Experiment TWO: Bleach Oxidation of Isoborneol Reaction (15 pts) –accurate drawing with ChemDraw Procedure Isoborneol (1.32 g, 8.5 mmol), NaOCL (1 mL, 7.6 mmol), and acetic acid (1.7 mL) was vigorously stirred in a flask. The solution was then heated to 50°C. NaOCl (15 mL) was added dropwise to the solution over a 10 minute time period. Parafilm was then used to seal the flask, while being stirred and heated (50°C). Samples of the solution where taken every 5 minutes and subjected to a starch-iodide paper to check for excess NaOCl. Once the test produced positive results (purple color), a minimal amount of saturated NaHSO3 was then added to the solution to produce a negative test. The solution was then cooled by a ice-water bath. …show more content…
Camphor is produced by oxidizing a secondary alcohol, isoborneol, into a ketone. The melting point of the product was experimentally determined to be 169°C. Comparing 169°C litature value of 174-179°C, it can be assumed that the product was not completely purely.1 To improve purity, procdure could be examined. Allowing the reaction more time to occur, along with more through filtering may increasing purity. Additionally, the heating during sublimation could be done slowly inorder not to burn the product. The mass of the crude product was 0.77 g, where the purified product was 0.03g. Comparing the pure product to the amount of isoborneol used, the percent yield was found to be 2.4%. To improve this low percent yield the procedure should be again be examined. Reducing the amount of product lost during transfers, filtration, and sublimation would improve yield. Better transfer would involve more through washes of glassware. Moreover, the yield of the sublimation process was very low (3.9%). To address this issue more time should be allotted for the product to collect on the cold finger. To further examine the purity and identity of the produced specie(s), mass spectrometry, gas chromatography, and NMR could be considered. Understanding what the impurities found in the reaction are may offer insight as how to improve the …show more content…
Considering that the reaction was done a micro scale the amount of waste is limited (Prevention #1). Bleach was used in this reaction instead of a chromium compound. Bleach is less hazardous in comparison, therefore less hazardous chemical syntheses (#3) was followed. Consider that all waste can be safely disposed with merely water, and that the chemicals used are at most irritates, then potential for harmful chemical accidents is limited (Inherently Safer Chemistry for Accident Prevention #12). 2. Consider that sublimation involves the transition of a solid to a gas. Iodine will exist was a solid where Bromine will not. Molecules of iodine will experience a strong intermolecular forces, London dispersion, due to the location of location of its electrons. Bromine will experience weaker forces, considering the electrons are closer to the nuclei (consider the small atomic radius compared to iodine. 3. Consider that the difference between the reactant and product’s NMR spectrum will differ due to the change of the an 2o alcohol to a ketone. Isoborneol would there for have two more speaks than what would be seen in the camphor spectrum. These peaks would include a single peak from the OH proton along with a peak from the proton found on the carbon that that OH group is attached (approx. 3.5 ppm). Camphor would lack this two protons, thus causing smaller splitting patterns than would be seen in the isoborneol
Additionally, during testing, it was discovered using the pH section of the testing
In addition, phenolphthalein was added as an indicator. The aliquots were titrated against sodium hydroxide (NaOH) solution until end point was reached, after which volume of NaOH consumed was recorded. The value of the rate constant, k, obtained was 0.0002 s-1. The experiment was then repeated with 40/60 V/V isopropanol/water mixture and a larger value of k = 0.0007 s-1 was obtained. We concluded that the rate of hydrolysis of (CH3)3CCl is directly proportional to water content in the solvent mixture.
If the water has been dispensed into another container, this reaction would have continuously run toward to the products side. Following the isolation of the ester, a drop of Isopentyl Acetate was placed into an infrared spectrometer. When bonds within molecules absorb photons at different frequencies the IR spectrometer produces a graph to represent the bonds within the ester
Although 3 pentanol is polar with an alcohol group attached to its end, its hydrocarbon chain decreases its solubility in water, making it possess a lower affinity for the stationary phase and elute first. In the second fraction, only one main peak could be identified at 3265.26 cm-1 that matched the provided IR spectra. This peak represents another alcohol group which limits it down to 3-methyl-butanol, 2 heptanol, 2 octanol, and 1 hexanol. Since this was the second fraction, it must be more polar than the first fraction to elute last. Therefore, by elimination, the second fraction was identified as 3-methyl-butanol.
