ORGANIC

CHEMISTRY
Laboratory Guide

This module provides guidelines for safety, Laboratory

Report and note book. It’s also providing students with
Laboratory Manual for subject of Organic Chemistry
(CLD 10302).

2nd EDITION
SEPT 2015
 Laboratory Information

Before each lab session, you should prepare by reading the lab manual, reference book and
summarized it in a jotter book. We expect you to have a good understanding of the purpose,
details of the procedure, the use of all chemicals and any significant hazards, and the underlying
science of the experiment when you come to lab.

2
 CONTENTS

Preface

Laboratory safety Guidelines

Safety Declaration Form

Chemistry Laboratory Report Guidelines

Laboratory Notes Books Guidelines

Experiment

1 Synthesis and Characterization of Alkane, Alkene, and Alkyne

(Saturated and Unsaturated Hydrocarbon)

2 Recrystallization of Benzoic Acid

3 Conversion of Ethyl Alcohol to Ethyl Acetate

4 Saponification of Fats: Soap Production

REFERENCES

APPENDICES

3
 PREFACE

This manual provides laboratory guidelines, safety declaration form, Chemistry Lab
Report guidelines and Laboratory Manual for subject of Organic Chemistry (CLD
10302).

The primary purpose of this manual is to compile all necessary information regarding
laboratory component in one manual.

The manual contains four parts. Part 1 provides a description of laboratory guidelines
and safety declaration form. It is compulsory for student to understand all those
guidelines and submit safety declaration for recording purposes. Part 2 is laboratory
report guidelines containing all requirements such as format and arrangement in order to
produce good quality of laboratory report. Part 3 is guidelines for preparation of
laboratory notes book. Part 4 is compilation of laboratory manual that will provide
student practical guidelines in Organic Chemistry.

There may be shortcomings which we had overlooked but hopefully these should not
hinder the process of enhancing laboratory skill.

DR MOHD ZULKHAIRI BIN ABDUL RAHIM

DR NORZAHIR BIN SAPAWE
Mdm NOR AINI BT BUROK
Ms NORHAYATI BT MOHD IDRUS

4
 PART 1

LABORATORY SAFETY GUIDELINES

General Guidelines

1. Conduct yourself in a responsible manner at all times in the laboratory.

2. Be familiar with your lab assignment before you come to the lab. Follow all
written and verbal instructions carefully. If you do not understand a direction or
part of a procedure, ask the instructor before proceeding.
3. No student may work in laboratory alone. The lab instructor or co-coordinator
grant exceptions on a case by case basis.
4. When first entering a laboratory, do not touch any equipment, chemicals or other
materials in the laboratory area until you are instructed to do so.
5. Do not eat, drink beverages or chew gum in the laboratory. Do not use laboratory
glassware as containers for food or beverages.
6. Smoking is not allowed in any indoor area.
7. No music allowed in the laboratory. Radio (including walkman) and other
entertainment devices are not permitted.
8. No cellular phone is allowed in this laboratory.
9. Perform only those experiments authorized by the instructor. Never do anything
in the laboratory that is not called for the laboratory procedures or by your
instructor. Carefully follow all instructions, both written and oral. Unauthorized
experiments are prohibited.
10. Observe good housekeeping practices. Work areas should be kept clean and tidy
at all times.
11. Horseplay, practical jokes, and pranks are dangerous and prohibited.
12. Always work in a well-ventilated area.
13. Bring only your laboratory instructions, worksheets and report to the work area.
Other materials (books, purses, backpacks, etc) should be stored in the cabinet.
14. Know the locations and operation procedures of all safety equipment including
the first aid kit, eyewash station, safety shower, spill kit and fire extinguisher.
15. Be alert and proceed with caution at all times in the laboratory. Notify the
instructor immediately of any unsafe condition you observe.
16. Label and equipment instructions must be read carefully before use. Set up and
use the prescribed apparatus as directed in the laboratory instructions provided by
your instructor.
17. Experiments must be personally monitored at all times. You will be assigned a
laboratory station at which to work. Do not wander around the room, distract
other students or interfere with laboratory experiments or others.
18. Write your name and equipment use every time you come in to the laboratory in
the log book.
19. Defeating safety devices or using equipment in a manner other than that which is
intended will be grounds for dismissal from the lab.

5
 Clothing
1. Safety goggles and safety jacket must be worn whenever you work in lab.
2. Gloves should be worn whenever you use chemicals that cause skin irritations or
need to handle hot equipment.
3. Mask should be worn every time you prepare the chemicals.
4. Safety shoes and hard hat should be worn at all times while in the laboratory.
5. Contact lenses should not be worn in the laboratory unless you have permission
from your instructor.
6. Dress properly during a laboratory activity.
7. Long hair, dangling jewelry and loose or baggy clothing are a hazard in the
laboratory. Long hair must be tied back and dangling jewelry and loose or baggy
clothing must be secured.
8. Sandal, open-toed shoes, high heels or shoes with holes in the sols will not be
worn in the lab.
9. Short and skirts are not permitted.
10. Instructor and laboratory assistant have a right dismiss to you from the laboratory
if they found that you are not wearing proper safety clothing.

