Camphor Reduction Lab Report

4039433
Results and Discussion
The rationale for oxidation and reduction reactions was determining the final product structure of camphor. Camphor contains a sp2-hybridized center, following the experiment and reduction process, a new stereocenter is created since it converted to sp3-hybridized center. Furthermore, this enables the formation of two different products. Reduction of camphor elicits two potential different products: borneol and isoborneol (see Figure 1). A mixture of camphor, methanol, and sodium borohydride (NaBH4) was boiled and vacuum filtered. The organic material was dissolved in dichloromethane (CH2Cl2) and small amounts of anhydrous sodium sulfate (NaSO4) was added for the reduction process. Reduction involves an increase in the number of carbon-hydrogen bonds; in order to ascertain the final structure of the reduction of camphor, NMR spectroscopy, IR spectroscopy, melting point analysis can be carried out, and the thermodynamics and kinetics assist in determining the final product.

Figure 1. Reduction of camphor to borneol and isoborneol. Borneol has an -OH group in a pseudo-axial position while the -OH group in isoborneol is pseudo-equatorial. When examining the product stability, the

A mixture of 0.25 g of camphor (1.64 mmol), 1.5 mL of methanol, and 0.25 g of sodium borohydride (6.60 mmol, NaBH4) was boiled for 2 minutes. Moreover, the addition of 10 mL of ice deionized water resulted in a white solid after the organic solution was vacuum filtered. The organic solid was dissolved in 10 mL of dichloromethane (CH2Cl2) and small amounts of anhydrous sodium sulfate (NaSO4) to dry. The organic solution was decanted and evaporated for melting point (203.3-203.8 °C), NMR, and IR spectroscopy. Product formation and heats of formation (borneol = -1.203675E6 kJ/mol, isoborneol = -1.203687E6 kJ/mol) were analyzed. 1H NMR (CDCl3, 400 MHz): δ 3.62 (dd, 1H), 4.01 (t, 1H). IR (cm-1): 1734 (C=O), 2949 (sp3 CH’s), 3373