I Will Survive: 8 Weeks in Organic Chemistry Lab!
Organic Chemistry 3412
Spring 2019
Rachael DixonDixon 2
Table of Contents
Title Page Number
1. Introduction 3
2. Week One: Synthesis of 2-Nitrofluorene 4
a. IR
b
...
I Will Survive: 8 Weeks in Organic Chemistry Lab!
Organic Chemistry 3412
Spring 2019
Rachael DixonDixon 2
Table of Contents
Title Page Number
1. Introduction 3
2. Week One: Synthesis of 2-Nitrofluorene 4
a. IR
b. 1H-NMR
c. Lab Carbon Copies
3. Week Two: Reduction of 2-Nitrofluorene to 2-Aminofluorene 7
a. IR
b. 1H-NMR
c. 13C-NMR
d. Lab Carbon Copies
4. Week Three: Synthesis of 2-Iodofluorene by a Diazonium Reaction 11
a. IR
b. 1H-NMR
c. 13C-NMR
d. Lab Carbon Copies
5. Week Four: Synthesis of an Acetamide 15
a. IR
b. 1H-NMR
c. Lab Carbon Copies
6. Week Five: Synthesis of an Imine by Reaction of an Amine with an Aldehyde 19
a. IR
b. 1H-NMR
c. Lab Carbon Copies
7. Week Six: Synthesis of a Benzyl Amine by Reduction of an Imine 23
a. IR
b. 1H-NMR
c. 19F-NMR
d. Lab Carbon Copies
8. Week Seven: Pd-Catalyzed Suzuki Reaction using a Boronic Acid 26
a. IR
b. Lab Carbon Copies
9. Week Eight: Benzylic Air Oxidation of 2-Nitrofluorene to 2-Nitrofluorenone 29
a. IR
b. Lab Carbon Copies
10. Conclusion 32
11. Summary Data Table 33
IntroductionDixon 3
Over the course of eight weeks, many different fluorene compounds were synthesized.
The first reaction was nitrating fluorene to produce 2-Nitrofluorene. 2-Nitrofluorene was used to
synthesized 2-Aminoflourene in week two via a reduction as well as 2-Nitroflourenenone via air
oxidation in week eight. The amine produced in week two was used to synthesize 2-Iodofluorene
in week three via Diazonium reaction, an acetamide in week four, and a fluorinated imine in
week five. The fluorinated imine produced in week five was used to synthesize a benzyl amine in
week six via reduction. The 2-Idofluorene produced in week three was then used to synthesize a
benzonitrile in week seven via a Pd-Catalyzed Suzuki reaction.
In each of the experiments, thin layer chromatography (TLC), melting points, and
infrared spectroscopy (IR) were gathered as data. These techniques were used to confirm product
purity, as that was a major goal of this project. Along with this collected data, Dr. Stephens also
provided the respective 1H-NMR, 13C-NMR, and 19F-NMR for our labs. It was also important to
have a relatively good yield of product, which was achieved most weeks. Overall, each reaction
was successful regarding product purity.
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