Handling Chemicals
1. Treat chemicals with respect and understand the chemicals you are using with
Material Safety Data Sheet (MSDS). The MSDS are available in the analytical
room.
2. All chemicals in the laboratory are to be considered dangerous. Do not touch,
taste or smell any chemical unless specifically instructed to do so.
3. Check the label on chemical bottles before removing any of the contents. Take
only much chemical are you need. Smaller amounts often work better than larger
amounts.
4. Label all containers and massing papers holding dry chemicals.
5. Never return unused chemicals to their original containers.
6. Never use mouth suction to fill a pipette. Use pipette bulb or pipette filler.
7. Acids must be handled with extreme care. Always add acids slowly to water, with
slow stirring and swirling, being careful of the heat produced, particularly with
sulfuric acid.
8. Handle flammable hazardous liquid over a pan to contain spills. Never dispense
flammable liquids anywhere near a flame or source of heat.
9. Never take chemicals or other materials from the laboratory area.
10. Take good care when transferring acids and other chemicals from one part of the
laboratory to another. Hold them securely and in the method demonstrated by the
instructor as you walk.
11. All wastes generated during the course of an experiment must be disposed of
according to the lab instructor’s directions.
12. Never mix chemicals in sink drains.
13. Sinks are to be used only for water and those solutions designated by the
instructor.

6
14. Solid chemicals, metals, matches, filter paper, and all other insoluble materials are
to be disposed of in the proper waste containers, not in the sink.
15. Checks the label of all waste containers twice before adding your chemicals waste
to the container.
16. Cracked or broken glass should be placed in the special container for “broken
glass”.
17. Keep hands away from your face, eyes, mouth and body while using chemicals.
Wash your hands with soap and water after performing all experiments.

Personal Hygiene
1. Wash hands before leaving the lab and before eating.
2. Gloves should be removed before leaving the lab, using telephones, or entering
common areas

Accidents and Injuries

1. Report any accidents (spill, breakage, etc) or injury (cut, burn, etc) to the
instructor immediately, no matter how trivial it may appear.
2. If you or your lab partners are hurt, immediately tell to the instructor.
3. If a chemical should splash in your eye(s), immediately flush with running water
from the eyewash station for at least 20 minutes. Notify the instructor
immediately.
4. Spills should be cleaned up immediately.

Handling Glassware and Equipment

1. Inserting and removing glass tubing from rubber stopper can be dangerous.
Always lubricate glassware (tubing, thistle tubes, thermometer, etc) before
attempting to insert it in a stopper. Always protect your hands with tower or
cotton gloves when inserting glass tubing into, or removing it from a rubber
stopper.
2. When removing an electrical plug from its socket, grasp the plug, not the
electrical cord.
3. Hands must be completely dry before touching an electrical switch, plug or outlet.
4. Examine glassware before each use. Never use chipped or cracked glassware.
5. Never use dirty glassware.
6. Do not immerse hot glassware in cold water; it may shatter.
7. Report damaged electrical equipment immediately. Look for things such as frayed
cords, exposed wires and loose connections. Do not use damaged electrical
equipment.
8. If you do not understand how to use a piece of equipment, ask the instructor for
help.
9. Be careful when lifting heavy objects. Lift comfortably, avoid unnecessary
bending, twisting, reaching out, and excessive weights, lift gradually and keep in
good physical shape.

7
10. Do not transfer a glassware form one laboratory to another without permission
from instructor.

Heating Substances
1. Do not operate a hot plate by yourself. Take care that hair, clothing, and hands
are a safe distance from the hot plate at all times. Use of hot plate is only allowed
in the presence of the teacher.
2. Heated glassware remains very hot for a long time. They should be set aside in a
designated place to cool, and picked up with caution. Use tongs or heat protective
gloves if necessary.
3. Never look into a container that is being heated.
4. Do not place hot apparatus directly on the laboratory desk. Always use an
insulated pad. Allow plenty of time for hot apparatus to cool before touching it.
5. If leaving a lab unattended, turn off all ignition sources and lock the doors.

Ended the Experiments

1. At the end of the laboratory sessions, you should;
 Shut-off main gas outlet
 Turn-off the water inlet
 Desk top, floor area and sink are clean
 All equipment is cool, clean and arranged
2. All equipment use should be flushed using deionized water.

8
 SAFETY DECLARATION FORM

Dean / Head of Campus

Universiti Kuala Lumpur
Malaysian Institute of Chemical and Bioengineering Technology (UniKL-MICET)
Lot 1988 Vendor City, Taboh Naning, 78000 Alor Gajah,
Melaka, Malaysia.

Dear Sir,

SAFETY DECLARATION

I ………………………………..………………………………………………………….
ID No ………………………. declare that I have read and understood the safety rules and
regulations in UniKL-MICET. I hereby agree to abide by all the rules and regulations
stated in the safety guidelines.

 I hereby understood the contents and will disciplinary action will be taken
against me, if I do not abide by the stated rules.
 I am fully responsible for all my actions during laboratory sessions.

Thank you.

