Honors Project: Organic Chemistry
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Transcript of 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
Component of Turmeric Indian Spice
Anti-Cancer and Anti- Inflammatory Properties
Synthesis of Derivatives Acetyl Acetone
Curcumin
OO
X YX,Y = H,Cl;Cl,Cl;H,Br;Br,Br
O O
HO
CH3O
OH
OCH3
Synthesis of Curcumin
Halogenation Using N-Bromosuccinamide (NBS) or N-
Chlorosuccinamide (NCS)
N
O
O
X + HX X2 N
O
O
H+
X2
OO
H H
+
OO
X Y
X,Y = H,Cl;Cl,Cl;H,Br;Br,Br
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 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 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 WorkContinuation 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