Recorded October, Robertson, J. Neither of these ought to be present in camphor, and were not present in the literature IR as shown by SDBS or the lab standard obtained by Bard. Since normal phase gas chromatography was used, the more polar compound would stick to the column longer; therefore borneol would have to be more polar to have a longer retention time. Better handling of chemicals and tighter experimental procedures would help to avoid significant losses of products in multistep reactions such as these in the future. This can also be seen in the gas chromatography data in how the isoborneol peak is much larger than the borneol peak. The solid was dissolved in CH2Cl2 Biochem J. Results and Discussion: Based off of the data, both isoborneol and borneol were synthesized from the reduction of camphor as seen in the gas chromatography data so the experiment was successful. Reference IR spectrum of - -camphor purchased from Sigma Aldrich. Since there is still a camphor peak on the gas chromatography spectra, the reduction reaction did not go to completion. This solid is then collected over a Hirsh funnel and allowed to dry. As for the weak O-H stretch, it could be representing water or the alcohol in isoborneol. References: Pavia, D. Camphor was first obtained and dissolved in methanol.
There was, once again, significant melting point depression. Therefore, this demonstrates that the product has a hydroxyl component as in isoborneol and borneol.
This indicates that the amount of product lost from camphene to isobornyl acetate, and from isobornyl acetate to isoborneol was mild in comparison to what was lost between isoborneol and camphor.
The initial step was the acid-catalyzed electrophilic addition of camphene to give isobornyl acetate, followed by saponification to give isoborneol, and finally oxidation with sodium hypochlorite to form camphor. The gas chromatography also shows evidence of the reaction proceeding when reducing camphor into borneol and isoborneol.
Results and Discussion: Based off of the data, both isoborneol and borneol were synthesized from the reduction of camphor as seen in the gas chromatography data so the experiment was successful. Overall, this reduction reaction of camphor into isoborneol was completed relatively successfully.
Conclusion The purpose of this experiment was to synthesize camphor in a multistep synthesis beginning with camphene. All of this most likely means there was a mixture of unreacted isobornyl acetate and isoborneal on the sample.
Oxidation of borneol to camphor reaction scheme
The IR spectrum of following product, isoborneol, was questionable due to the presence of a carbonyl stretch indicative of isobornyl acetate. The camphor had an incense-like smell and the isoborneol—borneol mixture had a similar odor. Metabolism of Camphors and Related Compounds. C indicated the presence of impurities in the sample. Dissolve this solid in methylene chloride then add anhydrous sodium sulfate to remove any water in solution. To a stirred solution of ketone 1. Camphor's IR spectrum was similar to the literature but indicated some water or alcohol as well as a C-O bond. The results for the final product, camphor, were similarly puzzling. Reference IR spectrum of - -camphor purchased from Sigma Aldrich. Isobornyl acetate was successfully synthesized with an IR spectrum that matched the literature, although only two thirds of the expected amount of product resulted. Sodium borohydride was slowly added in portions and the mixture was heated.
This could mean that some isobornyl acetate remained in the sample. The difference between the observed melting point of
based on 115 review