Student name

Section

‫جامعة كل للـعرب‬

Faculty of Pharmacy
Department of Pharmaceutical Chemistry and Pharmacognosy

Laboratory Manual for

Pharmaceutical Organic Chemistry (0905211)
Prepared by

Dr. Ghassan Abu Sheikah (Ph.D) Dr. Nina Sakhnini (Ph.D)

Dr. Adel Ardakani (Ph.D) Rasha Al-Kurdi (B.Sc.)

Edited by
Dr. Mumen Amer (PhD.)
Summer Semester
2020-2021

i
Aims

The course is designed to provide the student with a knowledge and understanding of the
basic experimental principles of pharmaceutical organic chemistry. The experiments will
provide first hand experience for the student and should equip him/her with the ability to
solve a wide range of synthetic chemistry problems relating to pharmaceutical products.
This course is designed to link the theoretical knowledge obtained in both courses (0905
& 0901224) based on their textbook Organic Chemistry, William H . Brown and Thomas
Poon as a reference with practical synthetic applications.

Abbreviations and some explained terms:

mg milligram g 10-3 Kg
g gram 1 Kg 103 g or 1000 g
Kg kilogram mmol milimole 10-3 mol
ml milliliter Mole 1000 mmol.
L liter dil. diluted
Temp temperature (°C) % percentage × 100
m.p. melting point B.P. British Pharmacopoeia
b.p. boiling point USP United States
M molarity Pharmacopoeia
N normality vol. Volume
Mol mole wt. Weight
M wt. molecular weight (g/mol) w/w Weight per weight
V volume (ml or L) w/v Weight per volume
Conc. concentrated aq. Aqueous
[] concentration ~ Approximately
ppt Precipitate e.g. Example
1L 103 ml or 1000 ml EtOH Ethanol
10 -3 L 1 ml n- normal (straight) chain
Sol. Solution

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 1. Table of Contents: Page

Aims and list of abbreviations i

Table of Contents 01
Introductory 03
1-Laboratory Work Rules 03
1-1 General Instructions and Safety Rules. 03
1-2 Hazards in Organic Chemistry Laboratories. 04
1-3 Laboratory Accidents and First Aid. 04
1-3-1 Poisons 04
1-3-2 Gas 05
1-3-3 Fires 05
1-3-4 Eye Accidents 05
1-3-5 Burns 06
Hazard Symbols and their designations. 07
Table 4-1: The hazards of chemicals used in the following experiments 08
2-Common organic lab apparatus. 09
2-1 Simple apparatus. 09
3-Some techniques used in organic chemistry laboratory. 12
3-3 Cleaning the Glassware. 12
3-4 Drying the glassware. 13
3-5 Calculation of Yields. 13

1
4-Experiments 14
Exp.1: Synthesis of Aspirin. 14
Exp.2: Recrystallization and Measurement of meting point. 17
Exp.3: Synthesis of p-nitroacetanilide. 20
Exp.4: Chemical drawing; PC Drawing Lab Report 34
Exp.5: Synthesis of Quinoline Derivative. 22
Exp.6: Haloform Reactions: Synthesis of Iodoform. 33
Exp.7: Synthesis of Azodystuff.Synthesis of phenyl azo-2 naphthol. 24
Exp.8: Reaction of Esterification: Preparation of n-Butyl acetate. 31
Exp.9 and 10: Separation of a mixture of water-insoluble compounds
by chemical extraction. 26
Exp.11: Separation of Benzoic Acid from Acetanilide mixture. 29
Exp.12: Synthesis of Paracetamol and Phenacetin. 35

Periodic Table 37
Glassware 38
Boiling chips & reflux, Instructions for using the vacuum pump 40
Fluting filter paper 41
Lab Instructions 43
Organic Lab Reports 45

2
Introductory
1-Laboratory Work Rules
1-1 General Instructions and Safety Rules
Before beginning any preparation in the laboratory, the student must carefully study the
complete details of the experiment as well as the underlying theory. He/she should not
only have a clear idea of what is to be done, but he should also be ready to answer clearly
and correctly the questions concerning the different steps of his work.
The student should have a designated note-book. The information recorded for each
experiment generally includes:
• Any new instructions (e.g. the particular cautions) given by the lecturer or the
person in charge of the Laboratory.
• The principle of the experiment and the reaction equations, in addition to physical
properties (e.g. melting point, boiling point, density, etc, of the compounds used
in the preparation.
• Their own observations.
• The results, for example, the calculation of the percentage yield of the product,
m.p. or b.p. range etc…
The following rules should always be observed and strictly followed at all times:

➢ No work should be allowed in the laboratory without a full-length, clean and

white protective coat, gloves and suitable eye protection.
➢ Follow strictly the experimental instructions given in your laboratory manual.
➢ Do not start without the approval of the lecturer.
➢ Each student must wear a safety spectacles or goggles at all times.
➢ Smoking, drinking and eating are strictly forbidden inside the laboratory.
➢ Student should bring a towel and soap for personal use.
➢ You should keep your working area as clean as possible because it is an indicator
of your proper technique.
➢ Glassware should be carefully examined before starting, do not use any unclean
or broken/cracked glassware.
➢ Take extra care when using flammable solvents (see section 1-2.).
➢ Do not follow a reaction by looking from the top of the tube or any flask
containing the reaction medium, due to splashing hazard.
➢ Make sure to ALWAYS close the reagent bottle after use with its own stopper, to
avoid any contamination.
➢ Make sure that the reagent you are about to use is the one you should use.
➢ Use the same pipette/spatula for the same reagent.
➢ Do not overuse gas, water, electricity or chemicals.
➢ Solid waste and used filter paper must not be thrown into the sink.

3
 ➢ Do not leave the laboratory without the approval of the instructor and make sure
you have closed the water, gas and electricity (hot plate, electric water bath,
etc....) sources.

1-2 Hazards in Organic Chemistry Laboratories.

The main sources of danger in the laboratory are usually the chemicals and the butane gas
used in Bunsen burners.
Many chemical substances used in organic chemistry laboratories are hazardous or very
dangerous. As a general rule: every unknown chemical should be considered hazardous.
The unsafe handling of chemicals would potentially lead to an accident and injury to
yourself and to others.
The danger may usually occur by different ways:
• By direct contact with different parts of the body (e.g. contamination of the hands,
contamination of the face or eyes with drops splashed from a solution when
heated unsafely in an open flask). The goggles should always be used in the
laboratory in order to protect eyes and the major part of the face.
• By inhalation of toxic vapors (e.g. bromine, chlorine, and other toxic vapors
produced from the reaction mixtures). In these cases, the manipulation should be
done in the fume hood where there is good ventilation.
• By combustion of the flammable compounds (e.g. volatile solvents such as
diethyl ether, acetone, methanol etc…). These compounds should never be
handled in the vicinity of a naked flame. The vapors of diethyl ether for example
may spread along the top of a bench, particularly if driven by a draft of air,
several meters to reach the source of ignition. The correct procedure for such
solvents is to heat in a flask fitted with reflux condenser by means of electric
water bath or a suitable hot plate.
• Some dangerous compounds should never be handled unless a special neutralizing
solution is present in the vicinity (5-10%w/v sodium thiosulfate or diluted
ammonia are used to neutralize the bromine liquid).
The Bunsen burner should be used with extra care because it is a major source of
laboratory accidents. Student should always make sure that the tubing connections of the
Bunsen burner are in good conditions to avoid any leakage which could lead to a fire or
an explosion. It is always demanded, after finishing the work, to make sure that you have
switched off the Bunsen burner and closed the main gas source.

