Advanced Pharmaceutical Organic Chemistry Practical Text

See discussions, stats, and author profiles for this publication at: https://www.researchgate.
net/publication/348555466
A Practical Handbook of Advanced Pharmaceutical Organic Chemistry
Book · January 2021
CITATIONS READS
0 225
4 authors, including:
Jithendar Reddy Narender Boggula

Assam down town University CVRS College of Engineering
20 PUBLICATIONS 37 CITATIONS 59 PUBLICATIONS 254 CITATIONS
SEE PROFILE SEE PROFILE
All content following this page was uploaded by Jithendar Reddy on 07 February 2024.
The user has requested enhancement of the downloaded file.

As Per PCI New Syllabus
PRACTICAL HANDBOOK OF
ADVANCED PHARMACEUTICAL
ORGANIC CHEMISTRY
As Per PCI New Syllabus
PRACTICAL HANDBOOK OF
ADVANCED PHARMACEUTICAL
ORGANIC CHEMISTRY
Narender Boggula
Associate Professor
School of Pharmacy, Anurag Group of Institutions,
Venkatapur, Ghatkesar, Telangana, India - 500088
Dr. M. Ram Mohan

Professor
School of Pharmacy, Anurag Group of Institutions,
Venkatapur, Ghatkesar, Telangana, India - 500088.
Deepika B
Associate Professor
Nalanda College of Pharmacy, Cherlapally,
Nalgonda, Telangana, India - 508001.
Jithendar Reddy Mandhadi

Assistant Professor
Vaageswari College of Pharmacy, Thimmapur,
Karimnagar, Telangana, India - 505527.
TAURUS PUBLISHERS
# 3-2-330, Chappal Bazar, Kachiguda, Hyderabad - 500 027.
Ph: 9000002723
All rights are reserved. No part of this publications which is materiel protected by
this copyright notice may not be reproduced or transmitted or utilized or stored in
any form or by any means now known or hereinafter invented, electronic, digital
or mechnaical including photocopying, scanning, recording or by any information
storage or retreval system, wothout prior written permission from TAURUS
PUBLISHERS.
© 2020, by Publisher, all rights reserved
ISBN: 978-81-938138-7-4
125/-
TAURUS PUBLISHERS
# 3-2-330, Chappal Bazar, Kachiguda, Hyderabad - 500 027.
Ph: 9000002723
PREFACE
It is a matter of my duty and delight to bring out the book “Practical Handbook of
Advanced Pharmaceutical Organic Chemistry”. The idea of writing this book was
convinced when our own students found difficulty in getting a book suited to their
academic needs.
I feel immense pleasure to introducing “Practical Handbook of Advanced

Pharmaceutical Organic Chemistry” to the students of pharmaceutical sciences.
Primarily this book has been written for the D.Pharmacy, B.Pharmacy and Pharm
D students. The major thrust has been to make the book more students friendly.
The practical contents of the book are vital in the field of pharmaceutical sciences.
Experiments have been explained according to the syllabus.
The importance of a laboratory course attached to a theory course is undisputable

in science subjects. Chemistry is a practical science and an appropriate correlation
between the theory and practical leads to better understanding. Every effort has
been made to include these recent trends and knowledge in this book. Most of the
information in this book has represented in a very simple manner. The aim of this
book is to make the subject easy and understandable to the students.
We have made every possible effort to make this book informative and
useful to the teachers and students. I will be grateful to all the teachers and students
who will be kind enough to point out my mistakes that have escaped my attention.
Suggestions for future improvement are always welcome.
It is hoped that the book will be received favourably as an effective practical book
by both students and faculty of pharmacy.
The structure of this book is simple, self-explanatory and easy for the readers to
grasp the subject.
Authors
ACKNOWLEDGEMENTS
To write a book of this magnitude, it needs lot of patience, skills and expertise over
the subject, which I have gained because of opportunity given to me by my teachers
and friends. Writing a book is harder than we thought and more rewarding than we
could have ever imagined. We express our immense gratefulness to almighty for
will-power, patience, courage and dedication towards work has made me possible
for successful completion of this handbook.
I honestly acknowledge and warm gratitude to my parents, fellow colleagues and

