Experiment 20 Lab Report

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Experiment 20: Qualitative Organic Analysis Unknown 2 Valentina Espinosa Canon Professor Memari November 2nd, 2023

2 Espinosa Materials and Method. Refer to Memari, Behnoush. CHM 2211L - Broward College-Central. Available from: VitalSource Bookshelf, (5th Edition). Macmillan Higher Education, 2023. Results: melting point of oxidized derivative was 154 – 156 C. Oxidized derivate: 3-chlorobenzoic acid. Unknown: 3-chlorotoluene. Discussion: In this laboratory experiment, the primary objective was to identify an unknown organic compound from a list of potential candidates. The identification process was accomplished through the oxidation of the unknown with potassium permanganate and followed by the determination of the melting point of the resulting oxidized derivative. In our experiment, the unknown compound was identified as 3-chlorotoluene through these procedures. The melting point of the oxidized derivative was determined to be in the range of 154 – 156°C, and it was identified as 3-chlorobenzoic acid. This information led to the final identification of the unknown compound as 3-chlorotoluene. The determination of the boiling point of the unknown compound was suggested but optional in our case. This decision was justified by the fact that the possible unknowns had close boiling points. This made it difficult to differentiate them based on this property alone. Although the solubility of the unknown compound could provide valuable information about its functional group, it was deemed unnecessary in this experiment. This is because all potential

3 Espinosa unknowns were aromatic compounds with alkyl side chains. Due to these compounds will not dissolve in water, HCl, NaOH, or H2SO4. The melting point of the oxidized derivative led to the identification of 3-chlorobenzoic acid. This in turn allowed for the confident identification of the unknown compound as 3- chlorotoluene. In conclusion, this experiment provided a comprehensive learning experience in organic compound identification. It highlighted the importance of using a combination of chemical reactions, physical properties, and analytical techniques to narrow down and identify unknown compounds accurately. Conclusion: The successful identification of an unknown organic compound was achieved by implementing a series of well-structured chemical reactions and physical property measurements. The ultimate goal was to determine the identity of the unknown compound from a list of potential candidates. These included toluene, 2-chlorotoluene, 3-chlorotoluene, 4- chlorotoluene, 2-nitrotoluene, o-xylene, and m-xylene. The experiment began with the oxidation of an unknown compound using potassium permanganate. The subsequent measurement of the melting point of this oxidized derivative was pivotal in the identification process. In this specific experiment, the melting point range of the oxidized derivative, determined to be between 154 – 156°C, led to the identification of the unknown compound as 3-chlorotoluene, as confirmed by its conversion to 3-chlorobenzoic acid.

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4 Espinosa While the procedure initially suggested measuring the boiling point of the unknown compound, it was ultimately deemed optional. This decision was supported by the fact that the possible unknowns had closely aligned boiling points, making this property less discriminatory in the identification process. The solubility test, which can be insightful in revealing the functional group of a compound, was omitted in this experiment. This omission was justified by the fact that all potential unknowns were aromatic compounds with alkyl side chains, and these compounds are inherently insoluble in common solvents such as water, HCl, NaOH, or H2SO4. Therefore, conducting solubility tests on these compounds would not have provided differentiating information. The precise measurement of the melting point of the oxidized derivative was highlighted as a critical aspect of the identification process. A narrow melting point range signified a pure compound, whereas a broader range indicated impurities or residual moisture. It is noteworthy that, although the procedure suggested the use of a 1H NMR spectrum for additional confirmation, it was not necessary or utilized in this specific experiment. The absence of conflicting data and the unambiguous correspondence between the melting point data and the identity of the unknown compound rendered the 1H NMR spectrum superfluous. In conclusion, this laboratory experiment provided a valuable learning experience for identifying organic compounds. It emphasized the importance of combining chemical reactions, physical property measurements, and analytical techniques to accurately pinpoint unknown compounds. The adaptable approach, where certain steps were optional based on the nature of

5 Espinosa the unknown compounds, facilitated a practical and efficient identification method. Ultimately, the experiment was successful in confidently identifying the unknown compound as 3- chlorotoluene based on a robust amalgamation of data.

6 Espinosa Bibliography: Memari, Behnoush. CHM 2211L - Broward College-Central. Available from: VitalSource Bookshelf, (5th Edition). Macmillan Higher Education, 2023.

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