ORGANIC

CHEMISTRY LABORATORY I
BSK1402

EXPERIMENT:

_________________________________________

STUDENT
MATRIX NO.
COURSE
SECTION
DATE

1
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

FACULTY OF INDUSTRIAL SCIENCES AND TECHNOLOGY

UNIVERSITI MALAYSIA PAHANG
FORMAT OF REPORT
The following check list is intended as a guide to the presentation and content investigation
report.

1. FORMAT
(5%)

2. ABSTRACT
One page is for abstract. In this page, you must summarize your report including
scope of the report, description of the precise problem, method used, results and
conclusion. Abstract must be short and clear. Abstract writing is the last session after
all the contents are completed.
(15%)

3. INTRODUCTION
Description of the motive of your report (why and how). Including theory and
objectives of the experiment
(15%)

4. METHODOLOGY
A brief flow diagram on the process of the experiment.
(5%)

*(Note: 1-4 can be done by Group)

5. RESULTS AND DISCUSSION

This part is very important. You must include your observation of the experiment and
also the result obtained during your experiment, in form of:
a. Results
i. Tables
ii. Graphs
iii. Diagrams (bar charts, pie charts, etc.)
iv. Written statements
v. Calculation

b. Discussion
i. Comparison of results with values obtained from other sources (if any)
ii. Comparison of results with your observation.

2
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

iii. Degree of accuracy achieved, having regard to random and systematic

errors.
(40 %)
6. CONCLUSIONS
Brief statement of achievement in relation to the objective of investigation and
summarize your result and discussion.
(10%)

7. REFERENCES

References to sources of information are usually given in the following form:

a. From books
Example:
Atkins, P & Julio, D. P. (2005). Elements of Physical Chemistry (4th ed.).
Freeman, Oxford.

b) From periodicals (ojurnal, papers…)

Example:
Warren S. W., 2000. Essential Physical Concepts for Chemistry. The Physical
Basis of Chemistry (2nd Edition), p 32-59

(5%)

8. APPENDIX
Attachment of your data that has been approved by instructors.
(5%)

*(Note: 5-8 must be done individually and hand writing)

3
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

TABLE OF CONTENT:

EXPERIMENT 1: Melting Point Determination of Mixed Chemical

EXPERIMENT 2: Extraction Technique: Liquid-Liquid Extraction

EXPERIMENT 3: Distillation Technique: Separation and identification of liquid organic

mixture.

EXPERIMENT 4: Isolation of caffeine from tea.

EXPERIMENT 5: Esterification of butanol with acetic acid

EXPERIMENT 6: Cross-Aldol condensation reaction between benzaldehyde and ketone

EXPERIMENT 7: Technique of Crystallization

EXPERIMENT 8: Organic functional group test (aldehydes and ketones)

4
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

ASSESMENT

● Laboratory Safety.
● Marks Scheme
 Report (individual) : 60%
 Observation : 10 %
 Test : 30%
 Total : 100%

● Report
 All reports must be submitted to the lecturer at any time (during office hours)
within 1 week after lab session or before starting the next experiment.
 All data collection must be endorsed by the lecturer before the laboratory
time is ended (before the students leaving the laboratory).
 There might be an interview for all groups during every report submission. All
group members are compulsory to attend to the interview.

● Soft Skill Evaluation

 Soft skill evaluation will be conducted at all times during the laboratory
activities as well as in report preparation.

● All areas in soft skill that will be evaluated are based on the UMP's standard soft skill
evaluation.

● Attendance
 Attendance is compulsory.
 Student who cannot attend to the laboratory as schedules, please submit a
letter with strong justification.
 Failing to do so, he/she will be not given a chance to re-do and re-evaluate for
that particular experiment.

5
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

SAFETY
Remember: "SAFETY IS ALWAYS THE NUMBER ONE PRIORITY"

√ Should any problem arise inform the instructor/lecturer immediately.

√ Do not put yourself in danger.
√ If you think something is unsafe STOP and consult the instructor/lecturer before
continuing.