my dear brothers for helping the authors for supporting directly and indirectly to
bring this book in time.
Preparing this book was a collective adventure and I am most grateful to all authors
for their cooperation and for the time and the effort they spent to write their respective
contributions. I appreciate also their patience, especially as the editing process took
much more time than initially expected.
Last but not least, we would also express a special thank to publishers for their
encouragement and publishing the book.
“The greatest challenge in life is discovering who you are. The second greatest is
being happy with what you find.”
Authors
SAFETY GUIDELINES
The organic chemistry laboratory has the potential to be very dangerous. This is
why it is extremely important that you follow all safety guidelines when you are in
the laboratory. As an ethical chemistry laboratory student you must make sure that
you understand and follow all safety precautions. Ignoring safety precautions may
result in a serious injury to yourself or another student. Any student working in an
unsafe manner is a danger to other students and will be asked to leave the laboratory.
Always adhere to the following safety guidelines:
 Wear eye protection. Chemicals can cause serious damage to your eyes, in-
cluding blindness. To prevent chemicals and other hazardous substances from
coming in contact with your eyes, safety glasses or goggles must be worn at
all times you or someone else is working in the laboratory. (If you must adjust
or clean your eye protection, step outside of the laboratory to do so.) Goggles
offer the best protection and are particularly recommended to guard against
splashes and explosions.
 Dress appropriately for lab. The less skin that is exposed, the better! Sandals
are not allowed in the laboratory because they expose your toes to chemical
spills and broken glassware. Shoes must be close-toed and offer the best pro-
tection when they are made from a non-porous material. Long-sleeved shirts/
blouses and long pants are recommended. If you choose to wear a shirt that
exposes your midriff, you must wear a lab coat. Lab coats are also recom-
mended to protect clothing you value. Avoid loose-fitting clothing and acces-
sories (e.g., scarves, ties, long necklaces, etc.) because they may cause spills
or come in contact with hazardous chemicals. Hair that is longer than shoulder
length must be tied back.
 Wear appropriate gloves. Gloves are required at all times when you are han-
dling chemicals and items that have been exposed to chemicals. Keep in mind
that different gloves protect against different types of chemicals. However,
once you have gloves on, this does not mean that you are free to touch every-
thing! For example, you do not want to rub your eye with a gloved hand once
you have handled chemicals. A good rule of thumb is to not touch anything
with your gloves that you do not want chemicals on. Obtain a new pair of
gloves if they develop a rip or tear.
 Keep the lab clean and neat. Avoid cluttering the lab bench or hood. Clutter can
lead to spills, so return items promptly to their proper locations. Do not place
personal items, such as bags and backpacks, on the floor as they may cause
others to trip. Promptly notify the laboratory instructor of any spills and clean
them up as instructed. Spills must be cleaned up as soon as possible to prevent
others from exposure to the spilled chemical. Inform the laboratory instructor
of any conditions that seem unsafe.
 Know how to transport chemicals safely. If you must transport a chemical out-
side of the laboratory, the chemical must be in a closed container (i.e., no open
beakers). Additionally, large bottles and particularly hazardous chemicals must
be transported in a safety carrier.
 Perform only authorized experiments. Unauthorized experimentation may ex-
pose you and your lab mates to unforeseen hazards.
 Do not bring food, drinks, or cosmetics into the laboratory. Eating, drinking, or
applying cosmetics in the laboratory can introduce toxic or corrosive chemi-
cals into your system. You particularly want to avoid any contamination to
your mouth or eyes.
 Immediately report all incidents to the laboratory instructor. An incident is any
injury or situation that might result in an injury. The laboratory instructor will
best know how to handle the situation and may also use the information you
provide to help other students avoid a similar difficulty.
 Read labels carefully. Only use the correct chemicals in the proper concentra-
tions. The wrong chemical or concentration could result in a violent reaction.
 Label vials and flasks. If you do not label a vial and then forget what it con-
tains, you will not know how to properly handle and dispose of its contents.
 Never pipette by mouth. Many organic chemicals are toxic or corrosive.
 Carefully inspect glassware for damage. Broken glassware may cause cuts, and
chipped or cracked glassware may break and spill its contents unexpectedly.
 Use caution when heating reactions. Avoid open flames whenever possible.
Use a stir bar or fresh boiling chip to avoid bumping (the sudden eruptive
release of vapour). Bumping can cause hot liquid to spray out of its flask. A
closed system should not be heated because the resulting increase in pressure
may cause an explosion that propels reagents or pieces of glass. Always insure
that an opening is present when heating a reaction. Do not heat any distilla-
tion pot to dryness because overheating could cause the remaining residue to
detonate.
 Vent separatory funnels into a fume hood or snorkel. Venting can cause the
release of harmful vapours. Never point the end of the separatory funnel at
someone’s face.
 Handle hot objects with caution. Hot glass, metal, or sand is often indistin-
guishable from cool glass, metal, or sand. Cautiously touch objects that have
been heated before handling them.
 Never work alone. Never use mouth suction. Never open the lid of a spinning
centrifuge. Do not perform any unauthorized experiments. Come and see your
instructor if you would like to perform an additional interesting or fun experi-
ment. He is probably willing to let you do it.
 Intimation. In case of accident, alert fellow students and immediately take an
appropriate action. Explain to your faculty/lab in-charge what happened and
seek further help if necessary.
CONTENTS
S. No. Experiment Name Page No.

1. Introduction to glassware and equipments used 1
2. Different techniques involving in the preparation of organic 15
compounds
3. Determination of melting point 21
4. Determination of boiling point 23
5. Determination of acid value 25
6. Determination of saponification value 26
7. Determination of iodine value 28
8. Synthesis of acetanilide 30
9. Synthesis of aspirin 32
10. Synthesis of benzanilide 33
11. Synthesis of phenyl benzoate 34
12. Synthesis of p-bromoacetanilide 35
13. Synthesis of benzil 37
14. Synthesis of cinnamic acid 38
15. Synthesis of 1-phenylazo-2-naphthol 39
16. Synthesis of dibenzalacetone 41
17. Synthesis of 2,4,6-tribromoaniline 42
18. Synthesis of m-dinitrobenzene 43
19. Synthesis of benzoic acid 44
20. Synthesis of benzophenone oxime 45
21. Synthesis of p- nitroacetanilide 47
22. Synthesis of p-nitroaniline 48
23. Synthesis of p- bromoaniline 49
24. Synthesis of salicylic acid 50
25. Synthesis of 5-nitrosalicylic acid 51
26. Synthesis of benzoic acid 52
27. Synthesis of nitrobenzene 54
28. Synthesis of 2-iodobenzoic acid 55
29. Synthesis of cyclohexanone 57
30. Synthesis of picric acid 59
31. Synthesis of hippuric acid 60
32 Microwave Assisted Hydrolysis of Benzamide 61
33 Synthesis of Tetrahydrocarbazole 62
34 Synthesis of Benzoin 63
35 Synthesis of Phthalimide 65
36 Systematic Quantitative Analysis of Organic Compounds 66
37 Separation of Organic Binary Mixture 77
Experiment - 1
INTRODUCTION TO GLASSWARE
AND EQUIPMENTS USED
Pharmaceutical Chemistry is concerned primarily with modification of structures