1-3 Laboratory Accidents and First Aid.

In the case of accident always call or notify the instructor (staff member) as soon as
possible.
1-3-1 Poisons
Solids or liquids:
1. In the mouth but not swallowed, spit out at once and wash repeatedly with water.

4
 2. If swallowed call the doctor immediately. In the meantime, give an antidote
according to the nature of poison:
a) Acids (e.g. sulfuric acid, hydrochloric acid including oxalic acid), dilute by drinking a
lot of water, followed by lime water or milk of magnesia, milk may then be given.
b) Caustic alkalis (e.g. concentrated solution of sodium hydroxide...), dilute by drinking a
lot of water followed by vinegar, lemon or orange juice, or solution of lactic acid or citric
acid, milk may then be given.
c) Salt of heavy metals, give milk or egg white.
d) Arsenic or mercury compounds, give an emetic immediately: e.g. one teaspoonful of
mustard or one teaspoonful of salt dissolved in warm water.
1-3-2 Gas
Remove the victim to the open air and loosen tight clothes around the neck. If chlorine or
bromine fumes are inhaled in small amount, inhale ammonia vapor or gargle with sodium
bicarbonate solution. Afterwards the patient should drink warm dilute peppermint or
cinnamon water, to soothe the throat and lungs. If breathing has stopped, apply artificial
respiration.
1-3-3 Fires
Burning cloths: prevent the person from running. Make the victim lie down on the floor,
or throw him down if necessary, and wrap the fireproof blanket firmly around the ignited
clothes until the fire is extinguished.
Burning reagents: turn out all gas burners and switch off all electrical hot plates in the
vicinity, remove everything which may ignite. Do not attempt to put out the fire,
unless:
• A small fire (e.g. liquid in a beaker or flask or an unbroken oil bath) may be
extinguished by covering the opening of the vessel with a clean damp cloth.
• For larger fires, dry sand may be employed. The use of sand has some
disadvantages that the compound or the reaction mixture is usually lost and glass
apparatus around may be broken under the weight of the sand. Alternatively
several extinguishers could be used. These are usually charged with carbon
dioxide under pressure, with “Halon” compounds such as: CF3Br, CBrClF3, etc...
or with carbon tetrachloride under high pressure of CO2, it should be noted that
carbon tetrachloride should not be used if sodium or potassium is present as a
violent explosion may be result, and the laboratory must be ventilated
immediately after extinguishing the fire in order to disperse the highly poisonous
phosgene vapor which is formed.
• For burning oil or organic solvents, do not use water as it will only spread the fire.
An extinguisher charged with dry powder (sodium bicarbonate, calcium
carbonate, etc...) under high pressure of CO2 could be used; it is also suitable for
fires caused by magnesium and metal hydrides.

1-3-4 Eye Accidents

• In every eye accident doctor should be consulted immediately plus having to do
some first aid before that.

5
 • Acid splash: with dilute acids the eye should be washed several times with
sodium bicarbonate solution 1%w/v. In case of strong acids, eye should first be
washed with a lot of water and then with sodium bicarbonate solution 1%w/v.
• Alkalis: proceed as for acids but wash with 1%w/v boric acid solution in place of
bicarbonate solution.

1-3-5 Burns
• Burns caused by dry heat (e.g. flame, hot objects, etc...): for slight burns, apply a
little of Vaseline or glycerin. For larger burns in which the skin is reddish or
blistered apply rapidly an ointment for burns and call for a medical aid at once.
• Burns on the skin caused by acids (conc. H2SO4, etc...) wash immediately and
thoroughly with a large quantity of water, then with saturated sodium bicarbonate
solution and finally with water. For serious acid burns, follow this by applying a
disinfectant, drying the skin and covering with an ointment for burns.
• Burns on the skin caused by alkalis (conc. NaOH solution, etc...), wash with a
large volume of water then with 1%v/v acetic acid and finally with water. For
serious burns, follow this by applying a disinfectant, drying the skin and covering
with an ointment for burns.

The nest two pages: Figure 1-1: Safety Hazard Categories and table 1: the hazard and
chemicals used in the following experiments

6
7
For more information you can visit many websites, an example is:
http://www.actiocms.com/msdsxchange/english/index.cfm

8
2-Common organic laboratory apparatus.
2-1 Simple apparatus.
Students should know the name and the use of different basic glassware and the apparatus
used in the preparation of organic compounds. Fig 2.1 shows some of these apparatus:

• Flasks:

Erlenmeyer Flask Filtration flask Round bottom flask

Volumetric flask Stopper flask

• Funnels :-

Buchner funnel Filter funnel Separatory funnel

9
• Pipettes:

Volumetric Pipette Graduated Pipette Pipette filler

• Other tools and glassware:

Burette Beaker Graduated cylinder

Watch glass
(Glass dish)

10
 Spatula Condenser

Washing bottle Test tube brush Wire gauze

Test tube holder

Mortar and Pestle Test tube holder (rack)

Crucible and lid

Glass rod
Clamp

11
 Petri dish

Burette clamp
Evaporating dish

Test tube
Rubber stopper
Dropper

Fig 2.1

3- Some technique used in organic chemistry.

3-1 Cleaning the Glassware.

All glassware should be perfectly clean and, for most purposes, dry before being used in
preparative work in the laboratory. Student should have the habit of cleaning all glass
apparatus immediately after use, because the nature of the dirt will be known at the time
and furthermore, the cleaning process becomes more difficult if the dirty apparatus is
allowed to stand for longer time.
The Simplest way to clean an apparatus is to use a test tube brush with a commercial
household washing liquid/powder.
The most widely used cleansing agent is the mixture of chromic acid (CrO3) and
concentrated sulfuric acid. This mixture possesses a powerful oxidizing and solvating
properties.
It should be emphasized that there is no universal cleansing mixture. The student must
take into account the nature of the substance to be removed and act accordingly. Cleaning
can be achieved by rinsing the vessel with a few ml of benzene, or diethyl ether (for
organic materials), with a dilute HCl (for basic residues) or, with dilute sodium hydroxide
(for acidic residues).
12
Student have to follow the following steps when the “chromic acid” cleaning mixture is
to be used:
• Rinse the vessel with water to remove organic matters (particularly the reducing
agents), drain away the water as much as possible.
• Introduce into the vessel a sufficient quantity of the “chromic acid” mixture.
Spread the liquid over the soiled surface by occasional rotation. Allow to stand for
a short time and return the main quantity of the mixture to the stock bottle.
• Rinse the vessel successively with tap and distilled water.
• If a black solid (carbonaceous materials) remains a after the above treatment,
introduce into the flask small volume of the cleaning mixture, heat the flask
gently on the free flame until the acid commences to fume. Allow to stand for a
short time, pour out the liquid into the stock bottle and then continue as above.

3-2 Drying the glassware.

Small glass apparatus may be dried by leaving it in a steam oven, or in an electrically
heated oven maintained at 100-120 ºC for one to two hours.
If an apparatus is wet with water, it could preferably be dried by draining as completely
as possible, then rinsing with methanol, followed after draining with a little amount of
ether or acetone. The final drying is then achieved with the aid of a heat gun.
3-3 Calculation of Yields.
The theoretical yield in an organic reaction is the amount which would be obtained under
ideal conditions if the reaction had proceeded to completion. The yield (sometimes called
the actual yield) is the amount of pure product which is actually isolated in the
experiment. The percentage yield is computed from the ratio between the weight of the
pure product obtained and the weight calculated.