IMPORTANT RULES
1. Please remember that may be we share the lab with other classes or other person
who are working in same lab, therefore do not leave anything out after the lab
session is finished. Place your unknowns and standard solutions vials in beakers and
lock them in your drawers or arranged places. Any unattended or unlabeled container
will be properly disposed without asking.
2. Always return all chemicals to the cabinet immediately after use.
3. Keep your work area always clean, in particular when working with instruments or
in the balance room. Your lab-book will not be validated until your work area is
clean. Point deductions will be taken off your experiment marks if this conduct is
persistent.
4. Do not leave standard solutions in volumetric flasks. Once you are done with the
preparation, transfer the solution to a labeled vial for storage. Include the Group
number and other important information in the labels; a lot of people may be doing the
same experimen t at the same time. Rinse the volumetric flasks thoroughly before
returning them to the cabinet.
5. Yes, you must have a lab notebook and you must write everything in black or blue ink (no
pencils). When correcting something do not white-out, scratch the error with a single line
and write the correction above or below.
6. Remember to record the unknown sample number for each experiment.
7. Always wear a lab coat and safety glasses and please, no sandals!
8. Read the operating instructions for every instrument before you use it. If you have
any questions about anything stop and ask!
9. Be aware of the due dates for each experiment (you will be penalized for late
submissions), If you can’t make it for any reason notify the instructor/lecturer in advance,
not after the fact.
10. Working in groups requires an even share of the responsibilities so do not drag your feet,
talk to your partner. If problems arise don't wait until it's too late, talk to the
instructor/lecturer about it.
11. PLAGIARIZE is to take and use another person’s ideas, writings or inventions as one’s
own. Note that plagiarism is illegal and unethical. Plagiarizing old laboratory reports
will not be tolerated! Any evidence of such activities will result in no points for
that exercise. Further disciplinary actions will be taken at the discretion of the
instructor/lecturer.

6
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 1

Title

Melting Point Determination of Mixed Chemical

Introduction

Melting point can be defined as the temperature at which a solid changes to a liquid.
For pure substances, the melting or fusion process occurs at a single temperature, the
temperature rise with addition of heat being arrested until melting is complete.

Melting points reported in the literature, unless specifically stated otherwise, have
been measured under an applied pressure of 1 atm (105 pascals), usually 1 atm of air. Upon
melting, all substances absorb heat, and most substances expand; consequently an increase in
pressure normally raises the melting point. A few substances, of which water is the most
notable example, contract upon melting; thus, the application of pressure to ice at 32°F (0°C)
causes it to melt. Large changes in pressure are required to produce significant shifts in the
melting point.

For solutions of two or more components, the melting process normally occurs over a
range of temperatures, and a distinction is made between the melting point, the temperature at
which the first trace of liquid appears, and the freezing point, the higher temperature at which
the last trace of solid disappears, or equivalently, if one is cooling rather than heating, the
temperature at which the first trace of solid appears.

Objectives

1. To determine the melting point of the mixture of EDTA and Gallic acid.
2. To observe the physical and chemical changes during the heating.

Chemicals

Ethylenediaminetetraacetic acid (EDTA) and Gallic Acid.

Apparatus

Melting point apparatus, electronic weighing machine, and capillary tubes.

7
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Experimental Procedures

1. Make 5 different chemical compositions with each component weigh 100 milligram
as follows:

100% EDTA
75% EDTA-25% Gallic Acid,
50% EDTA-50% Gallic Acid,
25% EDTA-75% Gallic Acid,
0% EDTA-100% Gallic Acid.

Each component has to mixed homogenously preferably by grinding using pestle and
mortar.

2. Put some of each of the above chemical compositions into 2 capillary tubes.
3. Measure the melting points of the chemical compositions in the capillary tubes using
the apparatus provided.
4. Plot the graphs of the melting points vs the chemical compositions
5. Explain the results obtained.

8
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 2

Title

Extraction Technique: Liquid-Liquid Extraction

Introduction

Liquid-liquid extraction, also known as solvent extraction and partitioning, is a

method to separate compounds based on their relative solubilities in two
different immiscible liquids, usually water and an organic solvent. It is an extraction of a
substance from one liquid phase into another liquid phase. Liquid-liquid extraction is a basic
technique in chemical laboratories, where it is performed using a separatory funnel. This type
of process is commonly performed after a chemical reaction as part of the work-up.
In other words, this is the separation of a substance from a mixture by preferentially
dissolving that substance in a suitable solvent. By this process a soluble compound is usually
separated from an insoluble compound. Solvent extraction is used in nuclear
reprocessing, ore processing, the production of fine organic compounds, the processing
of perfumes and other industries.
Liquid-liquid extraction is possible in non-aqueous systems: in a system consisting of
a molten metal in contact with molten salt, metals can be extracted from one phase to the
other. This is related to a mercury electrode where a metal can be reduced, the metal will
often then dissolve in the mercury to form an amalgam which modifies its electrochemistry
greatly. For example it is possible for sodium cations to be reduced at a mercurycathode to
form sodium amalgam, while at an inert electrode (such as platinum) the sodium cations are
not reduced. Instead water is reduced to hydrogen. A detergent or fine solid can be used to
stabilize an emulsion, or third phase.

