Analysis:

The most common technique for purifying organic solid compounds is recrystallization, which
relies on the different solubilities of solutes in a solvent. Recrystallization does not involve a
chemical reaction; the crude product is simply dissolved into solution, and then the conditions are
changed to allow crystals to re-form. As the crystal develops, they select only the correct
molecules, which fit into the crystal lattice and ignore the wrong molecules. Therefore, impurities
are excluded from the crystal lattice and the purity of the final product increases. Recrystallization
is a very effective way of obtaining a pure sample, but it is very important that the proper solvent
is used.
The solubility of the compound in the solvent used for recrystallization is important. In the ideal
case, the solvent would completely dissolve the compound to be purified at high temperature,
usually the boiling point of the solvent, and the compound would be completely insoluble in that
solvent at room temperature or at zero oC. In addition the impurity either would be completely
insoluble in the particular solvent at the high temperature, or would be very soluble in the solvent
at low temperature. In the former case, the impurity could be filtered off at high temperature, while
in the latter case the impurity would completely stay in solution upon cooling.
In the experiment, 1g of low grade benzoic acid was used as the solid to be purified using
recrystallization. The benzoic acid was dissolved using hot/nearly boiling distilled H2O, which is
added in small portions just enough for the solid to be dissolved (about 75ml).
There was a purple color impurity that is observed when dissolving the solid and for the
decolorization process of the experiment, activated charcoal was used. Activated charcoal is finely
divided carbon often used to decolorize a solution. The small particles of activated charcoal
provide a large surface area to which large colored molecules may become adsorbed. In the
experiment, the pure crystals of benzoic acid still contains a tinge of blue. The amount of charcoal
added may have been insufficient to fully filter out the impurities.

𝑀𝑎𝑠𝑠 𝑟𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑧𝑒𝑑 𝑠𝑎𝑚𝑝𝑙𝑒

% 𝑌𝑖𝑒𝑙𝑑 = 𝑥 100 =
𝑀𝑎𝑠𝑠 𝑐𝑟𝑢𝑑𝑒 𝑠𝑎𝑚𝑝𝑙𝑒

0.437g
% 𝑌𝑖𝑒𝑙𝑑 = 𝑥 100 = 43.7%
1g

The yield for a recrystallization can never be 100%. After performing the experiment, we only
obtained 43.7% of pure benzoic acid. While the chilled solvent is saturated and should release
some crystals, at least some of the desired material will remain dissolved in the cold solvent and
will be lost when the crystals and solvent are separated. The primary necessary source of mass loss
is to the solvent. Moreover, additional mass will be lost to physical handling, and some of the lost
mass is simply the impurities that will be removed.
Conclusion:
The purpose of this laboratory experiment was to recrystallize impure benzoic acid. Once the two
products were dissolved and started cooling, crystallization immediately took place, since the
solution was fully saturated. However, there was a high decrease in yield during recrystallization,
probably for at least four reasons. The first reason was that some of the compound stuck to the
glass of the flask when pouring it into the funnel. The second reason was that some of the dried
compound stuck to the actual funnel paper when transferring into a container. Also, some
compound was lost during the transfer from the funnel to the container, as some was spilled on the
counter. Finally, the fourth reason is the impurities of the compound stayed dissolved in the solvent
when drying the crystals.
An ice bath lessens the solubility of the solvent. Making the compounds in the solution precipitate
or in this case, recrystallize more quickly. By putting the solution in the ice bath we are thereby
“forcing” recrystallization to take place thus having smaller, less purer substances than that of the
slow cooling solution. The latter produces bigger, purer, and finely shaped crystals since the
solubility of the solution is at a constant rate.
POST-LAB QUESTIONS

1.)
If no crystal growth occurs, to mediate this problem the following should be done:
1.Reduce the temperature of the solvent
2. Evaporate some of the solvent
3. Add a seed crystal or scratch the surface of the vessel
4. Blend into the solvent a second liquid in which the solute is less soluble
2.)
Having the set up heated before filtration and keeping the solution hot so the solute stays
dissolved will prevent crystals from forming on the paper and in the funnel. As the filtrate begins
to accumulate, heating or filling the receptacle beaker with boiling water will also help to prevent
any crystallization in the funnel or on the filter paper.
3.)
Characteristics of a Good Recrystallization Solvent:
1. The recrystallization solvent should NOT dissolve the substance to be purified at room
temperature, but it should dissolve it well at the solvent’s boiling point
2. The solvent should dissolve soluble impurities well at room temperature.
3. The solvent should not dissolve insoluble impurities even at the solvent’s boiling
point. These insoluble impurities can then be removed by gravity filtration.
4. The solvent must not react with the substance to be purified.
5. solvent’s boiling point must be lower than the compound’s melting point
6. an abundant quantity of crystals must be recoverable from the cool solvent
In a nutshell, the choice of solvent for a recrystallization is crucial. For a successful
recrystallization
the dissolving power of the solvent must be “mediocre”, neither too good nor too bad for the
following reasons:
• If the solvent is too good, then even when the solvent is cold the sample will remain
dissolved and you won’t be able to harvest any crystals.
• If the solvent is too bad, then even when the solvent is hot it still won’t be able to dissolve
the sample, and the impurities won’t be freed from the original sample.
An effective solvent must be mediocre, good enough to dissolve the sample at high
temperature (so that the impurities are freed), but weak enough so that at least some of
your sample crystallizes out after cooling (so that you get at least some yield harvested.)

4.)