LABORATORY MANUAL

SKO 3023
ORGANIC CHEMISTRY I

Department of Chemistry
Faculty of Science and Mathematics
UNIVERSITI PENDIDIKAN SULTAN IDRIS
No Experiment Pages

0 Safety Rules and Regulations In Chemistry Laboratory 3

0 Guideline To Write Lab Report 5

1 Conformation and Optical Isomerism 7

2 Preparation of cis and trans Isomer 10

3 Solubility Tests 15

4 Synthesis of tert-butyl chloride 19

5 Selecting an Appropriate Solvent 21

6 Recrystallization 23

SAFETY RULES AND REGULATIONS IN CHEMISTRY LABORATORY

1. DO NOT ENTER the laboratory without the permission of the laboratory instructor.
2. All bags should be placed on the rack provided. All gadgets (handphone, tablet, etc) are
NOT ALLOWED during experiments.
3. Please wear a proper attire to work in the lab (Short pants, short skirt, “purdah”,
sleeveless shirt are not permitted).
4. Wearing jewellery is not permitted in the laboratory.
5. Long hair and scarf must be properly manageable.
6. DO NOT wear contact lenses.
7. Wearing personal protection equipment (PPE) is compulsory in laboratory such as lab
coat, cover shoes and safety glasses, gloves and etc.
8. Student are NOT ALLOWED to smoke, drink, eat, play around and run in laboratory
9. Know the location of all safety equipment.
10. No experiment can be performed without the permission of the laboratory instructor.
11. Read the label on the container of a chemical twice to make sure you are using the right
chemicals. Follow the instructions properly. DO NOT waste chemicals. Use required
amount only.
12. DO NOT contaminate chemicals. Once chemical has been removed from their containers,
DO NOT put it back into the stock container.
13. DO NOT use cracked or chipped glassware.
14. NEVER use mouth suction when using a pipette. Use a pipette filler/bulb.
15. DO NOT leave any heating, vigorous or rapid reaction unattended.
16. Always use fume hood when working with flammable organic compounds, strong acid and
base, volatile solvent, corrosive and toxic materials.
17. DO NOT heat flammable materials directly.
18. Make sure your surrounding is safe before using Bunsen burner.
19. While heating chemicals in test tubes, NEVER point the tubes to yourself or others.
20. Waste chemicals must be disposed properly by placing them in waste container provided.
Ask your instructor how to discard used reagents.
21. Broken apparatus, water and gas leakage must be reported to laboratory assistant on
duty immediately.
22. In case on fire or hearing emergency siren, evacuate the laboratory quickly in orderly
manner. In case of small accident or small fire occurs, try to overcome them wisely.
23. Report any accidents (minor or major) to your laboratory instructor. This accident must be
recorded in log book “CATATAN KEMALANGAN”.
24. Clean all glassware and place them appropriately before leaving laboratory. Make sure to
switch off instruments, water and gas supplies.
25. Final year project students should require permission from supervisor and head of
department if they want to work after normal working hours.
AN EXPERIMENT DONE WELL IS......
AN EXPERIMENT DONE SAFELY
 GUIDELINE TO WRITE LAB REPORT

OBJECTIVE
State the objective clearly in a complete sentence. A few explanatory sentences may be
included, if needed.
The objective should answer the question: What is the lab objective designed to determine?

EXPERIMENTAL PROCEDURE
The experimental methods should give a detailed description in your own words of how YOU
accomplished the experimentation (Passive voice sentences).
*Tips: This should include equipment used in the experiment as well as how it was used. The
description should have sufficient detail so that another experimenter could duplicate your
efforts.
Use sketches and diagrams to describe the experimental set-up. Label the main components.
Tips: Any information copied directly from Lab manuals or other references should be stated
within quotes and referred, otherwise, it is considered plagiarism.