having known physiologic or pharmacologic effects and with analysis of drugs.
Modern drug design as compared with, “Let’s make a change on an existing
compound or synthesize a structure and see what happens”, and is fairly recent
discipline, still in its infancy. It is based upon modern chemical techniques utilizing
recent knowledge of disease mechanism and receptor properties. Organic chemistry
is a sub-discipline of chemistry that studies the structure, properties and reactions of
organic compounds, which contain carbon in covalent bonding. Study of structure
determines their chemical composition and formula. Study of properties includes
physical and chemical properties, and evaluation of chemical reactivity to understand
their behaviour. The study of organic reactions includes the chemical synthesis of
natural products, drugs, and polymers, and study of individual organic molecules in
the laboratory and via theoretical (in-silico) study.
Laboratory glassware refers to a variety of equipment used in scientific work,

and traditionally made of glass. Glass can be blown, bent, cut, molded, formed
into many sizes and shapes, and is therefore common in chemistry, biology, and
analytical laboratories. Many laboratories have training programs to demonstrate
how glassware is used and to alert first–time users to the safety hazards involved
with using glassware. Glassware used as laboratory apparatus offers a wide range
of containment and transport functions for solutions and other liquids used in
laboratories. Most laboratory glassware is manufactured with borosilicate glass, a
particularly durable glass that can safely be used to hold chemicals being heated
over a flame and to contain acidic/corrosive chemicals. All laboratory glassware
should be cleaned immediately following use to prevent chemical residue from
congealing or hardening.
The synthesis, purification, and identification of compounds are perhaps the most
common tasks of the chemist. The techniques used for synthesis vary greatly,
but always require decisions about what type of glassware to use, whether to heat
or cool the reactants, and so on. The purification of solid products is often done
PRACTICAL HANDBOOK OF ADVANCED PHARMACEUTICAL ORGANIC CHEMISTRY
by recrystallization, while liquids are purified by distillation. Compounds can
be identified by a great variety of sophisticated techniques, but often the initial
task is to determine what elements are present and in what amounts. Elemental
composition can be done by many procedures, but classical gravimetric and
volumetric analyses remain among the most reliable. The operations given here are
for the basic techniques that you will encounter in these procedures of purification
and identification.
Beakers
Conical flask
Round bottom flask (single neck)

Round bottom flask (triple neck)
Round bottom flask (four neck)
Round bottom flask (double neck)

Flat bottom flask
Glass rod
Spatula

Burette stand
Burette
Copper water bath

Water pipes for condenser
Analytical balance
Funnel

Bent tube
Adaptor
Reflux condenser
Digital balance
Measuring cylinder
Iodine flask

Separating funnel
Thiele tube
Volumetric flask
10 PRACTICAL HANDBOOK OF ADVANCED PHARMACEUTICAL ORGANIC CHEMISTRY
China dish
Stereo models
Test tube holder

11
Test tube
Nessler cylinder
Test tube stand

Tripod stand
Bunsen burner and tripod stand with mesh
Thermometer
13
Heating mantle
Electric water bath
Watch glass
Hot plate
Hot air oven
Melting point apparatus

15
Experiment - 2
DIFFERENT TECHNIQUES INVOLVING IN THE

PREPARATION OF ORGANIC COMPOUNDS
Several techniques employed for the determination of identity and purity, as well as
for purification.
Synthesis:
Since each chemical synthesis is unique, there is no absolutely formulaic procedure
by which all compounds can be produced. Most synthesis procedures do share a
number of commonalities which will be discussed on this page. If the reagents that
are being used in the reaction are not properly mixed (they are not homogeneously
incorporated) the rate of reaction will be drastically slowed. The solvent that is
being used not only has to be able to support the reaction without interference; it
must also dissolve the starting materials. The product may or may not be soluble in
the solvent. If the product is insoluble in the solvent it will precipitate and therefore
be easily separated from the residual starting materials.
Many reactions produce heat; care must be taken when dealing with such situations.
Frequently, stirring can be utilized as a means of dispersing the heat. Also, if the
heating problem is anticipated, the reagents can be combined slowly to avoid
excessive heating. Also keep in mind that although a reaction may be exothermic,
it may be necessary to heat it to increase the rate at which the reaction occurs. After
the synthetic procedure has been carried out, the product must be separated from
by-products and the reagents that were used to make the product. In some cases,
the product will precipitate from solution and can be isolated simply by filtration.
This is the case for most of the syntheses shown below. If the product is soluble in
the solvent, it will be necessary to remove some or all of the solvent. Unfortunately,
removal of the solvent usually leaves behind not only the product but also any un-
reacted starting materials or by-products. An undesired compound must then be
separated from the product. If the product is a solid, recrystallization can be used to
purify it. A solvent can be chosen that will dissolve the product but will not dissolve
the unwanted starting materials and by-products, or, the solvent may dissolve the
impurities but not the product. If the product is a liquid; it can be distilled to remove
impurities that have boiling points different from that of the product. There are also
chromatographic techniques that can be used for both solids and liquids.
After the substance has been isolated it must be identified. Even though the synthetic
procedure was devised to allow you to prepare a certain compound, the substance
obtained in the reaction may not actually be that compound. In order to identify
the substance you generally need to perform several measurements of physical and
chemical properties.
Filtration:
Filtration is a physical, biological or chemical operation that separates solid matter
and fluid from a mixture with a filter medium that has a complex structure through
which only the fluid can pass. Solid particles that cannot pass through the filter
medium are described as oversize and the fluid that passes through is called the
filtrate.
1. Flute filter paper if necessary. Fluting is desirable when a rapid filtration is