Yours faithfully,

……………………………….
Name:
Student ID No:
Group:
Subject:
Date:

9
 PART 2

CHEMISTRY LAB REPORT FORMAT

You should type your lab report. Make sure that you check your document for any spelling
errors. Each lab report is worth 100 points. You should also read the student handbook on the
subject of plagiarism. Your data and observations will be similar, but your interpretations
should not be written identically. You may not copy another student’s lab report in part or in its
entirety. If you are found guilty of this infraction, you and the person from whom you copied
will both lose points or shared total marks. In extreme cases or repeated offenses, both students
may receive a zero for the lab.

Result & Discussion

Analyze all data qualitative and quantitative. Then transfer finding into Table, Graph,
Histogram and Pie chart if necessary. This includes any observations. Make sure that your
graphs have titles, labeled axes with units, and legends. You should include the proper units
with any numbers, as well as use the proper number of significant figures based upon the lab
equipment used. DO NOT place any calculations or data analysis in this section. It may be a
good idea to reproduce here any data tables that you completed during the lab. Base on above
point, discuss on your findings and relate to your theory and objective of experiment.

Example:
Table 1: X versus Y

Samples X (unit) Y (unit)

A
B
C
D

10
 50
45 y = 4.4557x + 0.9714
40 R2 = 0.9893

parameter X (unit)
35
30
25
20
15
10
5
0
0 2 4 6 8 10 12
parameter Y (unit)

Figure 1: Relationship between X and Y

Conclusions

This is the most important section. Please include the summary of the results and relate in brief
the findings / results with the theory. Answer the questions, “What did you learn?”, “Did I
accomplish the purpose?”, “How would I improve the experiment next time?”.
Recommendation is optional. The conclusion should be one paragraph of 5 – 7 sentences.

References

Write down any sources such as your textbook, the Internet, electronic
encyclopedia, books, etc. that you used.

 A list of lab manuals, books, reports, journal, world wide web (www) etc.
 Arrangement (year, alphabetical order)
 Author, title, publisher, year, chapter or page number

Example:
Smith J.M and Van Hess H.C., Introduction to Chemical Engineering Thermodynamics,
McGraw-Hill, New York, 2001, p229.
Rahim M.Z.A., Sapawe N., Yusof N.N.M. and Idrus N.M., Introduction to Chemical
Engineering Thermodynamics, Journal of Chemical Sciences, 2001, 20-30.

Appendix

Here is where you attach any material that you think is pertinent to the lab report such as
summary of calculation involved. Also answer any questions here that are in the lab report.
You do not have to re-write the questions, but label and number them appropriately.

11
 PART 3

LABORATORY NOTEBOOKS

You are required to use a bound notebook in CLD 10004 Lab to record all primary data and
observations. You should prepare your notebook before coming to a lab by writing the
title of the experiment on a new numbered page, summarizing relevant information from
the lab manual, and starting calculations involving molar masses, etc. Take note of
theoretical ideas and special instructions given by your instructor at the start of each
experiment. Your notebook should be a complete record of your work in lab. Notes should be
able to understand in the future, not just during the current experiment. Good note taking in a
lab is a valuable skill that you can learn with a little effort and practice.

Guidelines to be followed:
1. Always bring your notebook with you to lab. You will be graded on the completeness of
your previous note taking and your preparation for the current experiment. You may use
your notebook during a lab quiz.
2. Number the pages sequentially and reserve space at the beginning for a table of contents.
3. Take your notebook during laboratory hours and record all values directly in it – not on
loose scraps of paper.
4. Specify each measured quantity by name and include the units.
5. If you make a mistake in your notebook, simply draw a solid line through the error and write
the correction nearby.
6. Tables greatly simplify data entry; they should be set up before coming to lab.
7. Write down all observations if necessary – don’t rely on your memory.
8. Save time by doing trial calculations in your notebook before filling out any report sheets.
9. Save time by making preliminary sketches of graphs (flow Chart) on the ruled lines in your
notebook.

12
 EXPERIMENT 1

SYNTHESIS AND CHARACTERIZATION OF ALKANE, ALKENE AND ALKYNE

(SATURATED AND UNSATURATED HYDROCARBON)

OBJECTIVE

1. To synthesize methane, ethane and ethyne

2. To characterize the prepared methane, ethane and ethyne

INTRODUCTION
Saturated Aliphatic Hydrocarbon

Alkane

Methane is first member of the family of hydrocarbons. It can be prepared in the laboratory by
the reduction of any halogenated derivatives of alkane. This type of reaction involves the
replacement of one or more atoms of halogen. The generalized scheme is:

RX HX
reduction

The chemical properties of methane are characteristic of the alkanes as groups. A convenient
test for alkanes which distinguishes them from unsaturated aliphatic hydrocarbons consist of
treatment with bromine in carbon tetrachloride. If it is an alkane; almost no reaction occurs in
the dark. In bright artificial light or in sunlight, the bromine colour is gradually discharged as
the substitution reaction proceeds and hydrogen bromide (HBr) is evolved. To test for HBr,
blow your breath gently across the mouth of the reaction tube. HBr, if present, will dissolve in
the moisture of your breath to form a cloud of droplets.