RESULTS AND DISCUSSION

This is the most important part of the report. Summarize your results in the introductory
sentence. Relate your results to your objective. Present the results in the easiest way for your
reader to understand: graphs, tables, figures, etc.
Spread sheets are often an ideal tool for organizing the data, analyzing the data, and generating
graphs and tables. All tables and figures should be accompanied by comments or discussions
in the text of report; use a numbering system for identification of each one.
All figures and tables must have numbers and captions. While the table captions should be
placed over the table, figure captions should be placed below the figure.
Explain the results of the experiment, comment on the results you obtained, compare obtained
results with expected results, give probable reasons for discrepancies from the correct results,
answer any questions outlined in the instructions and solve any problems that may have been
presented. Tell why things happened, not only that they did happen. Implementation errors
should be discussed here.

CONCLUSIONS
State your discoveries, judgments and opinions from the results of this experiment and relate it
with your experiment objectives. Suggest ways to improve the results of this experiment.
REFERENCES
List the book, publication or website that you referenced in writing your report. Provide authors,
publisher, date of publication, page number, etc.
*Tips: Follow the standard format for typing a reference:
[1] Little, P., and Cardenas, M., “Use of Studio Methods in the Introductory Engineering
Design Curriculum,” Journal of Engineering Education, Vol. 90, No. 3, 2001, pp. 309-318.
[2] Nunally, J., Psychometric Theory, 2nd ed., New York, N.Y.: McGraw-Hill, 1978.
[3] Lister, B., “Next Generation Studio: A New Model for Interactive Learning,”
www.ciue.rpi.edu/pdfs/nextGenStudio.pdf
EXPERIMENT 1
CONFORMATION AND OPTICAL ISOMERISM

1.1 OBJECTIVE
Upon completion of this experiment, student will be able to:
1. explain the concept of conformation and optical isomerism.

1.2 INTRODUCTION
Stereochemistry is the study of molecules in space and how the atoms in a molecule are
arranged in space relative to one another. In this experiment, we focus in two aspect of
stereochemistry; conformation and optical isomerism.
Conformation: Group bonded by only a sigma (δ) bond can undergo rotation. The temporary
molecular shapes that result from rotation of the groups about single bond are called
conformations of a molecule. Each possible structure is called a conformer. An analysis of the
energy changes associated with a molecule undergoing rotation about single bonds is called
conformational analysis.
Optical isomerism occurs when the molecule doesn’t have a plane of symmetry in the molecule.
All the optical isomers have the same physical properties such as melting points, boiling points,
solubility except the rotation of the plane polarized light.

Figure 1.1: Molecular model set

Apparatus
Molecular model set

1.3 PROCEDURE
By using the molecular model, draw all the structures of the molecule and answer all the
questions.

A. Conformation
1. Draw a perspective view and Newman projection of ethane for the following
conformation. Which conformation is more stable? Explain.
a) Staggered
b) Eclipsed
2. Construct the models of following molecules and draw the potential energy diagram
versus the degrees of rotation (0° – 360°).
a) Ethane (C1-C2 bond)
b) Propane (C1-C2 bond)
c) Butane (C2-C3 bond)
3. Construct the model of cyclohexane. Draw chair and boat conformations for cyclohexane
and label the hydrogen axial and hydrogen equatorial. Which conformation is more
stable, why?
4. Construct the model of chair conformation and draw the Newman projection for the
following molecules. Which conformation is the most stable? Explain.
a) 1-methylcyclohexane (through C1-C2 and C5-C4)
b) 1,2-dimethylcyclohexane (through C1-C2 and C5-C4)
c) 1,3-dimethylcyclohexane (through C1-C6 and C3-C4)
d) 1,4-dimethylcyclohexane (through C1-C2 and C5-C4)

