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Regina Chen

Section 202
Instuctor: Qitian Lin
Date of Experiment: 6.3.13
Date of Report: 6.10.13
Microscale Laboratory Techniques: Recrystallization and Extraction

In medicine and industry pure compounds are used. Often, the compounds that are obtained
from natural sources or the product of chemical reactions are impure, and these impurities may
be due to the presence of side reactions, unreacted starting materials, inorganic materials and
solvents. To isolate pure compounds scientists have devised laboratory techniques and two
examples are recrystallization and extraction. Recrystallization involves dissolving the solid in a
solution with high temperature, running the hot solution through a filter to separate out the
impurities, and finally allowing the solution to cool, and crystals to reform.
Extraction is the technique of removing compound(s) from a mixture in a solid, liquid or gas
phase, to a different phase. A common everyday example is making coffee; we boil the coffee
beans to extract the caffeine into the water. The laboratory technique described here extracts a
base from a mixture containing an acid and a neutral compound.

In practicing these techniques, the expectation is to get as large as possible percent recovery.

Table of Reagents and Products
Reagent(s) and
weight (g)
(and %

What is this? 135.07 need this? .104 0 grams

Benzoic Acid
122.12 How to
know if
does not
0 grams


128.17 How to
know if
does not
.645 grams


Diethyl Ether

74.12 __

Sodium Hydroxide
40.00 __

Hydrochloric Acid
36.46 __

The experimental procedure was obtained from the laboratory handout and Experimental
Organic Chemistry by J.C. Gilbert and S.F. Martin, pages 107-108, 161-162.
For the first part of the experiment, 0 grams of acetanilide crystals was obtained (and melting
point not available).
Percent Recovery = weight of pure crystals recovered x 100 = _0______ = 0 %
weight of original sample .104
For the second part of the experiment, 0 grams of benzoic acid was obtained (and melting point
not available).
Percent Recovery = weight of pure crystals recovered x 100 = _0______ = 0 %
weight of original sample .104
.645 grams of naphthalene were obtained and the melting point determined was 70-75 degrees
Percent Recovery = weight of pure crystals recovered x 100 = .645______ = 35 %
weight of original sample 1.84

Discussion and Interpretation of Results
The results for acetanilide and naphthalene did not match expectations. There was zero percent
recovery. For acetanilide, in the first attempt, a large amount of crystallization occurred inside
the test tube as the hot solution was being poured out onto the filter. Then, on top of the filter
there was additional crystallization. It appeared that the total amount of recrystallization during
the hot filtration process was approximately in the same amount as the original crude acetanilide.
This observation lead to the prediction (which came true) that the filtrate might not produce any
crystals. In a second trial, there was an attempt to improve the technique by using a smaller test
tube (to reduce surface area for crystallization) and to boil the solution for a longer time (to
ensure the solution maintained a high enough temperature during the pour so as to prevent
crystallization). In this trial, there was less crystallization (pre-filtrate). However, after the
filtrate cooled down, there was no recrystallization. Due to lack of time, there were no further
trials. However, some ideas were formulated about possible ways to improve the technique in
the future. One way might be to use more solvent. The 1 mL of solvent used was a small
amount that it was not enough for the vacuum filter to pull through. The majority of the 1 mL of
solvent might have absorbed into the paper filter, making it hard for it to be vacuumed out.
For the benzoic acid, there was also zero percent recovery. However, in this filtrate there was
crystallization. It was during the second filtration step that the crystals were lost. That is, they
were poured onto the filter, and after applying vacuum, there were no longer any visible crystals
to scrape from the filter paper. The small amount combined with the thinness/fragility of the
crystals made them very hard to ultimately recover. In the future, probably producing more
crystals by adding more HCl would result in a higher percent recovery.
Recrystallization and extraction are two laboratory techniques that can be used to isolate pure
compounds. However, to obtain a near one hundred percent recovery can be difficult due to
factors such as human error, and limitations in amount of solvent available because of costs.
Post-lab Questions:
24. A second crop of crystals is probably less pure because the vacuum filtrate now has more
impurities in it (compared to the first crop filtrate), and these impurities are likely to precipitate
out with the crystals.
26. Operating at the temperature extremes of hot and cold ensure that the solute crystalizes
at the appropriate moments during the filtration process. To elaborate, during step one the goal
is to filter our impurities, not the desired solute. This can be done by having the solution at a
hot temperature (such as boiling point) so that the solute remains soluble in solution and passes
through the filter. Then in step two, the goal is reverse of step one; now it is desirable to filter out
the solute, not the impurities. To get the solute to precipitate out, a cold temperature is needed.
Also, operating at these temperature extremes ensures that precipitation will occur. This is
because the extent of precipitation of a solute depends on the difference in solubility in the
solvent at temperatures between the upper (hot) and lower (cold) extremes.
p. 168
7. (a) and (b)