Unsaturated Aliphatic Hydrocarbons

Unsaturated aliphatic hydrocarbons have one or more multiple (double or triple) carbon-carbon
bonds per molecule.

13
 Alkenes

The distinguishing feature of the alkene hydrocarbons is the carbon-carbon double bond. The
synthesis of alkene can be accomplished by elimination of atoms or groups from two adjacent
carbon atoms. The production of 2- methyl -2- butane from t – amyl alcohol is an example of
the acid catalysed dehydration of alcohols.

Two tests can be carried for an alkene i.e:

a. Bromine, dissolved in carbon tetrachloride, adds rapidly to alkenes at room temperature

to form dibromides

H H

3RHC CHR + Br2 R C C R

Br Br

Evidence for the reaction is the disappearance of the bromine colour, even in the dark with no
evolution of hydrogen bromide

b. Baeyer Test. Alkenes react with neutral permanganate solution to form glycols.

OH OH

+ 2MnO4 + 2 KOH
3RHC CHR + 2 KMnO4 + 4H2O 3 R C C R
Dark Brown
Purple H H Precipitate

Alkynes

The distinguishing features of an alkynes is a carbon-carbon triple bond. Alkynes give positive
Baeyer Test for unsaturation with aqueous potassium permanganate. This experiment contains
two parts: Part A, you will synthesize methane, ethane and ethyne; and Part B, you will
characterize prepared methane, ethane and ethyne.

14
 MATERIALS AND METHODS

Chemicals:

10 g Zinc dust
60 ml Ethanol
5 ml Chloroform
1 ml 10% copper sulfate solution
1g Aluminium oxide
3 Small pieces of calcium dicarbide
6 ml Tetrachloride
12 ml 0.3% solution of potassium permanganate
1 ml Acidified potassium permanganate
6 ml Alkaline potassium permanganate
# Rocksil wool

Methods:
Part A

Preparation of Methane by reduction of chloroform

1. Add 10 g of zinc dust into a 50 ml round – bottomed flask mounted in a ring stand
2. Add 10 ml of ethanol and 10 ml of water
3. Fit the flask with a rubber stopper and a delivery tube for collection of the gas over water.
4. Add to the mixture 5 ml of chloroform and 1 ml of 10 % copper sulfate solution.
5. The reaction may require several minutes to start. If it becomes too rapid, cool the flask in a
pan of cold water.
6. After the air in the flask has been displaced, collect (over water) at least 6 test tubes of
methane by keeping the bottles (or test tubes) inverted over the water.

Figure 1: Apparatus for the synthesis of methane by the reduction of chloroform

15
Preparation of Ethene

1. Place Rocksil wool at the bottom of test tube. Drop 8 – 10 drop of ethanol until the rocksil
wool has been soaked up with ethanol.
2. Place about 1 g of aluminium oxide halfway along the tube (Fgure 2).
3. Fit a cork and delivery tube to the test tube and heat the aluminium oxide with a gentle
flame.
4. Collect at least 6 test tubes of ethene by displacement of water.

Figure 2: Apparatus for the synthesis of ethene

Preparation of Ethyne

1. Place 2 or 3 small pieces of calcium dicarbide in the a test tube (Figure 1.3) and arrange
the apparatus for collection of ethyne
2. Add 2 or 3 drops of water at a time.
3. Collect at least 6 test tubes of ethyne by displacement of water

Figure 3: Apparatus for the synthesis of ethyne

16
 Part B

Characterization Tests for Methane, Ethene and Ethyne

1. Prepare FIVE sets of tubes, each set consist of 3 test tubes containing methane, ethene, and
ethyne).
2. To set 1A and 1B, add 1 ml of a 4% solution of bromine in carbon tetrachloride. Stopper
all the test tube. Place one set of tubes (set 1A) containing methane, ethene and ethyne in
your drawer for 15 minutes. Leave the other the other set (set 1B) in bright light
(preferably sunlight).After 15 minutes, observe the results. Open the stopper and blow
your breath across the mouth of each tube. Note and record any difference.
3. To set 2A, swirl about 2 ml of a 0.3 % solution of potassium permanganate in test tubes
containing methane, ethene and ethyne. Record your observations.
4. Set 2B; shake the tubes containing methane, ethene and ethyne with alkaline potassium
permanganate solution (made by dissolving about 0.1 g of anhydrous sodium carbonate in
1 cm3 of 1 % potassium permanganate solution). Record your observations.
5. Set 2C; add about 1 cm3 of acidified potassium permanganate (by adding 1 cm3 of
sulphuric acid to 0.5 ml of 1% potassium permanganate solution). Record your
observations.

