Borneol: An Oxidation-Reduction Scheme
Borneol; An Oxidation-Reduction Scheme
Nicolas Gibson
Lab Time: Tuesday 11:30 am
Abstract: In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this experiment show that camphor was produced during oxidation (0.6576 g). The IR spectrum shows a strong peak at 1740 cm-1 representing a carbonyl compound, which was concluded to be a ketone by the 2,4-DNP test and the deshielded peak at 218.4 ppm in the 13C NMR spectrum. The product of the reduction reaction was isoborneol (0.1591 g). The IR spectrum indicates a medium, broad peak from 3000-3500 cm-1 representing a hydroxyl group. The hydroxyl group is confirmed from the chromic acid test and the peak in the 13C NMR spectrum with a chemical shift of 80 ppm. These results support the hypothesis. Steric approach control states that steric hindrance will control the stereoselectivity of a reaction and direct the reducing agent to the less hindered face. In this case the endo face is the least hindered and will produce isoborneol. Further evidence from comparing the 13C NMR spectrum of borneol to isoborneol will show a difference in chemical shifts of one of the methyl bridge carbons that will conclude in what position the hydroxyl group is situated.
Introduction: This laboratory experiment focuses on the procedures of oxidation and reduction reactions. Oxidation is a reaction that results in a loss of electron density around a carbon
Nicolas Gibson
Lab Time: Tuesday 11:30 am
Abstract: In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this experiment show that camphor was produced during oxidation (0.6576 g). The IR spectrum shows a strong peak at 1740 cm-1 representing a carbonyl compound, which was concluded to be a ketone by the 2,4-DNP test and the deshielded peak at 218.4 ppm in the 13C NMR spectrum. The product of the reduction reaction was isoborneol (0.1591 g). The IR spectrum indicates a medium, broad peak from 3000-3500 cm-1 representing a hydroxyl group. The hydroxyl group is confirmed from the chromic acid test and the peak in the 13C NMR spectrum with a chemical shift of 80 ppm. These results support the hypothesis. Steric approach control states that steric hindrance will control the stereoselectivity of a reaction and direct the reducing agent to the less hindered face. In this case the endo face is the least hindered and will produce isoborneol. Further evidence from comparing the 13C NMR spectrum of borneol to isoborneol will show a difference in chemical shifts of one of the methyl bridge carbons that will conclude in what position the hydroxyl group is situated.
Introduction: This laboratory experiment focuses on the procedures of oxidation and reduction reactions. Oxidation is a reaction that results in a loss of electron density around a carbon
References: 1. University Of Winnipeg Organic Chemistry 2203 Lab Manual, 2014, Pages 7-11. 2. McMurry J.; Organic Chemistry, 8th edition.; Brooks/Cole Cangage Learning., 2012, Pages 277,281,437,440-441,465,473 and 645. 3. Zubrick, J.W.; The Organic Chem Lab Survival Manual, 8th edition.; John Wiley & Sons Inc., New York, 2011, Pages 281-283. 4. McMaster University: Department of Chemistry. Isomerization of an Alcohol by Oxidation-Reduction: Borneol, Camphor, and Isoborneol. http://www.chemistry.mcmaster.ca/~chem2o6/labmanual/expt7/2o6exp7.html (accessed March 5, 2014). 5. University of Texas. Oxidation-Reduction Scheme: Borneol – Camphor – Isoborneol. http://www.utdallas.edu/~scortes/ochem/OChem_Lab2/recit_notes/exp35_ox_borneol.pdf (accessed March 6, 2014) 6. Chemical Book. L(-)-Borneol(464-45-9)13CNMR. http://www.chemicalbook.com/SpectrumEN_464-45-9_13CNMR.htm (accessed March 9, 2014). 7. Chemical Book. DL-Isoborneol(124-76-5)13CNMR http://www.chemicalbook.com/SpectrumEN_124-76-5_13CNMR.htm (accessed March 9, 2014).