Objectives

Separation of benzoic acid from two organic compounds mixture (naphthalene and benzoic
acid).

Chemicals

Naphthalene, benzoic acid, dichloromethane, sodium hydroxide, distilled water and

hydrochloric acid.

Apparatus

Beaker (4x50 mL), separation funnel, graduated cylinder, thermometer, ice bath, glass rod,
pH paper, vacuum filter, Buchner funnel, clamp, suction flask, filter paper, dropper.

9
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Precaution

1. Beware of handling hydrochloric acid.

2. Do not pour chemicals in the sink.

Experimental Procedures

1. Dissolve a mixture of 0.5 g of benzoic acid and 0.5 g of naphthalene in 25 mL of

dichloromethane.
2. Make sure the separatory funnel was clean and the outlet was closed.
3. Put the solution into a separatory funnel of an appropriate size and add 25 mL of 10%
aqueous NaOH.
4. Determine which one is the organic phase and which one is the aqueous phase.
Extract thoroughly and allow the two phases to separate completely.
5. Wash the aqueous phase with 10 mL of dichloromethane.
6. Pour the aqueous layer into a small beaker and cool it to about 15 ºC.
7. While stirring, add enough ice-cold concentrated HCl (drop by drop) until a pH of 1 is
obtained.
8. Vacuum filter the solid into a Büchner funnel, using filtrate to rinse the precipitate
from the beaker into the funnel.
9. Dry the product, weigh it and calculate the percent recovery based on the amount of
the initial mixture.

Questions

1. Why dichloromethane were used as a solvent?

2. Why NaOH and HCl were added and please write the equations?
3. How to test the organic and aqueous phase in the mixture?
4. Describe one industrial application of liquid extraction?

10
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 3

Title

Distillation Technique: Separation and identification of liquid organic mixture.

Introduction

Distillation is a method of separating mixtures based on differences in

their volatilities in a boiling liquid mixture. Distillation is a unit operation, or a physical
separation process, and not a chemical reaction.
Commercially, distillation has a number of uses. It is used to separate crude oil into
more fractions for specific uses such as transport, power generation and heating. Water is
distilled to remove impurities, such as salt from seawater. Air is distilled to separate its
components-notably oxygen, nitrogen, and argon-for industrial use. Distillation
of fermented solutions has been used since ancient times to produce distilled beverages with a
higher alcohol content. The premises where distillation is carried out, especially distillation of
alcohol, are known as a distillery.
The application of distillation can roughly be divided in four groups: laboratory
scale, industrial distillation, distillation of herbs for perfumery and medicinals (herbal
distillate), and food processing. The latter two are distinct from the former two in that the
distillation is not used as a true purification method but rather to transfer all volatiles from the
source materials to the distillate.
The main difference between laboratory scale distillation and industrial distillation is
that laboratory scale distillation is often performed batch-wise, whereas industrial distillation
often occurs continuously. In batch distillation, the composition of the source material, the
vapors of the distilling compounds and the distillate change during the distillation. In batch
distillation, a still is charged (supplied) with a batch of feed mixture, which is then separated
into its component fractions which are collected sequentially from most volatile to less
volatile, with the bottoms (remaining least or non-volatile fraction) removed at the end. The
still can then be recharged and the process repeated.
In continuous distillation, the source materials, vapors, and distillate are kept at a
constant composition by carefully replenishing the source material and removing fractions
from both vapor and liquid in the system. This results in a better control of the separation
process.

Objectives

To separate a liquid mixture of an alcohol into their component parts and identification by
comparing the experimental boiling points to literature values.

Chemicals

10mL of each (methanol, 1-propanal and 1-butanol)

11
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Apparatus

Round bottom flask (50 mL), graduated cylinder, thermometer, clamp, adapter, stopper,
water bath, beaker, condenser, water hose.

