TITLE
Purification of Solid Organic Compounds by Recrystallization
AIM OF THE PRACTICAL
To purify solid organic compounds (salicylic acid, benzoic acid, 4-diethylamino benzaldehyde, and
phenacetin)
by recrystallization and determine the most suitable solvent(s) based on solubility and crystallization
behavior.
INTRODUCTION AND THEORY
Recrystallization is a common purification technique for solid organic compounds. It is based on the principle
that the solubility of a compound increases with temperature. An ideal solvent dissolves the compound when
hot
but not when cold. The impurities either remain dissolved in the cold solvent or are filtered out from the hot
solution.
A compound is dissolved in a minimum amount of hot solvent, filtered, then cooled to allow the purified solid
to
crystallize. The purity is checked using melting point analysis, as pure substances have sharp melting points.
The choice of solvent is critical. It must:
- Dissolve the compound well at high temperature but poorly at low temperature.
- Not react chemically with the compound.
- Either dissolve impurities at all temperatures or not dissolve them at all.
- Be safe and easy to remove (low boiling point preferred).
EXPERIMENTAL
Materials:
- Salicylic acid, Benzoic acid, 4-diethylamino benzaldehyde, Phenacetin
- Solvents: distilled water, acetone, benzene, glacial acetic acid
- Test tubes, droppers, water bath, ice bath, spatula, filter paper, funnel, beakers
Procedure:
1. About 0.1 g of each compound was placed in a clean test tube.
2. 1 mL of the selected solvent was added dropwise with shaking.
3. If the solid did not dissolve, it was heated gently in a water bath.
4. Additional solvent was added in 0.5 mL increments until the compound dissolved completely or up to 3 mL.
5. The hot solution was filtered if undissolved impurities were present.
6. The filtrate was cooled to room temperature and then in an ice bath.
7. Formation of crystals was observed and recorded.
8. If no crystals formed, the test was repeated with different solvents or mixed solvents if needed.
RESULTS
(See table in original explanation)
DISCUSSION
The effectiveness of recrystallization depended on the solubility characteristics of the compound in each
solvent.
Water was effective for polar compounds like salicylic acid, benzoic acid, and phenacetin due to hydrogen
bonding.
4-diethylamino benzaldehyde, being more non-polar, was better recrystallized from benzene, a non-polar
solvent.
Acetone generally dissolved most compounds too well, preventing crystallization upon cooling.
The solvent selection followed the principle "like dissolves like."
CONCLUSION
Each compound had an optimal solvent for recrystallization:
- Salicylic acid -> Distilled Water
- Benzoic acid -> Water or Acetone
- 4-diethylamino benzaldehyde -> Benzene
- Phenacetin -> Water
QUESTIONS
1. Why is acetone not suitable for recrystallizing most of the compounds tested?
2. Why is it important to cool the solution slowly during recrystallization?
3. How can you induce crystallization if none forms on cooling?
REFERENCES
1. Vogel's Textbook of Practical Organic Chemistry, 5th Edition, Furniss et al., pp. 857-860
2. Morrison & Boyd, Organic Chemistry, 6th Edition, Chapter 3 - Purification of Organic Compounds
3. Laboratory Manual, Department of Chemistry, (Your Institution), 2024 Edition
