After successfully isolating the eugenol and acetyleugenol, all that was left was to weigh each product. Once the lab was completed and the masses of the products were weighed, a 1.8% recovery of acetyleugenol as well as a 4.59% recovery of eugenol were obtained. These values may seem low, but in reality they may not be. This is because the amount of eugenol and acetyleugenol initially contained in the 25 grams of cloves is unknown. However, it is possible there were sources of error that occurred during the lab. A mechanical source of error would be spilling small amounts of solution while transferring it to different containers (beakers/flasks). Other sources of error could include incomplete reaction. This may be due to a lack of mixing …show more content…
when solutions were placed in the separatoy funel. In the end the two desired products were successsfully isolated, thus leading to a successful lab. There is a key difference between the structures of eugenol and acetyleugenol.
This difference is that eugenol has a alcohol group (OH) coming off its benzene ring while acetyleugenol has an ester group coming off its ring instead. This important stuctural difference is what allowed the separation between eugenol and acetyleugenol. This can be seen during extraction when the sodium hydroxide was added to the methylene chloride layer containg the eugenol and acetyleugenol. The OH group on the eugenol is able to react with the sodium hydroxide as seen in the mechanism diagram above. This reaction leads to eugenol going into the sodium hydroxide layer while the acetyleugenol is left in the methylene chloride layer. The eugenol’s OH group reacts with the negativle charged OH from the NaOH. The reaction leads to the eugenol’s OH group becoming a negativly charged oxygen. This negativley charged oxygen then reacts with the positivly charged Na from the NaOH and forms an eugenol salt. Eugenol salts dissolve in water, thus allowing the eugenol to be take from the sodium hydroxide layer to the water. The acetyleugenol has an ester group instead of an OH group, so it cannot under go this same extraction …show more content…
process. Spectral differentiation is commonly utilized to differentiate between two different compounds. This method is considered more reliable then relaying on comparing melting points. This is because if two substances have similar melting/boiling points it will be difficult to differentiate between the two. Similar melting/boiling points are not an issue for spectral differentiation. There are several unique spectra that can be used to determine molecular formulas and structures of certain molecules. The different types of spectra include Mass spec, IR, HNMR, and C NMR. These spectra were used in this lab to differentiate between eugenol and acetyleugenol. Mass spectrometry focuses on how much both parts of a molecule weights after the molecule is separated/cut at a specific point.
Both molecules in this lab have their own unique mass spec. This means that each molecule can be cut in a certain way which allows them to be differentiated from one another. The molecules focused on in this lab are eugenol and acetyleugenol. A clear distinction between their two mass spectra is that the acetyleugenol has an ion peak representng its mass at 206. The eugenol has an ion peak at 178 representing its mass. This is logical because the difference in mass between the two molecules is by the ester group acetyleugenol has. Eugenol has an OH group instead of an ester group. This causes the mass of the eugenol to be lower than the mass of acetyleugenol. There is a unique fragmentation at 17 that is only seen in mass spec for the eugenol. This fragmentation is caused by the eugenol being cut at the point where the OH group is coming of the aromatic ring. This fragmentation is impossible for acetyleugenol achieve because it has an ester group instead of an OH
group. Infrared spectrometry focuses on specific functional groups found on molecules. Different molecules will have unique/different IR spectra due to their different structures. For example, a molecule with a carbon double bonded to an oxygen will have a sharp deep peak that can be observed at around 1720. On the other hand, a molecule without a carbon double bonded to an oxygen will not have that peak. IR Spectroscopy was used to differentiate between eugenol and acetyleugenol. A difference between the IR spectra of eugenol and acetyleugenol can been seen at around 3500. The IR Spec for eugenol has a broad peak at 3500, due to its OH group. Acetyleugenol does not have this peak because it lacks an OH group. Another difference can be seen in the IR spec for acetyleugenol. The IR spec for acetyleugenol has a deep sharp peak at around 1720. This peak is caused by the carbon doubled bonded to the oxygen in acetyleugenol’s ester group. Eugenol does not have this peak because it lacks a carbon double bonded to an oxygen. Hydrogen NMR spectrometry focuses on hydrogens. Being able to properly read a molecule’s H NMR spec will reveal a lot of information about that molecule. For instance, with just the molecular formula and H NMR spectra, the structure of the molecule can be found. The peaks on the spectra reveal how many hydrogens and adjacent hydrogens there are in a molecule. For example, if there are 6 peaks together, it can be said there are 5 adjacent hydrogens. Eugenol and acetyleugenol have unique H NMR spectra. A difference in their spectra can be seen in the H NMR spec for eugenol. Eugenol has an 1H peak at about 5.75 ppm. This peak is causes by the OH group on eugenol. Acetyleugenol lacks this peak