Introduction
An elimination reaction is when an atom or group of atoms, the leaving group, leaves the molecule along with the loss of a hydrogen atom that is part of an adjacent carbon that results in an alkene (Ketcha, 98). Dehydration is an example of an elimination reaction. Just likes its opposite (hydration, the addition reaction), it could also result in multiple products: one product would be “major” where it is one that was mostly form as it is mostly stable, and one is the “minor” which is less stable then the major and least likely to form (Ketcha, 98).
The mechanism of dehydration is a three step process. First the protonation of the -OH, then the loss of the H-O-H + Leaving group, resulting in a carbocation intermediate, and finally the removal of H+
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Procedure
(Ketcha, Daniel; Turnbull, Kenneth; Grieb, Jonathan. Organic Chemistry Laboratory Experiment, “Dehydration of 2-Methylcyclohexanol and Gas Chromatography.” Cincinnati, OH: Van Grinner Publishing, 2016.)
2-Methycyclohexanol (15mL) were added to H3PO4 (1mL) and H2SO4 (3 drops) in a 100mL round bottom flask. The distillation apparatus was assembled and the mixture was moderately heated to avoid bubbling during the distillation process. During this time, some of the equipment was not 100% secured, and some product was lost. Distillation was stopped when a black, oily substance started to form at the bottom of the flask. The distillate was collected in the Erlenmeyer flask, at the temperature of 109 degrees C. The organic layer was dried using the anhydrous MgSO4. The MgSO4 was filter off and the alkene mixture was collected. The liquid alkene was weigh.
The final product was analyzed using the gas chromatography, where the retention time of each product was determine and compared to the standard
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
Experiment 55 consists of devising a separation and purification scheme for a three component mixture. The overall objective is to isolate in pure form two of the three compounds. This was done using extraction, solubility, crystallization and vacuum filtration. The experiment was carried out two times, both of which were successful.
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
Introduction: The fundamental techniques of organic chemistry lab, commonly known as SIPCAn, include separation, isolation, purification, characterization, and analysis (1). Through SIPCAn, students learn the fundamental techniques of organic chemistry laboratory. Mastering these techniques are necessary in order to perform more complicated experiments and to carry out organic reactions and synthesis. The information gained from SIPCAn included boiling point, melting point, and density can be used to identify unknown compounds. Simple distillation was used to purify a compound by separating it from a
The purpose of this experiment is to practice common organic laboratory techniques inside the lab to get one oriented to the basic methods of procedure that can be used for later experiments. This experiment involves the separation of benzoic acid from a more crude form, consisting of benzoic acid, methyl orange, a common acid/base indicator, and cellulose, a natural polymer of glucose (Huston, and Liu 17-24). The technique that is used to perform this separation is called extraction. Extraction is a systematic process of separating mixtures of compounds, taking advantage of the affinity differences of compounds to separate them (Padias 128-37). This technique recognizes the principle that “like dissolves in like,” that is,
In this experiment, 0.31 g (2.87 mmol) of 2-methylphenol was suspended in a 10 mL Erlenmeyer flask along with 1 mL of water and a stir bar. The flask was clamped onto a hotplate/stirrer and turned on so that the stir bar would turn freely. Based on the amount of 2-methylphenol, 0.957 mL (0.00287 mmol) NaOH was calculated and collected in a syringe. The NaOH was then added to the 2-methylphenol solution and allowed to mix completely. In another 10 mL Erlenmeyer flask, 0.34 g (2.92 mmol) of sodium chloroacetate was calculated based on the amount of 2-methylphenol and placed into the flask along with 1 mL of water. The sodium chloroacetate solution was mixed until dissolved. The sodium chloroacetate solution was poured into the 2-methylphenol and NaOH solution after it was fully dissolved using a microscale funnel.
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, there are one hundred known samples being tested under nine different conditions. Reversed-phase HPLC is being used with water and methanol as the solvents. The columns used are C8, C16, and C18. The number represents the length of carbon chains within the column. Each sample is run on each column under three different solvent ratios: 30%/70% water/methanol, 50%/50% water/methanol, and 70%/30% water/methanol.