Precaution

1. Beware of handling hot apparatus.

Experimental Procedures

1. Pour 10 mL of each chemical into a 50 mL round bottom flask.

2. Attach the flask to a simple distillation apparatus and securely clamp each piece of
glassware as you assemble the apparatus.
3. Heat the distillation flask using a water bath.
4. Using small beaker, collect the first fraction that distills at a reasonably constant
temperature (2-3o C), noting the temperature range of the distillate.
5. When the next fraction starts to distill, place a new beaker to collect the next
component.
6. Repeat step 5 for the last component of chemical.
7. After the distillation is completed, lower the heating mantle so that the distillation
system cools down for 10 minutes before disassembling.
8. Compare your experimentally obtained boiling point to the literature values.

Experimental Data

1st distillate 2nd distillate 3rd distillate

Volume obtained after distillation (mL).
Percentage of each recovered pure
compound based on 10.0 mL of starting
chemical.
Boiling point range (°C)
Identity of the unknown compound

Questions

1. Discuss the process that experienced by the liquid that is being distilled and elaborate
why molecular weight affects the distillation temperature.
2. With respect to the condenser used in the distillation, why should the lower rather
than the upper hose barb be used for the water inlet?
3. Given 5 compounds, namely; acetonitrile, tert-butanol, styrene, benzaldenyde and
styrene oxide. Draw the structure, state the molecular weight and suggest the flow of
distillation compound from mixture and why you suggesting that?
4. Describe one industrial application of distillation?

12
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 4

Title

Isolation of caffeine from tea.

Introduction

Caffeine is a bitter, white crystalline xanthine alkaloid that acts as

a psychoactive stimulant drug and a mild diuretic. Caffeine was discovered by a German
chemist, Friedrich Ferdinand Runge, in 1819. He coined the term "kaffein", a chemical
compound in coffee, which in English became caffeine. Caffeine is also part of the chemical
mixtures and insoluble complexes guaranine found in guarana, mateinefound in mate,
and theine found in tea; all of which contain additional alkaloids such as
the cardiac stimulants theophylline and theobromine, and often other chemicals such
as polyphenols which can form insoluble complexes with caffeine.

In humans, caffeine is a central nervous system (CNS) stimulant, having the effect of
temporarily warding off drowsiness and restoring alertness. Beverages containing caffeine,
such as coffee, tea, soft drinks and energy drinks enjoy great popularity. Caffeine is the
world's most widely consumed psychoactive substance, but unlike many other psychoactive
substances it is legal and unregulated in nearly all jurisdictions. In North America, 90% of
adults consume caffeine daily.

Caffeine is found in many plant species, where it acts as a natural pesticide, with high
caffeine levels being reported in seedlings that are still developing foliages, but are lacking
mechanical protection; caffeine paralyzes and kills certain insects feeding upon the
plant. High caffeine levels have also been found in the surrounding soil of coffee bean
seedlings. It is therefore understood that caffeine has a natural function as both a natural
pesticide and as an inhibitor of seed germination of other nearby coffee seedlings thus giving
it a better chance of survival.

Tea is a common source of caffeine instead of coffee. Although tea contains more
caffeine than coffee, a typical serving contains much less, as tea is normally brewed much
weaker. Besides strength of the brew, growing conditions, processing techniques and other
variables also affect caffeine content. Certain types of tea may contain somewhat more
caffeine than other teas. Tea contains small amounts of theobromine and slightly higher
levels of theophylline than coffee. Preparation and many other factors have a significant
impact on tea, and color is a very poor indicator of caffeine content. Teas like the pale

13
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Japanese green tea gyokuro, for example, contain far more caffeine than much darker teas
like lapsang souchong, which has very little.

Caffeine is also a common ingredient of soft drinks such as cola, originally prepared
from kola nuts. Soft drinks typically contain about 10 to 50 milligrams of caffeine per
serving. By contrast, energy drinks such as Red Bull can start at 80 milligrams of caffeine per
serving. The caffeine in these drinks either originates from the ingredients used or is an
additive derived from the product of decaffeination or from chemical synthesis. Guarana, a
prime ingredient of energy drinks, contains large amounts of caffeine with small amounts
of theobromine and theophylline in a naturally occurring slow-release incipient.

