Brominated hydrocinnamic acid underwent an elimination reaction (E2) to produce cinnamic acid. The goal of the elimination experiment was to remove the bromine and a hydrogen from brominated cinnamic acid, using the strong base KOH, to produce crude cinnamic acid. The reaction is shown in Scheme 1.
The crude cinnamic acid was dissolved then recrystallized. The goal for recrystallizing crude cinnamic acid was to purify the acid and filter out any impurities. Recrystallization is one method used to purify a compound. Using a hot solvent, the compound is dissolved. It is then cooled to produce pure crystals. “As the crystal develops, impurities are excluded from the crystal lattice, thereby completing the purification process.”1 The key to recrystallization is the solvent used. “The solute must be relatively insoluble in the solvent at room temperature but much more soluble in the solvent at a higher temperature. At the same time, impurities that are present must either be soluble in the solvent at room temperature or insoluble in the solvent at a high temperature.”2 The solvent must be able to dissolve the product and the impurities for recrystallization to take place. Once dissolved, the solution cools first to room temperature before placing it in an ice bath, for “gradual cooling is conducive to the formation of large, well-defined crystals.”2 Once cooled, the solution is placed into the ice bath to further the recrystallization of the compound. The crystals are then
An Erlenmeyer flask was used to accommodate the largest volume of recrystallization solvent calculated and was cooled in an ice bath to increase the yield of crystals. The solid was collected by vacuum filtration and washed with a small amount of ice water. The product is then dried to a constant mass by use of an oven and weighed. A small amount of the unknown was compared to two samples of acetanilide and phenacetin for a melting point range to determine the identity. The temperature of the unknown was recorded when the first trace of liquid can be seen and when the unknown was completely liquid.
Discussion The third experiment of the semester involves identifying an unknown component of Panacetin, a common pain relief medication, separated and precipitated in the previous experiment. Although Panacetin’s label reports this third ingredient as Tylenol, there is controversy over the true classification of the third substance. This Panacetin label also reports that the unknown constituent makes up 50% of the composition of Panacetin, compared to aspirin’s 40% composition and sucrose’s 10% composition, meaning that it is currently unknown what half of the drug people ingest is identified as. Research results have failed to repeatedly show that the third component of Panacetin is Tylenol, which leads to the hypothesis
During recrystallization, the solution was to be cooled to room temperature before placing it in an ice bath. Doing this allows enough time for the crystals to be formed because as the temperature decreases, the rate of crystallization slows down. If the solution was placed in the ice bath too quickly, then the cold would have blocked out the impurities and trapped them in the solution. The more impurities present, the lower the melting point so data would have been inaccurate. Also, if the melting point apparatus wasn’t set up correctly, the data would have been imprecise.
What is the stereochemistry for the bromination of trans-cinnamic acid, and how is it formed?
Discussion: In the synthesis of 1-bromobutane alcohol is a poor leaving group; this problem is fixed by converting the OH group into H2O, which is a better leaving group. Depending on the structure of the alcohol it may undergo SN1 or SN2. Primary alky halides undergo SN2 reactions. 1- bromobutane is a primary alkyl halide, and may be synthesized by the acid-mediated reaction of a 1-butonaol with a bromide ion as a nucleophile. The proposed mechanism involves the initial formation of HBr in situ, the protonation of the alcohol by HBr, and the nucleophilic displacement by Br- to give the 1-bromobutane. In the reaction once the salts are dissolved and the mixture is gently heated with a reflux a noticeable reaction occurs with the development of two layers. When the distillation was clear the head temperature was around 115oC because the increased boiling point is caused by co-distillation of sulfuric acid and hydrobromic acid with water. When transferring allof the crude 1-bromobutane without the drying agent,
The recrystallization technique utilizes the ability of a compound to dissolve within a hot solvent and produce a solution. As this solution cools, the solute reforms without impurities in a crystal lattice structure.1 For this to work properly, an appropriate solution that will not dissolve the solute at low temperatures, but will at high temperatures, must be used.1 There is no single solvent that will work well for every solute’s recrystallization; different solvents are better suited for some solutes than others.2 Some impurities that do not dissolve within the solvent can be filtered out while the solution is still hot, while other impurities that readily dissolve within the solvent shouldn’t recrystallize with the pure substance (as they are not concentrated enough to
The product was placed in a Craig tube and several drops of hot (100°C) solvent (50% water, 50% methanol, by volume) was added and heated until all of the crystals dissolved. The Craig tube was plugged and set in an Erlenmeyer flask to cool. Crystallization was induced once the mixture was at room temperature by scratching the inner wall of the tube. It was then placed into an ice bath for ten minutes until crystallization was complete. The tube was then
The product was then suspended in 2 ml of water with a stir rod in a 50 ml Erlenmeyer flask and heated to boiling. Water was added in one milliliter increments until all the product was dissolved (18 ml added total). The saturated solution was allowed to slowly cool, and gradual white crystal formation was observed. Recrystallized product was collected once more by suction filtration with the Hirsch funnel once crystallization ceased. Collected product dried on a watch glass for a week, weighed 0.14 g (1.2 mmol), and the melting point was 139°-141°
If the starting cinnamic acid contained the mixture of cis and trans isomers, the product would be the mixture of erythro- 2,3-dibromo-3 phenylpropanoic acid and threo-2,3-dibromo-3 phenylpropanoic acid, which would result in a broad range melting point.