17
 FLOW CHART [10 Marks]

(Hints: Draw a flow chart of the experiment in this page, simplify the procedure & include the
calculation of dilution)

18
 RESULTS [20 Marks]

Observation

No Test
Methane Ethene Ethyne

SET 1A

1 Tubes left in darkness

SET 1B

2 Tubes left in a bright

light

SET 1A & 1B

3 Blowing across the

mouth of each of the test
tubes

SET 2A

4 2 ml of 0.3% potassium
permanganate solution

SET 2B

5 1 ml alkaline potassium
permanganate

SET 2C

6. 2 ml acidified potassium
permanganate solution

**NOTE: GIVE REASON FOR EACH OBSERVATION.

19
 DISCUSSION [30 Marks]

(Hints: Discuss your findings and relate to your theory and objective of experiment)

20
 CONCLUSION [10 Marks]

(Hints: Conclusion should contain summary of the results and relate in brief the findings /
results with the theory)

21
 RECOMMENDATION [10 Marks]

(Hints: Suggest improvements in apparatus or measurement procedure, or experimental

procedures for future)

22
 TUTORIALS [10 Marks]

1. What do 'saturated' and 'unsaturated' mean when applied to hydrocarbons? Give

examples of a saturated hydrocarbon and an unsaturated hydrocarbon.

2. Give five (5) sources of methane.

3. Describe reactions that are characteristics of alkanes, alkenes and alkynes.

4. Write a balanced equation for the reaction which methane was obtained by the
reduction of chloroform.

5. Provide two (2) other methods of collecting gas that can be used in this experiment.

23
 REFERENCES [5 Marks]

(Hints: Write down any sources such as your textbook, the Internet, electronic encyclopedia,
books, etc. that you used)

24
 APPENDICES [5 Marks]

(Hints: Attach all the printed data from this experiment and jotter notes at this page)

25
 EXPERIMENT 2

RECRYSTALLIZATION OF BENZOIC ACID

OBJECTIVE

(1) To purify benzoic acid by recrystallization

(2) To determine the melting point of pure benzoic acid

INTRODUCTION

The products of chemical reactions can be impure. Purification of your products must be
performed to remove by-products and impurities. Liquids are customarily purified by
distillation, while solids are purified by recrystallization; sometimes called simply
"crystallization”. Recrystallization is a method of purifying a solid. There are two types of
impurities: those more soluble in a given solvent than the main component and those less
soluble. If there are any impurities that have the same solubility as the main component, then a
different solvent needs to be chosen.

When organic substances are synthesized in the laboratory or isolated from plants, they will
obviously contain impurities. Several techniques for purifying these compounds have been
developed. The most basic of these techniques for the purification of organic solids is
recrystallization, which relies on the different solubilities of solutes in a solvent. Compounds,
which are less soluble, will crystallize first. The crystallization process itself helps in the
purification because as the crystals form, they select the correct molecules, which fit into the
crystal lattice and ignore the wrong molecules. This is of course not a perfect process, but it
does increase the purity of the final product.

Organic compounds that are solids at room temperature are usually purified by
recrystallization. The general technique involves dissolving the materials to be recrystallized in
hot solvent (or solvent mixture) and cooling the solution slowly. The solid that crystallized out

26
from the solution is very pure material. During the recrystallization process, solid impurities
(Such as dust, filter paper, etc.) that do not dissolve in hot solution are normally eliminated
through filtration. The dissolved impurities remain in cold solution while the pure compound
recystallize out of the solution. The general procedure for recrystallization is as shown in the
flow chart below:

27
 MATERIALS AND METHODS

Chemicals:
Benzoic acid
Distilled water

Apparatus:
Conical flasks
Hirsch / Buchner funnel
Watch glass
Filter funnel
Capillary tubes
Beaker

Methods:

PART A

1. Weight about 1.0 g benzoic acid into a 100 ml conical flask. Add 15 ml water and anti –
bumping granules (3-5 pieces).
2. Heat the mixture on a hot plate until the solvent boils. Add successive small volumes of
water (2-3 ml) [if required] and continue boiling until all benzoic acid has dissolved
(apart from insoluble impurities).
3. While waiting for the solution to boil, prepare the fluted filter paper and put it in the
funnel. Put the funnel fitted with fluted filter paper in the oven until it is ready to be used.
4. Heat 20ml water in a beaker. Filter the hot mixture of benzoic acid through a fluted filter
into conical flask. If the filtration is done in batches, keep the remaining solution hot
throughout the filtration process.
5. If crystallization occurs on the filter paper, add a minimum volume of boiling water to
redissolve the crystals, and allow the solution to pass through the funnel. Add hot solvent
in small volumes until all crystals are dissolved. After filtration, boil the filtrate to
produce a more concentrated solution.

28
6. Cover the conical flask with a watch glass and allow the solution to cool to room
temperature, then in an ice-bath after the crystallization has occurred. If no
recrystallisation occurs at this stage, it may be due to the fact that too much solvent was
used. Concentrate the solution by heating on the hot plate and cool.
7. When all the benzoic filter the crystals through a Hirsch/ buchner funnel by rinsing the
flask with some of the filtrate. Wash the crystal with a little cold water and dry. Place the
filter paper containing crystals in a watch glass and leave it for at least four (4) hours to
air dry.

NOTE: DO NOT FORGET TO TAKE THE WEIGHT OF FILTER PAPER WITH AND
WITHOUT BENZOIC ACID.