Objectives

To extract the caffeine from tea leaf

Chemicals

Calcium carbonate, tea leaf, ice, dichloromethane, anhydrous sodium sulfate.

Apparatus

Beaker, hot plate, separation funnel, Erlenmeyer flask, filter paper, water bath.

Precaution

1. Beware of handling hot apparatus.

Experimental Procedures

1. To a 200 mL beaker containing 10g tea leaf and three grams of calcium carbonate,
add 100 mL of boiling water. Set the beaker on the hot plate and boil gently for 15
min.
2. Cool the aqueous solution to room temperature using an ice bath and filter the
solution using gravity filtration.
3. Pour the filtrate it into a 200 mL separatory funnel. Extract [gently shake/swirl the
mixture for at least 5 minutes] the tea solution two times, ( first time 30 mL and the
second time 25 mL) with dichloromethane [CH2Cl2]. Combine both extracts in a 200
mL Erlenmeyer flask. [Take care not to shake the separatory funnel so vigorously
as to cause an emulsion to form. If you should get an emulsion that does not
break].

14
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

4. Dry the combined CH2Cl2 extracts with five grams of anhydrous sodium sulfate.
Swirl for several minutes to allow enough time for the sodium sulfate to become
hydrated with the water.
5. Gravity filters the dry CH2Cl2 solution into a pre-weight 100 mL beaker.
6. Place the beaker on a water bath and evaporate the contents to dryness at low-
medium heat (80 oC). Weigh the flask to find the crude mass of caffeine. (Watch the
beaker carefully as you boil it down to makes sure you do not burn the caffeine).
7. Calculate the approximate percentage of caffeine in your tea, using the mass of the
theoretical mass of 5% of crude caffeine in the tea leaf.

Questions

1. Why is the ethyl acetate layer above the water layer?

2. Do you think your final mass of caffeine represents all of the caffeine originally in
your tea leaves? List two places where you could have “lost” some of your final
caffeine (not including human error).
3. Draw the structure of caffeine and state what is the other compound is present in tea
leaf.

15
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 5

Title

Esterification of butanol with acetic acid

Introduction

The ester group is an important functional group that can be synthesized in a number
of different ways.

The low-molecular-weight ester has very pleasant odors and indeed is the major
components of the flavor and odor aspects of a number of fruits. Although the natural flavor
may contain nearly a hundred different compounds, single esters approximate the natural
odors and are often used in the food industry for artificial flavor and fragrances.

Esters can be prepared by the reaction of a carboxylic acid with an alcohol in the
presence of a catalyst such as concentrated sulfuric acid, hydrogen chloride, p-
toluenesulfonic acid, or the acid form of an ion exchange resin:
`

O O
+
║ H ║
CH3COH + C4H9OH ⟺ CH3COC4H9 + H2O
Acetic acid butanol butyl acetate

This Fischer esterification reaction reaches equilibrium can be shifted by adding more
of the acid or of the alcohol, depending on cost or availability. The mechanism of the reaction
involves initial protonation of the carboxyl group attack by the nucleophilic hydroxyl, a
proton transfer, and loss of water followed by loss of the catalyzing proton to give the ester.

Chemicals

1-butanol, acetic acid, H2SO4

Apparatus

16
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Necked round bottom flask, thermometer, condenser, connector

Experimental Procedures

1. In this experiment , the class is divided into two with one section do the experiment
using an apparatus which consists of a two necked round bottom flask equipped with
a thermometer and condenser
2. While, the other section do the exactly the same experiment but the same apparatus
equipped with a connector modeled after that of Dean and Stark.
3. The mixture of equimolar quantities of 1-butanol and acetic acid is placed in the flask
along with an acid catalyst concentration H2SO4. (Stirring reduces bumping).
4. The mixture then is heated up to reflux.
5. The vapor, the temperature of which is 90.7oC, condenses and runs down back to the
flask but for the Dean & Stark apparatus the vapor will run down to the sidearm,
which is closed with a cork forming two layers.
6. The layers separate, with the denser layer remaining in the sidearm while the lighter
layer runs down into the reaction flask.
7. The reaction with ordinary apparatus is continued for about 3 hours but for the Dean
& Stark apparatus the reaction is stopped when there is no more lower layer produced.
8. Compare the smell and the purity of the results of the two reactions.
9. Explain the different results obtained.

