1 / 17

Honors Project: Organic Chemistry

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

kaethe
Download Presentation

Honors Project: Organic Chemistry

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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 + 1.5094g 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 + .8342g 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 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

  13. 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

  14. TLC of Bromination Reaction in Acetone

  15. Results 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

  16. 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

More Related