To tube 2 and tube 3 a boiling chip is added. The two tubes are boiled to remove any residual ether. Next, the tubes are cooled to room temperature and placed into an ice bath to allow for crystallization. The solution is then removed from the solid in each tube and discarded. To tube 2 and 3 ~0.5 ml of H2O is added for recrystallization, the tubes
The solution is then cooled and recrystallization of the solute occurs. For a solvent pair to
The purpose of this experiment is to separate a mixture of salicylic acid and naphthalene using extraction, recrystallization and sublimation techniques. Extraction is the separation of compounds from a mixture based on their relative solubilities in different solvents. Sublimation is the process of separation by which a substance transitions from the solid phase into the gas phase, skipping the liquid phase. Recrystallization involves dissolving a substance in an appropriate solvent then crystallizing it as it cools (impurities remain in solution). The melting points of the substances were determined in order to assess their purity and the percent recovery of pure naphthalene and salicylic acid were calculated. According to the results, the melting point of pure naphthalene was between 86°C -89°C range, whereas for pure salicylic acid was 167°C -170°C. Both determined melting points were higher compared to the literature value of 80.26°C and 158.6°C for pure naphthalene and salicylic acid respectively. Lastly, the percent recovery for pure naphthalene and salicylic acid were 17.7% and 71.2% accordingly.
The purpose of this lab was to synthesize the ester isopentyl acetate via an acid catalyzed esterification (Fischer Esterification) of acetic acid with isopentyl alcohol. Emil Fischer and Arthur Speier were the pioneers of this reaction referred to as Fischer Esterification. The reaction is characterized by the combining of an alcohol and an acid (with an acid catalyst) to yield and ester plus water. In order to accomplish the reaction, the reactants were
Recrystallization was done to remove impurities from the sample. The percent recovery of benzoic acid during recrystallization is 23.02%. The difference between the pure and impure samples was observed by comparison of melting points. It was found that impure sample had a lower and wider melting point range of 120.1-122.2 (C). The pure sample melting point range was 121.3-122.5 (C). These ranges helped determine purity by comparing the known melting point of pure benzoic acid.
Next, a research paper by Aysegul and Christian (2001), a study where it focused on the effects of sucrose concentration during citric acid accumulation by Aspergillus niger. It was hypothesised that different levels of sucrose concentration can determine the regulation of the citric acid production rate. Due to its regulation, the metabolism took place at several levels including the control of gene expression, translational control, control of enzyme activity and control through the spatial distribution of enzymes (Panneman et al., 1996; Kubicek et al., 1977 & 1978; Wolschek et al., 1996; Visser et al., 1992). Therefore, a number of the enzymes involved in hexose utilisation are regulated as well by inhibitors, activators and protein phosphorylation or dephosphorylation. It is believed that the citric accumulation is known to be stimulated by high sugar concentration suggesting it may be influenced by osmotic stress. The main goal of this research paper was to investigate the phosphorylated proteins produced during the osmotic stress conditions due to high sucrose concentrations as the possible role of protein phosphorylation due to osmotic stress has not been investigated in Aspergillus niger ATCC 11414 under citric acid production conditions in the past. Basically, an increase in citric acid accumulation with increasing concentrations of sugar is not surprising as it may simply