17
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 6

Experiment: Cross Aldol Condensation reaction between benzaldehyde and ketone

Objective: 1.To synthesize chalcone derivatives via cross Aldol Condensation reaction.
2. To learn the separation technique using Thin Layer Chromatography

Chemical/Apparatus:
4-methoxybenzaldehyde (molecular weight: 136.15 g/mol)
Acetophenone, (molecular weight: 120.15 g/mol)
Ethanol
NaOH (1M) Solution
Round bottom flask
Magnetic stirrer bar & magnetic stirrer
Filter paper, Buchner funnel, vacuum flask, clamp
Thin Layer Chromatography plates
Hexane, ethyl acetate
Measuring cylinder (10 mL)

Introduction:

Chalcones or chemically known as1,3-diaryl-2-propen-1-ones are the key precursors

to all flavonoids (Figure 1). Chalcones can be formed via the shikimate or
acetate/mevalonate pathways. They are the secondary metabolites that responsible for the
yellow pigments found in certain flowers(Harborne 1966; Ono et al. 2006). As a matter of
fact, the color of flowers in most angiosperms has significant role in pollination (fertility and
pollen germination) by attracting pollinator (e.g. insects and bird) for plant growth and
reproduction purposes. These compounds not only restricted to flowers but also widely
distributed in fruits, vegetables, spices, teas, soy and many different parts of plant (Iwashina
2000). Together with flavonoids, they play an important role in the chemosystematics,
biochemistry, physiology and ecology of plants, including UV light protection(Kootstra
1994), enzyme inhibition, pathogen protection(Treutter 2005), insect antifeedants(Morimoto
et al. 2003) and molecular signaling in symbiotic systems or allelopathic (Abdel-Lateif et al.
2012). A number of research works have suggested that they might have benefits to human
health and can be potentially used as nutraceuticals with array of interesting biological
activities(Nowakowska 2007).

FIGURE 1 The general structure and numbering of chalcones. A and B define the order
of ring introductionor ring formation in synthesis(Chimenti et al. 2009)

18
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Chalcone can be synthesized by reacting benzaldehyde and acetophenone via cross

aldol condensation or Claisen-Schmidt condensation in the presence of base or acid.
Basically, cross aldol condensation is a carbon-carbon bond forming reaction that is useful
for synthesizing β-keto compounds like chalcone.

Procedure:
Synthesis
1. Weight 1 mmol of benzaldehyde and 1 mmol of acetophenone (Please calculate how
many grams required for 1 mmol of each starting material prior to running the
experiment). Place both starting materials into 100mL round bottom flask containing
20mL of ethanol.
2. Stir the reaction mixture until all starting material is dissolve.
3. Carefully load dropwise10mL of 1M NaOH solution into reaction mixture.
4. Continue stir for 1 hour. Check the reaction progress using Thin Layer
Chromatography technique every 20 min using Hexane: Ethyl acetate 4:1 ratio as
solvent system. (Please refer to procedure below)
5. Filter the products obtained using Buchner funnel.
6. Dry the resulting yellow solid at an oven overnight.
7. Weight the yellow solid obtained.

Thin Layer Chromatography

1. Prepare 4mL of hexane and 1mL of ethyl acetate using measuring cylinder.
2. Place into 100 mL beaker and cover with petri dish to avoid solvent from evaporate

Questions

5. Calculate the percent of yield.

19
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 7

Title

Technique of Crystallization

Introduction

Crystallization is the (natural or artificial) process of formation of

solid crystals precipitating from a solution, melt or more rarely deposited directly from a gas.
Crystallization is also a chemical solid-liquid separation technique, in which mass transfer of
a solute from the liquid solution to a pure solid crystalline phase occurs.