Percentage Yield = Actual yield x 100

Theoretical yield

After a little experience in the organic chemistry laboratory, the student will soon find
that the yields frequently do not approach the theoretical values. This may be due to one
or more of the following causes:
• The reaction may not proceed to completion because the reverse reaction may
occur under the given conditions and a state of equilibrium is established.
• A portion of some of the reactants may be consumed in some side reactions which
lead to non-desired side products.
• Some of the desired product may be lost by further chemical changes before it can
be isolated.
• Some of the product may be lost in the process of separation and purification.
• Some of the reagents may not be completely pure.

13
4-Experiments
Exp 1: Aspirin Synthesis

Aspirin is the common name for the compound acetylsalicylic acid, widely used
as a fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the
willow family of plants, was derived from willow bark extracts. In folk medicine, willow
bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid is
administered in the form of aspirin which is less irritating to the stomach than salicylic
acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. A
small amount of a strong acid is used as a catalyst which speeds up the reaction. In this
experiment, phosphoric acid will be used as the catalyst. The excess acetic acid will be
quenched with the addition of water. The aspirin product is not very soluble in water so
the aspirin product will precipitate when water is added. The synthesis reaction of aspirin
is shown below:

Since acetic acid is very soluble in water, it is easily separated from the aspirin
product. The aspirin isolated in this step is the “crude product”. A “purified product” can
be obtained through recrystallization of the crude product in hot ethanol. In this
experiment, the crude product will be the desired product. The percent yield of the crude
product will be determined for this reaction.
The melting point range of pure aspirin is 138-140⁰C and the melting point range
of the salicylic acid starting material is 158-161⁰C. If impurities are present in your crude
sample, the melting point range for your product will be lower than the range of pure
aspirin. Also, your melting point range may be greater than 2 degrees.

14
Procedure:

1. Use a balance to weigh a 50 mL Erlenmeyer flask. Place about 2 g of sylicylic

acid in the flask and weigh again. In the fume hood, the instructor will transfer 5.0
mL of acetic anhydride from a burette into the flask. Add 5 drops of 85%
phosphoric acid (catalyst) to the flask.
2. Clamp the flask in a beaker of tap water supported on a ring stand over a burner
flame. Stir if needed to dissolve the salicylic acid. Heat the water to boiling, and
shut off the flame. Keep the flask in the hot water bath for 10 more minutes.
3. While the flask is still in the water bath, slowly add 2 mL of distilled water to the
flask to decompose any excess acetic anhydride.
4. After a minute, remove the flask from the water bath and add 20 mL of distilled
water. Let the flask cool to room temperature. As the solution cools, crystals of
aspirin will appear. Cool the solution further by placing the reaction flask in an
ice bath. Chill 5-10 mL of distilled water in a separate container.
5. Weigh a watch glass and filter paper on the balance.
6. Set up a Büchner funnel on a vacuum flask connected to a water aspirator. Place
the filter paper in the funnel and moisten with distilled water from a squirt bottle.
Turn on the aspirator and transfer the aspirin slurry into the funnel. Wash the
crystals with 5 mL of the cold distilled water. Note: Instructions hoe to
vacuum pump is at page ……

15
 7. Transfer the filter paper and aspirin to a pre-weighed watch glass and allow to air
dry in your locker until the next lab period.
8. It is safe to discard of the filtrate down the sink with water. Why?
9. Determine the theoretical yield and the percent yield of the aspirin product.

Questoions:

I. Compare the melting point of you aspirin product to the theoretical melting point

(138-140⁰C). Is the crude product above or below this mark? Explain why this is the

case.

16
Exp 2: Recrystallization and measurement of Melting point

Definition:

Solid Organic compounds when isolated from the reaction mixture/organic reactions are
seldom pure, they are usually contaminated with a small amount of other compounds
(impurities) which are produced along with the desired product, there is a laboratory
technique used for purification of a crude solid with impurities based on their different
solubility into pure crystals using a small amount of suitable boiled solvent known as
recrystallization.

The purification of solids by crystallization is based upon differences in their solubility in

a given solvent or mixture of solvents in its simplest form.

Before starting the recrystallization method you should select a suitable solvent for your
solid then:

A- Preparation for Recrystallization:

1. Solvent of re-crystallization selection:

The successful of re-crystalliztion and the purification of impure crystalline
compounds is usually depends on finding the right solvent (this is a combination of
trials and errors) and affected by crystallization from a suitable solvent or mixture of
solvent and The most desirable characteristics of a solvent for re-crystallization
are as follows:
1. A high power for the substance to be purified at elevated T and a
comparatively low solvent power at the laboratory T or below.
2. It should dissolve the impurities readily to a small extent.
3. It should yield well-formed crystals of the purified compound.
4. It should be capable of easy removal from the crystals of the purified
compound, i.e. possess a relatively low boiling point.
5. It should be chemically inert, i.e. does not react chemically with the
substance to be purified.
6. It should be non toxic. if two or more solvents appear to be equally
suitable for recrystallization, the final selection will depend upon such
factors as ease of manipulation, toxicity, flammability and cost.
7. A polar substance is more soluble in polar solvents and less soluble in
non-polar solvents.
17
 8. Solvents should be: cheap, available, non volatile, like dissolves like
(polar solid with polar solvent).

2. Caution: The vapors of chemical solvents are toxic and therefore recrystallizations
involve their use must be conducted in an efficient fume hood, excessive
inhalation of any vapor should be avoided.
3. Crystallization process can be illustrated by observing how snow recrystallize
to ice without melting.
4. Determination of amount of solvent through Dissolving the solute in the
solvent as in the following way:
I. Add a small portion of boiling solvent to the beaker that contains the
impure sample and boiling chips.
II. Heat the beaker contaning the solute and continue adding boiling solvent
increamently until all of the solute has been dissolved.if additional solvent
can be added with no appreciable change in the amount of solute
present,the particulate matter is probably is insoluble impurities.

B Reccrystallization procedure:-

1. Dissolve the crude solid using a small amount of suitable at or near the boiling
point by applying heat to the solution using water bath (if the solid is affected by
T or if the solvent boils below 80°C) or Hot plate if not until you get a clear
solution (you can use glass rod to enhance the dissolution) sometimes you will see
insoluble impurities in the solution after you dissolving the solid, this is may be
due to the filter paper fibers.

2. Hot Gravity filtration for the hot solution, this is usually done through a fluted
filter paper or small piece of cotton (faster than the filter paper, more efficient in
impeding the insoluble impurities and dust, that the hot solution may dissolve the
fiber that made the filter paper) supported in a relatively large funnel with a short
wide stem, separation of crystals in and clogging of the them is thus reduced to a
minimum. The funnel should be warmed in an electric or steam oven before
filtration is started, when it should be supported in a conical flask of sufficient
size to hold all the solution, the conical flask is stood on an electric hotplate or
steam bath and the filtrate is kept boiling gently so that the warm solvent vapors
maintain the T of the solution undergoing filtration, and thus prevent premature
deposition of crystals on the filter or in the neck of the funnel.

18
 - If the solid does separate out on the filter it must be scraped back into the
first flask, re-dissolved and re-filtered.
- After filtration, the solution must always be clear before cooling is
attempted.
Note: Hot gravity filtration:this step is an optional if there is no visible particulate
matter and the solution is the expected color (most Organic compounds are white
or light yellow).