altogether because it does not have an OH group. Another difference can be seen in the H NMR for acetyleugenol. Acetyleugenol has a 3H peak that reaches to 7 ppm. This ring represents the hydrogens on the aromatic ring. Eugenol has a similar peak, however its location is more upfield. This difference in position is caused by the ester group on the acetyleugenol. The ester group interacts with the aromatic ring causing the 3H peak to be further downfield. The last spectra is the carbon spectra. This spectrum deals with different types of carbons in a molecule. The different carbons are as follows: CH3’s, CH2’s, CH’s, and C’s. CH3 is represented by a “q”, CH2 is represented by a “t”, CH is represented by a “d”, and C is represented by an “s”. Baring this information in mind, molecules can be differentiated by comparing their carbon spectra. There are key differences that can be seen in the carbon NMR graphs for eugenol and acetyleugenol. One difference is that there is a “q” carbon peak located at about 20 ppm on the graph for acetyleugenol. Eugenol lacks this peak altogether because it lacks an ester group (which acetyleugenol has). Another difference can be seen in the graph of acetyleugenol. It has an “s” carbon peak at around 170 ppm. This is due to the carbon making the double bond with the oxygen in the ester group. Eugenol lacks this peak along with an ester group.
The experiment was not a success, there was percent yield of 1,423%. With a percent yield that is relatively high at 1,423% did not conclude a successful experiment, because impurities added to the mass of the actual product. There were many errors in this lab due to the product being transferred on numerous occasions as well, as spillage and splattering of the solution. Overall, learning how to take one product and chemically create something else as well as how working with others effectively turned out to be a
The unknown bacterium that was handed out by the professor labeled “E19” was an irregular and raised shaped bacteria with a smooth texture and it had a white creamy color. The slant growth pattern was filiform and there was a turbid growth in the broth. After all the tests were complete and the results were compared the unknown bacterium was defined as Shigella sonnei. The results that narrowed it down the most were the gram stain, the lactose fermentation test, the citrate utilization test and the indole test. The results for each of the tests performed are listed in Table 1.1 below.
Extraction is a separation method that is often used in the laboratory to separate one or more components from a mixture. Sucrose was separated at the beginning because it is the most immiscible and it’s strongly insoluble. Next Acetylsalicylic Acid was separated which left Acetanilide alone. Variety steps could have led to errors occurring. For example the step of separation, when dichloromethane layer was supposed to be drained out, it could be possible some aqueous layer was drained with it. Which could make the end result not as accurate. Also errors could have occurred if possibly some dichloromethane was not drained out. Both way could interfere with end result of figuring the amount of each component in the mixture. The solids percentage were 22.1% more than the original. That suggests that solids weren’t separated completely which clarifies the reason the melting points that were recorded were a slightly lower than the actual component’s melting point. The melting point for Acetylsalicylic Acid is 136 C but that range that was recorded during the experiment was around 105 C to 118 C. The melting points were slightly lower than the literature value. Sucrose was the purest among all component due to its higher melting point which follows the chemical rule that the higher the melting point the more pure the component
Saturated sodium chloride solution, also known as brine solution, is used to wash the distillate mixture. The distillate mixture is the phosphoric acid the co-distilled with the product. The brine solution also removes most of the water from the 4-methylcyclohexane layer. When six drops of 4-methylcyclohexene were added with two
This experiment synthesized luminol (5-Amino-2,3-dihydro-1,4-phthalazinedione) and used the product to observe how chemiluminescence would work. The starting material was 5-nitro-2,3-dihydrophthalazine-1,4-dione, which was, after addition of reaction agents, refluxed and vacuum filtered to retrieve luminol. Using two stock solutions, we missed our precipitated luminol with sodium hydroxide, potassium ferricyanide, and hydrogen peroxide, in their respective solutions, in a dark room, to observe the blue light
Triphenylmethyl Bromide. A 400 mL beaker was filled with hot water from the tap. Acetic acid (4 mL) and solid triphenylmethanol (0.199 g, 0.764 mmol) were added to a reaction tube, with 33% hydrobromic acid solution (0.6 mL) being added dropwise via syringe. The compound in the tube then took on a light yellow color. The tube was then placed in the beaker and heated for 5 minutes. After the allotted time, the tube was removed from the hot water bath and allowed to cool to room temperature. In the meantime, an ice bath was made utilizing the 600 mL plastic beaker, which the tube was then placed in for 10 minutes. The compound was then vacuum filtered with the crystals rinsed with water and a small amount of hexane. The crude product was then weighed and recrystallized with hexane to form fine white crystals, which was triphenylmethyl bromide (0.105 g, 0.325 mmol, 42.5%). A Beilstein test was conducted, and the crystals produced a green to greenish-blue flame.
