MANUAL AMALI SKO3013 SEM 1 20222023 (4)

LABORATORY MANUAL

SKO 3013
BASIC ORGANIC CHEMISTRY

Department of Chemistry
Faculty of Science and Mathematics
UNIVERSITI PENDIDIKAN SULTAN IDRIS

NO EXPERIMENT PAGES

0 SAFETY RULES AND REGULATIONS IN CHEMISTRY LABORATORY

0 GUIDELINE TO WRITE LAB REPORT

1 CONFORMATION AND OPTICAL ISOMERISM

2 PREPARATION OF CIS AND TRANS ISOMER

3 SOLUBILITY TESTS

4 SAPONIFICATION OF AN ESTER

5 THIN LAYER CHROMATOGRAPHY

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.
Spreadsheets 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, students should 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.

Apparatus
Molecular model set

1.3 PROCEDURE

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

Part 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 and draw chair and boat conformations for cyclohexane. Label the axial
hydrogen and equatorial hydrogen. Which conformation is more stable and 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)

Part B. Optical isomerism
1. Determine the absolute configuration (R or S) for each of the following molecules using

the molecular models.

2. 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)?

1.4 QUESTION
1. When the compound does not has a plane of symmetry, is it optically active? Explain.
1.5 REFERENCE
1. Bruice, P. Y. (2016). Organic Chemistry. 8th Ed., USA: Pearson Education.

1.6 WORKSHEET Explain
A. Conformation Explain
1) Staggered Potential energy diag

Eclipsed

2) Ethane (C1-C2 bond)

gram

Propane (C1-C2 bond) Potential energy diag

Butane (C2-C3 bond) Potential energy diag

3)

gram
gram

4) 1-methylcyclohexane (through C5-C4)
(through C1-C2)

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

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

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

Explain
Explain
Explain
Explain

B. Optical Isomerism b)
1) a)

Absolute configuration : Absolute configuratio
2) a) Mirror

b) Mirror

________________
DATE

on :
r image

r image

_____________________________
LECTURER’S SIGNATURE/STAMP

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 maleic acid.
2. differentiate chemical and physical properties of each isomers.

2.2 INTRODUCTION

Maleic acid and fumaric acid have the same molecular formula: C4H4O4. 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.

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

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

2.3 PROCEDURE

Part A. Conversion of maleic acid to fumaric acid
1. Weigh 2 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 and 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
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.

Maleic acid can also lose a molecule of water and form maleic anhydride. Fumaric acid
cannot do this. Explain.
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.

2.6 WORKSHEET Fumaric acid

Part A. Conversion of Maleic Acid to Fumaric Acid
1) Mass of Fumaric acid

Percentage yield
Melting point of Fumaric acid
Melting point of Maleic acid
Part B. Comparison of The Two Isomers
Solubility observations

Maleic acid

Observations

Chemical properties Maleic acid Fumaric acid
pH using pH paper

magnesium ribbon
sodium carbonate

________________ _____________________________
DATE LECTURER’S SIGNATURE/STAMP

EXPERIMENT 3
SOLUBILITY TESTS

3.1 OBJECTIVES

Upon completion of this experiment, students should be able to:
1. classify the unknown compound as acid, base and 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 an acid, base and
neutral.

Chemicals
Distilled water
5% Sodium hydroxide (NaOH)
5% Sodium hydrogen carbonate (NaHCO3)
5% Hydrochloric acid (HCl)
Concentrated sulphuric acid 3M
Amine, phenol, carboxylic acid, alkane, alkene, aldehyde
Sample X

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 tube which contain 1 mL water.
2. Add 2 drops or approximately 10 mg of solid of unknown sample into the test tube.
3. Shake the test tube slowly and observe the changes.
4. Repeat Step 1 by replacing water with 5% NaOH, 5% H2SO4, and 5% HCl, as shown in

Table below.
5. Repeat Step 1 with sample X and determine it functional groups.

CAUTION: Sodium hydroxide (NaOH) and hydrochloric acid (HCl) are toxic and corrosive.

CAUTION: Concentrated sulfuric acid (H2SO4) is toxic and oxidizing. Use fume hood when
working with H2SO4.
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.
6. Record observation.

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.

3.6 WORKSHEET

Solubility (Soluble or Insoluble)

Alkane Alkene Phenol Carboxylic Aldehyde Amine
acid

Water
NaOH
H2SO4
HCl

________________ _____________________________
DATE LECTURER’S SIGNATURE/STAMP

EXPERIMENT 4
SAPONIFICATION OF AN ESTER

4.1 OBJECTIVE

Upon completion of this experiment, students should be able to:
1. explain saponification process

4.2 INTRODUCTION

An ester can be separated into its components of carboxylic acid and alcohol using hydrolysis
reaction in the presence of strong base. This reaction, called saponification, results in the
formation of an alcohol and a carboxylate salt.

