Elimination Lab Report-2

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Temple University *

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2202

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Chemistry

Date

Jan 9, 2024

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docx

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4

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Experiment 9: The Elimination of Reaction: Dehydration of 2-Butanol Objective: The goal of this lab is to reflect the variety of techniques available to acid-catalyzed elimination reactions of 2 alcohols via carbocation intermediates and gas chromatography. Experimental Procedure: The procedure was followed as described in Mayo, pages 209-214, with the modifications provided in the Canvas document provided for this module. No additional modifications were added to the procedure. Reaction Scheme: Data Table and Results: 2-Methyl-cyclohexanol Phosphoric acid 1-Methylcyclohexane 3-Methylcyclohexene Mol. Formula C 7 H 14 O H 3 PO 4 C 7 H 12 Amount (mg) 1.538 Amount (mL) 2.0 0.5 mmoles 16 8.6 1.538 Molar Mass 114.19 97.99 96.17 Concentration N/A
85 wt% H2O Density (g/mL) 0.93 1.685 0.811, 0.801 Lit. bp (C) 163-166 158 110-104 Peaks Retention Time % Area 1(1-methylcyclohexene) 2.033 16.31 2 (methylene cyclohexene) 2.250 75.83 3 (3-methylcyclohexene) 6.917 7.86 Observations: The acid’s smell was extremely strong The collection of the distillate was taking longer than expected Temperature was initially group up quickly but after reaching the temperature required for the collection, it started to drop drastically making it difficult to collect the liquid and carry on with the experiment. Some steam started to form in the apparatus. The solution was clear before it was added to the apparatus. No product was formed Class data was utilized due to the product not being formed when the experiment was performed. 170 was reached for the sand bath temperature. Calculations: Theoretical Yield of Cyclohexane Products: 2-Methyl-cyclohexanol :
Volume : 2mL Density : 0.93g/mL Mass = Volume x density = 2mL x 0.93g/mL =1.86g Molar Mass: 114.19 g/mol Moles = = = 16mmoles Phosphoric Acid: Volume : 0.5mL Density : 1.685 g/mL Mass = Volume x density = 0.5mL x 1.685g/mL =0.843g Molar Mass: 97.994 g/mol Moles = = = 8.6 mmoles Theoretical Yield calculations: Moles of cyclohexene product = 16mmoles Molar Mass (product) = 96.17g/mol Mass= moles x molar mass = 0.016mol x 96.17g/mol = 1.538 g Yield of products Mass of tared test tube: 12.624g Mass of tared tube + product: 13.634g Yield of product = (Mass of tared tube + product) - (Mass of tared test tube) = 13.634g - 12.624g =1.01g % Yield of products: % Yield = x100 % Yield =( ) x100 % Yield = 0.65g x 100 % Yield = 65.67
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Gas Chromatogram Screen Shot: Questions: Reaction mechanism of E1 Elimination reaction of 2-methylcyclohexanol with phosphoric acid: Product based on Gas Chromatography Graphs: Peak area 1 of 3-methylcyclohexene is 16.31 mm2 Peak area of 2 of 3-methylcyclohexene is 7.86 mm2 The relative peak area ratio is : 16.31 : 7.86 = 32.62 : 15.72 The relative peak areas are consistent with the expected product distribution for the dehydration of 2-methylcyclohexene. Based on the generated peaks from the GC, 1-methylcyclohexene have the highest peak which consists of 16.31mm2 as it is a major product and more stable while 3-methylcyclohexene have a smaller peak area which is 7.86 mm2 as it is a minor product and therefore more unstable. Works Cited: 1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5thed.; John Wiley & Sons, Inc., 2011; pp 209-214. 2 .Modifications for Expt 9: Elimination Reaction : Dehydration of 2-Butanol.