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How proton NMR is different in starting material and product? What aspect is useful to determine if you successfully made the product?

How proton NMR is different in starting material and product? What aspect is useful to determine if you successfully made the product?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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How proton NMR is different in starting material and product? What aspect is useful to determine if you successfully made the product?

Oxidation of Fluorene Prelab: Write in your notebook the physical properties (molecular formula, molar mass, solubility, m.R, k.R) and the Reaction Scheme for this reaction (includes structure of fluorene and the product, 9-fluorenone). Obtain and turn-in the IR (KBr) and H-NMR literature spectra for the fluorene and 9-fluorenone from the SDBS website. Include your advance procedures in your notebook. Reaction Scheme: О, NaOH Catalyst Introduction: Oxidation of alkanes is notoriously difficult. However, the benzylic position of Fluorene can be oxidized in basic conditions by oxygen with a catalyst such as Aliquat 336 (twicaprvlmethylammonium chloride). Caution: NaOH is toxic and corrosive. Avoid contact and wash affected area immediately with water. Waste: Any hexane filtrates should be disposed of in the Red solvent waste recovery canister. Aqueous filtrates may be poured down the drain. Procedure: Mix 0.8 g of fluorene with 8 mL of hexanes (bottle top dispenser) in a 50 mL Erlenmeyer flask with a stir bar. Add 4 mL of 10 M NaOH (use gloves). Add 10 drops of Aliguat 336 and stir the mixture vigorously for 1 hour. The stirring rate should produce a froth on the surface. Transfer the reaction to a 15 mL centrifuge tube or test tube, cool in an ice bath for 2-3 minutes and carefully remove the lower aqueous layer with a pipet. Collect the solid, crude fluorenone on a Buchner funnel via vacuum filtration. Wash with small amount of 1 M HCl (~2 mL) and then water. Dry the sample on the filter for a few minutes. Get a mass of the product before continuing. Recrystallize the crude product from cyclohexane. Dissolve your product in a minimum of hot cyclohexane (generally ~13 mL/gram crude product) and cool to RT, then an ice bath until product crystals form. Do not cool too long. You will freeze the cyclohexane. Filter the recrystallized product. Dry and obtain the mass and melting point. Obtain an IR using KBr. Calculate the percent yield for the reaction. Fluorene CAS Registry No.: 86-73-7 Fluorenone CAS Registry No.: 486-25-9
Transcribed Image Text:Oxidation of Fluorene Prelab: Write in your notebook the physical properties (molecular formula, molar mass, solubility, m.R, k.R) and the Reaction Scheme for this reaction (includes structure of fluorene and the product, 9-fluorenone). Obtain and turn-in the IR (KBr) and H-NMR literature spectra for the fluorene and 9-fluorenone from the SDBS website. Include your advance procedures in your notebook. Reaction Scheme: О, NaOH Catalyst Introduction: Oxidation of alkanes is notoriously difficult. However, the benzylic position of Fluorene can be oxidized in basic conditions by oxygen with a catalyst such as Aliquat 336 (twicaprvlmethylammonium chloride). Caution: NaOH is toxic and corrosive. Avoid contact and wash affected area immediately with water. Waste: Any hexane filtrates should be disposed of in the Red solvent waste recovery canister. Aqueous filtrates may be poured down the drain. Procedure: Mix 0.8 g of fluorene with 8 mL of hexanes (bottle top dispenser) in a 50 mL Erlenmeyer flask with a stir bar. Add 4 mL of 10 M NaOH (use gloves). Add 10 drops of Aliguat 336 and stir the mixture vigorously for 1 hour. The stirring rate should produce a froth on the surface. Transfer the reaction to a 15 mL centrifuge tube or test tube, cool in an ice bath for 2-3 minutes and carefully remove the lower aqueous layer with a pipet. Collect the solid, crude fluorenone on a Buchner funnel via vacuum filtration. Wash with small amount of 1 M HCl (~2 mL) and then water. Dry the sample on the filter for a few minutes. Get a mass of the product before continuing. Recrystallize the crude product from cyclohexane. Dissolve your product in a minimum of hot cyclohexane (generally ~13 mL/gram crude product) and cool to RT, then an ice bath until product crystals form. Do not cool too long. You will freeze the cyclohexane. Filter the recrystallized product. Dry and obtain the mass and melting point. Obtain an IR using KBr. Calculate the percent yield for the reaction. Fluorene CAS Registry No.: 86-73-7 Fluorenone CAS Registry No.: 486-25-9
%Transmittance 3850.03812.94798.47 3741.43730.33707.54685.71 3666.6645.3625.71 2922.22 2852.36 2357.00 1693.87 1651.18 1557.00 1454.95 1376.69 Hill 9-Fluorono Thu Jun 24 23:03:01 2021 (G 40 35 30- 20 15 10 5. 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers (cm-1) Collection time: Thu Jun 24 23:02:41 2021 (GMT-04 Thu Jun 24 23:02:58 2021 (GMT-04:00) FIND PEAKS: Spectrum: Region: 4000.00 Absolute threshold: Sensitivity: Peak list: Hill 9-Fluoronone 400,00 36.904 50 Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: 36.708 35.162 36.680 1376.69 Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: 1454,95 1557,00 1651.18 36.550 1693.87 36.474 2357.00 35.438 2852.36 2922.22 3625.71 30.354 27.767 34.506 34.421 3645.33 34.663 3666.69 3685.71 3707.54 3730.33 3741.41 3798.47 34.648 34.739 34.623 34.359 34.754 Position: Position: Position: 3812.94 3850.03 34.632 33.904
Transcribed Image Text:%Transmittance 3850.03812.94798.47 3741.43730.33707.54685.71 3666.6645.3625.71 2922.22 2852.36 2357.00 1693.87 1651.18 1557.00 1454.95 1376.69 Hill 9-Fluorono Thu Jun 24 23:03:01 2021 (G 40 35 30- 20 15 10 5. 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers (cm-1) Collection time: Thu Jun 24 23:02:41 2021 (GMT-04 Thu Jun 24 23:02:58 2021 (GMT-04:00) FIND PEAKS: Spectrum: Region: 4000.00 Absolute threshold: Sensitivity: Peak list: Hill 9-Fluoronone 400,00 36.904 50 Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: Intensity: 36.708 35.162 36.680 1376.69 Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: Position: 1454,95 1557,00 1651.18 36.550 1693.87 36.474 2357.00 35.438 2852.36 2922.22 3625.71 30.354 27.767 34.506 34.421 3645.33 34.663 3666.69 3685.71 3707.54 3730.33 3741.41 3798.47 34.648 34.739 34.623 34.359 34.754 Position: Position: Position: 3812.94 3850.03 34.632 33.904
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