LRCamphor.docx - Oxidation of Borneol and Reduction of Camphor Alisha Seay Organic Chemistry Lab Fall 2019 Purpose The purpose of the first lab

LRCamphor.docx - Oxidation of Borneol and Reduction of...

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Oxidation of Borneol and Reduction of Camphor Alisha Seay Organic Chemistry Lab Fall 2019
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Purpose The purpose of the first lab experiment was to examine to see if Oxone could replace common toxic chromium oxidizing agents and if sublimation could be used to purify a solid. The second part of this experiment was then to reverse reaction one by reducing the camphor product back into borneol or isoborneol. The purpose of the second experiment was to test the stereoselectivity of the product and to determine whether it was preferred to have and endo or an exo attack. The purity of the experiments and their products were then tested using melting point, IR spectroscopy, 1 H NMR spectroscopy and gas chromatography. Reaction Scheme Oxidation of Borneol Reduction of Camphor
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Mechanism The reaction mechanisms are drawn out in the lab manual on pages 136 and 142. 1 The sodium chloride acts as the catalyst in the mechanism for oxidizing the Oxone. The Oxone is then reduced throughout the mechanism due to this. The oxidation state changes throughout the mechanism because the carbon goes from one bond to the oxygen and a bond to hydrogen to two bonds to the oxygen and no bonds to hydrogen. When it comes to the stoichiometry of the reduction of camphor with sodium borohydride, one molecule of sodium borohydride is used in the mechanism to reduce four camphor molecules. In an actual lab, excess sodium borohydride would need to be used along with methanol. The borate ester intermediate replaces the hydrogens on each of the Boron bonds and makes an oxygen- boron bond. The each oxygen is attached to a bicyclic ring. The positively charged sodium ion is then near the negatively charged Boron ion as an ionic bond. Procedure The procedure was followed as directed from the lab manual. 1 The procedure was not deviated from. The sublimation apparatus consisted of a
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150 mL beaker containing the crude product to be purified. A 100 mL round bottom flask containing ice on top of the beaker and paraffin wax around the top of the beaker and the bottom of the flask to prevent any gas or air from escaping. The apparatus then placed on top of a hot plate in the hood. Reagents Table Day 1: Oxidation of Borneol to Camphor Compou nd Molecu lar Weight (g/mol) Gra ms mL mm ol Densi ty (g/mL ) Melti ng Point (°C) Solubil ity Hazard s (1S)- Borneol 154.25 1.0 0.9 9 6.5 0.99 208 Soluble Irritant Oxone 614.7 2.4 2.0 9 3.9 1.15 70 Soluble Corrosiv e NaCl 58.44 0.11 0.0 5 1.88 0.902 801 Soluble KHSO5 152.2 1.2 1.0 45 1.95 1.15 120 Soluble Corrosiv e (1S)- Campho r 152.25 0.98 0.9 9 6.5 0.992 174- 179 Soluble Flamma ble Table 1: Properties referenced from PubChem Day 2: Reduction of Camphor to Borneol Compou nd Molecu lar Weight (g/mol) Gra ms mL Densi ty (g/mL ) Melti ng Point (°C) Solubil ity Hazard s NaBH 4 37.84 0.40 0.428 1.07 250 Soluble Flamma ble, corrosiv e, acute toxic, irritant and health hazard Ethyl Acetate 88.1 11.1 10 0.902 -83.8 Soluble Irritant and Flamma ble
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(1S)- Campho r 152.25 0.4 0.397 0.992 174- 179 Soluble Flamma ble Methan ol 32.042 5.05 4 0.792 -98 Miscibl e Flamma ble, Acute toxic and health hazard (1S)- Isoborn eol *** Soluble Irritant (1S)- Borneol 154.25 0.405 0.409 1.01 202 Soluble Irritant
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