3. Gradual cooling for the hot solution at room T to deposit the crystals thus
causing the dissolved substance to crystallize out, then wash the container with
cold water from the out side followed by putting it in an ice bath to form fine
shape and large crystals (sudden cooling will affect the crystal shape and broke
it), you can use the glass rod to enhance the formation of crystals through nucleus
creation.
a. If large crystals are desired, any solid which may have separated from the
filtered solution should be re-dissolved by warming then wrapping the
flask in a towel or cloth, and allowed to cool slowly.
b. If small crystals are required, the hot saturated solution should be stirred
vigorously and cooled rapidly in a bath of cold water or of ice.
c. If crystallization does not take place rapidly, this maybe due to the
absence of suitable nuclei for crystal growth. The flask should be
scratched below the surface of the solution with a glass rod, the fine
scratches on the wall (and the minute fragments of glass produced) may
serve as excellent nuclei for crystal growth.

4. Separating the crystals from supernatant solution (the mother liquid) by

vacuum/Suction filtration using the filter paper fitted in a Buchner funnel which
fixed on filter flask connected to the vacuum with a rubber tube.

5. Air Drying of the crystals or dry the crystal in an oven at 75°C for 30 minutes.

Measurement of melting point

After drying, the level of purity of the resulting solid is tested by taking a melting
point range of the solid and comparing it to an accepted melting point range if one exists
or by TLC (thin layer chromatography) or by spectrophotometer method.
If the solid found impure is again re-crystallized from fresh solvent and the process is
repeated until the pure compound is obtained, this often means until the melting point is
unchanged, but confirmation by the other method specified above is desirable.

19
Exp 3: Synthesis of p-nitroacetanilide.

Principle
Mono-substituted product of primary amine can not generally be prepared by direct
action of appropriate reagent, it is usually necessary to protect the amine group, for
example by acetylation. Thus the aniline can be transformed to acetanilide by action of
acetic anhydride. The nitration of acetanilide leads to p-nitroacetanilide (main product)
and minor amount of the ortho isomer.
O O O

HN CH3 HN CH3 HN CH3

HNO3/H2SO4 NO2
+

NO2
major minor
Procedure
• In 250 ml conical flask, dissolve 2 g of finely powdered, dry acetanilide in 3 ml of
glacial acetic acid (using a graduated cylinder).
• Stir the mixture and add immediately, using the dispenser, 4 ml concentrated
sulfuric acid (caution). The mixture becomes warm and a clear solution results
upon stirring the solution.
• Surround the conical flask with ice.
• Put into a small test tube, 1 ml of concentrated HNO3 (caution), using the
dispenser, and pipette 0.6 ml of concentrated H2SO4, stir the reaction mixture and
make it cold by using the same ice bath above.
• When the temperature of the solution in the Erlenmeyer flask falls to 2-4 ºC, (use
a thermometer), run in the acid mixture (HNO3 – H2SO4) gradually while the
temperature is maintained below 10 ° C.
• After all the mixed acid has been added, remove the conical flask from the
freezing mixture and allow it to stand at room temperature for 15 minutes.
• Pour the reaction mixture into 250 ml beaker containing nearly 25 g, of crushed
ice. The crude nitroacetanilide (yellow) is at once precipitated. Allow to stand for
ten minutes.
• Filter with suction on a Buchner funnel fitted with a filter flask and connected to
the water vacuum pump, wash the precipitate thoroughly with cold water until
free from acid, (test the wash water by litmus paper), and then drain well.

20
 Recrystallization of p-nitroacetanilide
• Place a small beaker filled with ethanol in your ice bath.
• Recrystallize the pale yellow product from alcohol (caution), filter at the pump,
wash with a little amount of cold alcohol and air dry on a filter paper (the yellow
o-nitroacetanilide remains in the filtrate).
• Place the filter paper on a white paper, write your name, section, product name
and physical state.
• Determine the weight and melting point, calculate the percentage yield. The
melting point of the pure product (colorless crystalline solid) is 214 °C.

Question
1) Explain why the main product is the para-isomer.
2) Explain the mechanism of the above SE reaction.
3) Draw the structures of nitronium ion, nitrosonium ion, sulfonium ion.
4) If the nitration is made on the free aniline, write the expected products of this reaction.
5) How can you prepare the p-nitroaniline?

21
Exp 5: Synthesis of Quinoline Derivative (a) and (b).

Principle
The quinoline nucleus is the heterocyclic component of several naturally occurring
alkaloids of which the antimalarial compound, quinine, is the best known. It is also
present in synthetic antimalarial (e.g. Chloroquine) and the amebicide, 5-chloro-8-
hydroxy-7-iodoquinoline (Enterovioform).
Cl

N I N
OH
Quinoline 5-chloro-8- hydroxy-7-iodoquinoline

The Following two-step synthesis yields 2-hydroxy-4,8-dimethylquinoline (4) which can

be written in two possible tautomeric forms (4a) and (4b) as shown bellow:
CH3

+ O O O
-EtOH H2SO4
NH2 H3C O CH3 O
CH3 N
ethylacetoacetate H
o-toluidine (2) CH3 acetoacetyl-o-toluidine
(1)
(3)
CH3 CH3

Or
N OH N O
H
CH3 (4a) CH3 (4b)

2-hydroxy-4,8-dimethylquinoline

Procedure
a) Synthesis of acetoacetyl-o-toluidine (3)
• Heat a mixture of 3.08 g (3.0 ml) ethylacetoacetate (2) and 2.5 g (2.53 ml) o-
toluidine (1) rapidly to its boiling point in a dried 100 ml round-bottom flask for 3
minutes on a heating mantle with a couple of boiling chips.
• Pour the resulting solution into a small beaker and allow it to cool in an ice bath
until a solid product (pale yellow) should precipitate.
• Recrystallize the solid product from ethyl acetate, decant, filter and wash twice
with cold dilute HCl 10% (5-10 ml) followed by distilled water wash (20 ml) on
the filter paper.
• Air dry the product on a pre-weighed filter paper.
• Record the melting point and the yield.

22
b) Synthesis of 2-hydroxy-4,8-dimethylquinoline (4)
• Add 1 ml of concentrated sulfuric acid (caution) slowly with swirling to 1 g of
acetoacetyl-o-toluidine (3) from step a above in a 100 ml conical flask and
subsequently maintain the flask at 100 °C for 15 minutes on a water bath.
• Pour the resulting solution into 20 ml of water after cooling to room temperature.
• Collect the white solid product and recrystallize carefully from aqueous ethanol,
wash with cold water.
• Air dry and place the pre-weighed filter paper on a white paper, write your name,
section, product name.
• Record the percentage yield and melting point.

Questions
1) Draw the structure of quinine.
2) Which one of the two tautomer (4a) and (4b) is a more accurate representation of the
molecule (the predominant form)?
3) Explain the mechanism of the above two-step synthesis.
4) Devise a synthesis of 2,4-dihydroxyquinoline

23
Exp 7: Synthesis of azodystuffs: Synthesis of phenyl azo-2 naphthol

Principle
The preparation of an azodye consists of the following two step process:
Step1: The diazotization of an aromatic compound containing a primary amino group
(diazonium salt preparation)
Stcp2: The formation of azodye: This involves the coupling of the above diazonium salt
with a solution of phenolic substance in dilute alkali or with a solution of an aromatic
amine in dilute acid. This process is called diazo-coupling reaction.

