The objective of the experiment was to synthesize a sample of cyclohexene by using an E1 reaction, which involved cyclohexanol.
Procedure Part A- Preparation of Cyclohexene
• Prior to beginning the procedure, a distillation setup was constructed in order to prepare for a later step in the procedure; a diagram of the construction was included in Figure 1.A. In a clean 50-mL Erlenmeyer flask, 5 mL of water were placed, and, with extreme caution, 4.0 mL (8.0 g, 0.08 mol) of concentrated sulfuric acid were added to the flask while swirling; it was emphasized that this acid can be highly corrosive and should be handled with care, especially while pouring it into the water1. It was observed that the flask began to heat up as the acid was added, and began to release a gas for a brief moment. Afterwards, the diluted acid was allowed to cool to about room temperature and 3.2 mL (3.0 g, 0.030 mol) of cyclohexanol were added to the mixture. The contents of the flask were carefully transferred to a 25 mL round-bottom flask that was attached to the distillation setup. The contents were distilled at a steady pace, making sure that all the junctions and flasks were clasped appropriately in order to avoid any accidents. The distillation was allowed to continue until the liquid found in the starting flask turned black and began to emit a white gas. It was noted that at around 53 °C distillate began to form, and at around 92 °C the liquid turned black. Approximately 2.8 mL of distillate
A 0.5 g of sodium tungstate dihydrate was weighed and transferred into a 50-mL round-bottom flask with a magnetic stir bar. Approximately 0.6mL of Aliquat 336 was then transferred carefully into the round bottom flask using a 1mL syringe. The round bottom flask and its contents were then set up in an oil bath. 11mL of 30% hydrogen peroxide and 0.37 g of potassium bisulphate were added to the reaction mixture in the round bottom flask and stirred using a magnetic stirrer. Lastly, 2.5mL of cyclohexene was added using automatic dispenser and the mixture stirred. A condenser was fitted on the round bottom flask, clamped and attached to water horses. The reaction mixture was then heated on the oil bath and the reflux process initiated for an hour while stirring the mixture vigorously. Half way while rinsing, any trapped cyclohexene in the condenser was rinsed. After 1 hour, the round bottom flask was rinsed
14 mL of 9 M H2SO4 was added to the separatory funnel and the mixture was shaken. The layers were given a small amount of time to separate. The remaining n-butyl alcohol was extracted by the H2SO4 solution therefore, there was only one organic top layer. The lower aqueous layer was drained and discarded. 14 mL of H2O was added to the separatory funnel. A stopper was placed on the separatory funnel and it was shaken while being vented occasionally. The layers separated and the lower layer which contained the n-butyl bromide was drained into a smaller beaker. The aqueous layer was then discarded after ensuring that the correct layer had been saved by completing the "water drop test" (adding a drop of water to the drained liquid and if the water dissolves, it confirms that it is an aqueous layer). The alkyl halide was then returned to the separatory funnel. 14 mL of saturated aqeous sodium bicarbonate was added a little at a time while the separatory funnel was being swirled. A stopper was placed on the funnel and it was shaken for 1 minute while being vented frequently to relieve any pressure that was being produced. The lower alkyl halide layer was drained into a dry Erlenmeyer flask and 1.0 g of anhydrous calcium chloride was added to dry the solution. A stopper was placed on the Erlenmeyer flask and the contents were swirled until the liquid was clear. For the distillation
In this experiment, we used distillation to separate a mixture of cyclohexane and toluene. We used two types of distillation simple and fractional. The experiment was carried out by mixing the cyclohexane and toluene in a round bottom flask, and the mixture was heated to boiling (in sand bath) and vaporized. The vapor then condensed by the condenser where the water was running through to cool the vapor back to liquid. Since this was a mixture of two liquids, the temperature was continuously increasing throughout the process. The different boiling points of cyclohexane and toluene allows the separation to occur. Cyclohexane has a boiling point of 81 °C and toluene has a boiling point of 111 °C, since cyclohexane has a lower boiling point it
1.5mL of phosphoric acid including 3-4 boiling chips were also added to the 25mL flask. The short path distillation apparatus was set up as shown in Figure 1. A heating mantle was used to heat up the 25mL flask. The solution was distilled to the receiving flask until a small amount of liquid remained in the initial RBF flask. At this point the presence of thick grey smoke pulling over into the entire apparatus was observed. The apparatus was then left to cool down. Through the use of pasture pipette, the aqueous layer from the distilled solution was drawn out. Sodium carbonate was then added to the remaining organic solution in order to check the pH and to verify the basicity of the solution. The aqueous layer was again drawn out from the solution. Next, 0.5g of sodium sulfate was added to the remaining organic layer and was swirled until the liquid appeared to be dry and clear. The alkenes were transferred into a clean 10mL flaks using another clean pasture pipe. The apparatus from the first distillation was rinsed off with
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
The organic solution was then transferred to a sample vial and labeled as reaction B. Another two mL of diethyl ether was placed with the NaHCO3 and then combined with the clear product and was sealed in the sample vial. This vial was also placed in the freezer until the product could be tested by gas
Objective: The objective of the experiment was to determine the distribution coefficient (the equilibrium concentration ratio) of iodine between the immiscible solvents water and cyclohexane. This experiment was a study of equilibrium. The distribution coefficient will be derived from the data obtained by performing a chemical analysis for iodine in the water layer.
