Post Lab #7

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University of South Florida *

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2210L

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Chemistry

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Dec 6, 2023

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Project #7 The SN2 Reaction Factors Affecting SN2 Reaction ***** TA: ***** Work Alongside *****
INTRODUCTION SN2 reaction happens in a single concerted step. The mechanisms involve the development of a leaving group and the creation of a bond to the nucleophile simultaneously (Weldegirma, 2021). The nucleophile, an electron-rich species, attacks the backside of electron- deficient species and inverts the configuration. During the process, the leaving group deflects the nucleophile from undertaking from the front side. In order for an SN2 to perform, there needs to be a strong nucleophile; the stronger the nucleophile, the faster the reaction will occur. The more sterically hindered the electrophile, the more readily it reacts under SN2. A slow reaction rate is caused by the alkyl groups branching off of beta and alpha carbons, preventing the nucleophile from attacking the backside of the species. (Kubelka & Bickelhaupt, 2017). Therefore, methyl substrate is more reactive. Additionally, tertiary groups are favored. SN2 reactions prefer polar aprotic solvents because polar protic solvents block the true properties of a nucleophile. (Hamlin, Swart, & Bickelhaupt, 2018). EXPERIMENTAL SECTION Add 5mL of the solvent to three test tubes in 1:5:4 ratio; Add 20 drops of triethylamine to test tube #1, then 20 drops of tripropylamine to test tube #2, then 20 drops of ethyldiisoproylamine to test tube #3 Add 10 drops of iodomethane to each test tube; then, discard waste into salt waste jars Get 3 new test tubes and add 20 drops of triethylamine to each tube with 15 drops of iodoethane to test tube #1, 15 drops of 1-bromopropane to test tube #2, and 15 drops of 2-bromopropane to test tube #3; observe the subsequent reaction
Get the unknown amine and a dry test tube and add 40 drops of the unknown chemical into the tube Add 20 drops of iodomethane slowly; then add 2mL of solvent Allow the tube to stand for 10-15 minutes (Cool the tube in ice bath if it gets too hot) Use vacuum filtration to get precipitate Allow solid to dry and identify the melting point to identify unknown substrate TABLE OF CHEMICALS Chemical Name Chemical Structure Molecular Formula Molecular Weight Boiling Point Melting Point Chemical Appearance Acetone C 3 H 6 O 58.08 g/mol 56.2ºC -95.35ºC Flammable and irritant Diethyl Ether C 4 H 10 74.12 g/mol 34.6ºC -116.3ºC Flammable and skin/eye irritant
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Pentane C 5 H 12 72.15 g/mol 36.1ºC -130ºC Flammable, skin/eye irritant, health and environmental hazards Triethylamine (CH 3 CH 2 ) 3 N 101.19 g/mol 89ºC -113.7ºC Corrosive, irritant, and flammable Tripropylamine C 9 H 21 N 143.27 g/mol 156ºC 93.5ºC Flammable, corrosive, toxic and skin/eye irritant Iodomethane CH 3 I 141.94 g/mol 42.43ºC -66.5ºC Health, toxic, and skin/eye irritant Iodoethane C 2 H 5 I 155.97 g/mol 72.2ºC -111ºC Flammable and skin/eye irritant 2-Bromopropane C 3 H 7 Br 122.99 g/mol 60ºC -89ºC Flammable, and health hazards Idiisopropylamine C 8 H 19 N 129.25 g/mol 127ºC -46ºC Flammable, corrosive, toxic, and skin/eye irritant 1-Bromopropane C 3 H 7 Br 122.99 g/mol 71ºC -110ºC Flammable, skin/eye irritant, and health hazards
Methyltributylam monium Iodide C 13 H 30 IN 327.295 g/mol N/A 189ºC Skin/eye irritant Trimethylphenyla mmonium Iodide (C 6 H 5 )N(CH 3 ) 3 I 263.12 g/mol N/A 187ºC Corrosive, toxic, and skin/eye irritant Benzyltrimethylam monium Iodide (C 6 H 5 )CH 2 (C H 3 ) 3 I 277.14 g/mol N/A 178ºC skin/eye irritant Methyltripropylam monium Iodide (CH 3 CH 2 CH 2 ) 3 N(CH 3 ) 3 I 315.28 g/mol N/A 20ºC N/A RESULTS Amines Test Tube Time of Precipitation Formation Texture Appearance #1 10 seconds Cloudy White #2 2 minutes Cloudy White #3 More than 15 minutes Cloudy White Alkyl Halide Test Tube Time of Precipitation Formation Texture Appearance #1 20 minutes Cloudy White #2 N/A N/A N/A #3 2 minutes Cloudy White Unknown Melting point Determined structure Identity
Unknown 175ºC (C 6 H 5 )CH 2 N(CH 3 ) 3 Trimethylphenylamm onium Iodide DISCUSSION Based on the results from the experiment, it can be implied that steric hindrance is present as a rate of an SN2 reaction. Steric The triethylamine CONCLUSION Based on the experiment, the theoretical background and results are connected. REFERENCES Weldegirma, Solomon. 2021. “Experimental Organic Chemistry: Laboratory manual for CHM 2210L and CHM 2211L.”Lab handbook. University of South Florida. Tampa, Fl. P. 119 Hamlin, T. A., Swart, M., & Bickelhaupt, F. M. 2018. Nucleophilic Substitution (SN 2): Dependence on Nucleophile, Leaving Group, Central Atom, Substituents, and Solvent. Chemphyschem : a European journal of chemical physics and physical chemistry , 19 (11), 1315–1330. Kubelka, J., & Bickelhaupt, F. M. 2017. Activation Strain Analysis of SN2 Reactions at C, N, O, and F Centers. The journal of physical chemistry. A , 121 (4), 885–891.
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