Methyl Benzoate Synthesis Lab Report

Atoms are the basic units of matter and all life is based on them. Life on earth is based on the element carbon. It is a highly versatile atom able to form four covalent bonds with itself or other atoms such as hydrogen and water. Atoms combine to form molecules and those that are carbon based are referred to as organic molecules. Organic molecules occur in four different types in living cells; carbohydrates, lipids, proteins and nucleic acids. They are also known as hydrocarbons due to the presence of both hydrogen and carbon. Carbohydrates are made up of carbon, hydrogen and oxygen in the ratio 1:2:1. They are important sources of energy and are classified in three main groups; monosaccharides, disaccharides and polysaccharides.

Different procedures were used to isolate benzil from the ether layer and benzoic acid from the aqueous layers. To isolate benzil, anhydrous MgSO4 was added to the flask containing the ether layer solution. MgSO4 removes the remaining water in the ether layer solution. After making sure that enough amount of MgSO4 present in the solution, the ether solution was filtered by using gravity filtration. During filtration, MgSO4 was removed from the solution and the ether solution was collected in 25 ml flask. To separate benzil from the filtered ether solution, the beaker containing the ether solution was heated until the ether evaporated. After letting the beaker to cool to room temperature, the mass of the beaker with the benzil crystals was measured. From the combined mass of the beaker and the benzil crystals and from the predetermined mass of the beaker, the mass of the collected crystals was calculated to be 0.266 gram.

In the first acid extraction of benzocaine, the compound was dissolved in the organic solvent of dichloromethane. When the mixture was shaken with HCl, benzocaine’s amine group gained a proton and became more soluble in water than dichloromethane. This allowed the newly formed hydrochloric salt to migrate to the aqueous layer. However, the addition of NaOH to the acidic aqueous layer regenerated benzocaine by deprotonation, making it insoluble in the aqueous layer. The precipitation of an ionic salt was therefore recovered by vacuum filtration and had a tested melting point range of 85.1C-87.4C compared to 88C-90C, the literature melting point of benzocaine. The similarity in melting point ranges, but low percent yield of 30.37% proves that the extract was somewhat successful. Lower yields may be the result of spillage performed in the lab. In the second basic extraction, the organic layer now included benzoic acid and benzamide. When treated with NaOH to deprotonate benzoic acid, the newly formed sodium benzoate transitioned to the aqueous layer as a sodium salt. Benzoic acid is regenerated once again after the addition of HCl and became insoluble in the aqueous layer after protonation. Its precipitation was then filtered out for a 65.87% recovery. Compared to its literature melting point of 122.41C, the resulting 120.9C-123.5C melting range of the sample also supports the accuracy of the separation due to its similarities and high percent yield. In conclusion, the usage of base and acid liquid extraction was mostly successful in this experiment because it was able to efficiently and properly isolate the impure mixture into two separate components of benzocaine and benzoic acid. By performing the techniques of extraction and vacuum filtration, the similarities between literature and tested

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.

Samples of benzophenone, malonic acid, and biphenyl were each tested with water, methyl alcohol, and hexane. Benzophenone was insoluble in water as it is nonpolar while water is highly polar. Benzophenone was soluble in methyl alcohol, dissolving in 15 seconds, because methyl alcohol is intermediately polar as benzophenone is nonpolar. Methyl alcohol is polar but not as much as water. Thus, the nonpolar benzophenone was soluble in methyl alcohol. Benzophenone was partially soluble in hexane because hexane is nonpolar as is benzophenone. Thus, benzophenone was dissolved in hexane. Malonic acid was soluble in water because both malonic acid and water are polar. It took 25 seconds for malonic acid to dissolve in water. Malonic acid was soluble in methyl alcohol because malonic acid is polar and methyl alcohol is intermediately polar, allowing malonic acid to dissolve in the methanol in 15 seconds. Malonic acid was insoluble in hexane because hexane is nonpolar while malonic acid is polar. Biphenyl was insoluble in water as water is highly polar whilst biphenyl is nonpolar. Biphenyl was partially soluble in methanol which is intermediately polar whilst biphenyl is nonpolar, allowing it to dissolve a little. Biphenyl was soluble in hexane because both biphenyl and hexane are nonpolar molecules. Biphenyl dissolved in hexane in 10 seconds.

