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Multistep Synthesis Lab Report

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The first stage of this multistep synthesis resulted in a successful yield of isobornyl acetate, as stated in Table 2 of page 6. A sample of 1.635 g of isobornyl acetate was produced, which corresponds to an 83.5% yield. The infrared (IR) spectrum illustrated in Figure 1 of page 5 shows the presence of sp3-hybridized carbons around 2990 cm-1. According to Table 2, sp3-hybridized carbons should appear as strong bands in the range of 2850.00-2960.00 cm-1, which holds true for the experimental spectrum. The HC–H and dimethyl signals predicted to appear at 1420.00-1470.00 cm-1 are found at around 1410.00 cm-1 of the experimental spectrum. Also, the sharp, strong band at 1733.37 cm-1 indicates the presence of a carbonyl group that belongs to an …show more content…

This is a significantly lower percent yield of product compared to the first step, so it was not as successful of a synthesis. In terms of purity, a melting point range and infrared spectrum were obtained. According to Table 1 of page 5, the measured melting point range of the product was 206.5–210.4 °C. This nearly four-degree range is fairly small, which means that there was little contamination in the product. The obtained melting point range matched closely with the literature melting point of isoborneol being 212 °C (Physical Constants of Organic Compounds). In addition, the obtained IR spectrum also signifies high purity of isoborneol in the sample. As demonstrated in Scheme 2 of page 2, isoborneol contains a hydroxy group in the equatorial position, which means that it is an alcohol. The predicted stretches of an alcohol are located around 3300.00 cm-1 and from 3380.00-3500.00 cm-1 in the literature spectrum, Figure 4. The IR spectrum on Figure 3 of page 7 depicts a broad stretch between 3320.00-3480.00 cm-1, signaling the presence of an alcohol functional group. There is also a sharp stretch at 2948.99 cm-1 that reflects sp3-hybridized carbons in the sample. When compared to the literature IR spectrum on page 7, the hydroxy group stretch and sharp stretches in the fingerprint region match …show more content…

After the oxidation reaction was performed, 0.973 g of product was made, corresponding to a 92.7% yield of crude camphor. This is very high. In order to purify the crude camphor, sublimation of the sample resulted in 0.485 g of purified camphor, or a very low 46.2% yield, as seen in Table 1. However, the sample had somewhat high purity. The obtained melting point range of the purified camphor was 171.1–173.2 °C, which is close to the literature melting point of 178.7 °C. As predicted to be around 2850.00-2960.00 cm-1, a sharp stretch is located at 2956.00 cm-1, confirming the presence of sp3-hybridized carbons. Furthermore, there are two prominent peaks at 1371.01 cm-1 and 1388.89 cm-1 that are representative of the HC–H dimethyl stretches that are at 1380.00 cm-1 and 1385.00 cm-1 in the literature spectrum. Lastly, a ketone’s stretch should be around 1710 cm-1, and there is a stretch around 1750 cm-1 in the literature spectrum and a strong stretch at 1743.67 cm-1 in the obtained spectrum. Thus, a ketone group is present in the product. The fingerprint region in the IR spectrum was examined more closely for purity to compare with the standard spectrum, which is seen in Figure 7 of page 9. This stacked IR spectra compared the camphor sample to isoborneol and camphor standards to evaluate contamination of isoborneol in the product. Many of the bands of the obtained

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