Dehydration of 2-methylcyclohexanol Authors: Johnny Presley Abstract: Dehydration of 2-methylcyclohexanol to 3-methylcyclohexene is simple distillation where dehydration was used to prepare the final product. The results of the experiment showed that the 3-methylcyclohexene was formed via an E1 reaction from 2-methylcyclohexanol with a 1:1 ratio of sulfuric acid and phosphoric acid. However, some H2O was left over, which was seen when we look at the IR and see a small water peak. This could be due to the fact that not enough sodium sulfate was added and not for long enough. These results were confirmed by the quality tests that showed that a precipitate formed when KMnO4 was added to the solution and in the IR spectroscopy peaks showed peaks at 3022.62cm-1 which matches an alkene, further showing that the formation of 3-methylcyclohexene was successful with a percent yield of 56.46%. Introduction: The major reaction that happened was an E1 reaction (otherwise known as a unimolecular elimination reaction). In this reaction the removal of an HX substituent group results in the formation of a double bond via beta hydrogen elimination4. In an E1 reaction the deprotonation of hydrogen in the beta position occurs and from here a carbocation is formed, which results in the formation of an alkene product. This happens when the OH group on the 2-methylcyclohexanol is hydrated by H2SO4, which allows the OH to become an H2O. Since H20 is a better leaving group now it will
In an oxidation reaction, the number of C-H bonds decreases or the number of C-O bonds increases, while in a reduction reaction, the number of C-H bonds increases or the number of C-O bonds decreases. In the oxidation step of this reaction, 4-tert-butylcyclohexanone is formed from when a C-H bond is lost while a C-O bond is gained to create a carbonyl. In the reduction step, 4-tert-butylcyclohexanol is formed when the carbonyl is converted into an alcohol when a nucleophilic hydride attacks the carbonyl. Whether the OH is in the
Stoichiometry is a very important part of chemistry. Stoichiometry refers to calculating the masses of molecules and their products . The reactants are usually given and stoichiometry is used to find the products of the equations as well balancing the equation. An example of this would be sodium chloride (NaCl). Stoichiometry will say that if there are ten thousand atoms of sodium and one atom of chlorine, only one molecule of sodium chloride can be made and that fact can never be changed.
The carbon-carbon double bond of alkenes represents a site that has a high electron intensity. This site is susceptible to oxidation. Depending on the conditions or reagents used to initiate the oxidation of alkenes, various products can be obtained. With relative mild oxidation, it is only the pi bond of an alkene that is cleaved resulting in the production of 1,2-diols or epoxides. However, when there is more vigorous
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
Whereas for simple distillation, the compounds need to be around 80C apart in order for proper separation to occur. Thus, cyclohexane and toluene were not able to be properly separated since the boiling point for cyclohexane was 80.74C while the boiling point of toluene was 110.6C—there two boiling points are fairly close to one another. Thus, the mole fraction for cyclohexane and toluene were fairly low when compared to cyclohexane and
Figure 1. Reaction mechanism for the reduction of cyclohexanone to adipic acid, using the oxidizing agent nitric acid.
A small beaker was placed under the arm of the distillation head to catch the distillate. Foil was wrapped around the neck of the round-bottomed flask and a wet paper towel was wrapped around the arm of the distillation head to create a condenser. The flask was heated gently so that the distillate dropped at a rate of two drops per minute. The temperature was recorded as every drop was collected. The distillation began at around 55.0 ℃. The distillation was stopped after 29 drops were collected to prevent the solution from being distilled to dryness. See attached data. The known boiling point of 1-butanol is 117.5 ℃ (Lemonds). The known boiling point of 1-propanol is 97 ℃ (Thiyagarajan). The known boiling point of acetone is 56 ℃ (Forss). The known boiling point of 2-butanone is 79.6 ℃ (Jiang). For unknown #3 the boiling point of the first substance seemed to be around 56 ℃ and the boiling point of the second substance seemed to be around 111 ℃. Therefore unknown #3 seemed to be a mixture of acetone and 1-butanol.
Within this experiment a type of cycloaddition reaction was performed, called Diels-Alder reaction. This type of reaction involves both a 1,3-diene and an alkene, called the dienophile in this reaction. Within this reaction two new sigma bonds were formed at the 1 and 4 carbon atoms of the diene. Two other pi bonds are also formed simultaneously with the sigma bonds. Due to this concerted nature of the reaction the diene must be able to adopt a s-cis configuration, making the reaction stereospecific.
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, 1,2-cyclohexene was taken and made it 1,2-cyclohexanediol in two separate reactions. Two products were formed in each respective reaction: cis-1, 2-cyclohexene and trans-1, 2-cyclohexanediol. To figure out which product was formed in each reaction, TLC was used to test the stereochemistry from the products compared to the actual compounds. Each retention factor was compared to the actual product retention factors to see if the reactions had been done properly.
Introduction The Purpose of the experiment was broken into two parts both having to do with the purification and separation of different compounds and impurities. In part A was the distillation of cyclohexane and in part B it was about taking a 50:50 mixture of dichloromethane and cyclohexane and separating them through fractional distillation. Experimental Refer to Chemistry 2513 Lab Manual Introductory Organic Chemistry Part 1 Fall 2014. Look for this experiment between pages 21-24 Results Observations:
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
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.
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
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.