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    Deamination Lab Report

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    RyanJForte
    The document summarizes a chemistry experiment involving a six-step synthesis and final deamination reaction. In the final step, 4-bromo-2-chloro-6-iodoaniline was suspended in ethanol and reacted with sulfuric acid and sodium nitrite to replace the amino group with hydrogen, producing the target compound 1-bromo-3-chloro-5-iodobenzene. The product was isolated through extraction with dichloromethane, recrystallization, and filtration. Yield, melting point, and mass of the isolated product were measured.

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    Deamination Lab Report

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    RyanJForte
    645 views4 pages
    The document summarizes a chemistry experiment involving a six-step synthesis and final deamination reaction. In the final step, 4-bromo-2-chloro-6-iodoaniline was suspended in ethanol and reacted with sulfuric acid and sodium nitrite to replace the amino group with hydrogen, producing the target compound 1-bromo-3-chloro-5-iodobenzene. The product was isolated through extraction with dichloromethane, recrystallization, and filtration. Yield, melting point, and mass of the isolated product were measured.

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    Lab Report on Deamination experiment

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    The document summarizes a chemistry experiment involving a six-step synthesis and final deamination reaction. In the final step, 4-bromo-2-chloro-6-iodoaniline was suspended in ethanol and reacted with sulfuric acid and sodium nitrite to replace the amino group with hydrogen, producing the target compound 1-bromo-3-chloro-5-iodobenzene. The product was isolated through extraction with dichloromethane, recrystallization, and filtration. Yield, melting point, and mass of the isolated product were measured.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    645 views4 pages

    Deamination Lab Report

    Uploaded by

    RyanJForte
    The document summarizes a chemistry experiment involving a six-step synthesis and final deamination reaction. In the final step, 4-bromo-2-chloro-6-iodoaniline was suspended in ethanol and reacted with sulfuric acid and sodium nitrite to replace the amino group with hydrogen, producing the target compound 1-bromo-3-chloro-5-iodobenzene. The product was isolated through extraction with dichloromethane, recrystallization, and filtration. Yield, melting point, and mass of the isolated product were measured.

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    of 4

    Forte 1 Experiment # 9 April 16, 2013 Deamination Reaction Mechanism: Ryan Forte Partner: Eilish Welsh CHM 215L

    D03

    Forte 2 Observed Yield: The sixth and final synthetic step is the deamination sequence in which the amino group of the 4-bromo-2-chloro-6-iodoaniline was replaced with hydrogen. The amounts of each reagent used in the experiment were calculated in reference to the amount of 4-bromo-2-chloro-6-iodoaniline obtained from the last experiment. The experiment suspended 3.265 grams of 4-bromo-2-chloro-6-iodoaniline, in 16.325 mL of ethanol inside of a 250mL round-bottom flask. Then 6.53 mL of sulfuric acid was added drop wise. 1.126 mL of powdered sodium nitrite was then added in small portions to the reaction. A reflux condenser was then equipped onto the flask, and while be stirred, the mixture was heated at reflux for about ten minutes. 125 mL of hot water was added through the condenser and then the apparatus for simple distillation was set up. Steam distillation was completed and distillate was collected in a beaker located inside of an ice bath. During this step some product collected in the condenser so it was important to oversee that the condenser did not plug up. The distillate dripping became clear and the product was extracted with the use of dichloromethane. Solid was also rinsed with dichloromethane and the rinsings combined with the organic layer. The dichloromethane was then removed by the rotary evaporation and the residue was recrystallized from about 10 mL of methanol to give 1-bromo-3-chloro-5iodobenzene. The product appeared as long colorless needles in the solution. The mixture was vacuum filtrated to collect the needles. The product was then stored in a drawer and the melting point, percent yield and mass of isolated product were measured the following week.

    Forte 3 Calculations: 0.006 moles of product = 2.0 g of product Our isolated yield = 3.265 g y mL CH3CH2OH = y mL H2SO4 = y mL NaNO2 = Theoretical yield = 3.265 g ( Results: = 16.325 mL ethanol = 6.53 mL sulfuric acid = 1.126 mL sodium nitrite ) = 5.262 g

    Table 1: Results of Experiment The isolated weight of 1-bromo-3-chloro5-iodobenzene The melting point of 1-bromo-3-chloro-5iodobenzene The calculated percent yield of isolated 1bromo-3-chloro-5-iodobenzene

    Conclusion: The purpose of this experiment is the deamination sequence in which the amino group of the 4-bromo-2-chloro-6-iodoaniline was replaced with hydrogen.

    Forte 4 The final step of the six-step synthesis from aniline to 1-bromo-3-chloro-5iodobenzene was completed and producing product in the final step. The reaction in the final step begins with the in situ generation of nitrous acid. Nitrous acid then converts the amine to a diazonium ion, which then undergoes an oxidationreduction reaction with ethanol. In this reaction ethanol is oxidized and the diazonium ion is reduced. Nitrous acid is often prepared by the reaction of NaNO2 with HCl. For this reaction however that method would not work well. That method does not work well in this case because the chloride ion may be exchanged in solution with the other halogens on the aromatic ring. Similarly, the chloride ion may be exchanged for the Br substituent because Br- is a better leaving group than Cl-. As for the actual experiment the greatest source of error is the step in which the product may collect as a solid in the condenser. Here it is important to make sure that the condenser does not plug up completely. An error stated that can also occur would be throwing out the product, which can be confused after the rinsing of the condenser. The yield for this experiment is around 40%, so it has a low yield to begin with. However, product was obtained in this six-step synthesis and after being stored in a drawer for a week the melting temperature, isolated mass and calculated percent yield will be determined for 1-bromo-3-chloro-5-iodobenzene.

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