Honors Project: Organic Chemistry Rebecca Nagurney & Anthony Possanza

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

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

Synthesis of Curcumin

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

Chlorination Chlorinating Reagent: N-Chlorosuccinamide (NCS) Reaction: 1.0193g Acetyl Acetone + 1.5094g NCS + 15mL dichloromethane (CH2Cl2) Stir reaction for one week at room temperature Use thin layer chromatography (TLC) to check for product

Bromination Brominating Reagent: N-Bromosuccinimide (NBS) Reaction: .5112g Acetyl Acetone + .8342g NBS + 15mL THF (Tetrahydrofuran) Stir reaction for one week at room temperature TLC to check for product

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

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

TLC of Bromination Reaction in Tetrahydrofuran (THF)

Removing the Solvents Rotary Evaporator “Roto Vap”

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

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

TLC of Bromination Reaction in Acetone

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

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