Lab Report 9 Bleach Oxidation Essays

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Bleach Oxidation of 9-Hydroxyfluorene

The purpose of this experiment was to oxidize an alcohol (9-hydroxyfluorene) to a ketone (9-fluorenone) using aqueous sodium hypochlorite (bleach) as the oxidizing agent, while introducing techniques used in microscale experiments.

Reaction:

Results

1. Recrystallized Product Yield
Product yield = (actual yield/theoretical yield) x 100%

3mL 9-hydroxyfluorene x (1mL/1000mL) x (0.09 mol/L) = 2.7 x 10-4 moles
0.05g 9-fluorenone / (180.20g/mol) = 2.77 x 10-4 moles
Product yield: (0.000277 mol/0.00027 mol) x 100 = 102.5% yield

*Note: A recording mistake was made in the lab notebook, where the final product was supposed to be 0.05g (calculations above) and not 0.55g (calculations below).

0.55g
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The range determined in the experiment is approximately 2 degrees above the actual melting point range, indicating some impurities in the final compound. According to the IR spectrum, the product obtained is quite pure. The peaks in the table above indicate the presence of a carbonyl, specifically the C=O bond of a cyclic ketone and also the sp2-hybridized =C–H bond of an alkene. There is no broad peak ranging from 3200 cm-1-3600 cm-1, which would indicate the presence of the -OH group of an alcohol. Thus, there is likely no presence of starting material in the final product. The percent yield above 100% indicates that some liquid (hexanes) used to recrystallize the product was likely still in the flask when the product was weighed.

2. Price of Reagents

Jones Oxidation: 0.00027 moles of 9-hydroxyfluorene requires:
(.00027 mol)(1.1) / (2M) = .1485 L of 2M CrO3 in H2SO4. That would be 14.85mL. Therefore, ($88.70)(14.85/25) = $52.69

PCC Oxidation: .00027 moles of PCC would weigh: (.00027mol)(1.1)(215.56g/mol) = 0.064g. This costs ($25.20)(.064/25)= $0.06

Swern Oxidation: (0.00027 mol)(1.1)(78.13 g/mol) / (1.1 g/mL) = 0.02 mL of DMSO. ($28.70)(.02/100) = $0.01
(.00027 mol)(3)(101.2 g/mol)/(.725 g/mL) = 0.11 mL of Et3N
($24.50)(.11/100) = $0.27
(.00027 mol)(1.1)(126.93 g/mol) = 0.038g of Oxalyl chloride
($51.90)(.038/25) = $0.08
Total cost: 0.01+0.27+0.08 = $0.36

Bleach Oxidation: (.00027

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