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Experiment 36: Determination of the Structure of a Natural Product in Anise Oil

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Name CHE 173 Sec # January 25, 2005 Experiment 36: Determination of the Structure of a Natural Product in Anise Oil

Purpose: The purpose of this experiment is to isolate the major component of anise oil and determine its identity and structure using melting point determination and IR spectroscopy.

Introduction: The major component of anise oil has the chemical formula C10H12O. This compound is said to be hydrogen deficient, meaning that it contains less hydrogen atoms than would be needed for each of the carbon atoms to have the maximum amount of hydrogen atoms attached. The IHD, or index of hydrogen deficiency for this molecule is 10. This indicates that there must be five rings or double bonds in the structure. Each of these would …show more content…

After adding the anise oil, the mixture was allowed to heat for 20 minutes rather than 15 minutes as stated. Lastly, the IR spectrum analysis was previously prepared so no actual IR spectrum analysis was carried out during the course of the experiment.

Results: No substantial qualitative data was collected, except that the original reaction mixture turned a purple color. Upon the addition of anise oil and heat, the reaction mixture turned a brown color. And with the addition of NaHSO3 the mixture turned a white color. The mass of the final product sample was measured to be 0.08g (see Calculation 1). The melting point range for this sample was 172.8-185.4ºC in Trial 1 and 171.6-185.2ºC in Trial 2 (see Table 1). The IR spectrum of anise oil can be found attached. Peaks appear to exist at 3022.86, 3002.41, 2957.58, 2933.88, 2912.63, 2834.94, and 2723.19 (cm-1). Another set of peaks appear to exist at 1608.06, 1510.55, 1464.73, 1441.16, 1306.3, 1283.06, 1247.18, 1174.78, 1036.26, 964.58, 839.29, and 787.03 (cm-1). No other significant quantitative results were collected.

Discussion: As seen in the melting point determination, the average melting point range of the product was 172.2-185.3ºC. The melting points of the possible products are listed as 101ºC for o-methoxybenzoic acid, 110ºC for m- methoxybenzoic acid, and 185ºC for p- methoxybenzoic acid. As the melting point of the sample

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