Lab Report 9 Bleach Oxidation

Topics: Swern oxidation, Infrared, Redox Pages: 4 (864 words) Published: February 26, 2015
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 9-fluorenone / (180.20g/mol) = 3.0 x 10-3 moles
Product yield: (0.003mol/0.00027mol) x 100 = 1,111% yield.

2. The Rf values were not recorded in lab. However, spot results were recorded. The TLC plates 1-3 showed the presence of starting material (SM) in the crude product (CP) lane. TLC plate 1 was taken after adding the initial addition of 0.25mL of bleach. TLC plate 2 was taken after adding an additional 0.08mL of bleach because plate 1 still showed presence of SM in the CP lane. TLC plate 3 was taken after adding an additional 1mL of bleach for the same reason. However, TLC plate 4 did not show any SM in the CP lane and this was after adding an additional 3mL of bleach. The plate only showed a CP spot, indicating that the reaction had gone to completion.

3. IR Spectroscopy Peaks
Peak
Functional Group1
2362.05 cm-1
Very weak band
1712.90 cm-1
(Strongest peak)
C=O (ketone)
1598.22 cm-1
C=C (aromatic)
1450.50 cm-1
C=C (aromatic)
1150.63 cm-1
Very weak band
735.43 cm-1
=C–H (alkene)
669.78 cm-1
Very weak band
Attached is a published spectrum from: http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi

Discussion

1. According to the melting point measured, the final product was...
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