The crystallization process consists of two major events, nucleation and crystal
growth. Nucleation is the step where the solute molecules dispersed in the solvent start to
gather into clusters, on the nanometer scale (elevating solute concentration in a small region),
that becomes stable under the current operating conditions. These stable clusters constitute
the nuclei. However when the clusters are not stable, they redissolve. Therefore, the clusters
need to reach a critical size in order to become stable nuclei. Such critical size is dictated by
the operating conditions (temperature, supersaturation, etc.). It is at the stage of nucleation
that the atoms arrange in a defined and periodic manner that defines the crystal structure —
note that "crystal structure" is a special term that refers to the relative arrangement of the
atoms, not the macroscopic properties of the crystal (size and shape), although those are a
result of the internal crystal structure.
The crystal growth is the subsequent growth of the nuclei that succeed in achieving
the critical cluster size. Nucleation and growth continue to occur simultaneously while the
supersaturation exists. Supersaturation is the driving force of the crystallization, hence the
rate of nucleation and growth is driven by the existing supersaturation in the solution.
Depending upon the conditions, either nucleation or growth may be predominant over the
other, and as a result, crystals with different sizes and shapes are obtained (control of crystal
size and shape constitutes one of the main challenges in industrial manufacturing, such as for
pharmaceuticals). Once the supersaturation is exhausted, the solid-liquid system reaches
equilibrium and the crystallization is complete, unless the operating conditions are modified
from equilibrium so as to supersaturate the solution again.
Many compounds have the ability to crystallize with different crystal structures, a
phenomenon called polymorphism. Each polymorph is in fact a different thermodynamic
solid state and crystal polymorphs of the same compound exhibit different physical
properties, such as dissolution rate, shape (angles between facets and facet growth rates),
melting point, etc. For this reason, polymorphism is of major importance in industrial
manufacture of crystalline products.

20
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Objectives

1. To remove solid impurities from a liquid or a solution.

2. To collect a desired solid using recrystallization method.

Chemicals

Product from previous experiment, ethanol, saw dust,

Apparatus

Glass rod, hot plate, filter paper, Buchner funnel, vacuum flask, clamp.

Precaution

1. Beware of hot ethanol and instrument.

2. Do not pour chemicals in the sink.

Experimental Procedures

8. A mixture of product from previous experiment and saw dust (0.5g) was weight and
place in conical flask.
9. 10 mL of ethanol was added. Stir the mixture using glass rod until the mixture is fully
dissolve.
10. Occasionally add 1 mL portions of hot ethanol if the mixture is not dissolved.
11. Filter the mixture using gravity filtration method and collect the mother liquor in the
conical flask.
12. The solution obtained from the filtration is transferred into an ice bath.
13. When crystallization is complete, filter the solid using vacuum filtration method.
Rinse crystal with cold ethanol.
14. Dry the resulting crystal at an oven overnight.
15. Weight the crystal obtained.

Questions

6. Calculate the percent of recovery.

21
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

EXPERIMENT 8

Title: Organic functional group test (aldehydes and ketones).

Objectives

To classify of an organic compound

The following carbonyl compounds are provided for the tests below:

Aldehydes: Propanal and Benzaldehyde

Ketones: Propanone and Acetophenone

Aldehydes and ketones are organic compounds containing the carbonyl functional group,
C=O. Aldehyde has the general formula, RCHO while ketone has the general formula
RR1CO where R
1
and R are alkyl or aryl groups. An aldehyde or ketone will undergo a general reaction with
the
Brady reagent, 2,4-dinitrophenylhydrazine (2,4-DNPH), to produce 2,4-
dinitrophenylhydrazone which will appear as an orange or yellow precipitates. This reaction
is commonly used to ascertain the presence of a carbonyl group in a compound.

O R1
+ O2N NHNH2 O2N NHN C + H2O
R R1
R
NO2 NO2
(R = H, alkyl or aryl)

Reaction mechanism of 2,4-DNPH with an aldehyde or ketone:

22
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Aldehydes can be distinguished from ketones through several tests. One test involves the use
of a Schiff's reagent which will produce a violet-pink solution with aldehydes but not
ketones.

Another test that can distinguish aldehydes from ketones is through weak oxidizing agents
such as the Tollen's reagent (ammonium nitrate complex in ammonia solution). A positive
reaction is indicated by the formation of a silvery mirror on the side of the tube.

Iodoform test is a useful test for the identification of methyl ketones and secondary methyl
carbinols. This test involves a reaction in which the methyl group of the ketone is removed
from the molecule and produces iodoform (CHI3). A positive test is indicated by
the formation of yellow precipitates or suspension of iodoform.

