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Synthesis of isopentyl acetate reaction
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After receiving alarming news from the Cavendish Distilling Company or CDC, about their delicious Banana Elixir. It seems after Hurricane Floyd they lost the majority of their bananas’ and are now in need of an alternative source for a banana flavoring, to avoid bankruptcy. Luckily for the CDC, there is a known way to get the chemical that can be used in place of the oil from a banana. That chemical in this experiment will be known as isopentyl acetate. Isopentyl acetate is an Ester, an Esters are usually created from reacting a carboxylic acid with an alcohol, along this an acid catalyst. This gives an Ester and some products, usually water. In this experiment Acetate acid and Isopentyl alcohol will be used with a sulfuric acid catalyst to synthesize the isopentyl acetate. Unfortunately some reactions, including this one, is reversible and the reaction may not fully go in the direction wanted throughout the entirety of the synthesis. To no surprise even after Reflux, there will be some isopentyl alcohol and acetate acid that didn’t react together.
Refluxing is a laboratory procedure in which you can separate pure amounts of the mixture, by separating them using their different boiling points. In a reflux, the glassware will heat up at different temperatures and depending on the boiling points of the individual chemicals used, the chemicals will evaporate and then condense back down, due to the cooling system of running water attached to the reflux system. Although you can say the chemicals at split up they need to be actually separated, a separatory funnel was used to do this. Using a base and some water along with our mixture, the two acids used should react nicely with this added water and base. Giving a nice separation of a...
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...uccessfully, and smelled wonderfully of banana, but it wasn’t a quantity that would be every profiting. Although if the experiment was done again the results maybe more profitable, the CDC may still be in a bit of a pickle. That’s the trouble with hurricanes, banana trees don’t stand a chance. As to if the isopentyl acetate had any isopentyl alcohol left in it, I would assume not. The worry in this experiment whether any of the isopentyl acetate was lost if it had indeed traveled with the isopentyl alcohol durning distillation.
Works Cited
Portlock, David E., Catalyst: The penitence hall custom laboratory program for chemistry, “RECRYSTALLIZATION AND MELTING POINT MEASUREMENT”.Wright State University, Dayton, 2010. Pp.51-58.
Ketcha, Daniel L., “Organic Chemistry Laboratory: week four”. Power Points slides, Wright State University, Dayton, 2014. Pp. 1-6.
In the first section, the Synthesis of Aspirin, salicylic acid was weight to be 3.029 grams using mass by difference since it was weighed on a 150 milliliter beaker. 9.23 milliliters of the acetic anhydride and 14 drops of 85 percent phosphoric acid were added to this beaker. A Bunsen burner provided by the laboratory was then used to boil the just mixed combination by producing a flame underneath the positioned beaker on top, and then allowed to cool for several minutes after the Bunsen burner flame was terminated. Two quantities of distilled water were then added to this mixture to make it cool even further, which were 41 drops and 30 milliliters. After cooling for some time, this beaker was placed into an ice bath in order to start the crystallization process. A glass rod was used to scratch around the bottom and the sides to catch all of the crystallized Aspirin that was being formed during this whole process. Then, by using a Buchner funnel and filter paper, which was placed on top of the flask connected to a water aspirator with rubber tubing, the excess liquid was removed from the just scraped Aspirin crystals when the Aspirin was placed on the filter paper. Using a medicine dropper, the Aspirin crystals on the filter paper were washed with distilled water just so that any non-pure substances were removed from the crude product. When these crystals were then ultimately dry, they were placed on a watch glass and put into an oven for 30 minutes. Then they were weighed by mass by difference to yield 2.4667 grams of crude s...
need is water and an ester and we will end up with an organic acid produced as
Another simple improvement to the experiment could have been the addition of time to procedure A as well as possibly increasing the time heated under reflux. Since the entire procedure B had to be completed before the period of reflux was done, some of the steps and processes involved in procedure B were rushed or not given the adequate time allowed to produce the best sample of product. In general, the laboratory experiment was successful and turned out well to find that the bromide ion was the better nucleophile to both the n-butyl alcohol as well slightly toward the t-pentyl alcohol used in the
We thank the University of Oklahoma and the chemistry faculty for providing the space, instructions, and equipment for the development of this report and experiment.
