Benzoin

The original 1.0 gram of the 50/50 mixture of the benzoic acid and benzil contain 0.5 gram of benzil. Thus, from 0.5 gram of benzil, only 0.266 gram of benzil was collected. The percent recovery of benzil was calculated to be 53.2%. This low percent recovery could be due to filtration errors. Some amount of benzil remained on the filtration paper that contained the MgSO4. In order for determining the purity of the

The hydrobenzoin (meso) product of the benzil was isolated through the techniques of recrystallization and vacuum filtration. Because there NaBH4 was the limiting reagent in the experiment, 0.005604moles of NaBH4 should yield 1.2008g of hydrobenzoin (meso). The mass of the isolated product was 0.613g, resulting in a 51.1% yield. There are many reasons to account for the loss of 48.9% of

In this lab, liquid-liquid extraction was performed to isolate a mixture of benzocaine and benzoic acid. 2.0107 grams of the mixture was first weighed out for the trials. When HCl was added to the mixture for the first acid extraction of benzocaine, an emulsion formed during inversion and venting that prevented a defined separation of the two layers. 8 mL of water was therefore added before continuing the extraction. The addition of NaOH then turned the top aqueous layer basic, indicated by the pH strips that turned blue when tested. A vacuum filtration isolated 0.29 grams of benzocaine and a MelTemp apparatus measured the crystal’s melting point ranges to be 85.1C-87.4C. For the base extraction of benzoic acid, the aqueous layers were retrieved

21) After all of the solid dissolves, move the flask from the hot plate and allow it cool to room temperature. After a while, crystals should appear in the flask.

The product obtained had a melting point of approximately 107 °C and a weight of .324 grams. Some of the product would not dissolve in water and so was removed through vacuum filtration, which left .141 g not dissolved in solution. It took 13.2 mL of sodium hydroxide to turn the solution of the product dissolved in water pink. A molecular weight of 138.63 g/mol was calculated from the data. These results indicate that the product was 2-methylbenzoic acid, the Grignard reagent was 2-methylphenylmagnesium bromide, and the unknown bromide solution was 2-methylbromobenzene. Calculations showed that the limiting reagent of the Grignard preparation was magnesium and that the experiment had a 23.13 % yield.

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 range determined in the experiment is approximately 2 degrees above the actual melting point range, indicating some impurities in the final compound. According to the IR spectrum, the product obtained is quite pure. The peaks in the table above indicate the presence of a carbonyl, specifically the C=O bond of a cyclic ketone and also the sp2-hybridized =C–H bond of an alkene. There is no broad peak ranging from 3200 cm-1-3600 cm-1, which would indicate the presence of the -OH group of an alcohol. Thus, there is likely no presence of starting material in the final product. The percent yield above 100% indicates that some liquid (hexanes) used to recrystallize the product was likely still in the flask when the product was weighed.

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Objective: The objective of this experiment is to use acid-base extraction techniques to separate a mixture of organic compounds based on acidity and/or basicity. After the three compounds are separated we will recover them into their salt forms and then purify them by recrystallization and identify them by their melting points.

Discussion: As seen in the melting point determination, the average melting point range of the product was 172.2-185.3ºC. The melting points of the possible products are listed as 101ºC for o-methoxybenzoic acid, 110ºC for m- methoxybenzoic acid, and 185ºC for p- methoxybenzoic acid. As the melting point of the sample

The decanted liquid had to be placed back into the freezer in order to refreeze the crystals to allow them to be decanted off. This could have caused a portion of the product to have been lost, thus affecting the percent yield and purity of the final product. Furthermore, there was an oiled substance thought to be a contaminant in the product after the addition of hot methanol and hot water to the Erlenmeyer flask. This contaminant was left in the Erlenmeyer flask to see whether or not it had an effect on the final product, but once the activated charcoal was added into the Erlenmeyer flask, the contaminant seemed to have latched onto the charcoal. Since it latched onto the charcoal and the charcoal was filtered out by way of gravity filtration, the contaminant is thought to have been filtered out as well. While the contaminant seemed to have been filtered out by the gravity filtration, there could be a small portion of the contaminant that remained in the filtered-out product, thus affecting the percent yield and purity of the final product as

After dissolving benzoic acid in 1.0mL CH2Cl2 and 1.0mL 10% NaHCO3 solution, two layers are created, the top layer is 10% NaHCO3 solution and the bottom is CH2Cl2.

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The resulting benzocaine obtained from experimentation had a melting point of 188°C, while the theoretical range for benzocaine is between 121°C-123°C. The sodium sulfate impurities present, resisted melting in the compound. After the experiment was concluded, the IR and 1H-NMR spectra were obtained for 4-aminobenzoic acid and benzocaine. When the spectra were compared, it became clear that a reaction had occurred, since certain signals

The solution was then allowed to crystallize and the solid benzilic acid was dried, weighed, and used to obtain melting point and IR spectra.