PART B

1. After the crystal dry completely, weigh the pure benzoic acid recovered, calculate the %
recovered

2. Break the crystal into powder, fill the powder in three (3) capillary tubes.
3. Read the melting point using BUCHI B540.
4. Compare the result with the actual melting point of benzoic acid.

29
 FLOW CHART [10 Marks]

(Hints: Draw a flow chart of the experiment in this page, simplify the procedure)

30
 RESULTS [20 Marks]

1. Data on the impure Benzoic Acid

a) Mass of benzoic acid + weighing paper :

b) Mass of weighing paper :

c) Mass of impure benzoic acid :

2. Data for recrystallized benzoic acid

Mass of recrystallized benzoic acid +

a) :
weighing paper
b) Mass of weighing paper :

c) Mass of recrystallized benzoic acid :

Calculation of percentage recovery

d) :
(show calculation )

e) Melting point of recrystallized benzoic acid

3. Melting point of recrystallized benzoic acid (Theory) :

31
 DISCUSSION [30 Marks]

(Hints: Discuss your findings and relate to your theory and objective of experiment)

32
 CONCLUSION [10 Marks]
(Hints: Conclusion should contain summary of the results and relate in brief the findings /
results with the theory)

33
 RECOMMENDATION [10 Marks]
(Hints: Suggest improvements in apparatus or measurement procedure, or experimental
procedures for future)

34
 TUTORIALS [10 Marks]

1. What is the purpose of the recrystallisation process?

2. Explain why anti – bumping are added before any solution is heated?

3. Why is suction filtration favoured over gravitational filtration when separating pure
crystals from its supernatant liquid after the recrystallisation?

4. In general, water is not a good solvent for the recrystallisation. Explain this statement.

5. Provide the probable reason(s) of low or high melting point of your experimental benzoic
acid when compared to theoretical result.

35
6. List the usages of benzoic acid in industry.

7. State the class/family of benzoic acid in organic chemistry.

8. Draw the structure of benzoic acid.

9. How is benzoic acid been synthesized?

a. Write the chemical equation of above process.

b. Name the starting material, process name, catalyst being used and side product.

36
 REFERENCES [5 Marks]

(Hints: Write down any sources such as your textbook, the Internet, electronic
encyclopedia, books, etc. that you used.)

3
 APPENDICES [5 Marks]

(Hints: Attach all the printed data from this experiment and jotter notes at this page)

4
 EXPERIMENT 3

CONVERSION OF ETHYL ALCOHOL TO ETHYL ACETATE

OBJECTIVE

 To convert ethanol to ethyl acetate (ethyl ethanoate)

INTRODUCTION

Chemist use organic synthesis both to make larger amounts of useful natural compounds
and to invent totally new compounds in search of improved properties and biological
effects. This experiment provides a synthesis step to convert raw material such ethanol to
ethyl acetate. Reaction involved is called esterification.

carboxylic acid alcohol ester water

The reaction of a carboxylic acid with an alcohol to produce an ester plus water is known
as the Fisher esterification reaction. A mineral acid, usually sulfuric acid is used as a
catalyst.

5
 MATERIAL AND METHODS

Chemicals
Ethanol
Glacial acetic acid
Conc. Sulfuric acid
30% sodium carbonate solution
Calcium chloride
Granular anhydrous calcium chloride
Anti-bumping granules

Apparatus:
Round bottom flask
Water / Liebig condenser
Retort stand
Separating funnel

Method

1. Mix 50 ml of 95% ethanol and 50 ml of glacial acetic acid thoroughly in a 250 ml

round – bottomed flask.
2. Add slowly with cooling and shaking of 10 ml of concentrated H2SO4.
3. Ensure that the mixture is homogenous, then fit the flask with a reflux water –
condenser (Figure 1) and boil the mixture gently for 10 minutes. Cool the flask and
its content. If the flask and its content are not cooled sufficiently, there will be some
loss of material by evaporation.

Figure 1: Reflux set-up

6
4. Ensure that the mixture is homogenous, then fit the flask with a reflux water –
condenser (Figure 2) and boil the mixture gently for 10 minutes. Cool the flask and
its content. If the flask and its content are not cooled sufficiently, there will be some
loss of material by evaporation.

Figure 2: Reflux set-up

5. Rearrange the position of the condenser for distillation (Figure 3) and put a few
boiling chips in the flask. A filter flask, whose side arm is joined to a rubber tube
leading over the edge of laboratory bench, is used as a receiver. Ethyl acetate is
highly flammable. Therefore any vapors should be conducted off the table towards
the floor. Distilled off about 2/3 of the mixture.

Figure 3a: Distillation set-up

7
 Figure 3b: Distillation set-up

6. Transfer the distillate to a separating funnel (Figure 4) and add about 25 ml of 30 %

Na2CO3 solution. Stopper the funnel, invert it and shake it, opening the stopcock
from time to time.

