2-Methylcyclohexene Synthesis Lab Report

The design of this experiment aimed to synthesize 2-methylphenoxyacetic acid from 2-methylphenol and sodium chloroacetate by means on phenol alkylation. 2-Methylphenoxyacetic acid has been used to control the growth in plants and exemplifies a product of synthesis as it is a complex molecule constructed from two simple molecules. This synthesis proceeds by a nucleophilic substitution reaction, more specifically, via SN2 mechanism (see below). An SN2 mechanism's reactants are a nucleophile and a good leaving group (usually a halide ion). Once the crude product is obtained, it is purified by recrystallization with water and collected.

The purpose of this experiment was to practice the functional group transformation procedure. The process of the experiment included the dehydration of 2-methylcyclohexanol in the presence of phosphoric acid and heat. The products that were formed from the reaction were 1-methylcyclohexene and 3-methylcyclohexene. The mass of the final product solution was 0.502g with a percent yield of 18.7% and a boiling point range of 84.5-98.5oC.

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

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

We used TLC analysis to identify each product obtained from the dihydroxylation reactions by spotting a TLC plate with the product of our reaction, a solution of cis-cyclohexane, trans-cyclohexane, and a 50:50 mixture of the two. We then placed the plate in a beaker with ethyl acetate saturating the atmosphere to allow the TLC plate to develop. Finally, we compared Rf values of the components of the mobile phase, after the phase was completed. 100% ethyl acetate was used instead of 100% Hexane or a mixture of Ethyl Acetate, because ethyl acetate has high polarity and can separate the components of a mixture to elution, unlike hexane, which is non-polar, and therefore unable to separate the components of the mixture. A 50:50 mixture of both would not work, because the polar and non-polar compounds would neutralize the mixture, and thereby not separate the components of the mixture.

The goals in this lab were to have a reaction occur with 4-methylcyclohexanol and an acid catalyst to form our product of 4-methylcyclohexene via an E1 reaction. This reaction is accomplished by removing the –OH group on 4-methylcyclohexanol via dehydration and to have a double bond form via a loss of a hydrogen on a β-Carbon.

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 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.

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

Dispense .5 mL water into the already weighed conical vial, replace cap and face insert on its down side.

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 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

Figure 1. Reaction mechanism for the reduction of cyclohexanone to adipic acid, using the oxidizing agent nitric acid.

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

In this experiment, methyl benzoate was synthesized from benzoic acid and methanol with acid catalyze using Fisher Esterification. First benzoic acid and methanol were mixed in 100 mL round bottom flask. We cooled the mixture in ice and poured 3 mL of conc. H2SO4 and swirled to mix compounds. Then we refluxed the mixture for 1 hour. We let the solution cool and then decanted into a separatory funnel containing 50 mL of water and rinsed the round bottom flask with 35 mL of tert-butyl methyl ether and added that to a separatory funnel. We shook and vented thoroughly and drained the aqueous layer which contained a bulk of methanol and H2SO4. We washed the solution in the separatory funnel with 25 mL of water, followed by 25 mL of sat. sodium bicarbonate