Hydroboration/Oxidation of 1-Octene

Introduction
We have covered the hydroboration/oxidation reaction extensively in lecture. Now you will see how the reaction works in the laboratory by performing it on the the terminal alkene, 1-octene. One of the key goals of the experiment will be to see the regiochemistry of the reaction: will 1-octanol or 2-octanol be formed?

Procedure
Get a 5 mL conical-bottomed reaction vial and a small magnetic stir bar from the drying oven, put the bar in the vial, and quickly fit the vial with a septum and screw cap.  After allowing the vial to cool for a few minutes, add 1.00 mL of the 1M BH3*THF, using the syringe provided; use the calibrations on the syringe for measurement.  When not in use, the syringe should be stored inserted in the bottle of reagent!  The septum in the reagent bottle is difficult to pierce; try to put the needle through the septum in the same spot each time. When the vial has been charged with 1M BH3*THF, take the vial back to your bench and clamp it in place in an ice bath on a stir plate (note: no heat is to be applied in this experiment).

Using a 1 mL syringe fitted with a 2" needle, deliver 0.157 mL of 1-octene dropwise into the stirred vial.  After 15 minutes, open the vial and carefully deliver about 0.3 mL of methanol into the vial to destroy excess BH3; vigorous foaming may occur.  When foaming has subsided, add 1 mL of 2.5 M NaOH.  Immediately add 1 mL of 30% H2O2. Stir the mixture vigorously.  After 15 minutes, stop stirring and remove the upper organic layer to a 15 x 150 mm test tube.  Extract the lower aqueous layer with two 2 mL portions of ether, combining each organic layer with the original organic layer.  Extract the combined organic layers with one 3 mL portion of water, then one 3 mL portion of sat. NaCl.  Dry the organic layer with Na2SO4, and evaporate off the ether in a warm water bath. Run an NMR and GC on the product.

Report
In your report you must identify your product based on your NMR and GC evidence. Be sure to discuss what specific features of your spectrum and chromatogram led to your conclusion. Write out the mechanism that accounts for your product's formation and discuss why, theoretically, the other product did not form. Discuss how you can improve the percent yield and purity of your product.