1. Honors Project: Organic Chemistry
Rebecca Nagurney & Anthony Possanza

2. Objectives
Synthesis of a precursor to an organic molecule with anti-cancer properties
Learn invaluable laboratory skills
Reinforce learning of lecture topics

3. Curcumin Component of Turmeric Indian Spice
Anti-Cancer and Anti- Inflammatory Properties
Synthesis of Derivatives
Acetyl Acetone

4. Synthesis of Curcumin

5. Halogenation Using N-Bromosuccinamide (NBS) or N-Chlorosuccinamide (NCS)

6. Chlorination Chlorinating Reagent: N-Chlorosuccinamide (NCS) Reaction:
1.0193g Acetyl Acetone g NCS + 15mL dichloromethane (CH2Cl2)
Stir reaction for one week at room temperature
Use thin layer chromatography (TLC) to check for product

7. Bromination Brominating Reagent: N-Bromosuccinimide (NBS) Reaction:
.5112g Acetyl Acetone g NBS + 15mL THF (Tetrahydrofuran)
Stir reaction for one week at room temperature
TLC to check for product

8. Thin Layer Chromatography
Solvent system: 10:1 (Hexane: Ethyl Acetate (EtOAc))
Spot
Starting Materials
(Acetyl Acetone in EtOH)
Reaction Mixture

9. TLC Continued Rf = d1/d2 d1 = distance from origin to middle of spot
Allow solution to run up the TLC plate
Mark the solvent front before removing from the solution
Dry
Dip in 5% Phosphomolybdic Acid in EtOH
Place on hot plate and wait for spots to appear
Calculate Rf Value
Rf = d1/d2
d1 = distance from origin to middle of spot
d2= Distance from origin to solvent front

10. TLC of Bromination Reaction in Tetrahydrofuran (THF)

11. Removing the Solvents
Rotary Evaporator
“Roto Vap”

12. Column Chromatography
Fill column with gel
Load dry or wet
Wet is better!!!
Particles are fine and can get into your lungs!!
Run hexane through the column until the gel is compacted
Pour a layer of sand on top of the compacted gel

14. Column Chromatography
Load product on top of sand
Run hexane through the column and collect samples
Add 25mL Ethyl Acetate to Hexane to increase polarity of the solvent
Increase to a 50% Hexane 50% Ethyl Acetate solution
57 samples were taken

15. TLC of Bromination Reaction in Acetone

16. Results Favors mono-bromo product
Reaction in THF
Favors mono-bromo product
Slower moving (more polar) spot on TLC
Reaction in Acetone
Favors di-bromo product
Faster moving (less polar) spot on TLC

17. Future Work Continuation of honors work into the spring semester
Completion of synthesis of anti-cancer agent
We would like to sincerely thank Dr. Pham for her guidance and support