In order to isolate benzoic acid, benzocaine and 9-fluorenone, each component needed to be separated from one another. All three compounds began together in one culture tube, dissolved in methylene chloride and formed into a homogenous mixture. In this culture tube, two milliliters of aqueous three molar hydrochloric acid was added, which immediately formed two layers, the top acidic aqueous layer was clear in color and contained benzocaine, and the bottom organic formed was yellow and contained benzoic acid and 9-fluorenone. Benzocaine’s amino group is protonated by the aqueous layer hydronium. This protonation forms the conjugate acid of benzocaine, benzocaine hydrochloride. Thus, the conjugate acid, benzocaine hydrochloride is a salt in which is soluble in water and furthermore can be isolated from the organic mixture. When testing out the pH levels in benzocaine, the pH test strip was dark blue in color, indicating a pH level of around 5 to 7. When isolating benzoic acid, two milliliters of aqueous three molar sodium hydroxide was added, which deprotonates the carboxylic group in benzoic acid, forming its conjugate base, sodium benzoate. As with benzocaine hydrochloride, sodium benzoate is a water soluble ionic salt in the aqueous layer that can then be separated from the bottom organic layer containing the 9-fluorenone. The pH test strip was a vibrant red for benzoic acid, indicating a pH of 2. Now the 9-fluorenone is left, deionized water is added to remove any excess

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.

In this experiment, the Fischer Esterification of an unknown acid and an unknown alcohol was used to prepare an unknown ester. Sulfuric acid was used as a catalyst in the reaction which then was put under reflux. After cooling, the pH of the solution was raised to approximately 8 using sodium carbonate. Diethyl ether was added, then the aqueous layer was removed and the organic layer was washed with sodium chloride. The aqueous layer was removed again and sodium sulfate was added. The unknown product was then identified using gas chromatography (GC) to obtain the retention time.

Experiment 4A: Determination of a Partition Coefficient for Benzoic Acid in Methylene Chloride and Water, and Experiment 4B: Solvent Extraction I: Acid-Base Extraction Using the System Benzoic Acid, Methylene Chloride, and Sodium Bicarbonate Solution

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

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

At room temperature (25°C), esterification reactions are relatively slow, therefore requiring the rate of the chemical reaction to be increased for the products to be formed efficiently. This is implemented, by using a catalyst, such as concentrated sulphuric acid (H2SO4 (aq)), as well as by heating the mixture: using a heating mantle. As a result, the energy of the reactants can be greater than the activation energy, increasing the rate of reaction. Hence, as the reactants are relatively volatile, so reflux apparatus such as a pear-shaped flask and a Liebig condenser were used, to minimise the amount of reactants lost, as well as allow the reaction to take place at the highest temperature possible. In addition, boiling chips were added prior to reflux, to prevent bumping and a decrease a loss of volatile reactants, during the reflux

Purpose: The purpose of the experiment was to perform the acid-catalyzed Fischer Esterification of acetic acid and isopentyl alcohol to form isopentyl acetate, or banana oil, which is used in flavor industries. The equilibrium of the reaction was changed by adding an excess amount of acetic acid. The reaction was refluxed and product was purified by extraction and distillation. Isopentyl acetate was analyzed by infrared spectroscopy and 1H NMR spectroscopy.

Purpose: The purpose of this experiment is to synthesize methyl nitrobenzoate from methyl benzoate, concentrated nitric acid, and concentrated sulfuric acid via an

In this experiment, a Fischer Esterification reaction was performed with two unknown compounds. The unknown compounds, Acid 2 and Alcohol D, were identified by using the knowledge of the reaction that took place, and the identity of the product that was synthesized. The identification of the product resulted from analysis of IR and NMR spectra.