necessary, as in the filtration of the hot solution during a recrystallization.
2. Place filter paper in the funnel. Place the funnel either directly on top of the
beaker or on a ring stand above the beaker (Figure 2.1).
Figure 2.1: Beaker containing funnel
3. Wet the filter paper using a small amount of the liquid that is the solvent of the
mixture being filtered.
4. After the filtrate has been collected, pass a small amount of the wash liquid
through the filter paper to wash the residue.
5. Select a Buchner funnel of appropriate size for the amount of residue you are
collecting, not the amount of filtrate. Put a piece of filter paper in the funnel
that fits exactly and wet the paper using a small amount of solvent.
6. Place the funnel in a filter flask and connect the rubber tubing (Figure 2.2).
Using rubber tubing, the filter flask is connected to a trap, which in turn is
17
connected to an aspirator, which provides the vacuum.
7. After the filtrate has been collected, pass a small amount of pure solvent
through the filter to wash the residue.
Figure 2.2: A Buchner funnel in a filtration flask
Decolourization:
If the crude compound or product contains colour/coloured impurities, it is dissolved
in a suitable solvent by heating to get a clear solution. Then add a small amount
(pinch) of activated charcoal (decolourizing agent) and boil the solution. Then filter
the hot solution using filter paper and allow the filtrate to cool for the separation of
pure, colourless crystals.
Simple Distillation:
Simple distillation is a procedure by which two liquids with different boiling points
can be separated. Simple distillation (the procedure outlined below) can be used
effectively to separate liquids that have at least fifty degrees difference in their
boiling points. As the liquid being distilled is heated, the vapours that form will be
richest in the component of the mixture that boils at the lowest temperature. Purified
compounds will boil, and thus turn into vapours, over a relatively small temperature
range (2 or 3 0C); by carefully watching the temperature in the distillation flask,
it is possible to affect a reasonably good separation. As distillation progresses, the
concentration of the lowest boiling component will steadily decrease. Eventually the
temperature within the apparatus will begin to change; a pure compound is no longer
being distilled. The temperature will continue to increase until the boiling point
of the next-lowest-boiling compound is approached. When the temperature again
stabilizes, another pure fraction of the distillate can be collected. This fraction of
distillate will be primarily the compound that boils at the second lowest temperature.
This process can be repeated until all the fractions of the original mixture have been
separated.
Procedure:
1. Check the calibration of the thermometer that is to be used. This can be
accomplished by placing the thermometer in an ice bath of distilled water.
After the thermometer has been allowed to reach thermal equilibrium, place
it in a beaker of boiling distilled water and again allow it to reach thermal
equilibrium. If the temperatures measured deviate from the expected values by
more than two degrees, obtain a new thermometer and check its calibration.
2. Fill the distillation flask. The flask should be no more than two thirds full
because there needs to be sufficient clearance above the surface of the liquid
so that when boiling commences the liquid is not propelled into the condenser,
compromising the purity of the distillate. Boiling chips should be placed in
the distillation flask for two reasons: they will prevent superheating of the
liquid being distilled and they will cause a more controlled boil, eliminating
the possibility that the liquid in the distillation flask will bump into the
condenser.
3. Heat the distillation flask slowly until the liquid begins to boil. Vapours will
begin to rise through the neck of the distillation flask. As the vapours pass
through the condenser, they will condense and drip into the collection receiver.
An appropriate rate of distillation is approximately 20 drops per minute.
Distillation must occur slowly enough that all the vapours condense to liquid
in the condenser. Many organic compounds are flammable and if vapours pass
through the condenser without condensing, they may ignite as they come in
contact with the heat source.
4. As the distillate begins to drop from the condenser, the temperature observed on
the thermometer should be changing steadily. When the temperature stabilizes,
use a new receiver to collect all the drops that form over a two to three degree
range of temperature. As the temperature begins to rise again, switch to a third
collection container to collect the distillate that now is formed. This process
should be repeated; using a new receiver any time the temperature stabilizes
or begins changing, until all of the distillate has been collected in discrete
fractions.
a. Note: All fractions of the distillate should be saved until it is shown that the
desired compound has been effectively separated by distillation.
5. Remove the heat source from the distillation flask before all of the liquid is
vaporized. If all of the liquid is distilled away, there is a danger that peroxides,
which can ignite or explode, may be present in the residue left behind. Also,
when all of the liquid has evaporated, the temperature of the glass of the
filtration flask will rise very rapidly, possibly igniting whatever vapours may
still be present in the distillation flask.
I. Never distil to dryness. The residue left in the distillation flask may contain
peroxides, which could ignite or explode after all the liquid has distilled
away.
19
II. Make sure that all joints are secured very tightly. If any vapour escapes at the
connection points, it may come into direct contact with the heat source and
ignite.
III. Never heat a closed system, the increasing pressure will cause the glass to
explode. If the distillation flask has a tapered neck, the thermometer may be
placed in such a way as to block to flow of vapours up the neck of the flask; in
effect creating a closed system; make sure that if using a tapered neck flask, the
thermometer is not resting in the lowest portion of the neck.
Simple distillation is effective only when separating a volatile liquid from a non-
volatile substance or when separating two liquids that differ in boiling point by 50
degrees or more. If the liquids comprising the mixture that is being distilled have
boiling points that are closer than 50 degrees to one another, the distillate collected
will be richer in the more volatile compound but not to the degree necessary for
complete separation of the individual compounds.
The basic idea behind fractional distillation is the same as simple distillation only
the process is repeated many times. If simple distillation was performed on a
mixture of liquids with similar volatilities, the resulting distillate would be more
concentrated in the more volatile compound than the original mixture but it would
still contain a significant amount of the higher boiling compound. If the distillate
of this simple distillation was distilled again, the resulting distillate would again
be even more concentrated in the lower boiling compound, but still a portion of
the distillate would be the higher boiling compound. If this process is repeated
several times, a fairly pure distillate will eventually result. This, however, would
take a very long time. In fractional distillation, the vapours formed from the boiling
mixture rise into the fractionating column where they condense on the column’s
packing. This condensation is tantamount to a single run of simple distillation; the
condensate is more concentrated in the lower boiling compound than the mixture
in the distillation flask. As vapours continue to rise through the column, the liquid
that has condensed will revaporize. Each time this occurs the resulting vapours
are more and more concentrated in the more volatile substances. The length of the
fractionating column and the material it is packed with impact the number of times
the vapours will recondense before passing into the condenser; the number of times
the column will support this is referred to as the number of theoretical plates of the
column.
Since the procedures of simple distillation are so similar to those involved in