Part 1, week one, of this experiment consisted of the Synthesis of Cyclohexene and Simple Distillation. A 5ml short-necked, round-bottomed flask was obtained to add 3.0mL of cyclohexanol into it. Then, 0.75mL of 85% phosphoric acid using a pipette as well as adding a few boiling chips, to prevent bumping. The flask was then connected to the simple distillation apparatus. To set this apparatus up, micro-kit, such as the following, were used to build it: short-necked, round-bottom flask, Viton connector with a support rod. A distillation head with a 105° connecting adapter, air condenser, rubber connector, thermometer, thermometer adapter, Erlenmeyer flask that was used as the receiving flask, and a sand bath. The thermometer was carefully inserted into the rubber connector by holding the thermometer close to the adapter and sliding it in the connector using a twisting like motion; this was done while avoiding any forcing action which would have led to breaking of the thermometer. After the apparatus was built, the thermometer was fixed therefore its bulb was below the side arm and was not touching the sides of the glass; which ensured that the thermometer recorded the temperature of vapors which were distilling off. The apparatus was lowered making the round-bottomed flask rest in the sand bath and tilting it therefore the condenser end is resting on the Erlenmeyer flask. The sand bath was turned on to start heating the reaction mixture. The reaction was boiled for 10 minutes before distilling was proceeded. After the ten minutes, the temperature of the sand bath was increased and distilling of the cyclohexene was commenced. The distillation head was wrapped with aluminum foil to prevent heat from going out. A spatula was used to adjust the sand surrounding the round-bottomed flask to control the amount of heat that it tales in; it was adjusted therefore making the rate of distillation not faster than 2 drops per minute. Vapors were directed through the air condenser and were condensed back into liquid into the receiving flask. The simple distillation distilling temperature range was collected by recording the temperature of the first drop of distillate that is collect and the temperature of the last drop
The prime goal in implementing preparative gas chromatography was to separate components of a mixture. Afterwards, the identity of the separated parts was observed by the use of infrared spectroscopy. In the experiment, the unknown was labeled with the number 138R, and the identity was predicted to be 4-methyl-2-pentanone due to the presence of the functional groups: alkanes, and carbonyls on the IR spectrum.
analysis, also known as gas-liquid chromatography, is an extremely applicable and powerful method of environmental analysis. G.C. analysis is one of the few analyzing methods which has the capacity to measure nearly all gases, pesticides, and small as-well-as complex organic molecules [2]. As with other forms of chromatography, two different phases are needed, more specifically, for gas-liquid chromatography the mobile phase is a gas and the stationary phase is a liquid (usually of high boiling point such as hexane). The very small sample which is to be analyzed is injected into an oven, as depicted in figure 2, which is hot enough for the sample to vaporize and be carried into the column by a gas such as helium. How fast the sample travels through the column depends on how much time it takes moving with the gas in the column as opposed to being attached to the mobile phase. This amount of time in the column, or retention time, is measured by the detector. Every substance has a specific retention time. The graph generated by the computer-detector for our specific elimination reaction is shown
This experiments was performed in three parts. In Part 1, the organic solution was separated from the aqueous solution. First approximately 0.300 grams of 1,4-dimethoxybenzene, p-tert-butylbenzoic acid and p-tert-butylphenol was weighed and and placed in a 100-mL beaker with 25 mL of Et2O. Then, the solution was quantitatively transferred a 125 mL separatory funnel and added 10 mL of 0.5 M NaHCO3. The solution was shaken and vent until there was no CO2 being formed. The aqueous layers was drained into a 125 mL Erlenmeyer flask. Additionally, the organic layer was washed with 0.5 M NaHCO3 two more times and combined with the other aqueous solution. The organic layer was washed again with 10.0 mL of DI water and combined with the other aqueous
The two pentenes were trimethyl-1-pentene and trimethyl-2-pentene. The methods to reach this conclusion were different, then those used in the thin-layer chromatograph. A gas chromatograph consisted of a gaseous mobile phase, carrier gas, and a non-volatile liquid as the stationary phase in a heated system that collected its results from a flame ionized detector. A thin-layer chromatograph consisted of a volatile liquid mobile phase, and a silica layer on an absorbable paper as the stationary phase. The results of the TLC was observable on the TLC plate after the separation, as a graph was needed to physically see if the compounds in the gas chromatograph were separated. These differences in procedure relates to the type of chromatography that was needed to separate specific compounds based on their unique or similar
The purpose of the lab was to separate a mixture containing methanol, acetone, methyl ethyl ketone, ethyl acetate, propyl acetate and 2-pentanone using gas chromatography. The effect of temperature and pressure variance of the Mini GC on the chromatogram was analyzed and the best temperature-pressure profile was determined based on the results. Temperature programming was determined to give better separation than using a constant temperature. The gas chromatogram was analyzed and peaks were identified based on their behavior within the column. The first two peaks were identified as either acetone or methanol. The next two peaks were identified as 2-pentanone and Methyl Ethyl Ketone and the last two peaks were identified as Ethyl Acetate and Propyl Acetate.
Gas chromatography is the branch of chromatography in which the mobile phase is gas (called the carrier gas) and the stationery phase is liquid (GLC=Gas Liquid Chromatography). GLC has been widely used as in solid stationery phase it is difficult to deal with as there is a phase difference (Solid, Gas) and gas do not easily adsorb in solid. The separation on liquid stationery phase is based on either relative solubility’s of sample component in the stationery phase or a combination of relative solubility’s in the stationery phase.