What is the oxidation state of the affected carbon in the starting material and product

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
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What is the oxidation state of the affected carbon in the starting material and 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
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