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
3. The IR spectrum of the starting material shows a medium/strong C-O bond at around 1500cm-1, also the starting material shows a strong C-H bond at around 3000cm-1 and another medium C-H bond at 2865cm-1 indicating an aldehyde group whereas the product does not. The IR spectrum of the product shows a two weak broad O-H peaks at around
Lab 8 Purpose Using sodium borohydride as the reducing agent, to convert a ketone (camphor) to a mixture of secondary alcohols (isoborneol or borneol). The product mixture will be characterized by melting point and functional group tests (TLC and IR spectrum). Pre Lab 1. Structure of Camphor NaBH4 used as reducing agent to produce isborneol from camphor Structure of isoborneol Isoborneol with wedged and dashed lines 2. Isoborneol can be produced by reduction of camphor by using the NaBH4 in Methanol.
This was concluded by combining information on melting points and TLC; melting range narrowed when filtered product was mixed with the standard product. Also, the Rf value of the pure product is closely related to the Rf value of the standard. TLC of filtrate showed no movement of the substance in the mixture under 9:1 ratio declaring the substance to be extremely polar. Of the three potential unknown reactants, 4-methoxyphenol would be the most polar and therefore would travel least up the TLC plate. (Q14:Yield) 81.2% product yield was collected. “Matter cannot be created nor destroyed”, therefore some product could have filtered through. TLC of filtrate confirmed remnants of product present. Filtering the filtrate could have increased the yield. (Q15:Recovery) The percent recovery of the product makes sense because it is the mass of the crystallized product divided by the crude product: 94.9%. The percentage reflects the mass of pure product (without the presence of impurities). (Q16:MP) Melting point coincides with the unknown nucleophile being 4-methoxyphenol because when the standard product was combined with our pure product, the melting range narrowed. When compared to the melting ranges obtained when mixed with the other two possible products the melting ranges significantly decreased and widened. This is often an indication of impurities being present, but because this was a
present in the final product. If the IR of a molecule with an alcohol is present, there will be an IR peak between 3400 and 3200 cm^-1. However, if the experiment was done successfully by
Many techniques and skills were developed in this lab. Among them were dehydration, isolation, drying, and distillation. We used all of these techniques to get the product we were looking for. In addition to these experimental techniques we also verified our product via spectroscopy which is a new technique. Using IR spectroscopy we were able to
Which means that it did not have any neighboring hydrogens but it still had a hydrogen on the compound. The next peak was a multiplet around 6-7.1 ppm and had 5 similar hydrogens. According to the H NMR chemical shifts, 5 similar hydrogens and a ppm range from 6-8.0 ppm, this particular peak was an aromatic. More specifically a benzene with 5 similar hydrogens, and with another hydrogen with attached substituents. This aromatic also contains 4 degrees of saturation, satisfying the requirement that the compound needed to have DoU of 4. The next peak was a quartet around 3.4-3.5 with 2 hydrogens. The quartet meant that the compound had 3 neighboring hydrogens and that particular peak was a CH2. The last pear was a triplet around 1.2-1.4 ppm with 3 hydrogens on the compound. The triplet meant that compound that 2 neighboring hydrogens indicating that particular peak was a methyl group (CH3). This help determine that the CH2 and CH3 were bonded to one another creating an ethyl
The product that was obtained from the experiment was analyzed by weighing the product, obtaining melting point range and an IR spectrum. An NMR spectrum was unable to be obtained. The mass of the product was .4162 grams, with a precent yield of 17.34%. The low percent yield can be The melting point range that is expected from 4-cyclohexene-cis-dicarboxylic anhydride is 101-103°C. The actual range that was obtained from the melting point test was 82.9-93.2°C.
The IR has a big peak at 1705 cm-1, but what really proved the product to be cyclohexanone was the fingerprint region. The fingerprint region IR of the product matched perfectly with cyclohexanone. There were some peaks at 1449 cm-1, 1221 cm-1, 1118cm-1 and 734 cm-1. There was one indication at 1449cm-1 in the finger print spectra of the product that showed there was some indication of the cyclohexanol in there, which was the starting alcohol. This was to truly help identify what the unknown compound A was.
Also, when looking at the filtrate values under the short-wavelength, a value of 0.44 appears to hint at the existence of the cis,trans-isomer which has a literature value of 0.41. The three values for the filtrate under the long-wavelength make sense as well, being that the value of 0.28 belongs to the oxide, the 0.36 to the trans,trans, and the 0.44 to the cis,trans.
Through this experiment, I used IR and NMR to identify several unknown compounds. In order to identify my pure unknown compound, IR-12, I first looked for any medium to strong peaks on my IR spectra. The peaks that were useful in identifying my unknown were: a C-O bond of an ester at 1043.8, a C-O bond of an ester at 1243.6, a stretching C=O bond at 1743.2, a stretching alkyl C-H bond at 2860.4, and a stretching alkyl C-H bond at 2958.7. When figuring out which IR unknown was my compound, I first looked to see if my IR spectra showed an alcohol or an amine. Since my IR spectra didn’t show an alcohol or an amine, I was able narrow down my choices of possible compounds to twelve. Next, I looked for an aromatic ring in my IR spectra and since my IR didn’t show an aromatic ring, I was able to narrow down my choices to six possible compounds. Then I looked for any nitriles in my IR and since my IR didn’t contain any nitriles, I was able to narrow down my choice to five possible compounds. Then, I looked to see if my IR contained a ketone, an aldehyde, or an ester. My IR spectra didn’t contain a ketone or an aldehyde, however, it did contain an ester, which is how I was able to identify my unknown, IR-12.
In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this
The light yellow precipitate was collected by suction filtration using a Hirsch funnel. The product was washed with two 1-mL portions of cold methanol followed by two 1-mL portions of diethyl ether. The product was dried in the oven at 110°C. The IR spectrum as a KBr pellet was obtained for the product and inosine for analysis.
In order to achieve isoborneol from camphor, a mixture of camphor with methanol and sodium borohydride was heated for about two minutes. Data Table 1 demonstrates the measurements that were taken to prepare the reaction mixture. The addition of sodium borohydride caused the reaction to fizzed.
An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the
The product attained was a white, dry solid. The small amount of product lost during the second recrystallization was most likely do to impurities, which were filtered away with the methanol. Impurities that contributed to the low percent yield could be due to side reactions such as methyl o-nitrobenzoate and methyl p-nitrobenzoate. Although the percent yield attained was low, the product attained was fairly pure due to similarity in melting point and IR spectrum compared to standardly accepted values for methyl m-nitrobenzoate.