Experiment 18 Report

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Salt Lake Community College *

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2320

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Chemistry

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Dec 6, 2023

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Experiment 18: Qualitative Analysis of Select Functional Group in Organic Compounds Valentina Espinosa Canon Laboratory Partners: Dagmawit Duresa Professor Memari October 19th, 2023 Abstract This laboratory experiment aimed to identify and characterize unknown compounds by employing traditional chemical property tests. The primary objectives were to assess the compounds' purity, determine their primary functional groups, and utilize solubility and classification tests to narrow down their identities. Solubility tests in water, HCl, NaOH, NaHCO3, and concentrated H2SO4 were conducted to evaluate the compounds' chemical nature, followed by classification tests. Due to challenges in the practical laboratory setting, results were obtained from instructional videos. Based on these results, six unknown compounds were tentatively identified. Unknown 1 identified as an alkene, unknown 2 identified as an amine, unknown 3 as carboxylic acid, unknown 4 as an alcohol, Unknown 5 as a ketone or aldehyde, and unknown 6 as a ketone or aldehyde. These findings serve as a valuable foundation for further confirmation of functional group identities. They emphasize the importance of maintaining proper laboratory techniques to minimize errors and ensure accurate chemical property test results.
2 Espinosa Introduction In this experiment, the main objective is to identify and characterize pure substances using traditional chemical property tests. Before advanced spectrometric techniques, these tests were vital in chemical property determination. The initial step involves confirming the purity of the compound by assessing its boiling or melting point, with a narrow range indicating purity. After purity verification, the experiment focuses on identifying the compound's primary functional group. This could be alcohol, ketone, aldehyde, amine, carboxylic acid, or alkene. This identification process involves solubility tests and functional group classification tests, often accompanied by IR spectroscopy. Solubility tests play a critical role in functional group determination. Compounds are first tested for solubility in water, and the results reveal information about their polar nature. Subsequent tests involve examining solubility in various solutions, including HCl, NaOH, and NaHCO3, to narrow down the potential functional groups present. Strong and weak acids react differently in these solutions, aiding in the identification process. This experiment is a fundamental approach to characterizing chemical compounds based on their chemical properties and functional group characteristics. In the experiment, the solubility tests play a crucial role in guiding the selection of subsequent classification tests or narrowing down the options. Choosing the right classification tests is key because conducting all tests might be time-consuming and unproductive. Solubility test results help in this selection process, as different functional groups display distinct solubility behavior. 2
3 Espinosa Moreover, maintaining clean and dry glassware and equipment is essential to prevent false positive or false negative results. It's critical to note that even a negative result in a classification test can provide valuable information. Different reagents and conditions yield specific outcomes for substances with particular functional groups. This enables the distinction between different functional groups and the identification of specific functional groups in tested compounds. In this experiment, various classification tests are discussed to identify specific functional groups in given compounds. These tests include: 1. 2,4-Dinitrophenylhydrazine Test: This test detects ketones and aldehydes by producing a distinct colored solid derivative. 2. Alcoholic Silver Nitrate Test: This test distinguishes alkyl bromides, alkyl iodides, and carboxylic acids based on the formation of specific solid products. 3. Bromine in Carbon Tetrachloride Test: Used to identify alkenes by observing the disappearance of bromine's characteristic color upon reaction. 4. Ceric Ammonium Nitrate Test: This detects alcohols, with a by a color change in the ceric ammonium nitrate solution. 5. Ferric Chloride Test: Used for identifying phenols, which produce distinct colors in ferric chloride solution. 3
