4-Recrystallization of An Impure Acetanilide Sample
4-Recrystallization of An Impure Acetanilide Sample
Experiment No. 4
DISCUSSION
Figure 4.1. An impure solid in: (A) cold solvent in which it has low solubility, (B)
solvent that has been warmed up to dissolve all of the solid, and (C) solvent that
has cooled down to the original temperature. The crystallized solid is now pure,
while the impurities remain in solution.
If a solid material (impure) is placed in a solvent of low solubility, the solid will dissolve but
the rest will ‘sit there’. However, it doesn’t just ‘sit there’ since equilibrium is in effect. In
order for the entire solid to dissolve, heat must be introduced equal or near to its solvent
boiling point until the entire solid goes into the solution. Then, if the solution is cooled at
some temperature, the concentration of solute will exceed its solubility, and the solid will
start to come back out of a solution- it will crystallize. Now during the process of crystal
formation, a molecule will tend to attached to a growing crystal composed of the same
type of molecules because of a better fit in a crystal lattice of the same structure than for
the other molecules (impurities), which remain soluble into the solution. Finally, by the
time when the initial temperature is reached, all of the original material has formed
crystals, which can be filtered from the solvent.
The process does not only begin on selecting a good solvent and end on the
performing recrystallization but it must consider the rate of forming the crystals and the
percentage recovery of the pure solid. To handle this scratching the walls of the
container (It must be an Erlenmeyer flask!) with a glass rod to hasten the rate of crystal
nucleation or the solution can be ‘seeded’ (adding tiny crystals of the substance). If
none of these work consider vaporizing the solution because of too much solvent or work
out for a new solvent. There are other problems such as colored contaminants and
insoluble impurities. This is best remedied by adding activated charcoal and hot filtration.
The filter paper must be fluted and stemless funnel must be used to filter rapidly and
avoid crystallization. The residue and the flask must be washed with hot solvent. The
collected filtrate in the flask begins to form crystals as it reaches room temperature. The
best way to obtain a purer crystal is through slow cooling without agitating the solution.
The flask can be covered by a beaker but not stoppers. Ice-bath cooling is not
encouraged because it causes additional crystallization. The beauty of the crystals
formed in slower phase will compensate your patience rather than the crystals formed in
a speedy process.
In this experiment, five different solvents ranging in polarity will be utilized to determine
the good solvent for the recrystallization of acetanilide. After the proper solvent is chosen
for recrystallization of the impure sample, recovery of the pure acetanilide follows
together with the test for its purity.
TIME ALLOTMENT
MATERIALS
NChemicals/Reagents:
pure acetanilide, impure acetanilide, ice, activated charcoal, solvents:
distilled water, ethanol, acetone, toluene,
! Glasswares/Equipment:
hot plate, 5 test tubes (small), testube rack, testube holder, 1 mL pipet for
each solvents, 500 mL beaker, 250 mL, beaker, 100 mL beaker, 125 mL
Erlenmeyer flask (2), stirring rod, filtering funnel, filter papers, basin, Petri dish,
vacuum pump, Buchner funnel, sciccors
PRECAUTIONS
• Always wear your laboratory gown and safety goggles.
• Keep volatile & flammable liquids (e.g. ethanol, acetone) away from flame.
• Acetanilide is harmful if swallowed.
• Cool hot glasswares before washing.
• Do not weigh hot substances.
• Dispose organic wastes into its respective waste bottle.
PROCEDURE
Cool the contents of four test tubes in an ice bath and observe for any
reappearance of the crystals. If crystals do not appear in any of the test tubes, add a pin
head size of acetanilide crystal into the solution or scratch the inside wall of the test tubes
beneath the solvent surface with a stirring rod. Identify the solvent that is best in
recrystallizing an impure acetanilide mixture. Report your finding to your instructor.
essential that this operation be completed as quickly as possible in order that cooling is
minimized. It is also advisable to place only few mL of the hot solution into the funnel,
keeping the remainder of the solution in the flask hot by heating on a hot plate until it is
transferred to the funnel. If the filtrate remains to be colored, add a pinch of activated
charcoal, heat and refilter.
Allow the filtrate to cool slowly to room temperature undisturbed. Observe the
appearance of crystals. To induce the crystallization of more acetanilide, chill the flask in
an ice-water bath and scratch the walls of the flask in contact with the solution.
Dry the crystals transfer the crystals together with the filter paper into a Petri dish,
and place in an oven preheated to 105 oC. Keep it in the locker until the next laboratory
period. Weigh the dried crystals and filter paper to the nearest 0.0001 gram. Determine
the percentage of the pure crystals recovered from the impure sample. Determine the
melting point of the purified acetanilide in experiment #7.
REFERENCE
Pasto, Daniel J. et.al. (1992). Experiments and Techniques in Organic Chemistry. Prentice-
Hall Inc. New Jersey.pp 43 –46 and 391-392.
REPORT SHEET
Experiment No. 4
Name Score
Experiment Title
Ethanol, 78.5
Acetone, 56.2
Toluene, 110.6
System Description/Observation
Impure solid sample
Impure solid sample after the addition of
solvent
Dissolved mixture after the addition of
activated charcoal
Filtrate in the receiver
Pure acetanilide
Observation/Quantity
Color
State
Melting Approximate _______
point (oC) Mpt Range: ________
True value: _________
Density
Structure
GUIDE QUESTIONS
Write your answer on the space provided for the following questions.
3. Compare the melting ranges for the pure and impure acetanilide samples. What
can you tell from these? Describe the requirements for a good Recrystallization
solvent.
4. Compare the melting point of your purified acetanilide with that listed in the
literature. Discuss any discrepancies. Are they significant?
6. The solubility of compound A in ethanol is 0.8 g per 100 mL at 0oC and 5.0 g per
100 mL at 78oC. What is the minimum amount of ethanol needed to recrystallize
12.0 g sample of compound A? How much would be lost in the recrystallization?