fractional distillation, the apparatus that are used in the procedures are also very
similar. The only difference between the equipment used in fractional distillation
and that used in simple distillation is that with fractional distillation, a packed
fractionating column is attached to the top of the distillation flask and beneath the
condenser. This provides the surface area on which rising vapours condense, and
subsequently revaporize.
The fractionating column is used to supply a temperature gradient over which the
distillation can occur. In an ideal situation, the temperature in the distillation flask
would be equal to the boiling point of the mixture of liquids and the temperature
at the top of the fractionating column would be equal to the boiling point of the
lower boiling compound; all of the lower boiling compound would be distilled away
before any of the higher boiling compound. In reality, fractions of the distillate must
be collected because as the distillation proceeds, the concentration of the higher
boiling compound in the distillate being collected steadily increases. Fractions of
the distillate, which are collected over a small temperature range, will be essentially
purified; several fractions should be collected as the temperature changes and these
portions of the distillate should be distilled again to amplify the purification that has
already occurred.
Figure 2.3: Distillation apparatus. A distillation flask with a thermometer is placed

in a heating mantle and is connected to a condenser
21
Experiment - 3
DETERMINATION OF MELTING POINT
Aim: To determine the melting point of the given organic compound by using
Thiele’s apparatus.
Requirements: Thiele’s tube containing liquid paraffin, capillary tube, thermometer,

burner, thread.
Back ground: Determining the melting point of a compound is one way to test if the
substance is pure. A pure substance generally has a melting range (the difference
between the temperature where the sample starts to melt and the temperature where
melting is complete) of one or two degrees. Impurities tend to depress and broaden
the melting range so the purified sample should have a higher and smaller melting
range than the original, impure sample. Melting point of a solid is the temperature
at which a solid begins to change into liquid phase.
Melting point occurs when the temperature is reached at which the thermal energy
of particle is greater enough to overcome the intra crystalline forces that holds atom
in a portion, in case of ionic compounds. These extract crystalline forces over highly
powerful. These powerful interactions, in which the structural unit are molecules.
Figure 3.1: Melting point determination