Step1: Diazotization:
ArNH2 + HNO2/HX → ArN2+X-
Step2: Coupling
ArN2+X- + Phenolic compound (under dilute alkali media) → Azodye
ArN2+X- + Aromatic amine (under dilute acidic media) → Azodye

Reactions
The reaction equations of this preparation may be written as follows:
NaNO2 / HCl
NH2 N N Cl-
0-5 oC

Aniline Diazonium salt

OH
- NaOH 10% HO
C6H5 N N Cl +
C6H5 N N
-naphthol Azodye

Procedure
• Dissolve 2.45 ml (2.5 g) of pure aniline, from the dispenser bottle in the
fumehood, in a mixture of 8 ml of conc. HCl and 8 ml of water (caution)
contained in a 100 ml conical flask. Place a thermometer in the solution and
immerse the flask in a bath of crushed ice, cool until the temperature of the stirred
solution falls below 5 ºC.
• Dissolve 2 g of NaNO2 in 10 ml of water in a small beaker and chill the solution
by immersion in the ice bath.

24
 • Add the sodium nitrite solution in small volumes (1 ml at a time) to the cold
aniline hydrochloric solution and keep the latter well stirred with a glass rod. Heat
is evolved by the reaction, the temperature should NOT be allowed to rise above
10 °C (add few grams of ice to the reaction mixture if necessary). Otherwise
appreciable decomposition of the diazonium compound and of nitrous acid will
occur. Keep the diazonium salt solution cold.
• Prepare a solution of 3.9 g of pure 2-naphthol (grind using a pestle and mortar
then weigh) in 22.5 ml of 10 % NaOH solution in large beaker (sonicate until a
clear solution is obtained), cool the solution to 5 °C by immersion in an ice bath,
assisted by direct addition of about 10-15 g of crushed ice.
• Stir the naphthol solution vigorously and add the cold diazonium salt solution
very slowly with continuous stirring. A red color develops and red crystals of
phenyl-1-azo-2-naphthol soon separate.
• When all the diazonium salt solution has been added, allow the mixture to stand
in the ice bath for 10 minutes with occasional stirring.
• Filter the solution through Buchner funnel fitted with a filter flask and connected
to the water vacuum pump, wash well with water and drain thoroughly.
• CLEAN all your equipment, place the pre-weighed filter paper on a white paper,
write your name, section, product name and physical state.
• For purification recrystallize the product from glacial acetic acid (30-35 ml), filter
the crystals with suction, wash with a little alcohol (or methanol) to eliminate the
acetic acid and dry upon a filter paper. If the melting point is below 131 ºC
recrystallize the dry product from alcohol and calculate the percentage yield.

Questions
1) Explain the mechanism of the above two-step synthesis.
2) Explain the role of the following:
• The use of 10% aqueous sodium hydroxide in the coupling reaction.
• The low temperature (0- 10 °C) required for the diazotization reaction.
3) Draw the resonance form structures of benzene diazonium cation.

25
Exp 9: Separation of a mixture of water-insoluble compounds by
chemical extraction.

Principle
In the isolation of compounds from natural sources or after the completion of a reaction,
it is often necessary to separate mixture into acidic, basic or neutral components. The
chart in Figure 4-1illustrates the method.
You should separate an approximately 1 g portion of the mixture which is provided. In
each mixture there are at least two components of the following:
A carboxylic acid, phenolic compound, amine, carbonyl compound (aldehyde or ketone).
Caution
You should take a great care when using the diethyl ether, it is highly flammable and all
Bunsen Burners in the Laboratory should already be switched off.

Procedure
• Dissolve the mixture in about 30 ml of diethyl ether (caution).
Step 1: Extraction and separation of the carboxylic acids (Benzoic acid).
• When using a separatory funnel one must:
1. Shake with the stopcock closed and the funnel stoppered.
2. Shake gently and release any gas pressure buildup cautiously from stopcock. Do
NOT aim the funnel at another person.
3. Let the separatory funnel stand in the upright position and REMOVE the stopper
until the biphasic layers separate.
4. Drain the required (you must understand solubility) layer into a labeled flask.
• Shake the ethereal solution in a small separatory funnel with 20 ml of 10%
aqueous sodium carbonate solution (evacuate the build up of pressure and stand
until the two layers separate).
• Separate the lower aqueous phase, collect them in a 250 ml labeled beaker (A)
and repeat the extraction two times with further portions (10 ml for each) each
time separate the lower layer and add it to the beaker containing the aqueous
layer.
• Wash the alkali ethereal solution with 10 ml of water and add the wash water to
the aqueous alkaline extracts. Set aside the ethereal solution E1 for step 2.
• Acidify the alkaline extract with 10% HCl solution, shake and check the pH with
litmus paper.
a) If a solid acid forms (white foam), separate it by filtration, wash with a little
amount of cold water (why?) and then purify it by recrystallization from suitable
solvent.
b) If no solid forms, extract the acid aqueous solution two times with ether (20, 10
and 10 ml). Wash the ethereal extracts with 10 ml of salt saturated water (why?).

26
 Dry the ethereal solution over anhydrous sodium sulfate and then distill off the
ether using a Rotary Evaporator.

Step 2: Extraction and separation of phenolic compounds (β-naphthol).

• Extract the original ether solution (E1) with 10% sodium hydroxide solution (20,
10 and 10 ml), shake, evacuate, stand and separate the lower layer into a labeled
beaker (B).
• Wash the ether solution with 10 ml of water and add the wash water to the
aqueous alkaline extracts to beaker B, preserve the residual ether solution (E2) for
step 3.
• Acidify the aqueous alkaline extract with 10% hydrochloric acid (check with
litmus paper) and then continue as explained in step 1 (a or b).
Step 3: Separation an extraction of amines
• Extract ether solution (E2) with 10% hydrochloric acid (20, 10 and 10 ml).
• Wash the ether solution with 10 ml of water and add the wash water to the
combined acid extracts. Set aside the residual ether solution (E3) for step 4.
• Render the entire acid extracts alkaline with 10 % sodium hydroxide (check with
litmus).
• Saturate the aqueous extracts with commercial salt (why?), extract with ether (20,
10 and 10 ml) and then continue as explained above in step 1 (b).
Step 4: Separation of neutral compounds
• Filter ether solution (E3). Distill off the ether at Rotary Evaporator.

Questions
1) Write the reaction equation which would be carried out during the several steps of
extraction, and separation.
2) If the extraction of the original ethereal solution is started with 10% aqueous NaOH,
what would happen, explain why?
3) How could you identify the different components separated from the above given
mixture.
4) Draw the structure of the following compounds: Aniline, β-naphthol, phenol, benzoic
acid, benzaldehyde, acetophenone, salicylic acid, benzophenone, toluidine, ortho xylol.
Mention their water solubility and their physical state.
5) How can you separate a mixture of testosterone and estradiol? Write the reaction
equation.

27
Figure 4-1:

28
Exp 8: Separation of Benzoic Acid from Acetanilide mixture.

Principle
The separation of benzoic acid depends on the treatment of the mixture (benzoic acid +
acetanilide) with an aqueous solution of sodium carbonate and formation of water soluble
salt (sodium benzoate). The benzoic acid is then liberated by acidification of alkaline
filtrate.
2 C6H5COOH + Na2CO3 → 2 C6H5COO- Na+ + CO2 + H2O
C6H5COO- Na+ + HCl → C6H5COOH + NaCl
The acetanilide, which is not affected by the alkaline reagent, can be separated by
filtration.

