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Abstract
Recrystallization is a common method of purifying organic substances
through the difference in solubility at different temperature. In this
experiment, acetanilide was produced by acetylation of aniline with acetic
anhydride. The crude acetanilide was dissolved in a solvent in a heating
water bath. The solution was cooled slowly in an ice bath as crystals form
out. As the compound crystallizes from the solution, molecules of other
compounds dissolved in solution are excluded from growing crystal lattice,
yielding pure acetanilide.
I. Introduction
Organic compounds that are solid at room temperature are usually
purified by crystallization. Crystallization is the deposition of crystals from a
solution. During the process of crystal formation, a molecule have the
tendency to be attached to a growing crystal composed with the same type
of molecules because of a better fit in a crystal lattice of a molecule of the
same structure than for other molecule. (Pastro, John, & Miller) Lattice is a
fixed and rigid arrangement of atoms, molecules or ions. (Mullin, 1961)
Recrystallization is a method in which two crystallization processes was
performed. It is referred to the second crystallization. (Pavia, Lampman, Kriz,
& Engel, 1999) It depends on the difference of solubility of a substance in a
hot and in a cold solvent.
II. Experimental
A corn grain amount of pure acetanilide was placed into each of the
three test tubes. The first test tube contained 1-ml distilled water. The test
tube was shaken and placed in a warm water bath (37 – 40°C) for 1 – 5
minutes. Then, it was cooled through an ice bath. Solubility of pure
acetanilide was recorded. For methanol and hexane, the same procedure was
done.
On Table 1, there were three (3) solvent that was tested, distilled
water, methanol and hexane. Methanol is soluble while hexane is insoluble in
all system. This shows that acetanilide that will be place in this solvent
cannot undergo recrystallization. Nevertheless, recystallization will not occur.
In addition, extra precaution must be taken because methanol and hexane
are flammable and highly volatile. However, distilled water exhibits different
result; rather, it shows the desired solubility behavior of an ideal
recrystallizing solvent for acetanilide. At room temperature it was insoluble;
during heating it was soluble; and when placed upon cooling it was insoluble.
Water is quite suitable for melting points of pure organic compounds from
about room temperature to about 70°C in heating water bath.
Drying the crystals was done after filtration. The most common
method involves placing the crystals on a watch glass, a clay plate or a piece
of paper and allowing it to dry in air. Acetanilide crystals were dried by
pressing-in of crystals with filter paper. During the process, some of the
residue was not weighed because the particles were attached to some part of
the filter paper. Rushing the drying process resulted to reduction of the
yielded pure acetanilide. The weight of the pure acetanilide was reduced to
1.8997g.
IV. References
Books:
Chang, R. (2008). General Chemistry: The Essential Concepts (5th Ed.). New
York: McGraw-Hill. Pg. 81-85
Pastro, D. J., John, C. R., & Miller, M. S. (1998). Experiment and Techniques
in Organic Chemistry. New Jersey: Prentice Hall. Pg. 43-46
Pavia, D. L., Lampman, G. M., Kriz, G. S., & Engel, R. G. (1999). Organic
Laboratory Techniques: A Microscale Approarch (3rd Ed.). Harcourt College
Publiser. Pg. 558-576
Web sites:
ACETANILIDE (N-PHENYLACETAMIDE). (n.d.). Retrieved August 16, 2009 ,
from http://chemicalland21.com/lifescience/phar/ACETANILIDE.htm