DEPARTMENT OF CHEMISTRY

FACULTY OF SCIENCE AND MATHEMATICS

UNIVERSITI PENDIDIKAN SULTAN IDRIS

LABORATORY REPORT

SKO 3023
ORGANIC CHEMISTRY I

EXPERIMENT TITLE

5
SELECTING AN APPROPRIATE SOLVENT

NAME MATRIC NO.

WATI BINTI ZAFRI D20182085046

NELVIANA NAH ANAK TIMBANG D20182085048

LECTURER DR. YUHANIS BINTI MHD BAKRI

GROUP F
NO. ITEMS MARKS
DATE 25/05/2021
1. Objectives 1
LABORATORY − 2. Introduction 2
3. Procedure / Methods 3
4. Results / Worksheets 4
5. Discussion 4
6. Conclusion 2
………………………………. 7. References 1
8. Question / Answer (if any) 2
9. Formate 1
TOTAL 20
EXPERIMENT 5: SELECTING AN APPROPRIATE SOLVENT

5.1 OBJECTIVES

Upon completion of this experiment, student will be able to:

1. Find a good solvent for recrystallization process.

5.2 INTRODUCTION

Recrystallization is the primary method for purifying solid organic compounds.

Compounds obtained from natural sources or from reaction mixtures almost always contain
impurities. The impurities may include some combination of insoluble, soluble, and coloured
impurities. Each is removed in a separate step in the recrystallization procedure. In order for
recrystallization to be effective, the solid and the impurities should have different solubilities
in the recrystallization solvent. The purpose of this experiment is to identify the
appropriate solvent for the recrystallization technique. In this experiment, we dissolve
some organic compounds in the cold (room temperature) and hot (boiling) solvents and
determined the solubility.

5.3 PROCEDURE / METHODS

Refer to the jotter note attached.

5.4 RESULTS / WORKSHEETS

Tick (√) for the suitable solvent for the recrystallization process

Solvent
Ethanol Acetone Distilled Water
Sample

Benzoic acid √ √

Naphthalene √

Acetanilide √ √ √

Cinnamic acid √ √
5.5 DISCUSSION

Recrystallization is the most important method of purifying nonvolatile organic

solids. Recrystallization involves dissolving the material to be purified (the solute) in an
appropriate hot solvent. As the solvent cools, the solution becomes saturated with the solute
and the solute crystallizes out (reforms a solid). As the crystal develops, impurities are
excluded from the crystal lattice, thereby completing the purification process. The crystals
can then be collected, washed, and dried.

In recrystallization process we need to choose suitable solvent for the sample. In this
experiment, ethanol is suitable for recrystallization of naphthalene, acetanilide and cinnamic
acid. Acetone is suitable for recrystallization of benzoic acid and acetanilide. Distilled water
is suitable for recrystallization of benzoic acid, acetanilide and cinnamic acid. There are few
criteria in choosing the solvent. First, find the solvent with high temperature coeffiecient. The
solvent must not dissolve the compound at low temperature such as room temperature. Then
use a solvent that dissolve impurities readily or not at all. If the solvent dissolves the
impurities readily (even at room temperature) then the impurities will not become trapped in
the developing crystal lattice, but will remain dissolved in the solvent. If the impurities do
not dissolve (even at elevated temperatures) then they can be easily removed by gravity
filtration. Next, insuring the solvent will not react with solute. No chemical bonds must be
broken in the solute molecule. The crystal lattice is dissolved at elevated temperatures, but
this only involves overcoming the intermolecular attractive forces. Lastly use a solvent that is
non-flammable and volatile.
5.6 CONCLUSION

In recrystallization process we need to choose suitable solvent for the sample. In this
experiment, ethanol is suitable for recrystallization of naphthalene, acetanilide and cinnamic
acid. Acetone is suitable for recrystallization of benzoic acid and acetanilide. Distilled water
is suitable for recrystallization of benzoic acid, acetanilide and cinnamic acid. The ideal
solvent also should be able to dissolve very little or none of the compound at low temperature
(room temperature) and need to have different solubilities for the compound and the
impurities. To make sure that there is no chemical reaction between the compound and the
solvent, the ideal solvent should be inert with respect to the compound. No chemical bonds
must be broken in the solute molecule. A good solvent also should have a boiling point below
the melting point of the compound. A good solvent needs to be non-flammable, inexpensive
and volatile so that it can be easily removed from the resultant crystals by simply
allowing the solvent to evaporate.

5.7 REFERENCES

Atkins, P. W. (2010). Shriver & Atkins' Organic chemistry. Oxford: Oxford University Press

Afonso, C. A. M., Candeias, N. R., Simao, D. P., Trindade, A. F., Coelho, J. A. S., Tan, B.
&Franzen, R. (2017). Comprehensive Organic Chemistry Experiments for the
Laboratory Classroom. UK: The Royal Society of Chemistry.

Clayden J., Greeves N., Warren S. and Wothers P. (2001). Organic Chemistry, Oxford
University Press, United States

Sillberberg, M. S. (2013). Chemistry : The Molecular Nature of Matter and Change (Global
Edition). New York: McGraw-Hill.
5.8 QUESTIONS

1. What is the suitable solvent for recrystallization for each of the samples given?

Ethanol is suitable for recrystallization of naphthalene, acetanilide and cinnamic acid.

Acetone is suitable for recrystallization of benzoic acid and acetanilide. Distilled
water is suitable for recrystallization of benzoic acid, acetanilide and cinnamic acid.

2. How you test the suitability of a solvent for recrystallization?

First, find the solvent with high temperature coeffiecient. The solvent must not
dissolve the compound at low temperature such as room temperature. Then use a
solvent that dissolve impurities readily or not at all. If the solvent dissolves the
impurities readily (even at room temperature) then the impurities will not become
trapped in the developing crystal lattice, but will remain dissolved in the solvent.   If
the impurities do not dissolve (even at elevated temperatures) then they can be easily
removed by gravity filtration.  Next, insuring the solvent will not react with solute. No
chemical bonds must be broken in the solute molecule.   The crystal lattice is dissolved
at elevated temperatures, but this only involves overcoming the  intermolecular
attractive forces. Lastly use a solvent that is non-flammable and volatile.