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Preparation of Acetanilide
Recrystallization practicals report discussion
Discussion on preparing acetanilide
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Recommended: Preparation of Acetanilide
Title and Authors
Recrystallization
Devon King
Jean Kim
Chemistry 237-536
Results and Discussion
The product given, Acetanilide, was an impure product from a chemical reaction. It was purified through the process of recrystallization, where by-products and impurities were removed from the solid. This process gives a purer compound than what was originally given. Recrystallization is able to be used due to the solubility of the impure compound. Ideally, the whole solvent would completely dissolve in the water when the proper boiling point was reached. In this lab, the Acetanilide was soluble thusly this process would work properly. The end product of creating a pure substance was purified crystals.
The percent recovery was determined to find what percent of Acetanilide was recovered during recrystallization. At the beginning of the lab, 1.612grams of Acetanilide was weighed out. The dry crystals of Acetanilide weighed 0.979grams. The calculation goes as it is written below: Percent Recovered = (grams of
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The melting point helps to determine how close to a pure compound the extracted crystals were. When the dry crystals of Acetanilide were melted, they were found to have a melting point of 119.5°C. The melting point of pure Acetanilide that is recorded in literature is reported between 113-115°C. Knowing that this is the range of the melting point, it is possible that the Acetanilide recovered is relatively pure. The melting point found might not be in the reported range due to some errors throughout the laboratory procedure. Some errors that may have been possible are as follows: not completely dissolving the solvent, using too little solvent, improper weighing of original solvent, placing the solvent into the ice bath before it was completely cooled to room temperature, and not identifying where the crystals had completely
At this point the identity of the unknown compound was hypothesized to be calcium nitrate. In order to test this hypothesis, both the unknown compound and known compound were reacted with five different compounds and the results of those reactions were compared. It was important to compare the known and unknown compounds quantitatively as well to ensure that they were indeed the same compound. This was accomplished by reacting them both with a third compound which would produce an insoluble salt that could be filte...
Every 5 minutes, a small amount of mixture was dissolved in acetone (0.5 mL) and was spotted onto a thin layer chromatography (TLC) plate, which contained an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL). The bezaldehyde disappearance was monitored under an ultraviolet (UV) light. Water (10 mL) was added after the reaction was complete, and vacuum filtrated with a Buchner funnel. Cold ethanol (5 mL) was added drop-by-drop to the dried solid and stirred at room temperature for about 10 minutes. Then, the solution was removed from the stirrer and place in an ice bath until recrystallization. The recrystallized product was dried under vacuum filtration and the 0.057 g (0.22 mmol, 43%) product was analyzed via FTIR and 1H NMR
The C-H (sp3) hydrogens from our product displayed at wavelength 2959 cm-1 correlates to the methyl groups located on the ends of isopentyl acetate4. A really prominent, strong peak located at 1742 cm-1 shows that a C=O ester stretch is located in the product, along with at 1244 cm-1 the spectrum shows a strong peak representing the C(=O)-O stretch that is crucial to the structure of isopentyl acetate. Shown in my IR spectrum is a weak O-H (H-bonded) peak at 3464 cm-1 which shows that I have an impurity of isopentyl alcohol in my product. Isopentyl alcohol has similar boiling points and density as my product so the impurity could have easily boiled out with the isopentyl acetate during distillation. The isopentyl alcohol was also present in my 1H-NMR spectrum backing up the impurity peak at 3464
The theoretical weight was 599.6 mg. This yields a percent yield of 3.7%. Table 1 also illustrates the experimental melting point of 99.3-102.1◦C. A melting point that has a range larger than 3◦C is indicative of impurities in the sample. A few possibilities of impurities could have been unreacted norbornene, and water. Evidence that supports that there was unreacted norbornene in the final sample was the fact that the product was a jelly-like structure. Norbornene by itself has a jelly-like structure. However, once norbornene reacted with the acid-catalyst (H2O2), then it should have changed the chemical structure of the molecule and once the solution was brought back down to room temperature, crystals should have formed. Since a jelly-like, or oil-like product was present at the end of the reaction, then this is indicative that there was unreacted norbornene in the sample. The second impurity that may have been present in the final product was water. Instead of adding 3 mL of sodium bicarbonate and then 3 mL of brine, 3 mL of brine was added first and then 3 mL of sodium bicarbonate was added. This experimental error caused excess aqueous solution to be added to the diethyl ether. Since excess water was added to the final product, about 4x the amount of anhydrous sodium sulfate was needed in order to remove the water from the product. This was another indication that there was too much water in
Based on our observations during the separation techniques and some speculation, we were able to identify eight components of our mixture: graphite from the filtration residue, Epsom salt from crystallization, water and acetic acid through distillation, red and orange dye, iron metal, marble chips, and sand.