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4 Espinosa 6. Solubility Tests: These tests involve determining the solubility of compounds in HCl and NaOH to identify amines and carboxylic acids. Solubility depends on various factors, including the molecule's size and structure. 7. Solubility in Concentrated H2SO4: This test identifies unsaturated hydrocarbons, high molecular weight alcohols, aldehydes, or ketones. It is performed on compounds found insoluble in water, HCl, and NaOH. Each test provides information about the presence of specific functional groups in the compounds, helping to narrow down their identities. It's essential to use these tests selectively and sequentially to obtain meaningful results. Materials and Method. Six different Unknowns. Water. HCl. NaOH. H 2 SO 4. NaHCO 3 . 2,4-dinitrophenylhydrazine. Bromine in Carbon Tetrachloride. Ceric Ammonium Nitrate. Test tubes. Droppers. Part A: Determine the Purity of a Compound Measure the boiling or melting point of one of the given compounds. 4
5 Espinosa Verify with the instructor that the obtained boiling/melting point falls within an acceptable range. Part B: Test for Solubility Test the solubility of each compound in water, 5% HCl, 10% NaOH, and 10% NaHCO3. If a compound dissolves in a solution, determine its pH. For compounds insoluble in the above solutions, perform a solubility test in concentrated H2SO4. Classification Tests Based on the solubility results, perform classification tests for potential functional groups like alkenes, alcohols, aldehydes, and ketones. If the compound remains insoluble in concentrated H2SO4, it could indicate the presence of alkanes, alkyl halides, or aromatic compounds. Perform further classification tests as necessary and consider IR spectra if available. 2,4-Dinitrophenylhydrazones for Aldehydes and Ketones: Dissolve the sample (0.10 g solid or 4 drops of liquid) that did not dissolve in water, HCl, or NaOH but dissolved in H2SO4 in ethanol. Add 2,4-dinitrophenylhydrazine/sulfuric acid reagent. 5
6 Espinosa Allow crystallization at room temperature, heat if necessary. The absence of crystals might indicate the absence of an aldehyde or ketone functional group. Tollens' Test for Aldehydes: Mix 2 mL of 5% aqueous silver nitrate with 1 drop of 10% sodium hydroxide. Gradually add 2 M aqueous ammonia until dark Ag2O precipitate dissolves. Add 0.05 g of the compound and let it stand for 5-10 minutes. Observe for a silver mirror; its presence indicates an aldehyde. Bromine in Carbon Tetrachloride: Dissolve the sample (4 drops of liquid or 0.1g of solid) in ethanol or carbon tetrachloride. Slowly add a 5% solution of bromine in carbon tetrachloride drop by drop. Note observations, including the number of drops required for the bromine color to persist. Ceric Ammonium Nitrate Test for Alcohols: Add 1 mL of the compound to a dry test tube. Add ceric ammonium nitrate reagent and shake the solution. 6
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7 Espinosa Observe the solution for immediate red or red-brown color, indicating a positive test for alcohols. These tests help identify specific functional groups within the compounds and are conducted sequentially to narrow down the possibilities. Proper waste disposal and cleaning procedures are important after conducting the tests. Data: Table 1: Raw Data: Solubility in water Unknown Water Observations Unknown 1 No soluble Two layers formed, with a slightly oily layer on top containing visible oil droplets. Unknown 2 No soluble A cloudy solution was observed. Unknown 3 No soluble The solid did not dissolve. 7
8 Espinosa Unknown 4 No soluble solution remained cloudy with oil droplets moving up and down. Unknown 5 No soluble Solid did not dissolve. Unknown 6 No soluble Solution appeared oily. Table 2: Raw Data: Solubility in HCl Unknown HCl Observations Unknown 1 No soluble Two layers formed. Unknown 2 Soluble Solution became transparent and clear. Unknown 3 No soluble Solid did not dissolve. Unknown 4 No soluble Two layers formed. Unknown 5 No soluble Solid did not dissolve. Unknown 6 No soluble Two layers formed. Table 3: Raw Data: Solubility in NaOH Unknown NaOH Observations Unknown 1 No soluble Two layers formed. Unknown 3 Soluble Solid dissolved. 8
9 Espinosa Unknown 4 No soluble Two layers formed, with a slightly oily layer. Unknown 5 No soluble Solid did not dissolve. Unknown 6 No soluble Two layers formed with some white precipitate. Table 4: Raw Data: Solubility in H 2 SO 4 Unknown H 2 SO 4 Observations Unknown 1 Soluble Color changed to a light yellow. Unknown 4 Soluble Color changed to a light yellow. Unknown 5 Soluble Solid dissolved, and the color became very pale yellow. Unknown 6 Soluble Color changed to a light orange. Table 5: Raw Data: Classification Tests: 2,4-Dinitrophenylhydrazones for Aldehydes and Ketones Unknown C 6 H 6 N 4 O 4 Observations Unknown 1 No reaction Color did not change, and no crystals were observed. Unknown No reaction Color did not change, and no crystals were 9
