Madison McVey*with acknowledgement of partner Allen Jorgenson (Eugenol data)CHEM 237 – 549November 10, 2016Natural Products and Alkenes Lab ReportResults and Discussion:In this lab, students focused on isolating two natural products, acetogenins and terpenes. The acetogenin that students seeked to isolate was eugenol and the terpene, limonene. Using steam distillation to extract limonene from 10.283 g of an orange peel and extraction to isolate eugenol from 2.0 g of clove oil. Once the isolation methods were complete, classification tests were run on each product. The permanganate and bromine tests were conducted on the limonene product, both concluding positive results. The permanganate test was positive due to the brown precipitate that formed, where as the bromine test was positive because the when added to the tube, the color of the bromine disappeared. Because the results indicated the presence of double bonds and results were positive, the product was then analyzed by preparative gas chromatography. The GC report indicated a large limonene peak, as expected. The ferric chloride, permanganate, and bromine tests were performed on the eugenol product and then the product was analyzed using an IR spectrum comparedto the reference spectrum. The bromine test resulted in a reddish color indicating the presence of an alkyne or an alkene, whereas the presence of phenols was confirmed by the red color appearing during the ferric chloride test. Thepermanganate saturation test was considered positive as well because of the brown precipitate that formed. The IR spectrum was taken and compared to the reference spectrum, revealing peaks at 2983.80 cm-1 (C-H) and 1366.15 cm-1 (CH3) for alkanes, and a peak at 1638.07 cm-1 (C=C) for an alkene group. Had eugenol not been isolated, a large peak around 3500.00 cm-1 would have resulted to indicate the presence of an alcohol group. There was a slight curve here to indicate possible errors, however it was determined that there was enough data to accurately conclude that eugenol had been isolated. Possible errors that occurred in this lab could include not allowing the steam distillation to completely finish distilling or not adding enough calcium chloride to remove all of the water, thus effecting the IR results of the eugenol