Procedure
a) Separation of the mixture
• To a 100 ml conical flask, containing 20 ml of aqueous sodium carbonate
(10%w/v) taken from the appropriately labeled bottle fitted with a dispenser, pour
the mixture of benzoic acid (1 g) and acetanilide (1 g) in small portions with
continuous stirring (glass rod) until the benzoic acid dissolves completely. If the
benzoic acid does not dissolve (you still see CO2 gas bubbles evolves from the
flask) place in a sonicator for a few minutes (not more than 5).
• Using a 250 ml conical flask and filter funnel separate the insoluble acetanilide by
filtration on a filter paper and keep away the filtrate of sodium benzoate (A).
• Wash the acetanilide crystals three times with 5 ml of cold water in order to
eliminate the traces of alkali and any salts, add the wash water portions to the first
filtrate (A).
b) Purification of acetanilide
• Recrystallize the crude acetanilide by dissolving it in a suitable amount of boiled
water on a hot plate. Boil the solution in a water bath and filter it while “it is still
hot” through a small piece of cotton fitted in a funnel on a 250 ml conical flask.
• Cool in an ice filled ice bath and separate the crystals of acetanilide by filtration
under suction using a pre-weighed filter paper.
• Wash the crystals with 5 ml of cold water X 3 and drain well.
• Place the filter paper on a white paper, write your name, section, product name
and physical state.
• Air dry the crystals on a filter paper and determine their weight and melting point.

29
c) Precipitation and purification of benzoic acid
• Acidify the basic solution of sodium benzoate (A) by adding gradually a 10%v/v
of aqueous hydrochloric acid (verify the pH of the medium by the use of litmus
paper).
• Separate the benzoic acid by filtration under suction using a pre-weighed filter
paper and wash it three times with 5 ml of water.
• Purify it by recrystallization from water.
• Place the filter paper on a white paper, write your name, section, product name
and physical state.
• Dry the crystals and determine their weight, percentage yield and melting point.

Questions
1) Could you use another solvent for the crystallization of benzoic acid? Explain and give
an example.
2) Propose a method to separate and purify a mixture of Iodoform and benzoic acid,
knowing that the Iodoform is a yellow solid, very slightly soluble in water (practically
insoluble). One gram dissolves in 60 ml of cold ethanol.
3) Propose a method to separate a mixture of β-naphthol and benzoic acid, write the
reaction equations.
4) What is the expected amount of benzoic acid used in the given mixture regarding to
the amount (20 ml) of 10% aqueous sodium carbonate used in the above experiment?

30
Exp 8: Reaction of Esterification: Preparation of n-Butyl acetate.

Principle and mechanism

The interaction between an acid and an alcohol is a reversible process and proceeds very
slowly, for example:
CH3COOH + CH3(CH2)2CH2OH CH3COOCH2(CH2)2CH3 + H2O
Acetic acid n-Butyl alcohol reversible n-Butylacetate water

Equilibrium is attained only after refluxing for several days. If, however, about 3 percent
(on the weight of alcohol) of either concentrated sulfuric acid or of dry hydrogen chloride
is added to the mixture, the same point of equilibrium can be reached in a few hours. The
use of mineral acid as catalyst in the esterification was introduced by E. Fischer and
Speier in 1895.
When equimolecular quantities of acid, alcohol are employed, only about 2/3 of the
theoretically possible yield of ester is obtained. According to the law of mass action, the
equilibrium may be displaced in favor of the ester by the use of an excess of one of the
components. It is frequently convenient to use an excess of the acid, but if the acid is
expensive, a large excess of the alcohol is more generally employed. This method of
esterification, in general, gives good yields with primary alcohol substrates.
The mechanism of the acid-catalyzed formation of ester, which applies to the vast
majority of cases, involves the following steps:
• Attack by a proton on the negatively polarized carbonyl oxygen to produce an
oxonium ion (I). The carbonyl carbon thereby becomes more positive and more
susceptible to attack by the nucleophilic alcohol molecule.
• Attack of (I) by the alcohol to produce the addition product (II). This can form a
second intermediate (III) by proton transfer.
• Loss of a molecule of water from (III), followed by loss of a proton gives the ester
(IV).

O H H OH
-H+ O O
R OH
R OH R OH (I) R OH R'-OH OH
R' (II)

OH2 O
-H2O R C OH R C O -H+
R OH C
O O H R O
O R' R'
R' (III) R' (IV)

The above reactions are all reversible and an excess of one reactant must be
employed to favor ester formation.

31
Procedure
• Mix together 9.3 g (11.5 ml) of n-butyl alcohol and 15 g (15 ml) of glacial acetic
acid in a 100 ml round-bottomed dry flask.
• Add cautiously 0.2-0.3 ml of concentrated H2SO4 (use a small measuring cylinder
or a calibrated dropper pipette) and add a couple of glass beads to prevent
bubbling.
• Attach a Liebig condenser and reflux the mixture gently on a heating mantle for
1.5 hours.
• Pour the reaction mixture into about 60 ml of water placed in a separatory funnel,
shake, evacuate, stand until the layers separate and remove the upper layer of the
crude ester.
• Wash the crude ester with about 25 ml of water, followed by about 6 ml of
saturated sodium bicarbonate solution and with 12 ml of distilled water, after each
addition shake, evacuate, stand then remove the lower layers from each
separation.
• Pour the crude ester (the remaining upper layer in the separatory funnel) in a
small beaker and add 1.5 g of anhydrous magnesium sulfate (leave for 15
minutes).
• Filter through a small funnel containing a fluted filter paper or a small plug of
cotton or glass wool into a dry 10 or 100 ml graduated cylinder.
• For purification filter directly into a distilling flask with a condenser attached and
add two boiling chips and distill from wire gauze. Collect the pure n-butyl acetate
at 124-125 °C.
• Calculate the percentage yield and then dispose of the ester into the reagent bottle.

Questions
1) Propose a good method for the synthesis of the above ester, using an acid derivative
other than the acid itself. Explain the mechanism of the reaction and compare it with the
Fischer esterification.
2) Explain the role of the following:
• the use of one of the two reactants (alcohol or acid) in excess.
• the addition of traces of mineral acid.
• Clarify if the hydroxyl group in the formed water is resulted from the alcohol or
the carboxylic acid.

32
Exp 6: Haloform Reactions: Synthesis of Iodoform.

Principle and mechanism

Methyl Ketones CH3COR and the corresponding secondary alcohols CH3CHOHR react
with –OH, X2 to give the trihalogenomethane CHX3 (haloform reaction). Thus, acetone
CH3COCH3 yields the sparingly Iodoform, probably by the following series of reactions.

The –OH, I2 may be generated in situ from potassium iodide solution and sodium
hypochlorite (NaOCl) solution.
The mechanism of the reaction is probably as follows:
-
O OH O I2 O O O -
OH
H3C CH3 H3C CH2 H3C CH2I + I -
H3C CHI2 H3C CI3

O- O O
NaOH O
H3C CI3 H + CI3 CHI3 +
H3C O H3C O -
OH H3C O-Na+

Procedure
• Place a solution of 1.5 g of potassium iodide in 25 ml of water in a 250 ml conical
flask and add 0.5 ml acetone.
• Slowly add, with frequent shaking a 5% w/v solution of sodium hypochlorite* as
long as any yellow precipitate of Iodoform is formed (about 15 ml are required).

* Commercial 10-14 % sodium hypochlorite solution should be diluted with an equal

volume of water.

Questions
1) What is the pharmaceutical use of Iodoform?
2) Propose a mechanism for the reaction of ethanol with –OH, I2.

33
Exp 4: Chemical drawing lab

Pharmaceutical Organic Chemistry PC Drawing Lab

Student Name :-...............................................................................

Section :- ........................................................................................

