recrystallization and melting point lab report

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Apr 3, 2024

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Name and Date: Wyatt Collier 9/12/2022 Identifying the Identity of a Compound Utilizing Melting Point and Recrystallization Introduction: The purpose of the melting point lab was to determine the melting points of different organic compounds, and then use this information to identify the name of the compound. In the recrystallization lab, the purpose was to develop the necessary techniques needed for purifying solids. Melting point and recrystallization are important because they can help identify the identity of a compound and determine the purity of a substance. Because of the effect that impure compounds have on the crystal lattice, the structure has weakened intermolecular forces making it less stable, and in tum having a larger melting point range at a lower temperature. For instance, pure benzoic acid has a melting point range of 121°C - l 22°C, but impure benzoic acid has a melting point range of l l 8°C - 121°C. Chemical Properties and Safety: Name Chemical Formula Color Molecular Weight (g/mol) Density (g/mL) Melting Point (°C) Boiling Point (°C) Acetanilide CsH9NO A white to a gray solid 135.61 g/mol 1.214 g/mL 113°c - 114°c 304.0°C Benzoic Acid C7H6O2 White crystalline 122.21 g/mol 1.2659 g/mL 121°c - 122°c 249_2°c
substance Cinnarnic Acid C9HsO2 White crystalline powder 148.16 g l rnol 1.2480 g l rnL 132°c - 133°c 300°c Salicylic Acid C7H6O3 White to light tan solid 138.12 g l mol 1.443 g l mL 156°C - 158 °C 411.8°C Ethanol C2H6O Clear colorless liquid 46.07 g l rnol 0.7893 g l mL -114.1°C 78.2°c Chemical Flammable Irritant Corrosive Teratogen Mutagen Carcinogen Toxic Permeator Acetanilide X X N I A N I A N I A N I A X N I A Benzoic Acid N IA X X N IA N IA X X X Cinnarnic Acid N I A X X N I A X N I A X N I A Salicylic Acid N I A X N I A X N I A N I A X X Ethanol X X N I A X X X X X
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Experimental Procedure: Beginning with the melting point of the pure compounds procedure, a small sample of both benzoic acid and salicylic acid was placed on two separate watch glasses. From here, both individual samples were pulverized and used to prepare two separate capillary tubes. The capillary tubes were then placed into the Mel-Temp device along with the thermometer placed into the aluminum block, the power button turned on, and then the voltage adjusted. The voltage was set at around 4 until the thermometer read about 90-95°C. After the temperature reached the low nineties, the voltage was set to a low setting so that the temperature would not rise too quickly. The melting point range for benzoic acid was between 120-122°C and the salicylic acid melting point range was 154-157°C. Moving on to the melting point of the known compounds, equal parts ofbenzoic acid and salicylic acid were combined on a watch glass, and then grinded up. A capillary tube was then used to collect some of the mixed compounds. Same as before, the capillary tube was placed into the Mel-Temp apparatus and observed for the melting point range. After the procedure was complete, the melting point range of the mixture ofbenzoic acid and salicylic acid was l 10-113°C. The recrystallization procedure started with the recrystallization of dirty benzoic acid. Around one gram (1.038g) of dirty benzoic acid was placed in an Erlenmeyer flask along with 30 mL of water and a stir rod. Using filter paper and a short stemmed funnel, the mixture was then transferred to another Erlenmeyer flask that was sitting on the hot plate. After the filtration was complete, around 5mL of water was used to rinse out the remaining mixture from the filter. Once this second filtration had finished, the flask was put onto the countertop and let cool until small
crystals started to form. After cooling, the same flask was then placed into an ice bath to allow the compound to complete the precipitation process. The mixture was then transferred to a Buchner funnel to complete the filtering of the crystals. Once the crystals were dry enough, they were placed into a capillary tube and tested for their melting point in the Mel-Temp apparatus. The remaining crystals were then placed on a watch glass to fully dry and then weighed to find the overall percent recovery. The melting point range for the dirty benzoic acid was between 118-121°C. After going through the entire procedure, the weight of the crystals recovered was 0.082 grams, which equated to a 7.89% recovery rate. The recrystallization of the unknown compound: compound A. Around two grams of compound A (2.005g) was placed into a 125mL Erlenmeyer flask. 