Experiment 1: Separation and Purification of Solid Product
I. Laboratory Objectives
1. To apply the basic principles of drug synthesis, separation, and purification
techniques.
2. To be able to synthesize a crude extract for use in the synthesis of drugs.
3. To determine the concepts involved in separation and purification of crude
extracts in the synthesis of drugs.
4. To determine the different factors affecting the purity of drugs.
II. Reactants and Products
Note: Because recrystallization is a physical purification process rather than a
chemical transformation, no new chemical species are synthesized. Instead, the
process isolates a pure substance from a crude mixture.
Starting Material (Crude Input): Impure Benzoic Acid (Recorded mass:
1.01 g)
Isolated Substance (Purified Output): Recrystallized Benzoic Acid
(Recorded mass: 0.323 g)
III. Chemical Structure & Process Representation
Physical Phase Transition Equation
+
C7H6O2 (Impure Solids) + H2O (Hot) Filtration∧Cooling
→
C7H6O2 (Pure Crystals)
Structural Formula of Benzoic Acid
IUPAC Name: Benzoic acid
Molecular Formula: C6H5COOH
IV. Principles and Experimental Rationale
1. Core Principles Involved
The recrystallization of benzoic acid is governed by temperature-dependent
solubility; its hydrophobic benzene ring and hydrophilic carboxylic acid group allow
it to dissolve in hot water as kinetic energy overcomes intermolecular forces, but as
the solution cools, solubility drops sharply, forcing the molecules to selectively
organize into a pure crystalline lattice. During this process, activated charcoal
leverages its high surface area to physically adsorb large, colored, and resinous
impurities prior to hot filtration. Lastly, the purity of the isolated substance is
reflected in its melting point behavior, where a pure compound exhibits a sharp,
distinct thermal range, whereas residual impurities disrupt the uniform crystalline
matrix, requiring less thermal energy to break the lattice and resulting in a
characteristically depressed and broader melting point range.
The foundational mechanism of recrystallization. Benzoic acid features a
hydrophobic benzene ring and a hydrophilic carboxylic acid group. It is
soluble in hot water because the increased kinetic energy easily breaks the
intermolecular bonds, but it is sparingly soluble in cold water. As the hot
solution cools, the solubility drops sharply, forcing the benzoic acid molecules
to selectively organize into a pure crystalline lattice. Activated charcoal has
an incredibly high surface area that physically adsorbs large, colored, and
resinous organic impurities from the hot mixture before filtration. Pure
substances have sharp, distinct melting points. Impurities disrupt the uniform
crystalline matrix, requiring less thermal energy to break the lattice structure.
This causes a lower (depressed) and broader melting point range.
2. Safety Measures and Precautions
The procedure requires handling liquids heated near boiling on a hot plate.
Use beaker tongs or heat-resistant gloves when handling hot glassware.
The solution must not be boiled too aggressively, which can prematurely
evaporate the distilled water solvent and alter the concentration required for
optimal crystallization.
When packing the fine glass capillary tubes for melting point determination,
handle them gently to avoid breakage and puncture wounds.
3. Experimental Outcome Rationale: Success vs. Failure Analysis
The recrystallization was only partially successful, resulting in a low recovery of
31.79% and low product purity. The minimal yield indicates significant material loss,
likely due to premature crystallization during hot filtration or over-washing with
insufficiently cold water. Furthermore, the severe melting point depression of 102°C
compared to the literature standard of 121°C–123°C confirms that substantial
residual impurities or lingering moisture remained trapped within the crystals,
disrupting the uniform lattice structure.
1. Acetic acid + Benzyl alcohol
2. Acetic acid + Decanol
3. Acetic acid + Hexanol
4. Acetic acid + Isopentyl alcohol
5. Acetic acid + Isopropyl alcohol
6. Acetic acid + n-octanol
7. Acetic acid + Propanol
1. Benzyl acetate + Water
2. Decyl acetate + Water
3. Hexyl acetate + Water
4. Isopentyl acetate + Water
5. Isopropyl acetate + Water
6. n-octyl acetate + Water
7. Propyl acetate + Water
Concentrated sulfuric acid is an aggressive dehydrating agent that causes
severe chemical burns. It must be dispensed dropwise with extreme caution,
ideally inside a functional fume hood.
During the purification steps, adding sodium bicarbonate to neutralize lingering
acetic acid produces a substantial volume of carbon dioxide gas:
The separatory funnel must be inverted and vented frequently to release this
gas pressure safely and prevent the stopper or liquid from spraying out under
pressure.
Both the reactant alcohols and the produced organic esters have low flashpoints
and are highly volatile. Heating steps must be performed using a regulated hot
plate or water bath rather than an open flame.
The successful chemical synthesis of benzyl acetate and isopropyl acetate was initially
verified by a distinct shift in their olfactory profiles, which transformed the reaction mixtures
into a pleasant, jasmine-like aroma and a specific, fruity apple/pear-like aroma, respectively.
This structural transformation was chemically confirmed through a verification test using
base hydrolysis; upon the addition of sodium hydroxide (), the ester bonds underwent a
complete breakdown, which was conclusively demonstrated by the total disappearance of
both the floral jasmine and fruity apple/pear scents from the solution.