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10 Espinosa 4 observed. Unknown 5 Reaction occurred Precipitate in the form of crystals was observed. Unknown 6 Reaction occurred Precipitate in the form of crystals was observed. Table 6: Raw Data: Classification Tests: Bromine in Carbon Tetrachloride Unknown Bromine in Carbon Tetrachloride Observations Unknown 1 Reaction occurred The brown color of bromine disappeared. Unknown 4 No reaction Brown color of bromine did not disappear. Table 7: Raw Data: Classification Tests: Ceric Ammonium Nitrate Test Unknown Bromine in Carbon Tetrachloride Observations Unknown 4 Reaction occurred Solution turned red. Table 8: Raw Data: Classification Tests: Sodium Bicarbonate. Unknown NaHCO 3 Observations 10
11 Espinosa Unknown 3 Reaction occurred Bubbles were observed, and then the solution completely dissolved. Table 9: Raw Data: Identification of functional groups. Unknown Functional Group Unknown 1 Alkene. Unknown 2 Amine. Unknown 3 Carboxylic acid. Unknown 4 Alcohol. Unknown 5 Ketone or Aldehyde. Unknown 6 Ketone or Aldehyde. Discussion: The experiment aimed to identify the primary functional groups within the compounds. This identification process involved solubility tests, and functional group classification tests. The solubility tests were crucial in narrowing down the potential functional groups within the compounds. The solubility behavior of compounds in different solvents provided valuable insights into their chemical nature. 11
12 Espinosa In the water solubility test, it was observed that Unknowns 1, 2, 3, 4, 5, and 6 did not dissolve, suggesting that they were not water-soluble. Unknown 1 and Unknown 5 displayed two layers with an oily appearance, indicating limited solubility in water. The results hinted at the possibility that these compounds were non-polar. In the HCl solubility test, Unknowns 2 was soluble, while the others (Unknowns 1, 3, 4, 5, and 6) did not dissolve. The solubility of Unknown 2 in HCl indicated that it had basic properties, as basic compounds tend to be soluble in acidic solutions. In the NaOH solubility test, Unknowns 3 displayed solubility, while the rest (Unknowns 1, 4, 5, and 6) did not dissolve. This solubility of Unknown 3 in NaOH suggested it contained an acidic functional group, as acidic compounds tend to be soluble in basic solutions. The lack of solubility in NaOH for the other compounds indicated their non-acidic nature. In the NaHCO3 solubility test, Unknown 3 exhibited a reaction by forming bubbles, suggesting the presence of a carboxylic acid functional group. In the concentrated H 2 SO 4 solubility test, Unknowns 1, 4, 5, and 6 dissolved and exhibited color changes, indicating the presence of specific functional groups. Based on the results of the solubility tests, further classification tests were performed to identify specific functional groups within the compounds. In the 2,4-Dinitrophenylhydrazone Test Unknowns 5 and 6 exhibited a reaction by forming crystals, suggesting the presence of aldehyde or ketone functional groups. The absence of crystals for Unknowns 1 and 4 indicated the absence of aldehyde or ketone groups. 12
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13 Espinosa For Bromine in Carbon Tetrachloride Test Unknown 1 displayed a reaction by the disappearance of the brown color of bromine, indicating the presence of an alkene. However, Unknown 4 did not show a reaction, suggesting the absence of an alkene. To confirm Unknown 4 identity a Ceric Ammonium Nitrate Test was performed. Unknown 4 displayed a reaction by turning red, indicating the presence of an alcohol. Based on the results of the classification tests and solubility tests, we can tentatively identify the functional groups in each of the unknown compounds. Unknown 1 is Alkene, Unknown 2 is an Amine, Unknown 3 is Carboxylic acid, Unknown 4 an Alcohol, Unknown 5 Ketone or Aldehyde and Unknown 6 Ketone or Aldehyde. Conclusion. The primary objective of this laboratory experiment was to identify and characterize unknown compounds functional group through the application of traditional chemical property tests. These time-honored tests played a crucial role in chemical analysis before the advent of advanced spectrometric techniques. 13