Figure 4a: Separating funnel set-up

8
 Figure 4b: Method to invert and shake the separating funnel

7. Allow the two layers to separate. Carefully run off and reject the lower layer,
ensuring that the sodium carbonate is removed as completely as possible.
8. Prepare a solution of 25 g of calcium chloride in 25 ml of water. Add if to crude
ethyl acetate in the funnel. Shake vigorously. Allow the mixture to separate. Run
off the lower aqueous as completely as possible.
9. Run the ethyl acetate into a small conical flask. Add a few lumps of granular
anhydrous calcium chloride. Shake occasionally until the liquid is clear.
10. Decant the liquid some anti-bumping granules. Arrange for distillation (with a 0 –
100 oC thermometer in the apparatus). Pre – weight the receiving flask. The
distilling flask should be placed in cold water bath, which is gradually heated.
11. The ether that is always formed in this reaction will distill off at 35 – 45 oC and
may be discarded. Continue to heat and collect the fraction that boils between 74 oC
and 79 oC.
12. Weight your product and calculate the percentage yield.

9
 FLOW CHART [10 Marks]

(Hints: Draw a flow chart of the experiment in this page, simplify the procedure &
include the calculation of dilution)

10
 RESULTS [20 Marks]

Volume of ethanol :
ml
Weight of ethanol :
g
Volume of acetic acid :
ml
Weight of acetic acid :
g
Theoretical yield :
g

Weight of receiving flask :

g
Weight of Product
+ receiving flask :
g
Weight of ethyl ethanoate :
(Actual yield)
g
Percentage yield :
%

**Show all calculations, otherwise will be NO MARKS.

11
 DISCUSSION [30 Marks]

(Hints: Discuss your findings and relate to your theory and objective of experiment)

12
 CONCLUSION [10 Marks]

(Hints: Conclusion should contain summary of the results and relate in brief the findings
/ results with the theory)

13
 RECOMMENDATION [10 Marks]
(Hints: Suggest improvements in apparatus or measurement procedure, or experimental
procedures for future)

14
 TUTORIALS [10 Marks]

1. (a) Write and balance the equation for the reaction of acetic acid with ethanol to
produce ethyl ethanoate and water.

(b) In the reaction of above example, how many grams of ethyl ethanoate would be
produced if 50 ml of ethanol were react with 50 ml acetic acid? Which is the
limiting reagent? (Given  ethanol : 0.8 g/ml and  acetic acid : 1.06 g/ml and  ethyl acetate :
0.9g/ml).

(c) Calculate the percentage yield if 50.0 g of ethyl ethanoate was obtained from the
experiment.

2. What is the function of reflux water condenser?

15
3. Why must the concentrated sulphuric acid be added slowly and with cooling?

4. What is the function of sodium carbonate solution and anhydrous calcium chloride?

5. Explain the phenomena of 2 layers formed in the separating funnel.

16
 REFERENCES [5 Marks]

(Hints: Write down any sources such as your textbook, the Internet, electronic
encyclopedia, books, etc. that you used)

17
 APPENDICES [5 Marks]

(Hints: Attach all the printed data from this experiment and jotter notes at this page)

18
 EXPERIMENT 4

SAPONIFICATION REACTION OF FAT: SOAP PRODUCTION

OBJECTIVE

(1) To synthesize a sample of hard soap

(2) To test the soap produced

INTRODUCTION

The procedure of making soap involves the basic hydrolysis (saponification) of a fat.
Chemically, fats are referred to as triglycerides. They contain ester functional groups.
Saponification involves heating fat with an alkaline solution. The alkaline solution
hydrolyzes the fat to alcohol and the salt of a long chain carboxylic acid (soap).When
common salt is added, the soap precipitates. The soap is washed free of unreacted
alkaline solution and molded into bars. This experiment contains two parts: In Part A,
you will synthesize Soap, while in Part B, you will test prepared soap.

O HO CH2

R C O CH2

O
O HO CH
R C O CH + 3 NaOH
3R C O Na +
O
HO CH2
R C O CH2
sodium salt of an acid (soap) glycerol
fat

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 MATERIALS AND METHODS

Chemicals
NaOH
95% ethanol
Fat
50% water/ethanol mixture NaCl solution
4% calcium chloride solution
Trisodium phosphate

Apparatus:
Conical flasks
Beaker
Filter funnel
Hirsh / Buchner funnel
Watch glass
Measuring cylinder

Methods:

Part A

Preparation of Soap

1. Prepare a NaOH solution (about 0.25 g sodium hydroxide dissolved in a mixture of

1.0 ml of distilled water and 1.0 ml of 95% ethanol).
2. Place about 0.25 g of fat in a 50 ml conical flask and add the prepared sodium
hydroxide solution to the flask.
3. Heat the mixture in a in a bath of 100 oC.
4. Cover the flask with some aluminium foil to help reduce evaporation. Swirl the
Erlenmeyer flask every few minutes. Use tong to do this.
5. The soap will precipitate from the boiling mixture within 20 minutes.
6. If you observe that some alcohol and water is evaporating from the flask, you may
add up to 0.4 ml of a 50 % water/alcohol mixture to replace the solvent.
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7. Heat the mixture for a maximum time of 25 minutes.
8. Place 4 ml of NaCI solution in a 15 ml beaker and transfer the saponified mixture
from flask to beaker.
9. Stir the mixture while cooling the beaker in an ice-water bath.
10. Collect the prepared soap on a Hirsch funnel of ice cold distilled water to remove
excess NaOH.
11. Continue to draw air through the filter for a few minutes to partially dry the
product. Test your soap with the procedure below.