Because the heating block readily increased in temperature, the temperature had to be adjusted accordingly to prevent the overheating the reaction. Initially, the color of the reaction turned into a dark green color and over time became a lighter shade with a minimal solid left. The reaction process lasted for 2 hours. As the reaction heated for 2 hours, a 50 mL beaker was weighed, approximately 12 mL of 20% ethyl acetate in hexane solution was added to a 25 mL Erlenmeyer flask, and 2.0 mL of saturated NaCl solution was added to a labeled test
Then 200 µl of the solution phenol/chloroform/isoamyl alcohol (25:24:1) was added to the tubes under the fume hood and tubes were placed on rotator and left to mix for 3 min. 200 µl of TE buffer was added and spun for 5 min at maximum speed, the water phase was transferred to new tubes. 1 ml of cold 96 % ethanol was added, mixed and then spun for 5 min at maximum speed at 4°C. the supernatant was discarded and the pellet re-suspended in 400 µl of TE buffer (40 mM Tris-Base, 20 mM acetic acid, 1 mM EDTA, pH 8.0). 6 µl of 7.5 M ammonium acetate was added and the pervious step was repeated.
As seen in table 1, the theoretical yield was .712 g of C_17 H_19 NO_3. The % yield of this experiment was 7.51 % of C_17 H_19 NO_3. . This low yield can be explained from a poor recrystallization technique combined with potential contamination. Throughout the experiment, the mixture changed color from green, orange, to yellowish lime, and eventually clear.
This lab only included double-replacement reaction which allowed for only one of 2 types of products. Products that chemically reacted (solid) or products that didn’t (aqueous). The insoluble products of these double replacement reaction occurred when the cations or anions of the reactant bonded with the cation or anion of the other reaction. When this happens the reactants get paired together with the reactant it bonded with and causes a replacement. This is shown evident in the lab in Station
Observations were then recorded. Solutions were disposed into the proper waste container, and distilled water was used to rinse the contents into the waste container. HCl was used to clean the centrifuge tubes. In the labeled centrifuge tubes, ten drops of each metal cation solution were put in. 15 M NH4OH solution was added into each tube until a precipitate or color complex was created.
The possible explanations and changes to make are similar to the previous questions. Conclusion and Future Experiment 18. The identity of the product and unknown were 4-tert-butylbenzyl phenol ether and tert-butyl phenol respectively. The key to making this discovery was the melting point and TLC results!
Then, the other part of cupric acetate which is acetate as the base attacks the proton in benzoin. Then, acetic acid was formed and also resonance will stabilize the radical and move the electron to form a double between carbon-carbon. After forming the double bond between carbon-carbon, the electrons in the double bond move between oxygen and carbon and form
10 mL of deionized water was added and stirred until fully dissolved. 5.0 mL of 3.0 M of hydrochloric acid was slowly pipetted into the mixture and stirred. The pH was checked to be less than two. The solution was placed into an ice bath to decrease the temperature to 10°C. A vacuum filtration apparatus was built with an Erlenmeyer flask with a vacuum arm and connected to a vacuum source and secured for safety using a ring hoop.
CHAPTER 4 SUMMARY OF RESULTS, CONCLUSION AND RECOMMENDATIONS Summary As the researchers completed the process of making the product which undergone extractions and pre-treatment, different tests we’re conducted in terms of physical and chemical properties in relation to the commercial ethanol. For the physical properties of BIT and commercial ethanol, the ethanol showed different measurements in physical properties of BIT and commercial ethanol such as the density, smoke emission, and heat. Based on the given data, BIT and commercial ethanol are close to each other in terms of density and smoke emission.
However, the percent yield of this experiment was 109.96% (Fig. 5). Ultimately, the product mass collected after the reaction was a greater amount than the initial mass used in the original
The problem at hand is that the reaction kinetics is not known and need to be determined to understand the reaction more thoroughly. There is a hypothesis that the reaction kinetics is exactly the same for different types of reactors. The purpose of