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Synthesis of Oil of Wintergreen

Synthesis of Oil of Wintergreen. Chemistry 1060 Laboratory. 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. Solvent front.

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Synthesis of Oil of Wintergreen

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  1. Synthesis of Oil of Wintergreen 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. Solvent front Rf = 3/5 = 0.60 5 cm 3 cm Origin Analysis • Thin Layer Chromatography (TLC) • Retention factor (Rf) values

  4. Analysis • Thin Layer Chromatography (TLC) • Salicylic acid (starting material) • Pure oil of wintergreen (from stockroom) • Isolated product • UV detection • Results • Isolated product • Rf pure oil of wintergreen • Salicylic acid removed?

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

  6. Analysis • 1H NMR

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

  8. Analysis • 1H NMR – Shielding

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

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

  11. Analysis • 1H NMR – Chemical Shifts, Complex Patterns

  12. Analysis • 1H NMR – Characterizing starting material and product salicylic acid methyl salicylate

  13. Summary • GoalsWeek 1: • To synthesize methyl salicylate, or oil of wintergreen, from salicylic acid and methanol • To isolate the product using liquid-liquid extraction 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

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