This chapter covers methods for purifying organic compounds and analyzing their composition.
Overview
graph TD
A[Purification] --> B[Physical Methods]
A --> C[Analysis]
B --> B1[Crystallization]
B --> B2[Distillation]
B --> B3[Chromatography]
C --> C1[Qualitative]
C --> C2[Quantitative]Purification Methods
Crystallization
For solid compounds with different solubilities at different temperatures.
Steps:
- Dissolve in hot solvent
- Filter hot solution
- Cool slowly
- Collect crystals
Distillation
Simple Distillation: For liquids with BP difference > 30°C
Fractional Distillation: For liquids with BP difference < 30°C (uses fractionating column)
Steam Distillation: For water-immiscible compounds
Vacuum Distillation: For high-BP compounds that decompose
Differential Extraction
Separates compounds based on solubility in immiscible solvents.
Chromatography
Separates based on differential adsorption or partition.
Types:
- Column chromatography: Uses adsorbent column
- TLC: Thin layer on glass plate
- Paper chromatography: Paper as stationary phase
- HPLC: High pressure, fine particles
Qualitative Analysis
Detection of Elements
Nitrogen: Lassaigne’s test (sodium fusion → NaCN)
- Test with FeSO₄ + FeCl₃ → Prussian blue
Sulfur: Lead acetate test (black PbS)
Halogens: Silver nitrate test after fusion
- AgCl: white, soluble in NH₃
- AgBr: pale yellow, partially soluble
- AgI: yellow, insoluble
Phosphorus: Ammonium molybdate test (yellow precipitate)
Quantitative Analysis
Carbon and Hydrogen (Liebig’s Method)
Compound + CuO → CO₂ + H₂O
- CO₂ absorbed by KOH (weigh increase)
- H₂O absorbed by anhydrous CaCl₂
Nitrogen (Dumas/Kjeldahl)
Dumas: Measure N₂ volume
Kjeldahl: Convert to NH₃, titrate
Halogens (Carius Method)
Heat with HNO₃ + AgNO₃, weigh AgX
Sulfur
Heat with HNO₃, precipitate as BaSO₄
Molecular Formula Determination
- Find percentage composition
- Calculate empirical formula
- Find molecular mass (vapor density method, etc.)
- Determine molecular formula
Practice Problems
A compound contains 40% C, 6.7% H, and 53.3% O. Find its empirical formula.
Explain how you would separate a mixture of benzoic acid and naphthalene.
Further Reading
- Organic Principles - Basic organic chemistry
- Hydrocarbons - Organic compounds