The data we gathered was tested to be as accurate as possible. Our prediction on the solvents did not support our data that we collected. The cause of this could be due to human error when washing the beets or the cutting of the beets. The beets were not perfectly cut the same size, so some beet pieces were bigger than others which can affect the final the final result. We followed each step and followed the time limits cautiously. I can say if we were to redo the experiment our results would be similar because we would attempt to do the experiment as close as we did the first
One of the best methods for determining mass in chemistry is gravimetric analysis (Lab Handout). It is essentially using the the mass of the product to figure out the original mass that we are looking for. Thus the purpose of our experiment was to compare the final mass in our reaction to the initial mass and determine the change in mass.
Benzyl bromide, an unknown nucleophile and sodium hydroxide was synthesized to form a benzyl ether product. This product was purified and analyzed to find the unknown in the compound.
The C-H (sp3) hydrogens from our product displayed at wavelength 2959 cm-1 correlates to the methyl groups located on the ends of isopentyl acetate4. A really prominent, strong peak located at 1742 cm-1 shows that a C=O ester stretch is located in the product, along with at 1244 cm-1 the spectrum shows a strong peak representing the C(=O)-O stretch that is crucial to the structure of isopentyl acetate. Shown in my IR spectrum is a weak O-H (H-bonded) peak at 3464 cm-1 which shows that I have an impurity of isopentyl alcohol in my product. Isopentyl alcohol has similar boiling points and density as my product so the impurity could have easily boiled out with the isopentyl acetate during distillation. The isopentyl alcohol was also present in my 1H-NMR spectrum backing up the impurity peak at 3464
The objective of this experiment was to perform extraction. This is a separation and purification technique, based on different solubility of compounds in immiscible solvent mixtures. Extraction is conducted by shaking the solution with the solvent, until two layers are formed. One layer can then be separated from the other. If the separation does not happen in one try, multiple attempts may be needed.
After performing the first Gas Chromatography, we took the organic layer, and mixed it with saturated Sodium Hydroxide. We performed this step to remove the (-OH) group from the Eugenol. The purpose was to make the water as a product, which can also be used as a solvent for the Eugenol that was ionized, for the two substances Acetyl Eugenol and Beta Caryophyllene. Again, we see the density differences in the solvents; we were able to take the organic layer. Finally, we transferred the layer into the beaker and dried, to perform the Gas Chromatography
One possible source of experimental error could be not having a solid measurement of magnesium hydroxide nor citric acid. This is because we were told to measure out between 5.6g-5.8g for magnesium hydroxide and 14g-21g for citric acid. If accuracy measures how closely a measured value is to the accepted value and or true value, then accuracy may not have been an aspect that was achieved in this lab. Therefore, not having a solid precise measurement and accurate measurement was another source of experimental error.
In this lab, we are finding the number of molecules in one mole. To do so we use Avogadro's number as a reference. Avogadro's number is 6.02 x 10^23 and the final calculation at the end of the experiment should be close to this number. Avogadro's number represents that if there is an equivalent number of gases that are present at the same temperature they will all contain the same number of molecules as each-other. Using the calculations given a number of molecules in a mole of oleic acid can be found.
There is also the potential of human error within this experiment for example finding the meniscus is important to get an accurate amount using the graduated pipettes and burettes. There is a possibility that at one point in the experiment a chemical was measured inaccurately affecting the results. To resolve this, the experiment should have been repeated three times.