B. Optical isomerism
By using the molecular model, draw all the structures of the molecule and answer all the
questions.
1. Compound does not has a plane of symmetry is it optically active or not optically
active. Explain why or why not.
2. Compound with stereogenic carbon (chiral carbon) does not possess a plane of
symmetry, true or false. If false, construct and draw an example of the symmetrical
compound with stereogenic carbon.
3. By using the molecular models, determine the absolute configuration (R or S) for each of
the following molecules.
F COOH

a) Cl H b) H NH2

Br CH3

OH CH3

c) Br CH3 d) HOH2C CH(CH2)3

CH2CH3 CHO
4. Construct the molecular models for the following molecules and draw their mirror image.
Determine whether the object and its mirror image were identical or a pair of enantiomer.
Which compound is unsymmetrical (optically active)?
H OCH3

a) Br H b) H OH

CH3 Cl

c) COOH d) CHO

OH H
H3C H3C
H OH

1.4 QUESTION

1. Compound does not has a plane of symmetry is it optically active or not optically active.
Explain why or why not.

1.5 REFERENCE

1. Bruice, P. Y. (2016). Organic Chemistry. 8th Ed., USA: Pearson Education.

1.6 WORKSHEET

A. Conformation
1) Staggered Explain

Eclipsed Explain

2) Ethane (C1-C2 bond) Potential energy diagram

Propane (C1-C2 bond) Potential energy diagram

 Butane (C2-C3 bond) Potential energy diagram

3) Model of cyclohexane

4) 1-methylcyclohexane
(through C1-C2 and C5-C4)
1,2-dimethylcyclohexane
(through C1-C2 and C5-C4)

1,3-dimethylcyclohexane
(through C1-C6 and C3-C4)

1,4-dimethylcyclohexane
(through C1-C2 and C5-C4)

Most Stable
B. Optical Isomerism
1) a) c)

Absolute configuration : Absolute configuration :

d)

b)

Absolute configuration : Absolute configuration :

4) a) Mirror image
 b) Mirror image

c) Mirror image

d) Mirror image

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SKO3023: Organic Chemistry I

EXPERIMENT 2
PREPARATION OF CIS AND TRANS ISOMER

2.1 OBJECTIVES

Upon completion of this experiment, students should be able to:

1. synthesize fumaric acid from malic acid.
2. compare chemical and physical properties of each isomers.

2.2 INTRODUCTION

Malic acid and fumaric acid have the same molecular formula: C 4H4O4. Each compound
contains two carboxyl groups, -COOH, and a double bond. The compounds are isomers
because their structures differ in the geometry, or arrangement in space of the atoms in the
molecule. Examine the structural formulas of the two acids shown below and note that in the
trans form the carboxyl groups are on the opposite sides of the molecule and in the cis form
they are on the same side. The fact that two isomers can be isolated indicates that rotation of
the molecule at the double bond is restricted.

Figure 2.1: cis (a) and trans (b) isomer

As a result of this geometrical difference, the cis isomer and the trans isomer have different
physical properties. In addition, some of their chemical properties differ because of the locations
of the two carboxyl groups.

In this experiment you will convert malic acid to fumaric acid by heating it in concentrated
hydrochloric acid (HCl). You also will compare some of the properties of each acid and attempt
to explain any differences in terms of structures. This should enable you to draw some
conclusions about which acid, malic or fumaric, is the trans form and which is the cis form.

Chemicals
Malic acid
Concentrated hydrochloric acid 12M
Magnesium ribbon (3 cm strips)
Sodium carbonate
pH paper

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Apparatus
Erlenmeyer flask 125 mL
Watch glass
Beaker 100 mL
Test tubes
Filter paper
Melting point apparatus