Results: Through a melting point reading, it was determined that the product obtained was 2,4-Dibromoanisol mp 55-58 C. The products obtained by my partners, were determined to be: (p-bromoacetanilide mp 160-165 C) and (2,4,6 tribromoaniline, mp of 108-110 C) respectively.
While this probably does not have a huge effect, crystallizing the product helps to eliminate impurities. The overall product yield for this reaction is 90.53%. Although this number seems high, indicating a very successful synthesis, it does not account for the fact that Part C began with a new sample of benzil. Had it been continued using the product from part B, the yield would be much lower.
The literature value is 34 to 38 °C and the experiment melting point was shown to be 30.5 to 34.4 °C with a range of 3.9. According to the literature value, methyl cinnamate is purified, but not completely because the melting range is not below 2.
After synthesizing a chemical, especially a drug, it is important to confirm the identity and purity of the product. You will perform three tests to examine the identity and purity of the aspirin that you synthesized. One test will detect the presence of leftover salicylic acid in the synthesized aspirin and allow you to determine its concentration. Government regulations stipulate that commercial aspirin must not contain residual salicylic acid since it is irritating to the mouth, throat, and stomach. Iron salts react with phenols to form a complex ion that has a purple color, therefore iron (III) chloride can be used to determine if your aspirin sample contains residual salicylic acid. The second test uses melting point to evaluate the purity of your aspirin product. You will measure the melting point of pure acetylsalicylic acid (135°C) as a comparison to your product. The melting point of a pure aspirin sample should be within 1°C of its known melting point. A compound that contains impurities will tend to melt over a range of temperatures and at temperatures lower than the fixed mp for the pure compound. For example naphthalene, an ingredient of mothballs, has a melting point of 80°C and a pure sample of naphthalene would most likely be observed to melt within 80-81°C. An impure sample of naphthalene might melt over a range from 75-80 °C. Impurities in the crystals of the compound weaken the structure, which results in the compound melting at a lower temperature. In addition, impurities will be unevenly distributed throughout a sample of a compound. This non-uniform composition results in some areas of the sample being more “pure” than othe...
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
Extraction is a separation method that is often used in the laboratory to separate one or more components from a mixture. Sucrose was separated at the beginning because it is the most immiscible and it’s strongly insoluble. Next Acetylsalicylic Acid was separated which left Acetanilide alone. Variety steps could have led to errors occurring. For example the step of separation, when dichloromethane layer was supposed to be drained out, it could be possible some aqueous layer was drained with it. Which could make the end result not as accurate. Also errors could have occurred if possibly some dichloromethane was not drained out. Both way could interfere with end result of figuring the amount of each component in the mixture. The solids percentage were 22.1% more than the original. That suggests that solids weren’t separated completely which clarifies the reason the melting points that were recorded were a slightly lower than the actual component’s melting point. The melting point for Acetylsalicylic Acid is 136 C but that range that was recorded during the experiment was around 105 C to 118 C. The melting points were slightly lower than the literature value. Sucrose was the purest among all component due to its higher melting point which follows the chemical rule that the higher the melting point the more pure the component
After washing it out, and driving off any remaining pet ether with a water bath and reaching a constant mass, the purified product had a mass of 0.272grams. A second TLC was ran to determine if the product was now pure. The plate was found to have two spots for the pure product, benzhydrol and biphenyl with Rf values of 0.67 and 0.15 respectively. It expected to see only one spot if the product was pure, so by TLC it was able to be determined there was not purification of the benzhydrol product. The pure product had a 73.1% yield, but this does not accurately reflect the yield as there were still impurities in the pure
The solvent should be easily removed from the purified product, not react with the target substances, and should only dissolve the target substance near it’s boiling point, but none at freezing. A successful recrystallization uses minimum amount of solvent, and cools the solution slowly, if done to fast, many impurities will be left in the crystals. Using the correct solvent, in this case ice water and ethyl acetate, the impurities in the compound can be dissolved to obtain just the pure compound. A mixed solvent was used to control the solubility of the product. The product is soluble in ethanol an insoluble in water. Adding water reduced solubility and saturates the solution and then the crystals
Analysis of Aspirin Tablets Aim --- To discover the percentage of acetylsalicylic acid in a sample of aspirin tablets. ----------------------------------------------------------------- In order to do this, the amount of moles that react with the sodium hydroxide must be known. This is achieved by using the method of back titration.
These were all naturally occurring substances. No refinement had occurred, and isolation of specific compounds (drugs) had not taken place.