14 Espinosa This identification process involved solubility tests and functional group classification tests. The solubility tests played a pivotal role in narrowing down the potential functional groups present in the compounds, offering insights into their chemical nature. It is important to note that, due to certain complications in the practical laboratory setting, the results discussed here were obtained from the professor's instructional videos. These complications arose from challenges related to identification and observation, which could impact the results accuracy. The solubility tests in water, 5% HCl, 10% NaOH, and 10% NaHCO3 served as a foundation for understanding the chemical properties of the compounds. Each of these solutions was chosen to assess the solubility of the compounds under different pH conditions and observe their interactions in acidic and basic environments. In the water solubility test, the compounds (Unknowns 1, 2, 3, 4, 5, and 6) were observed not to dissolve, indicating limited or no water solubility. In the case of Unknowns 1 and 5, two layers with an oily appearance were observed, suggesting reduced solubility in water. These results suggested the possibility of these compounds being non-polar or hydrophobic in nature. In the HCl solubility test, Unknown 2 was soluble, while the other compounds (Unknown 1, 3, 4, 5, and 6) did not dissolve. The solubility of Unknown 2 in HCl suggested the presence of basic properties, as basic compounds tend to dissolve in acidic solutions. The lack of solubility of the other compounds in HCl provided further information about their non-basic nature. In the NaOH solubility test, Unknown 3 was observed to be soluble. This solubility of Unknown 3 in NaOH indicated the presence of an acidic functional group, as acidic compounds 14
15 Espinosa tend to be soluble in basic solutions. The non-solubility of NaOH compounds indicated their non-acidic nature. In the NaHCO3 solubility test, Unknown 3 displayed a reaction by producing bubbles, suggesting the presence of a carboxylic acid functional group. In the concentrated H2SO4 solubility test, unknowns 1, 4, 5, and 6 dissolved and exhibited color changes, indicating the presence of specific functional groups. The light-yellow color change in Unknown 1, 4, 5 suggested the presence of an unsaturated hydrocarbon or a high molecular weight alcohol, aldehyde, or ketone. The light orange color change in Unknown 6 indicated the presence of a high molecular aldehyde or ketone. Based on the outcomes of the solubility tests, further classification tests were conducted to identify specific functional groups within the compounds. In the first test, 2,4- Dinitrophenylhydrazone was used. As a result of the formation of crystals, unknowns 5 and 6 showed reactions that suggest the presence of aldehydes or ketones as functional groups. The absence of crystals for unknowns 1 and 4 indicated the absence of aldehyde or ketones groups. By using a bromine-in-carbon tetrachloride test, Unknown 1's functional group identity was confirmed since it displayed a reaction resulting in the disappearance of bromine's brown color, indicating the presence of an alkene. However, Unknown 4 did not exhibit a reaction, suggesting the absence of an alkene. Then a Ceric Ammonium Nitrate Test was performed on Unknown 4. It displayed a reaction by turning red, indicating the presence of alcohol. Based on the results of the classification tests and solubility tests obtained from the professor's instructional videos, we can tentatively identify the functional groups in each of the unknown compounds. Unknown 1 is Alkene, Unknown 2 is an Amine, Unknown 3 is a 15
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16 Espinosa Carboxylic acid, Unknown 4 an Alcohol, Unknown 5 is Ketone or Aldehyde, and Unknown 6 is a Ketone or Aldehyde. In conclusion, despite the challenges faced in the practical laboratory, the combination of solubility tests and classification tests, along with the guidance from the professor's instructional videos, provided valuable information for identifying potential functional groups within the unknown compounds. Further confirmatory tests and the use of IR spectroscopy, if available, could help refine the identifications and provide more conclusive results. Overall, the laboratory experience was invaluable in providing us with a deeper understanding of the functional groups and their properties. The laboratory also gave them an opportunity to practice their laboratory skills. Bibliography: Memari, Behnoush. CHM 2211L - Broward College-Central. Available from: VitalSource Bookshelf, (5th Edition). Macmillan Higher Education, 2023. 16