2.3 PROCEDURE

Part A. Conversion of Maleic acid to Fumaric acid

1. Weigh 2.0 g of maleic acid in Erlenmeyer flask.
2. Add 4 mL distilled water and if necessary, warm the solution slightly to
dissolve the acid.
3. Add 5 mL of concentrated hydrochloric acid (HCl) in the solution.
CAUTION: Concentrated hydrochloric acid (HCl) causes severe skin burns. Immediately
wash the affected areas with cold running water and promptly report the accident to your
instructor.
4. Place the flask in hot water bath assembly as shown in the following
figure.
5. Heat until solid fumaric acid forms in the flask (approximately 5 min).
6. Cool the solution to room temperature by slowly placing the Erlenmeyer
flask into a cold water bath.
7. Pour the contents into a 100 mL beaker.
8. Allow the crystals to settle; then carefully decant and discard the
supernatant liquid from the beaker.
9. Rinse any remaining crystals in the Erlenmeyer flask with approximately
10 mL of cold distilled water and pour them into the beaker.
10. Again, decant and discard the supernatant liquid.
11. Using two additional 5 mL portions of cold distilled water, repeat the
washing procedure.
12. Dry the crystals of fumaric acid in oven until a consistent mass is
obtained.
13. Record the mass of the fumaric acid.
14. Calculate the percentage yield.
15. Determine the melting point of fumaric acid.
16. Determine also the melting point of maleic acid.

Part B. Comparison of the Two Isomers

Solubility
1. Place 0.1 g of fumaric acid and maleic acid into separate test tubes.
2. Add 2 mL of distilled water to each test tube

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3. Observe the solubility for both test tubes.

Chemical Properties
1. Prepare solution of 0.1 g of maleic acid into a beaker containing 20 mL distilled water.
2. Place 5 mL of each into three different test tubes.
3. Label the test tube as A, B and C.
4. Perform each of the following tests:
a) determine the pH using pH paper
b) add 3 cm strip of magnesium ribbon.
c) add a small amount of sodium carbonate.
5. After each test, record the observation.
6. Repeat step 1 to 5 with fumaric acid.
7. Compare results between maleic and fumaric acid.

2.4 QUESTIONS

1. Assume that equilibrium concentrations were achieved in Part A. Which acid is the most
stable?
2. Some diacids can lose a molecule of water when the two carboxyl groups react to form a
cyclic anhydride. Phthalic acid is a diacid that reacts as follows.

COOH
C
heat
O

COOH C

Maleic acid also can lose a molecule of water of water and form malic anhydride. Which
structural isomer, cis or trans, do you predict it is? Fumaric acid cannot do this. Explain.
3. What does each of the following experiments contribute to your knowledge of the
structure of each isomer?
a) The melting point determination.
b) The reactions of each with magnesium.
c) The reaction of each with sodium carbonate.

2.5 REFERENCES

1. McMurry, J. (2015). Organic Chemistry. 9th Ed., USA: Cengage Learning, Inc.
2. Zubrick, J. W., (2014). The Organic Chem Lab Survival Manual: A Student’s Guide to
Techniques. 9th Ed., USA: John Wiley & Sons, Inc.

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2.6 WORKSHEET

Part A. Conversion of Maleic Acid to Fumaric Acid

1) Mass of Fumaric acid 0.1581 g
2) Percentage yield
3) Melting point of Fumaric acid 303.7 ℃
4) Melting point of Maleic acid 152.9 ℃
Part B. Comparison of The Two Isomers
Solubility Observations

Chemical properties Observations

Test tube A

Test tube B

Test tube C

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EXPERIMENT 3
SOLUBILITY TESTS

3.1 OBJECTIVES

Upon completion of this experiment, students should be able to:

1. determine the unknown compound as acid, base and neutral.

2. classify the compound into strong acid and base, weak acid and base and also neutral.

3.2 INTRODUCTION

Solubility tests are extremely useful in determining the nature of the major functional groups
present in the unknown compound. The tests are very simple and require only a small amount
of sample. In addition, the solubility tests will determine whether the compound is a strong base
(amine), a weak acid (phenol), a strong acid (carboxylic acid) or a neutral compound (alkene,
aldehyde, ketone, alcohol, ester).