PROCEDURES

1. BRADY TEST

Dissolve about 0.5 mL or 50 mg of the compound to be tested in 2 mL 95% ethanol. Add 2 to

3 drops of this mixture into the test tube containing 3 mL 2,4-dinitrophenylhydrazine reagent
(Brady reagent).* Shake the tube and observe the formation of any precipitate. If no
precipitate forms immediately allow the mixture to stand for 5-10 minutes. Record your
observations.
*The 2, 4-dinitrophenylhydrazine reagent can be prepared by dissolving 3 g of 2,4-
dinitrophenylhydrazine in 15 mL concentrated sulfuric acid. This solution is added in to a
mixture of 20 mL water and 70 mL 95% ethanol with stirring and filtered.
2. SODIUM BISULFITE SOLUTION TEST
Add aldehyde or ketone (about 0.2 mL or 2 mg) into a test tube containing 1 mL alcoholic
sodium bisulfite solution.* Plug the test tube with a cork and shake thoroughly. Record any
observations.
*The alcoholic sodium bisulfite reagent can be prepared by adding 1 mL ethanol to 4 mL
40% aqueous solution of sodium bisulfite. The reagent must be filtered before use.

3. TOLLENS' TEST
Add 2-3 drops or 0.1 g of the compound that is to be tested to the Tollens' reagent*. Shake
the
tube slowly and note the formation of silver mirror/precipitate for the presence of an aldehyde
group. If there is no precipitate after 10 minutes, warm the mixture in a water bath at 30°C for
5-10 minutes. Record your observation.
*Tollens' reagent can be prepared by adding one drop of NaOH 10% solution to a 2 mL 5%
silver nitrate solution in a test tube. Add ammonia 5% solution drop by drop until all the
precipitate (silver oxide) dissolves. Avoid using excess ammonia in order to obtain a sensitive
reagent (The reagent must be prepared just before use and should not be stored).

23
Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

4. FEHLING'S TEST
Dissolve 0.2 g or 1 mL of the compound to be tested in 5 mL water and add 5 mL of the
Fehling's reagent* to the solution. Slowly shake the tube and heat the mixture to boiling. Cool
the mixture to room temperature and note the occurrence of any precipitation. Record your
observations.
*Fehling's solution can be prepared as follows:

Solution #1: Dissolve 17.32 g hydrated copper sulphate crystal in 200 mL water and dilute
the solution to 250 mL.
Solution #2: Dissolve 86.5 g sodium potassium tartrate and 35 g sodium hydroxide in 100
mL water and dilute the solution to 250 mL.
 To prepare the Fehling's reagent, mix 2.5 mL Solution #1 and 2.5 mL Solution #2
immediately before use.

5. SCHIFF'S TEST
Add 1-2 drops of the compound to be tested to 1 mL Schiff's reagent* in a test tube. Shake it
slowly and observe the color develop in 4-5 minutes. If the compound does not dissolve in
the Schiff's reagent, cap the test tube with a cork and shake it vigorously until an emulsion
forms. Record your observations.
*Schiff's reagent is prepared by dissolving 0.005 g p-Rosaline hydrochloride (Fuchsin) in 50
mL distilled water followed by addition of 2 mL saturated sodium bisulfite solution. After 1
hour, add 1 mL concentrated hydrochloric acid and then leave the solution to stand for 24
hours. This reagent is colorless and very sensitive.

24
 Chemistry Laboratory I (BSK1402) Faculty of Industrial Sciences & Technology

Experiment Observation Inference

Test for carbonyl group (>C=O): Orange red crystalline ppt. >C=O group
present.
Dissolve considerable amount of the sample in 2 ml of
rectified spirit (if necessary heat the sample to dissolve)
and then add excess 2,4-DNPH solution. Allow the
reaction mixture to stand in a beaker of cold water.

Differentiation between aldehydes and ketones:

(a) Fehling’s solution: Heat the sample with

Fehling’s soln (by mixing equal volume of (a) (i) Pink ppt. (a) (i) Aldehyde
Fehling’s soln No. 1 and 2) on a water bath for 4- present.
5 min. (ii) no pink ppt. (ii) Ketone present.

(b) Tollens reagent: Add small amount of the

sample to the Tollen reagent (prepare the reagent (b) (i) Silver mirror forms in (b) (i) Aldehyde
fresh) and observe the result in the cold. If no the inside wall of the tube. present.
reaction takes place in the cold, warm the (ii) Silver mirror is not (ii) Ketone present.
solution in a beaker of hot water. formed.

(c) Schiff’s reagent: Add small amount of the (c) (i) pink colour. (c) (i) Aldehyde
sample in 2 ml of Schiff’s reagent and shake the present.
mixture well. (ii) no pink color. (ii) Ketone
present.

25