Figure 3.2: Melting point determination using Thiele’s tube
Procedure:
1. Take a clean dry capillary tube and close one of the end by heating in the
flame.
2. Insert a little solid into the capillary tube and push the solid to reach the closed
end.
3. The sample should not be more than one third of the length of the capillary
tube.
4. Tie the capillary tube at the bulb-end of the thermometer with a thread.
5. Insert the thermometer into a bored cork and fix it into a Thiele’s tube containing
liquid paraffin.
6. The bulb of the thermometer should be inside the liquid but the open end of the
capillary should be above the surface of the liquid.
7. Heat the Thiele’s apparatus gently by waving the flame over the side tube.
8. A soon as the solid starts melting, note down temperature immediately.
9. If the compound melts slowly, then note down a second temperature where the
compounds completely melts.
23
Experiment - 4
DETERMINATION OF BOILING POINT
Aim: To determine the boiling point of the given organic compound by using
Thiele’s apparatus.
Requirements: Fusion tube, capillary tube, Thiele’s tube containing liquid paraffin,
thermometer, thread.
Back ground: Is the temperature at which a liquid changes its phase to vapour phase.
The boiling point of a substance is the temperature at which the vapour pressure
of a liquid equals the pressure surrounding the liquid and the liquid changes into a
vapour. The boiling point is the temperature at which the vapour pressure of a liquid
equals the external pressure surrounding the liquid. Therefore, the boiling point of
a liquid depends on atmospheric pressure. The boiling point becomes lower as the
external pressure is reduced.
The boiling point of a liquid varies depending upon the surrounding environmental
pressure. A liquid in a partial vacuum has a lower boiling point than when that liquid
is at atmospheric pressure. A liquid at high pressure has a higher boiling point than
when that liquid is at atmospheric pressure. For example, water boils at 100 0C (212
0F) at sea level, but at 93.4 0C (200.1 0F) at 1,905 metres (6,250 ft) altitude. For
a given pressure, different liquids will boil at different temperatures. The normal
boiling point (also called the atmospheric boiling point or the atmospheric pressure
boiling point) of a liquid is the special case in which the vapour pressure of the
liquid equals the defined atmospheric pressure at sea level, 1 atmosphere.
Figure 4.1: Boiling point determination using Thiele’s tube
Procedure:
1. Take a clean and dry fusion tube and to this add 2-3 drops of the liquid
sample.
2. Take a capillary tube and close one end by heating in a flame.
3. Insert the capillary tube into the fusion tube containing liquid sample keeping
the sealed end above the surface.
4. Tie the fusion tube to the bulb end of the thermometer.
5. Insert the thermometer into a bored cork and fix it into a Thiele’s tube containing
liquid paraffin.
6. The bulb of the thermometer should be inside the liquid but the upper half
portion of the fusion tube should be above the surface of the liquid.
7. Heat the Thiele’s apparatus gently by waving the flame over the side tube.
8. When a stream of bubbles rises from the bottom of the capillary tube, note
down the temperature immediately
25
Experiment - 5
DETERMINATION OF ACID VALUE
Aim: To determine the acid value of given oil.
Apparatus: Conical flask, burette, pipette, measuring cylinder, glass rod, volumetric
flask.
Chemicals: KOH, oxalic acid, alcohol, solvent ether, phenolphthalein indicator.
Principle: Acid value is the number of mg of potassium hydroxide or sodium

hydroxide required to neutralize the free fatty acid present in 1g of oil or fat. The
fresh oils and fats are nearly colourless and neutral in reaction. If they are exposed
to moisture and aerobic bacteria for the long time, they either gets oxidized or
hydrolyzed into aldehyde, ketones and acids, and develops a disagreeable odour
and there upon become rancid called rancidity.
Procedure:
Standardization of potassium hydroxide: Pipette out 10ml of 0.1N of oxalic acid
solution and transfer into a clean and dry conical flask. Add 2 drops of phenolphthalein
indicator and titrate against 0.1N KOH until the appearance of permanent pink
colour. Repeat the procedure till concordant value was obtained.
Each ml of 0.1N KOH ≡ 5.61 g of fatty acid
Assay: Weigh accurately 5g of oil and transfer into a clean and dry conical flask.
To this add a mixture of equal volumes of alcohol and solvent ether (15ml); shake
well the mixture till the solution becomes clear. Heat the solution for some time if
necessary. Then add 2-3 drops of phenolphthalein indicator and titrate it against
0.1N KOH solution. End point is colourless to pink.
Experiment - 6
DETERMINATION OF SAPONIFICATION VALUE
Aim: To determine the saponification value of given oil.
Apparatus: Conical flask, burette, pipette, measuring cylinder, glass rod, volumetric
flask, water bath.
Chemicals: HCl, KOH, sodium carbonate, phenolphthalein indicator, methyl orange

indicator.
Principle: The number of milligram of potassium hydroxide or sodium hydroxide

required for neutralizing the combined fatty acids and the free fatty acids resulting
from the complete hydrolysis (saponification) of 1g of fat or oil. Thus, the
saponification value is a measure of both free and combined fatty acids. 1 mole
of fat or oil contains 3 molecules of fatty acids therefore, 3 moles of potassium
hydroxide is required to neutralize 3 moles of fatty acids. The fatty acids present
in fat or oil cannot be directly estimated in the alkaline medium therefore excess
amount of alcoholic potassium hydroxide is made to react with fatty acids and the
remaining unreacted potassium hydroxide is back titrated with standard acid (HCl)
using, phenolphthalein indicator. Colour change will be from pink to colourless.
Significance:
Since it gives the measure of molecular weight as well as equivalent weight of fatty
acids. It is also used to check the purity of fat and oil. Therefore, if the saponification
value goes high above the normal range then it indicates that the oil has become
rancid and it is not fresh. If saponification value is less, it indicates that the fat or oil
is adulterated because the amount of the fatty acids of the fresh oil is replaced by the
fatty acids of the adulterant material.
27
Procedure:
Standardization of HCl: Standardize the HCl by using sodium carbonate in presence
of methyl orange as an indicator. Pipette out 10ml of 0.1N sodium carbonate and
add into a clean conical flask. Add few drops of methyl orange indicator and titrate
to get a concordant value.
Each ml of 0.5N HCl ≡ 28.05g of KOH
Assay of oil: Weigh accurately 2g of given oil and transfer into a clean conical
flask. To this, add 25ml of 0.5N alcoholic KOH, then keep the reaction mixture
in water bath for about 30 min and reflux using air/water condenser. Rotate the
flask frequently while boiling along with the contents. Then, cool the flask and add
1ml of freshly prepared phenolphthalein indicator and titrate the resulting mixture
against 0.5N HCl. Repeat this procedure by omitting the sample for the blank
determination.
Experiment - 7
DETERMINATION OF IODINE VALUE
Aim: To determine the iodine value of given oil using iodine monochloride
method.
Apparatus: Conical flask, burette, pipette, measuring cylinder, glass rod, spatula,
volumetric flask.
Chemicals: Conc. HCl, KI, Na2S2O3, potassium dichromate, iodine monochloride,

