Lab Report 9 Bleach Oxidation
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 quite pure. The melting point range determined
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 quite pure. The melting point range determined