Chemicals
Distilled water
5% Sodium hydroxide (NaOH)
5% Sodium hydrogen carbonate (NaHCO3)
5% Hydrochloric acid (HCl)
Concentrated sulphuric acid 3M
Unknown sample
Litmus paper

Apparatus
Test tubes

3.3 PROCEDURE

The amounts of material to use for a solubility test are somewhat flexible. Use 2-3 drops of a
liquid or approximately 10 mg of a solid. Unless the solid is already a fine powder, crush a small
amount of the solid on a watch glass with the back of a spatula. Do not weigh the solid; simply
use enough to cover the tip of a small spatula. Your instructor will demonstrate how to estimate
the correct amount. Place the appropriate amount of either your solid or liquid unknown in a
small test tube and proceed with the following solubility tests.
1. Prepare 7 test tubes which contain 1 mL water.
2. Add 2 drops or approximately 10 mg of solid of unknown sample into the test tube.
3. The following flow chart simplified the procedure of this experiment.

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4. Record the observation.

CAUTION: Sodium hydroxide (NaOH) and hydrochloric acid (HCl) are toxic and
corrosive. Concentrated sulfuric acid (H2SO4) is toxic and oxidizing. Use fume hood
when working with H2SO4.

3.4 QUESTIONS

1. Why is it unnecessary to determine the pH of the remaining acid-base solubility tests?

2. Write a general chemical reaction(s) for any positive solubility test result(s) that you
obtain for your unknown compound. Your reaction should demonstrate how any organic
compound with a specific functional group can dissolve/react in an aqueous solution.

3.5 REFERENCE

1. Clayden, J., Greeves, N. & Warren, S. (2012). Organic Chemistry. 2nd Ed., USA: Oxford
University Press, Inc.

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3.6 WORKSHEET

UNKNOWN

water

Soluble Insoluble

NaOH

Litmus paper Litmus paper Soluble Insoluble

(red - blue) (blue - red)

NaHCO3 HCl
Neutral

AMINE

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CARBOXYLIC ACID

Soluble Insoluble Soluble Insoluble

CARBOXYLIC ACID WEAK ACID (Phenol) WEAK ACID (Phenol) H2SO4

Soluble Insoluble

NEUTRAL
(Alkene, Alcohol, Ketone, Aldehyde)

INERT (Alkane, Alkyl halide)

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EXPERIMENT 4

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SYNTHESIS OF TERT-BUTYL CHLORIDE

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

1. synthesize tert-butyl chloride.

4.2 INTRODUCTION
Alkyl halide is also known as haloalkane or halogen alkane. Alkyl halide is a hydrocarbon group
which attached with at least one halide atom in the molecule. Alkyl halides always resemble the
parent alkanes in being colourless, relatively odourless and hydrophopic. Their boiling point is
always increasing as the parent chain increase, the longer the parent chain, the higher the
melting point. This is due to the increased strength of the intermolecular forces from London
dispersion to dipole-dipole interaction because of the increased polarity.
Alkyl halide can be prepared from alcohol by reacting them with a hydrogen halide, HX (X = Cl,
Br, or I). The mechanism of acid catalysed substitution of alcohols are S N1 and SN2, where “S”
stands for substitution while sub-“N” stands for nucleophilic, and the number “1” and “2” are
described as first order and second order respectively. The “1” or “2” is also represent the
reaction is unimolecular or bimolecular reaction. The secondary alcohols are more favor to react
with hydrogen halides by both SN1 and SN2 mechanisms. For primary or methyl alcohol, both
molecules undergo SN2 mechanism while tertiary alcohol undergoes SN1 mechanism.
R3COH > R2CHOH > RCH2OH > CH3OH
The order of reactivity increasing
Tertiary alcohols react readily with HX alone to form alkyl halide, while secondary and primary
require catalyzation in the halohydrogenation reaction. Zinc chloride acts as catalyst in the
reaction. In some condition, heat supply is needed in the reaction.