The three butene products have been verified to elute in the following order: 1-butene, trans-2-butene, and cis-2-butene. Theory: The dehydration of 2-butanol, a secondary alcohol, progresses readily in the presence of a strong acid like concentrated sulfuric acid (H2SO4). The reaction is completed via the E1 mechanism. Initially, the hydroxyl group is a poor leaving group, but that is remedied by its protonation by the acid catalyst (H2SO4) converting it to a better leaving group, H2O. The loss of this water molecule results in a secondary carbocation intermediate that continues to form an alkene in an E1 elimination.
The sought to determine the effects of mixing various levels of acids and bases to see which combination would have the most explosive reaction, and measure the resulting pH levels. I did this by testing an assortment of different pH levels of acids and bases, mixing them together and measuring the results. Most of the experiments resulted in a pH neutral solution, except for the Sulfuric Acid and the Sodium Hydroxide. By far, the Sulfuric Acid was the most explosive, followed by the Citric and Acetic acid.
Paturau, J.M. 1982. By-products of the cane sugar industry. Second ed. Elsevier scientific Publishing Co., New York. 366 pp.
The lab begins with reflux of the reaction to form an ester, followed by several extractions from an organic layer. To purify the ester, the compound is dried by gravity filtration with a drying agent, distilled using simple distillation, and recrystallized. The aldol condensation is reacted in a test tube and the solute is collected via vacuum filtration and recrystallized. The esterification procedure was performed first. To begin the lab, the heating mantle was set at the 6 setting, and the hot plate heat was turned on to low.
The purpose of conducting this experiment was to synthesise and characterise for the preparation of benzocaine via a fishcer esterification reaction by the means of amino benzoic acid alongside ethanol. The product was also precipitated from a solution in order to gain a pH of 8.The secondary aim was to esterify the reaction in an equilibrium reaction catalysed via the addition of acid shown below:
The goal of this experiment is to determine which products are formed from elimination reactions that occur in the dehydration of an alcohol under acidic and basic conditions. The process utilized is the acid-catalyzed dehydration of a secondary and primary alcohol, 1-butanol and 2-butanol, and the base-induced dehydrobromination of a secondary and primary bromide, 1-bromobutane and 2-bromobutane. The different products formed form each of these reactions will be analyzed using gas chromatography, which helps understand stereochemistry and regioselectivity of each product formed.
As a final point, the unknown secondary alcohol α-methyl-2-naphthalenemethanol had the R-configuration since it reacted the fastest with S-HBTM and much slower with R-HBTM. TLC was a qualitative method and ImageJ served as a quantitative method for determining which reaction was the faster esterification. Finally, 1H NMR assisted in identifying the unknown from a finite list of possible alcohols by labeling the hydrogens to the corresponding peaks.
Frey, Regina F., and Maureen J. Donlin. "Chemistry 257." Olfaction Tutorial. Washington University, 1998. Web. 4 Dec. 2013.
The solvent should be easily removed from the purified product, not react with the target substances, and should only dissolve the target substance near it’s boiling point, but none at freezing. A successful recrystallization uses minimum amount of solvent, and cools the solution slowly, if done to fast, many impurities will be left in the crystals. Using the correct solvent, in this case ice water and ethyl acetate, the impurities in the compound can be dissolved to obtain just the pure compound. A mixed solvent was used to control the solubility of the product. The product is soluble in ethanol an insoluble in water. Adding water reduced solubility and saturates the solution and then the crystals
In this experiment, the following chemicals were used; benzocaine, benzoic acid, ethyl acetate, sodium hydroxide, acetone, sodium benzoate, hydrogen chloride, methylene chloride, and glacial acetic acid.
J. Clayden, N. Greeves, S. Warren, P. Wothers. Organic Chemistry. 8th ed. 2007, Oxford University Press, p. 1186-1191.