Part : Draw the following compounds using the software to name your organic molecule

O
N

O
O

butyl acetate N-phenylacetamide

Part : Generate structures from the following chemical names

Aniline Ortho-toluidine

N N

Part : You should be able to draw mechanisms on this software, as shown bellow

H
: O: +
O
H
O
H+ ..
R + + HO
H+
R .. .. R
R O R O R O..
+O
H H

OH O
-H+
H + ROH
R O R OH
+

Remember to show every part of your work to your supervisor in order to get marked

34
Exp 12: Synthesis of Paracetamol and Phenacetin.

Principle
Phenacetin may be conveniently prepared in the laboratory from p-aminophenol. The
latter is readily acetylated with acetic anhydride to give p-acetyaminophenol, this is
ethylated in the form of sodium derivative to yield acetyl p-phenetidine (Phenacetin):
O O

NH2 HN CH3 HN CH3

O O O
Et-I
+
CH3 CH3 EtO-Na+aq

OH OH O
CH2CH3

p-Aminophenol Paracetamol Phenacetin

Procedure
a) Synthesis of Paracetamol
• Suspend 5.5 g of p-aminophenol in 15 ml of water contained in 100 ml beaker or
conical flask and add 6 ml of freshly distilled acetic anhydride.
• Stir the mixture vigorously and warm on a water bath, the solid dissolves.
• Cool the solution, filter the solid acetyl derivative at the pump and wash with a
little cold water.
• Recrystallize the solid from hot water, and dry upon filter paper in the air.
• Calculate the percentage yield and determine the melting point.
b) Synthesis of Phenacetin
• Place 0.4 g of clean sodium * (caution) in a dry 100 ml round bottomed flask
equipped with a reflux condenser. Add 10 ml of absolute alcohol through the
condenser and allow the reaction to proceed until all the sodium dissolves. If all
the sodium has not disappeared after the vigorous reaction has subsided, warm the
flask on water bath until solubility is complete.
• Cool the mixture and add 2.5 g Paracetamol.
• Introduce 3.75 g (2 ml) of ethyl iodide slowly through the condenser and reflux
the mixture for 20 minutes.
• Pour 25 ml of water through the condenser at such a rate that the crystalline
product does not separate. (If crystals do separate, reflux the mixture until they
dissolve).
• Cool the flask in the ice bath, collect the crude Phenacetin with suction and wash
with a little cold water.
• Dissolve the crude product in 20 ml of absolute ethanol, add 20 ml of hot water
and allow it to cool. Collect the pure Phenacetin at the pump and dry in the air.

35
 • Record the percentage yield and melting point.
* Caution: Sodium must be handled with great care and should never be allowed to come
into contact with water as a dangerous explosion may result (why?). It should be
distributed by the instructor. Even the scrap pieces of sodium should never be thrown into
the sink or the waste basket. They should be destroyed by adding in small portions to a
large quantity of methylated spirit.

Questions
1) Mention the pharmaceutical uses of Paracetamol.
2) Explain the mechanism of the above reactions.
3) Could you prepare the Phenacetin in an aqueous solution? Explain why.
4) Write a series of reaction for the synthesis of p-aminophenol from phenol.

36
37
38
39
Boiling chips & reflux definitions

Boiling chips are small, irregularly shaped stones added to liquids to make them boil
more smoothly. They provide nucleation sites so the liquid boils easily without becoming
superheated. Without boiling chips, a liquid being heated in a smooth container can
become superheated and "bump" in a sudden, sometimes violent release of vapor. This
sudden burp of gas can cause your solution and reagents to be thrown out of your
container, sometimes into fractional column or condenser, destroying a reaction.

Boiling chips are typically made of a porous material, such as alumina, calcium carbonate
or carbon, and often have a non-reactive coating of Teflon (PTFE). This ensures that the
boiling chips will provide effective nucleation sites, yet be chemically inert.

Never add boiling chips to an already hot liquid, as it could cause a large amount of vapor
to form all at once. This could cause hot liquid to be expelled from the container, possibly
causing heat or chemical burns

Reflux is a technique used in chemistry to apply energy to reactions over an extended

period of time.

A liquid reaction mixture is placed in a vessel open only at the top. This vessel is
connected to a Liebig condenser, such that any vapors given off are cooled back to liquid,
and fall back into the reaction vessel. The vessel is then heated vigorously for the course
of the reaction.

The advantage of this technique is that it can be left for a long period of time without the
need to add more solvent or fear of the reaction vessel boiling dry as any vapor is
immediately condensed in the condenser. In addition, as a given solvent will always boil
at a certain temperature, you can be sure that the reaction will proceed at the same
temperature; by careful choice of solvent, you can even control what that temperature is.
The constant boiling action also serves to continuously mix the solution. A beaker of
water between the reactants and the heat is often used as a safety precaution when using
flammable reactants and a Bunsen burner in order to keep the flame away from the
reactants.

Fig (1): Diagram of typical simple reflux apparatus

40
 Instructions for using the vacuum pump:

1. Connect the Büchner funnel to the filter flask and to the vacuum pump by means of a
rubber tube.
2. Site the filter paper (use proper size) on the Büchner funnel and wet it with suitable
clean solvent.
3. Turn the apparatus on, and filter your sample by slowly pouring it into the center of
the filter paper.
4. Rinse the solid on the filter paper with more clean solvent.
5. Turn the apparatus off when finished and clean the glassware.

Fluting filter paper

“Fluted “filter paper (LEFT) is used when you wish to

separate a liquid and a solid, keeping the liquid and
discarding the solid. This arrangement of folds in the
filter paper will allow the liquid to pass through it
very quickly and give you a lot of surface area on
which to collect the solid “impurity”.

If you wished to keep the solid sample and discard

the liquid, you would make a simple cone of the filter
paper (RIGHT). This would make it much easier to
remove the solid from the filter paper than if it was
on a fluted filter paper.
To “flute” filter paper, you do the following:

Fold the large circle of filter paper in half (2), then in quarters (3) being careful not to press the creases too hard as this tends to
weaken the paper and cause possible tears later on.
1 2 3

Take the straight edge on one side and fold back to the centre fold (4). Do the same on the other side (5). You should now have a
“fan” with alternating folds. Open the “fan” up with the centre fold going away from you (6).

41
4 5 6

Starting at one side, fold the straight edge up towards the first fold (7). Fold back along the preformed fold and then fold again
towards the centre fold (8). Reverse the direction of the centre fold (9). Continue folding back and forth until you get another
smaller-sized fan. ( 10, 11, 12)

7 8 9

10 11 12

Open the “fan” and look for the two areas called the “boxes”, where there are two folds going in the same direction instead of
alternating (13). Pinch the paper (14) to make another fold between the two folds in each box (15). Then invert the filter paper before
you place it in the glass funnel. [NOTE: inverting the filter paper will insure that any grease or dirt transferred from your fingers will
be on the “inside” of the filter paper rather than the “outside”, when it is being used. Whatever is collected on the inside of the filter
paper is something that will be disposed of.

