DEPARTMENT OF CHEMISTRY

FACULTY OF SCIENCE AND MATHEMATICS

UNIVERSITI PENDIDIKAN SULTAN IDRIS

LABORATORY REPORT

SKO 3023
ORGANIC CHEMISTRY I

EXPERIMENT TITLE

6
RECRYSTALLIZATION

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 6: RECRYSTALLIZATIONS

6.1 OBJECTIVES

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

1. Crystallize an impure benzoic acids.

2. Test the purity of the product after recrystallization process and calculate the
percentage of the yield.

6.2 INTRODUCTION

Recrystallisation is a very important purification technique, purifying substances by

removing unwanted by-products. It is also used to manufacture the correct crystal size and
shape of a material. These factors can have a very significant impact on how a medicine acts
when taken by a patient. The same principles and techniques of recrystallisation can be
applied both on a laboratory and industry scale.

The process depends on two principles; the fact that substances tend to be more
soluble in a hot solvent than in cold solvent, and that each solute tends to behave as though it
were alone in the solvent.

Using the correct solvent is a very important part of the process. The solute must be
insoluble in the solvent at room temperature, and as the temperature of the solvent increases,
the solubility of the solute also increases. It is also important that the impurities present are
soluble in the solvent at room temperature and insoluble at higher temperatures.

An excellent substance for showing this process is benzoic acid (C 6H5COOH). A

molecular crystal rather than an ionic crystal, shown by its low melting point of 122 °C,
benzoic acid is used as an anti-microbial agent and is found in toothpastes, mouthwashes,
cosmetics and deodorants.

Impure benzoic acid contains the impurities phthalic acid and benzylbenzoate. If the
impure sample is dissolved in a minimal volume of hot solvent – in this case boiling water –
and filtered to remove insoluble impurities, the resulting solution will contain dissolved
benzoic acid as well as dissolved impurities
6.3 PROCEDURE / METHODS

Refer to the jotter note attached.

6.4 RESULTS / WORKSHEETS

(A) Mass of benzoic acid used before recrystallization 1.82 g

(B) Mass of filter paper 0.18 g

(C) Mass of filter paper and benzoic acid 1.88 g

(D) Mass of benzoic acid (C-B) 1.70 g

(1.70 g / 1.82 g x 100)

Percentage yield (D/A x 100)
= 93.4%

Melting point (oC) 122 ℃

6.5 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 this experiment the yield of the experiment slightly over 90% which is 93.4%. This
yield can be cause by few reasons. The first reason is the impurities still remaining in the
product. This can be cause by the crystal no rinse thoroughly during filtration process. That is
why a suitable solvent is very important in recrystallization process to minimize loss of
product and reduce the impurities. A minimum of ice-cold solvent should be used for the
rinse and a minimum near boiling solvent should be used for recrystallization. The mass of
pure benzoic acid is 1.7g. This is because the hot solution is allowed to cool down at room
temperature for long period before place it at the ice bath. In this method, we get large size of
crystal.

Occasionally crystals will not form, even though the saturation point has been
reached. If a recrystallization solution has been allowed to cool and crystals have not formed,
it may be due to a condition known as supersaturation. If this happens, the crystallization may
induced by scratching the inside of the glass tube just below the surface of liquid using a
glass stirring rod. The tiny scratch provides a rough surface on which the crystallization may
begin.

The filter paper need to fold to increase the surface area to speed up the filtration
process. There might have some error of the mass of benzoic acid because of there are some
pure benzoic acid left on filter paper. So the mass of impurities that we get is less than the
actual mass that we should get. Moreover, some filtrate might be still left in the flask and not
being transferred to the filter also effect the result.
6.6 CONCLUSION

In this experiment the yield of the experiment slightly over 90% which is 93.4%. This
yield can be cause by few reasons. The first reason is the impurities still remaining in the
product. The mass of pure benzoic acid is 1.7g. This is because the hot solution is allowed to
cool down at room temperature for long period before place it at the ice bath. In this method,
we get large size of crystal. The filter paper need to fold to increase the surface area to speed
up the filtration process. There might have some error of the mass of benzoic acid because of
there are some pure benzoic acid left on filter paper. So the mass of impurities that we get is
less than the actual mass that we should get. Moreover, some filtrate might be still left in the
flask and not being transferred to the filter also effect the result.

6.7 REFERENCES

Armarego, W. L. F.; Chai, C. L. L (2003). Purification of laboratory chemicals. 5th ed.;

Butterworth-Heinemann: Amsterdam ; Boston; p xv, 609 p

Mayo, D. W.; Pike, R. M.; Forbes, D. C. (2011). Microscale organic laboratory : with
multistep and multiscale syntheses. 5th ed.; J. Wiley & Sons: Hoboken, NJ, p xxi, 681 p

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

Zubrick, J. W. (2014). The Organic Chem Lab Survival Manual: A Student’s Guide to
Techniques. 9th Ed. Hoboken: Wiley.