Chemicals
Boiling chip
tert-butyl alcohol
CaCl2 anhydrous
Concentrated HCl

Apparatus
Distillation apparatus
Erlenmeyer flask 50 mL
Separating funnel 100 mL

4.3 PROCEDURE
1. Measure 10 mL of tert-butyl alcohol and pour into the separating funnel. Add 60 mL
concentrated HCl. Make sure the stopcock of the separating funnel is closed. The total

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volume should not be greater than three-quarters of the funnel volume. Insert the
stopper in the neck of the separating funnel.
2. Shake the funnel vigorously for a few seconds. Release the pressure; then again shake
vigorously for 15 min until the solution reaches to equilibrium. If the acids layer is not
clear, continue shaking for another 5 min.
3. Leave the funnel until the layers are clearly separated. While waiting, remove the
stopper and place a beaker or flask under the separating funnel.
4. Carefully open the stopcock and allow the acid layer to drain into the flask. Drain just to
the point that upper liquid barely reach the stopcock.
5. Pour the raw tert-butyl chloride from the funnel into 50 mL dry and clean Erlenmeyer
flask. Add CaCl2 anhydrous and leave it for 10 min.
6. Prepare the distillation apparatus. Weight 50 mL Erlenmeyer flask for the distillation
product and record the value.
7. Pour the tert-butyl chloride in the distillation flask and add 2-3 boiling chips and start the
distillation process.
8. tert-butyl chloride yielded when the temperature is 48 - 52°C. Weight and record your
data.

4.4 QUESTION

1. Write the complete mechanism of reaction.

2. Primary and secondary alkyl halides are not synthesized using this method. Explain.

3. What is the purpose of distillation in this reaction?

4. What is the function of dehydrate CaCl2?

4.5 REFERENCES

Cranwell, P. B., Harwood, L. M. & Moody, C. J. (2017). Experimental Organic Chemistry.

3rd Ed. John Wiley & Sons Ltd.

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4.6 WORKSHEET

RESULTS

(A) Mass of empty Erlenmeyer flask

(B) Mass of Erlenmeyer flask and product

(C) Mass of product (B) – (A)

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DATE LECTURER’S SIGNATURE/STAMP

EXPERIMENT 5

SELECTING AN APPROPRIATE SOLVENT

5.1 OBJECTIVE

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

1. find a good solvent for recrystallization process.

5.2 INTRODUCTION

The essence of a recrystallization is purification. Messy, dirty compounds are cleaned up,
purified and can then hold their heads up in public again. The sequence of events you use will
depend a lot on how messy your crude product is and on just how soluble it is in various
solvents. You’ll have to remember a few things;

1. Find a solvent that will dissolve the solid while hot.

2. The same solvent should not dissolve it while cold.

3. The cold solvent must keep impurities dissolved in it forever or longer.

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Check on the color or crystalline form. This is important since;

1. A color in a supposedly white product is an impurity.

2. A color in a colored product is not an impurity.

3. The wrong color in a product is an impurity.

You can usually assume impurities are present in small amount. Then you don’t have to guess
what possible impurities might be present or what they might be soluble or insoluble in. if your
sample is really dirty, the assumption can be fatal. This doesn’t usually happen in an
undergraduate lab, but you should be aware of it.

Chemicals

Benzoic acid

Naphthalene

Acetanilide

Cinnamic acid

Ethanol

Acetone

Distilled water

Apparatus

Test tubes

Test tube rack

Glass rode

5.3 PROCEDURE

1. Weighed 0.01 g sample and place it in a test tube.

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2. Add 3 mL of a solvent into the tube and shake it. If the entire solid dissolves at room
temperature, then your solid is soluble. Do not use this solvent as a recrystallization
solvent.

3. If none (or very little) of the solid dissolved at room temperature and heat it. Shake it and
heat it carefully. You may have to heat the solvent to a gentle boil. Careful, solvents with
low boiling points often boil away and used water bath. If it does not dissolve at all, the
do not use this as a recrystallization solvent.

4. If the sample dissolved during heating, while undissolve at room temperature, you are on
the trail of a good recrystallization solvent.

