique 9.

Prelab - Make sure you include the moles to be used of all reactants and the theoretical yields of the products.

Overview - You will oxidize a chiral alcohol, borneol (endo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol) to the corresponding ketone, camphor (1,7,7-trimethylbicyclo[2.2.1]heptan-2-one) using sodium hypochlorite. TLC will be used to make sure the reaction is complete before purifying the camphor product and characterizing by IR and mp determination. This ketone will then be reduced back to an alcohol using NaBH₄ and we will observe the stereoselectivity of this reaction using ¹H NMR.

Procedure - We are carrying out Experiment 35A, B, C. The following are modifications and other notes to keep in mind when carrying out the procedures. 

    1. Use a regular jacketed condenser but do not connect water tubes or run water through as one normally would do. 

    2. Use the dry film method (p XXX) for the IR of the camphor product.

    3. I recommend using a screw cap vial in place of the 10-mL Erlenmeyer flask in the isolation of the first product.

    4. TLC will not be used.

    5. We will not obtain the IR spectrum or run a GC of the final product. Instead a mp and ¹H NMR spectrum will suffice. 

Report:

Assigned questions. Answer questions  2, 3, 5 and 6 in the lab manual.

Results and Discussion.

Make sure to integrate the NMR spectrum of the final product as described in the Part C procedure and present these results, as well as the Camphor TLC, IR and mp data, in your results tables.

Make sure to include discussions of all of the following:

• The yields obtained in each reaction and reasons for loss of yield.
• The completeness of the first reaction as indicated by TLC.
• The purity of the camphor product of the first step as indicated by IR and mp.
• Interpretation of the IR spectrum of camphor including peak assignments and a comparison to the literature spectrum.
• The stereoselectivity of the hydride reduction step (part C - ¹H NMR results). Explain thoroughly based on the structure of the reactant reactant. (You may want to examine a molecular model to check your explanation.)