6mL of ethanol were then added to the flask on the hot plate. Using a fluted filter paper inside of a short stemmed funnel, the mixture was transferred into a 100mL beaker that resided on the hot plate. After the first filtration was complete, around 4mL of ethanol was used to rinse the remaining compound out of the filter paper. The filtrate was then kept hot, and 10mL of water was gradually added. The flask was then removed and allowed to cool to room temperature. Once around ten minutes had passed and the flask had properly cooled, it was placed into an ice bath for another ten minutes. The Buchner funnel was then used to collect all of the crystals remaining from the compound. Midway through, the crystals were rinsed with a bit more ethanol (4mL) and allowed to dry. Once dry enough to transport, the crystals were transferred to a capillary tube to get the melting point, and then the rest was moved to a watch glass to get the remaining mass. After placing the capillary tube into the Mel-Temp apparatus, the melting point range came out to be between l ll-113°C. After weighing the remaining crystals, the total amount left over was 1.541 grams,
which is a recovery rate of 76.86%. Due to the melting point range, it can be concluded that the unknown compound was acetanilide. Data and Observations: Name of Compound Melting Point Range Benzoic Acid 120- 122DC Salicylic Acid 154- 157DC 50/50 Mixture 110- 113DC Mass of Dirty Benzoic Acid (g) 1.038 Mass of Crystals (g) 0.082 Melting Point of Crystals (DC) 118-121 % Recovery 7.90% Mass of Unknown Sample (g) 2.005 Mass of Recrystallized Solid (g) 1.541 Melting Point of Crystals (DC) 111- 113 % Recovery 76.86% Identity of Unknown Compound Acetanilide Observations During Recrystallization Procedure: When the dirty benzoic acid was on the hot plate, it didn't completely dissolve. There were small white particles moving around. These small white particles were likely the impurities within the dirty benzoic acid. When taking the melting point of the benzoic acid, the range was lower than the typical melting point and had a broader range than the typical pure benzoic acid.
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Calculations: Percent Recovery for Dirty Benzoic Acid: 0. 082/1. 038 = 0. 0789980732 * 100 = 7. 89% Percent Recovery for Recrystallization of Unknown Sample: 1. 541/2. 005 = 0. 7685785536 * 100 = 76. 86% Discussion and Conclusions: Through both procedures, the main focus was to be able to develop techniques in finding the melting point of different compounds, and with that, being able to determine the purity of the structure and the identity of the compound. During the first procedure, it became apparent that the more impure the substance was, the broader the range of the melting point would be as well as melting at a lower temperature than expected. For instance, pure benzoic acid has a melting point range of 120-122°C, but impure or "dirty" benzoic acid has a melting point range of 118-121°C. While the range only increases by one degree, the compound melts at two degrees lower than it usually does. The reason for this is that the more pure a compound is, the stronger the intermolecular forces in that compound are. As a compound becomes increasingly impure, the intermolecular forces follow suit and are less strong than they were before. Ultimately, the stronger the intermolecular forces are, the higher the boiling point because it takes a lot more work for it to fully break apart the compound. While salicylic acid and benzoic acid both have hydrogen bonding, salicylic acid has two hydrogen bonds in contrast to benzoic acid which only have one, so the melting point for salicylic acid is significantly higher because hydrogen bonding is the strongest intermolecular force. Because the 50/50 mixture of salicylic acid and benzoic
acid was an impure mixture, the melting point range dropped drastically. After completing the recrystallization ofbenzoic acid, the percent recovery rate came out to approximately 7.89%, which means that the majority of the dirty benzoic acid was lost throughout the procedure. On the contrary, after completing the recrystallization of the unknown acid, the percent recovery came out to approximately 76.86%, which was significantly more than the benzoic acid. Additionally, the melting point of the unknown acid ranged from l l l-l l 3°C, which directly correlates to the unknown compound being acetanilide.