5. Place the test tube (no longer hot) in an ice-water bath, and cool it to about 5°C or so. If
lots of crystals come out, this is good, and this is your recrystallization solvent.

6. Suppose your crystals don’t come back when you cool the solution. Get a glass rode into
the test tube, stir the solution, rub the inside of the tube with the glass rode, and agitate
that solution. If the crystals still don’t come back, perhaps you’d better find another
solvent.
7. Suppose, after all this, you still haven’t found a solvent, you will have to perform a mixed-
solvent recrystallization.

8. Repeat all the above procedure for each of the samples by using the different solvent.

5.4 QUESTIONS

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

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

5.5 REFERENCES

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.

5.6 WORKSHEET

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RESULTS

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

Solvent
Ethanol Acetone Distilled Water
Sample

Benzoic acid

Naphthalene

Acetanilide

Cinnamic acid

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EXPERIMENT 6
RECRYSTALLIZATION

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

Solid organic compounds are often contaminated with undesirable impurities. If the compound
has solubility considerably different from that impurity, crystallization from a suitable solvent (or
solvent mixture) provides a useful and simple method of purification. The terms crystallization
and recrystallization are often used interchangeably by practicing chemists.
Crystallization is a technique which chemists use to purify solid compounds. It is one of the
fundamental procedures each chemist must master to become proficient in the laboratory.
Crystallization is based on the principles of solubility: compounds (solutes) tend to be more
soluble in hot liquids (solvents) than they are in cold liquids. If a saturated hot solution is allowed
to cool, the solute is no longer soluble in the solvent and forms crystals of pure compound.
Impurities are excluded from the growing crystals and the pure solid crystals can be separated
from the dissolved impurities by filtration.
This simplified scientific description of crystallization does not give a realistic picture of how the
process is accomplished in the laboratory. Rather, successful crystallization relies on a blend of
science and art; its success depends more on experimentation, observation, imagination, and
skill than on mathematical and physical predictions. Understanding the process of crystallization
in itself will not make a student a master crystallizer; rather, this understanding must be
combined with laboratory practice to gain proficiency in this technique.

Chemicals
Benzoic acid
Activated charcoal
Distilled water

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Ice

Apparatus
Erlenmeyer flask
Heater
Cotton
Buchner funnel
Filter funnel
Filter paper
6.3 PROCEDURE

1. Weight approximately 1.0 g benzoic acid in an Erlenmeyer flask.

2. Add 20 mL distilled water.
3. Heat slowly and shake until the entire solid was dissolved.
4. Add slight excess of water to keep the solid dissolved.
5. If the solution is only slightly colored, the impurities will stay in solution. Put a small
amount (about the size of a pea) of activated charcoal, heat and swirl the flask.
6. Stir the flask and the solution should turn black. Try not to use too much of activated
charcoal. Why?
7. Set up the gravity filtration and filter of the carbon by using filter funnel into a clean
Erlenmeyer flask. The filter funnel must be warmed before you can filter your solution.
Why? This can be done by putting 10mL distilled water in a Erlenmeyer flask and heat it
to produce steam to warm the filter funnel.
8. Wash the crystals deposited on the filter paper with hot distilled water.
9. The filtered solution should be much cleaner than the original solution. If not, you’ll have
to add charcoal and filter again.
10. Cool the filtrate at room temperature and then place the flask to an ice bath for further
cooling.
11. Filter your product using Buchner funnel and wash it with cool distilled water.
12. Air dried your product before putting it in the oven.
13. Get the weight, calculate the percentage of the yield
14. Determine the melting point of your product.

4.5 REFERENCE

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

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4.6 WORKSHEET

RESULTS

(A) Mass of benzoic acid used before recrystallization

(B) Mass of filter paper

(C) Mass of filter paper and benzoic acid

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

Percentage yield (D/A x 100)

Melting point (oC)

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SKO3023: Organic Chemistry I

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DATE LECTURER’S SIGNATURE/STAMP

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