1. Synthesis and Analysis of Aspirin Chemistry 1060 Laboratory

2. Analysis Purity determination Thin Layer Chromatography (TLC) Separation and identification stationary phase – silica gel mobile phase – organic solvent Relative attraction to the two phases Polarity

3. Analysis Thin Layer Chromatography (TLC) Retention factor (R f ) values 3 cm 5 cm Solvent front R f = 3/5 = 0.60 Origin

4. Analysis Thin Layer Chromatography (TLC) Salicylic acid (starting material) Pure aspirin Isolated product UV detection Results Isolated product R f of pure aspirin salicylic acid removed? UV

5. Analysis Structure confirmation 1 H nuclear magnetic resonance ( 1 H NMR) - or proton magnetic resonance (PMR)

6. Analysis 1 H NMR

7. Analysis 1 H NMR radio-frequency region of the spectrum

8. Analysis 1 H NMR – Shielding

9. Analysis 1 H NMR – Chemical Shifts, Chemical Equivalency tetramethylsilane (TMS)

10. Analysis 1 H NMR – Chemical Shifts, Integration 3 1

12. Analysis 1 H NMR – Chemical Shifts, Complex Patterns

13. Analysis 1 H NMR – Characterizing starting material and product salicylic acid aspirin

14. Summary Goals Week 1: To synthesize aspirin, from salicylic acid and acetic anhydride To purify the product using recrystallization Week 2: To verify the purity and identity of the product using thin layer chromatography (TLC) To further confirm the identity of the product by nuclear magnetic resonance (NMR) spectroscopy