The main purpose of this experiment is to synthesize, isolate, extract and characterize 4-methylcyclohexe. The reaction is performed by performing a combined reflux and distillation procedure on the reactant 4- methylcyclohexanol along with catalysts concentrated sulfuric and phosphoric acid combined with heat. The combination of reflux and distillation procedure prevents the backward reaction through the formation of water. The reflux reaction is especially useful as the addition of heat during this process allows for an increase in the fraction of useful collisions. This allows the reaction to proceed faster.
Distillation is a method of separating two volatile chemicals on the basis of their differing boiling points. During this lab, students were given 30 mL of an unknown solution containing two colorless chemicals. Because the chemicals may have had a relatively close boiling point, we had to employ a fractional distillation over a simple distillation. By adding a fractionating column between the boiling flask and the condenser, we were able to separate the liquids more efficiently due to the fact that more volatile liquids tend to push towards the top of the fractionating column, thereby leaving the liquid with the lower boiling point towards the bottom. After obtaining the distillates, we utilized a gas chromatograph in order to analyze the volatile substances in the gas phase and determine their composition percentage of the initial solution. Overall, through this lab we were able to enhance our knowledge on the practical utilization of chemical theories, and thus also demonstrated technical fluency involving the equipment.
After the mixture finished refluxing, the flask was then cooled on ice. A sulfuric acid solution was then prepared by pouring 4.5 mL of concentrated H2SO4 over 50 grams of ice and then diluted to 75 mL by adding enough tap water to reach 75 mL. The sulfuric acid solution was then cooled on ice.
The purpose of the experiment is isolate the natural products -terpenes and acetogenins- and to observe their properties. The terpene used was used to isolate was limonene from a citrus peel, and the acetogenin that was used to isolate was eugenol from clove oil. The techniques used to isolate these two natural products was a steam distillation and extraction. The amount of eugenol that was recovered 2.39 grams. After the recovery of eugenol, an IR spectrum was obtained. The IR spectrum displayed the presence of an alcohol at 3529.37 cm-1 and an alkene at 1638.08 cm-1. Classification tests are used to determine what is present.The results for the classification tests for eugenol are shown below in the table.
The purpose of this experiment is to produce cyclohexene through the acid catalyzed elimination of water from cyclohexanol. Secondary alcohols like as cyclohexanol, undergo dehydration by E1 mechanism. In this experiment the important intermediate in the mechanism is the cyclohexyl cation. This intermediate can undergo both substitution and elimination reactions. In order to prepare the cyclohexene in a desired yield, it is imperative to the substitution reaction. In this experiment, the substitution reaction is suppressed by firstly, the use of strong acids with anions that are relatively poor nucleophiles ; secondly, a high reaction temperature that favours the elimination reaction as opposed to the substitution reaction; and lastly, the distillation of cyclohexene from the reaction mixture as it is formed. The dehydration of cyclohexanol is strategically done so as to have the product, cyclohexene, distilling from the reaction mixture as it is being formed; the distillation technique serves to remove the cyclohexene from contact with the sulphuric acid before polymerization occurs. In order to obtain pure cyclohexene from the crude distillate, one has to treat with the addition of calcium chloride that helps to get rid of the water and part of the cyclohexanol, thereafter, distillation aids in separating the rest of the cyclohexanol.
Cyclohexanol, secondary alcohol, undergoes dehydration by an E1 mechanism. To prepare a cyclohexene, it is essential to restrain the substitution reaction. In this experiment, the substitution reaction is completed by the use of strong acids with anions that are mostly poor nucleophiles, a high reaction temperature, and distillation of cyclohexene from the reaction mixture as it is formed. The side products of this reaction are similar to those that are encountered in the preparation of n-pentyl bromide, the only difference is that the alkene is no longer a side product but is now the desired product. The dehydration of Cyclohexanol is carried out in a way that the product Cyclohexene is distilled from the reaction mixture. The distillation
A 10 mL round-bottom flask was weighed both before and after approximately 1.5 mL of the given alcohol, 4-methyl-2-pentanol, was added. 3 mL of glacial acetic acid, one boiling chip, and 2-3 drops of concentrated sulfuric acid were added to the flask in that order. The reflux apparatus was assembled, the
An ice bath was prepared in a large beaker and a small cotton ball was obtained. 0.5 g of acetanilide, 0.9 g of NaBr, 3mL of ethanol and 2.5 mL acetic acid was measured and gathered into 50mL beakers. In a fume hood, the measured amounts of acetanilide, NaBr, ethanol and acetic acid were mixed in a 25mL Erlenmeyer flask with a stir bar. The flask was plugged with the cotton ball and placed in an ice bath on top of a stir plate. The stir feature was turned on a medium speed. 7mL of bleach was obtained and was slowly added to the stirring flask in the ice bath. Once all the bleach was added, stirring continued for another 2 minutes and then the flask was removed from the ice bath and left to warm up to room temperature. 0.8mL of saturated sodium thiosulfate solution and 0.5mL of NaOH solution were collected in small beakers. The two solutions were added to the flask at room temperature. The flask was gently stirred. Vacuum filtration was used to remove the crude product. The product was weighed and a melting point was taken. The crude product was placed into a clean 25mL Erlenmeyer flask. A large beaker with 50/50 ethanol/water