The goal of this experiment was to synthesize an alkene (4-methylcyclohexene) from an alcohol (4-methylcyclohexanol) by dehydration. The reaction, consist of 4-methylcyclohexanol, phosphoric acid, and sulfuric acid, was refluxed at a given time frame. The product was isolated by distillation and purified by adding sodium chloride to help the extraction. The final product had a 125% yield and was characterized by the IR spectroscopy and chemical reaction. The alkene resulted in a colorless liquid after adding molecular bromine dissolved in dichloromethane.
Introduction One of the most important things organic chemists do is synthesize new and complex structures from simpler structures by chemical reactions. The techniques done in
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By heating to refluxing, the temperature and thermal energy were controlled during the experiment. Heating the reaction is important because it is required in order for the bonds to break to cause a chemical reaction. Breaking bonds also means requiring energy and that is where activation energy comes into play. All chemical reactions has to overcome an energy barrier to generate the product from the reactant. The chemical yield is a measurement of how efficient the organic reactant was synthesized into the desired product. The chemical yield will be lower if there are unreacted reactants or too many side products in the reaction. Unless the product was isolated properly during the distillation, it will negatively affect the chemical yield too. The chemical yield is measured by dividing the number of moles of product to the number of moles of reactant then multiplying it by 100 to get the percentage. The final product formed was characterized by using an infrared spectroscopy and chemical reaction. The IR spectrum was expected to show a carbon double bond (alkene) and many C-H sp³ hybridization bonds (alkyl) from the final product. This was compared to the authentic sample with its vibrational bonds. Once done identifying how close the sample is with the authentic sample, that would be the evidence to support the product’s
The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.
During the synthesis chemical reaction, covalent bonds breaks and form new bonds (Arizona State University, 2017). This is what form new chemical structures. During this process, thermal energy is produced because of the chemical bonds being broken down. In this experiment, p-aminophenol was converted into acetaminophen using reflux, or heat. When external heat is added to a chemical reaction in a container, a closed container may cause an increase amount of pressure and the container will explode (MIT OpenCourseWare, 2010). Evaporation happens when a container is closed (MIT OpenCourseWare, 2010). It takes time and a specific heat temperature for a reaction to occur, so reflux solves this by allowing the solution to boil to the right temperature but it is continuously cooled to stay at that temperature which
Alcohol dehydrations are widely used in many industries to produce alkene. In this experiment 2-methylcyclohexanol was dehydrated to three possible products using phosphoric acid as a catalyst. The main tool for this experiment is the Hickman still. First, Drierite was added to the Hickman still so that any excess water formed during the experiment will be absorbed. It also acted as a boiling stone and addition surface to increase surface area. Next, 0.75 mL of 2-methylcyclohexanol is added to the still and right after 1 mL of phosphoric acid is added. The phosphoric acid (H3PO4) acts as a catalyst in order for the reaction to occur. The mixture is heated up to between 120o Celsius and 160o Celsius. If the temperature goes above 165oC then
After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some
There was an C-C double bond, as indicated by the peak at about 1609 cm-1. Sp3 C-H was also present as indicated from the peaks in the 3000cm-1 to 2850cm-1 region. The C-O bond of an ester is present, as indicated from the 1266cm-1 peak. From analyzing both the
The purpose of this lab was to carry out a dehydration reaction of 2-methylcyclohexanol by heating it in the presence of phosphoric acid and determining which alkene product would be the major product. Methylcyclohexanols were dehydrated in an 85% phosphoric acid mixture to yield the minor and major alkene product by elimination reaction, specifically E1. The alkenes were distilled to separate the major and minor products and gas chromatography was used to analyze the results and accuracy of the experiment. The hypothesis was the major product of the reaction would be the most substituted product. This conclusion was made because of
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 dehydration of 2-methyl-2-butanol was performed using sulfuric acid and phosphoric acid in order to synthesize alkene products 2-methyl-1-butene and 2-methyl-2-butene. After carrying out steam distillation to isolate the organic alkenes from aqueous components within the reaction mixture, the purity and characterization of the products were then assessed through various analytical methods including Gas Chromatography (GC), Infrared Radiation (IR) Spectroscopy, and Nuclear Magnetic Resonance (NMR) Imaging. Through the characterization of the final products, it was found that little impurities remained in the final reaction solution and according to the GC, no alcohol remained in the vial after the reaction was complete. The actual yield
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.
This experiment set out to synthesize 2-methyl-4-heptanone from the supplied starting materials containing four carbons. During week one, 1-chloro-2-methylpropane was reacted with magnesium to form the Grignard reagent. The Grignard was then reacted with butanal to produce 2-methyl-4-heptanol. Using IR spectroscopy, the success or failure of the formation of the alcohol was observed, concluding week one. During week two, 2-methyl-4-heptanol was oxidized in order to form our desired product of 2-methyl-4-heptanone. Both a GC and IR spectroscopy were observed in order to determine the presence of a newly formed ketone. The results of our experiment from the IR taken during week one showed no formation of an alcohol. The GC and IR spectroscopy
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 purpose of this lab is to understand the process of eliminating an alkyl halide to form an alkene. The experiment is carried out by first converting the alcohol, 2-methy-2-butanol, into the alkyl halide of 2-chloro-2-methylbutane that will then be put through dehydrohalogenation that favors elimination reaction (E2) to create a mixture of 2-methyl-2-butene and 2-methyl-1-butene. A fractional distillation will be taken to purify the mixture and an additional gas chromatography will be done to further analyze the mixture composition. A bromide test will be done to determine the product of an alkene in the experiment.
For this experiment, Alcohol D and Acid 2 reacted in the presence of concentrated sulfuric acid, resulting in a colorless solution with brown layer on top. After washes with sodium bicarbonate and brine, the pale-yellow liquid product was dried and then distilled. Distillation resulted in two colorless fractions, the second of which had a boiling point of 69-70 ˚C. This boiling point is unrealistic for any compound obtained in this experiment, so it was not used in identifying the product. After distillation, both fractions were spectroscopically analyzed. The IR and NMR spectra obtained for both fraction were identical, meaning both fractions contained exactly the same substance. Both fractions also smelled the same, like piña colada, therefore confirming this conclusion. This outcome also meant that the amount of product synthesized was 5.7393 g.
Part 2 to determine the empirical formula and percentage yield of the compound synthesized in Part 1. Spectrophotometry is a routine laboratory test that has the added advantage
The objective of this experiment is to successfully perform a dehydration of 1-butanol and 2-butanol, also dehydrobromination of 1-bromobutane and 2-bromobutane to form the alkene products 1-butene, trans-2-butene, and cis-2-butene. The dehydration reactions react under and acid-catalysis which follows an E1 mechanism. It was found that dehydration of 1-butanol yielded 3.84% cis-2-butene, 81.83% trans-2-butene, and 14.33% 1-butene, while 2-butanol is unknown due to mechanical issues with the GC machine. For the dehydrobromination, with the addition of a