Part B

Testing on prepared Soap

1. Remove about 0.01 g of soap from the filter paper and placed it in a clean 10 ml
graduated cylinder
2. Add 3 ml of distilled water, close the cylinder with your thumb and shake the
mixture vigorously for about 15 sec.
3. After about 30 sec standing, note down the level of the foam.
4. Check the pH of the aqueous solution.
5. Add 5 – 10 drops of 4% calcium chloride solution to the soap mixture from a
Pasteur pipette .Shake the mixture for 15 sec and allow it to stand for 30 seconds.
Observe the effect of addition the calcium chloride.
6. Then add 0.5 g of trisodium phosphate and shake the mixture again for 15 seconds.
After 30 sec. again observe the result.

21
 FLOW CHART [10 Marks]

(Hints: Draw a flow chart of the experiment in this page, simplify the procedure &
include the calculation of dilution)

22
 RESULTS [20 Marks]

Conditions Observation

1. Soap + 3 ml distilled water :

2. Test with litmus paper :

Mixture from No. 1 + 5-10

3. :
drops of 4% calcium chloride

Mixture from No. 2 + 0.5 g

4. :
trisodium phosphate

23
 DISCUSSION [30 Marks]

(Hints: Discuss your findings and relate to your theory and objective of experiment)

24
 CONCLUSION [10 Marks]

(Hints: Conclusion should contain summary of the results and relate in brief the findings
/ results with the theory)

25
 RECOMMENDATION [10 Marks]

(Hints: Suggest improvements in apparatus or measurement procedure, or experimental

procedures for future)

26
 TUTORIALS [10 Marks]

1. Give a definition of saponification.

2. Explain how soap can function as “dirt remover”.

3. Synthetic detergent functions in the same way as soaps. Give the advantages of
synthetic detergent over soaps.

4. Reaction of fat with NaOH will produced long chain carboxylic acid (soap) in form
of Bar. What would be happen if sodium Hydroxide (NaOH) is replaced by
potassium hydroxide (KOH).

5. Name the all types of chemical reaction in this experiment.

27
6. Explain the reason of your findings for the followings:

a. Soap + 3 ml distilled wáter

b. Soap mixture + 5-10 drops of 4% calcium chloride

c. Soap mixture + 0.5 g trisodium phosphate

28
 REFERENCES [5 Marks]

(Hints: Write down any sources such as your textbook, the Internet, electronic
encyclopedia, books, etc. that you used)

29
 APPENDICES [5 Marks]

(Hints: Attach all the printed data from this experiment and jotter notes at this page)

30
 APPENDICES

Mass Force
1 lbm = 0.453592 kg 1 lbf = 4.448222 N
1 ton = 2000 lbm 1N = 0.224809 lbf = 1 kg.m/s2
1 kg = 2.20462 lbm

Volume Density
1 ft3 = 0.028317 m3 1kg /m3 = 0.062428 lbm/ ft3
1 L = 0.001 m3
1 m3 = 35.32 ft3
1 cm3 = 0.06102 in3
1 gal =0.0037854 m3
1 gal/min = 6.31 x 10‾5 m3/s

Pressure

1 pascal (Pa) = 1 N/m2

1 atm = 760 mmHg = 760 torr
1 atm = 101.325 KPa

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 Table 1: Characteristic Infrared Absorption frequencies

Bond Compound Type Frequency range, cm-1

2960-2850(s) stretch
Alkanes
1470-1350(v) scissoring and bending
C-H
1380(m-w) - Doublet - isopropyl, t-
CH3 Umbrella Deformation
butyl
3080-3020(m) stretch
C-H Alkenes
1000-675(s) bend
Aromatic Rings 3100-3000(m) stretch
C-H Phenyl Ring Substitution Bands 870-675(s) bend
Phenyl Ring Substitution Overtones 2000-1600(w) - fingerprint region
3333-3267(s) stretch
C-H Alkynes
700-610(b) bend
C=C Alkenes 1680-1640(m,w)) stretch
C C Alkynes 2260-2100(w,sh) stretch
C=C Aromatic Rings 1600, 1500(w) stretch
C-O Alcohols, Ethers, Carboxylic acids, Esters 1260-1000(s) stretch
Aldehydes, Ketones, Carboxylic acids,
C=O 1760-1670(s) stretch
Esters
Monomeric -- Alcohols, Phenols 3640-3160(s,br) stretch
O-H Hydrogen-bonded -- Alcohols, Phenols 3600-3200(b) stretch
Carboxylic acids 3000-2500(b) stretch
3500-3300(m) stretch
N-H Amines
1650-1580 (m) bend
C-N Amines 1340-1020(m) stretch
Nitriles 2260-2220(v) stretch
1660-1500(s) asymmetrical stretch
NO2 Nitro Compounds
1390-1260(s) symmetrical stretch

v - variable, m - medium, s - strong, br - broad, w - weak

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 THIS IS THE END OF THE LABORATORY MANUAL ~

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