distilled water, starch mucilage as indicator, CCl4.
Principle: Iodine value is defined as the weight of iodine absorbed by 100 parts by
weight of fat or oil under certain specified conditions.
Significance: Iodine value mainly gives the indication of proportion of unsaturation

i.e. number of double bonds present in the acid component of triglycerides. In other
terms, triglycerides that are having more number of double bonds will show higher
iodine value and vice-versa. Iodine is sparingly soluble in water and also it react too
slowly. Iodine monochloride or bromine in pyridine is used in presence of sulphuric
acid as a reagent.
A scientist named Wij derived the iodine monochloride method A solution of iodine
monochloride in glacial acetic acid is called Wijs solution. Iodine value is determined
by mixing Wijs solution with fat or oil in carbon tetrachloride solution and glacial
acetic acid. When the absorption of iodine is complete; add excess amount of
potassium iodide produces the iodine, equivalent of residual iodine monochloride.
The iodine formed is then titrated with standardized sodium thiosulphate solution
using starch mucilage is indicator. Colour change is deep blue to colourless.
Iodine value =
Precautions:
 The reaction should be carried out at a temperature of 17 0C for half an hour.
 It is kept in dark condition to prevent side reactions like oxidation, substitution
and decomposition of reacting mixture.
29
 The iodine flask should be closed with stopper to prevent any loss of free io-
dine formed.
 Starch iodine indicator should be added at the end because iodine which is
present absorbed first by starch as a result no sharp end point is observed.
Procedure:
Standardization of Na2S2O3: Prepare 0.1N potassium dichromate solution in 100ml
volumetric flask. From this, pipette out 20ml into a clean iodine flask, then, add 6ml
conc. HCl and 1 spatula of KI to it. Keep the flask in dark place for 5 min. Titrate
the mixture against 0.1N Na2S2O3 using starch mucilage as an indicator. The end
point is to be change in colour from blue to green.
Each ml of 0.1N Na2S2O3 ≡ 0.01269g of iodine
Assay of oil: Weigh 0.2g of fat or oil and add to a clean conical flask. Add 10ml
of CCl4 and 20ml of iodine monochloride to flask by using a burette. Shake well
the iodine flask and keep in dark place for 30 min, rotate occasionally. To this, add
15ml of KI solution along with 10ml of distilled water. Before titrating, shake the
flask properly and titrate against 0.1N Na2S2O3 using starch mucilage as indicator
towards end point. Perform the blank titration in similar way by omitting the
sample.
Experiment - 8
SYNTHESIS OF ACETANILIDE
Aim: To prepare and submit acetanilide from aniline and report its percentage
yield.
Apparatus: Conical flask, pipette, measuring cylinder, stirrer, beaker, funnel.
Chemicals: Conc. HCl, aniline, acetic anhydride, sodium acetate, distilled water.
Principle: Acetanilide is also known as N-phenyl acetamide. It is prepared by

acetylation of aniline with either acetic anhydride or acetyl chloride. The replacement
of one or more active hydrogen atom from –NH2, -OH, -SH groups etc. from a
molecule by –COCH3 group is known as acetylation. Acetylation of an aromatic
primary or secondary amine may be readily achieved by using an acid chloride in
the presence of catalyst. However acetylation is more usually effected with acetic
anhydride rather than acetyl chloride. Primary amines react readily upon warming
with acetic anhydride to yield in the first instance, the mono acetyl derivative.
Ar NH2
+ (CH 3 CO) 2 O Ar N H CO CH3 + CH 3 COOH
If heating is prolonged and excess of acetic anhydride is employed variable amounts

of the diacetyl derivatives are formed.
Ar N H CO CH3 + (CH 3 CO) 2 O Ar-NH-(CO-CH 3)2 + CH 3 COOH
Conc. HCl or conc. H2SO4 is used as a common solvent and also as a catalyst.
Aniline dissolves in HCl forming the salt. Hence the lone pair of electrons is not
available to attack on the carbonyl carbon. Hence sodium acetate is added to get
the free aniline, which immediately reacts, with the acetic anhydride forming
acetanilide.
31
Procedure:
1. Place 2.5ml of conc. HCl, 2.5ml (2.45g) of aniline and 75ml of distilled water
in a 250ml of conical flask.
2. Stir properly until the aniline goes in to solution.
3. Add 3.3ml of acetic anhydride to the filtrate stir well and immediately pour
into the solution of 20ml of 33% sodium acetate.
4. Stir vigorously and cool in ice. Filter, wash with water and dry. Recrystallize
from hot water.
Experiment - 9
SYNTHESIS OF ASPIRIN
Aim: To prepare and submit aspirin from salicylic acid and report its percentage
yield.
Apparatus: Conical flask, water bath, glass rod, funnel, beaker, funnel, measuring
cylinder.
Chemicals: Salicylic acid, acetic anhydride, conc. H¬2SO4.
Principle: Aspirin is also known as acetyl salicylic acid. It is prepared by the phenolic
group of salicylic acid can be easily acetylated with the help of acetic anhydride in
the presence of a little conc. H¬2SO4 to yield acetyl salicylic acid. Here H¬2SO4
is acts as a catalyst. The reaction mixture is warmed to 50-60 0C to make faster. It
should not be boiled or heated for a long time, since these leads to hydrolysis of
aspirin to salicylic acid.
Procedure:
1. In a clean and dry 250ml flask, take 5g of salicylic acid and 10ml of acetic
anhydride; add 0.5ml of conc. H¬2SO4.
2. Shake the mixture thoroughly and heat on a water bath keeping the temperature
about 50-60 0C, for about 15-20 min with continuous stirring.
3. Allow the mixture to cool and add 80 ml of ice-cold water stir well and filter.
4. Recrystallize the product from 50% of acetic acid.
33
Experiment - 10
SYNTHESIS OF BENZANILIDE
Aim: To prepare and submit benzanilide from aniline and report its percentage
yield.
Apparatus: Iodine flask, dropper, funnel, beakers, digital balance, spatula, water
bath, stirrer, filter paper.
Chemicals: Aniline, benzoyl chloride, sodium hydroxide, distilled water.
Principle: Insertion of benzoyl moiety instead of an active hydrogen atom present in