13 14 15

42
 ‫نظام المختبر (‪(Lab Instructions‬‬

‫تسليم التقرير في المكان المخصص‬ ‫‪.1‬‬

‫امتحان قصير (في بعض األيام)‬ ‫‪.2‬‬
‫البدء بشرح الجزء النظري‬ ‫‪.3‬‬
‫أخذ الحضور و الغياب‬ ‫‪.4‬‬
‫البدء بتعليقات على الجزء العملي السابق‬ ‫‪.5‬‬
‫البدء بشرح الجزء العملي‬ ‫‪.6‬‬
‫اكمال الجزء المتبقي من العمل للتجربة السابقة و عمل حسابات‬ ‫‪.7‬‬
‫البدء بالجزء العملي و التقييم خالل العمل‬ ‫‪.8‬‬
‫مغادرة المختبر‬ ‫‪.9‬‬

‫على كل طالب قراءة التعليمات الخاصة بالمختبر‬

‫التعليمات‪:‬‬

‫‪ .1‬ارتداء معطف المختبر ‪ Lab Coat‬و إغالقه قبل الدخول الى المختبر‪.‬‬
‫‪ .2‬التواجد داخل المختبر في الوقت المحدد و التزام االنتظام لحين تواجد المسؤول‪.‬‬
‫‪ .3‬عدم مغادرة المختبر تحت أية ظروف إال بإذن من المسؤول‪.‬‬
‫‪ .4‬يمنع إدخال الطعام و الشراب إلى المختبر منعا باتا‪.‬‬
‫‪ .5‬يمنع استخدام الهواتف النقالة منعا باتا‪.‬‬
‫‪ .6‬على الطالب مراجعة لوحات االعالنات الخاصة بالمختبر بشكل دوري‪.‬‬
‫‪ .7‬يمنع الجلوس على البنشات فيوجد هناك كراسي مخصصة للجلوس‪.‬‬
‫‪ .8‬سوف يتم تخصيص مكان من المختبر لوضع الحاجيات الشخصية‪.‬‬
‫‪ .9‬يمنع التحويل الداخلي بين الشعب إال من خالل دائرة القبول و التسجيل بشكل رسمي‪.‬‬

‫التقارير‪:‬‬
‫‪ .1‬على كل طالب كتابة تقرير كامل و واضح منظم و مرتب و يقوم بتسليمه إلى المسؤول في نهاية‪/‬‬
‫بداية المختبر القادم و إحضاره في ملف ذو لون محدد يتم تحديده من قبل المسؤول‪.‬‬
‫‪ .2‬كتابة التقرير بقلم أزرق جاف ‪ /‬أسود فقط ال غير‪.‬‬
‫‪ .3‬يمنع نسخ التقرير من زميل آخر‪ ،‬و اذا تم ذلك فكال التقريرين يتم رصد العالمة صفر‪.‬‬
‫‪ .4‬ال تستخدم مطلقا اختصارات غير علمية‪.‬‬
‫‪ .5‬ال تنسى كتابة الوحدات في جزء الحسابات‪.‬‬
‫‪ .6‬لن يقبل تقرير مختبر ما لم يتم حضور التجربة العملية‪.‬‬
‫‪ .7‬يسلم التقرير حال دخول الطالب إلى المختبر مباشرة‪.‬‬
‫‪ .8‬يتم توزيع التقارير مرة أخرى في المختبر بعد تدقيقها لكتابة الحسابات من المختبر السابق و إعادة‬
‫تسليمها ليتم تدقيقها و تقييمها من قبل المسؤول‪.‬‬
‫‪ .9‬مدة مراجعة عالمة التقرير مع المسؤول تتم في نفس يوم توزيع التقارير فقط بعد اطالعك على‬
‫اإلجابة النموذجية‪.‬‬

‫العمل‪:‬‬
‫يتم تقسيم الطالب على هيئة مجموعات إختيارية من قبلهم في بداية الفصل و تسجيل أسمائهم ‪،‬كل‬
‫مجموعة مكونة من طالبين و عليهم‪:‬‬
‫‪ .1‬اإللتزام خالل الفصل بإستعمال خزانة األدوات الخاصة المعينة له و المحافظة على عدد و نظافة محتوياتها‪.‬‬
‫‪ .2‬تنظيف األدوات و تسليمها إلى المسؤول بعد اإلنتهاء من العمل‪.‬‬
‫‪ .3‬اإللتزام بالعمل بروح الفريق الواحد و بهدوء و اتقان مع الحرص على التعامل مع المواد الخطرة‪.‬‬
‫‪ .4‬تسليم نتيجة العمل‪.‬‬
‫‪ .5‬المحافظة على األدوات و األجهزة في المختبر و معرفة كيفية استخدامها‪.‬‬
‫‪ .6‬يلقى على عاتق كل مجموعة باالضافة إلى عملها بعض المسؤوليات األخرى و التي يتم تحديدها من‬
‫خالل المسؤول‪.‬‬

‫أي تقصير أو ازعاج يبدر من المجموعة سوف يتم تبديل أحد االعضاء فيها بما يتناسب و المصلحة العامة‪.‬‬

‫اإلمتحانات القصيرة و النهائية‪:‬‬

‫مذكور بعض التعليمات عنها في وصف المساق و اإلمتحان النهائي تعطى التعليمات في حينه‪.‬‬

‫‪43‬‬
 ‫الحضور و الغياب‪:‬‬

‫إن غيابك عن مختبر واحد سوف يؤثر في تقييمك و أدائك و عالماتك‪.‬‬

‫‪ .1‬يمنع التعوي ض في مختبر آخر غير الذي يسجل فيه الطالب اإل تحت ظروف قاهرة و بإذن من المسؤولين‪.‬‬
‫‪ .2‬في حال مصادفة يوم عطلة سوف يتم التعميم عن آلية التعويض الجماعي على لوحة إعالنات المختبر‪.‬‬
‫‪ .3‬على الطالب أن يتابع عدد غياباته حسب التعليمات‪.‬‬
‫‪ .4‬يمنع التعويض منعا باتا خالل فترة اإلمتحانات‪.‬‬

‫كسر األدوات الزجاجية‪:‬‬

‫على الطالب أن يعلم المسؤول مباشرة ويضع األداة المكسورة بحذر في الصندوق المخصص للنفايات‬
‫الزجاجية المكسورة و يوقع على نموذج الكسر‪.‬‬

‫أدوات على الطالب أن يحضرها كل مختبر‪:‬‬

‫‪Clean white lab coat, gloves, calculator, lab manual, marker, towel, goggle, mask, colored file‬‬
‫‪and badge.‬‬

‫التخلص من النفايات‪:‬‬
‫تذكر في أول مختبر‪.‬‬

‫أجهزة من حولك ال بد من معرفتها‪:‬‬

‫تذكر في بداية المختبر‪.‬‬

‫التقييم‪:‬‬
‫سوف يقيم الطالب على عمله و سلوكه و التزامه بالتعليمات و أدواته و التزامه بالوقت كما في النقاط التالية‬
‫بشكل أسبوعي‪:‬‬

‫)‪1. Attention to safety /Attendance time (… marks‬‬

‫)‪2. Towel / Hair / cap (….. marks‬‬
‫)‪3. Lab coat/ Goggles, gloves / (….. marks‬‬
‫)‪4. Team work / Attitude (….. marks‬‬
‫)‪5. Working methods (….. marks‬‬
‫(‪6. Cleaning tasks (….. marks‬‬

‫)‪Total mark evaluation (15 marks‬‬

‫مغادرة المختبر‪:‬‬

‫يمنع مغادرة المختبر إال ‪:‬‬

‫‪ .1‬بعد اإلنتهاء من العمل‪.‬‬
‫‪ .2‬تنظيف األدوات و مكان العمل‪.‬‬
‫‪ .3‬التوقيع على نموذج المختبر واعالم مشرف المختبر‪.‬‬

‫‪44‬‬
Name:……………………..
Tidiness Clarity Report
ASU- Pharmaceutical Organic Chemistry Lab Report

Notes:

The Date was the work performed:

/ /20
Title of the Experiment:

1-Introduction:

A- Objectives of the Experiment:

B- Reactions Involved:
Note: Put the amounts of reactants and products under the balanced equations for the reaction:

45
B- Calculation:

46
Fill the spaces below then put your result in the space provided, finally detach this paper
and put your product in the circle, then give it to your instructor:

Student Name(s) 1-
2-
Section

Product Name

Color

Purity

47