Chemicals
Ethyl benzoate
Hydrochloric acid
NaOH
Boiling chips
Litmus paper

Apparatus
Droppers
Hot plate
Reflux condenser
Round bottomed flask
Beaker
Buchner funnel
Filter paper

4.3 PROCEDURE

1. In a round bottom flask, mix 5 mL of ethyl benzoate with a solution of 3 g of NaOH in 15
mL of water.
CAUTION: Sodium hydroxide is a caustic substance. Do not touch this substance. Rinse
your skin with water immediately if it has a soapy feeling. Sodium hydroxide will cause
irreversible eye damage and blindness. Clean up any spilled material at once.

2. Fit the flask with a reflux condenser.
3. Add few boiling chips in the flask to prevent bumping.
4. Boil the mixture gently for at least 15 min or until ester layer has disappear.

5. Cool the flask at room temperature.
6. Dilute the product with 50 mL of water.
7. Separate the aqueous layer from the oily layer using a separating funnel.
8. While stirring, add dilute hydrochloride acid to the aqueous layer until the solution is acidic

to litmus paper.
9. Filter the precipitate using Buchner funnel.
10. Record your observation
11. Write chemical equation for the saponification of ethyl benzoate.

4.4 QUESTION

1. State two uses of saponification and explain.

4.5 REFERENCE

1. Plummer, D. T., (1987). An Introduction to Practical Biochemistry, 3rd edition, McGraw-Hill
Book Company (U.K.) Ltd., London.

4.6 WORKSHEET

Observations

Equations

________________ _____________________________
DATE LECTURER’S SIGNATURE/STAMP

EXPERIMENT 5
THIN LAYER CHROMATOGRAPHY

5.1 OBJECTIVES

Upon completion of this experiment, students should be able to:
1. distinguish polar and non-polar solvents.
2. perform analysis technique using thin layer chromatography.
3. differentiate the retention factor, Rf for different compounds.

5.2 INTRODUCTION

Thin layer chromatography (TLC) is a chromatographic technique that is useful for separating
organic compounds. TLC consists of a stationary phase immobilized on a glass or plastic plate,
and an organic solvent as mobile phase. The sample dissolved in a volatile solvent is deposited
as a spot on the stationary phase. Different component in the mixture moves with the different
rates by capillary action, due to the differences of behaviour between the mobile phase and the
stationary phase.

The retention factor, Rf is define as the distance travelled by the compound divided by the distance
travelled by the solvent.

Distance travelled by the compound a

Rf = =

Distance travelled by the solvent b

Figure 5.1: Thin layer chromatogram

Chemicals
Acetone
Chloroform

o-Nitroaniline
p-Nitroaniline
Unknown sample
TLC Silica gel F254 Aluminium sheets 20×20cm

Apparatus
Forcep
UV Lamp
TLC Spotter
TLC Glass Container
TLC Plate Cutter

5.3 PROCEDURE

1. Draw the origin (0.5 cm from the bottom) and solvent front line (0.5 cm from the top) of the
TLC plate (3x5 cm) using pencil.
Note: Use only pencil with blunt end (2B/HB). Do not use mechanical pencil.

2. Place all three samples using TLC spotter on the TLC plate on the origin line with correct
labelling.

3. Allow the sample to dry and place the TLC plate into the TLC container containing
chloroform (5 mL).
Note: Samples spotted have to be above the solvent level.

4. When the solvent reach the solvent front, remove the plate from the container with forceps.
5. Leave it to dry in room temperature.
6. Place the chromatogram under UV lamp and mark the spots using pencil.
6. Calculate the Rf value for each sample.
7. Record and discuss the result.

5.4 QUESTION

1. Discuss the identification of unknown compound from their distinguished Rf values.

5.5 REFERENCE

1. Skoog, D.A., Holler, F.J., Nieman, T.A. (2005). Principles of Instrumental Analysis. 5th
Edition, Thomson Asia Pte Ltd., Singapore.

5.6 WORKSHEET o-nitroaniline p-nitroaniline Unknown sample

Samples
Distance travelled
by the compound (a)
Distance travelled
by the solvent (b)

Retention factor, Rf

Thin Layer Chromatogram

________________ _____________________________
DATE LECTURER’S SIGNATURE/STAMP