hydroxyl (-OH) primary amino (-NH2) or secondary amino (-NH-) group is termed
as benzoylation reaction.
Benzanilide is obtained by benzoylation of aniline in the presence of dilute NaOH

solution (usually 10%) called Schotten-Baumann reaction. The aqueous NaOH
acts as a scavenger of HCl produced during the reaction which can promote side
reaction.
Procedure:
1. Place 2.6g (2.5ml) of aniline and 25ml of 10% aqueous sodium hydroxide
solution in a clean and dry iodine flask.
2. Then add 3.5ml (4.3g) of benzoyl chloride drop wise, stopper the flask and
shake vigorously for 15 minutes.
3. After 15 minutes, dilute it with 10ml distilled water and shaken vigorously.
4. Filter off the crude product; wash well with distilled water and drain.
5. Recrystallize from hot alcohol, filter the solution and collect the crystals and
dry in oven and weigh.
Experiment - 11
SYNTHESIS OF PHENYL BENZOATE
Aim: To prepare and submit phenyl benzoate from phenol and to report its percentage
yield.
Apparatus: Beaker, conical flask, measuring cylinder, water bath, stirrer, funnel.
Chemicals: Phenol, benzoyl chloride, sodium hydroxide, distilled water.
Principle: Phenyl benzoate is prepared by Schotten-Bauman’s reaction, which

involves reactions between phenol and benzoyl chloride in presence of sodium
hydroxide.
OCOC 6H 5
OH
AgNaOH
+ C 6 H 5 COCl + HCl
Phenol Benzoyl chloride Phenyl Benzoate
Procedure:
1. Dissolve 5g of phenol in 75ml of 10% sodium hydroxide solution in a clean
and dry conical flask.
2. Add 11g (9 ml) of redistilled benzoyl chloride; shake the mixture for 15-20
minutes.
3. After forming the product filter it and wash with minimum quantity of distilled
water till the odour of benzoyl chloride disappear.
4. Dry and weigh the product and calculate the percentage yield.
35
Experiment - 12
SYNTHESIS OF P-BROMOACETANILIDE
Aim: To prepare and submit p-bromoacetanilide from acetanilide and report its
percentage yield.
Apparatus: Beaker, conical flasks, dropper, funnel.
Chemicals: Acetanilide, glacial acetic acid, bromine solution, cold water.
Principle: By direct substitution of bromine of aniline gives sym-tribromo aniline

and nitration causes a vigorous oxidation reaction. But if the amino group is protected
as anilide group, then substitution becomes easy. Thus bromination of acetanilide
gives p-bromo acetanilide as the main product; a small quantity of o-isomer is also
formed simultaneously, which can be easily eliminated by crystallization.
Procedure:
1. Dissolve 1g of acetanilide in 5ml of glacial acetic acid in a dry conical flask.
2. In another small flask, 1ml of bromine in 5ml of glacial acetic acid and transfer
the solution and add bromine solution drop wise slowly and regularly shaking
the flask to ensure thorough mixing.
3. After the addition of all bromine, the solution will become of orange colour
due to slight excess of bromine.
4. Allow the mixture to stand at room temperature for about half an hour with
occasional shaking.
5. Pour the contents with stirring to about 100ml of cold water in a beaker.
6. Filter and wash the product with cold water and dry.
7. Recrystallize the product from ethyl alcohol.
(Or)
4.66g (0.05 mol) aniline is dissolve in glacial acetic acid (50ml) in a 100ml round
bottomed flask equipped with a magnetic stirrer. Cool the solution on an ice/water
bath before add a solution of bromine 8.0ml (0.155 mol) in glacial acetic acid (30ml)
drop wise from an addition funnel at such a rate, that complete decolourization is
achieved between each drop. During the addition the reaction mixture is stirred
continuously with magnetic stirring (if the acetic acid solidifies, remove the flask
from the ice/water bath momentarily). When all the bromine is added, stir the reaction
mixture 10 min (check TLC) before it is poured into water (250ml) containing a
pinch (ca. 1 g) of sodium bisulphite (NaHSO3). Filter off the precipitate and wash
with water. The product is recrystallize from a minimum of hot ethanol with a
spoonful of activated charcoal.
37
Experiment - 13
SYNTHESIS OF BENZIL
Aim: To prepare and submit benzil from benzoin and report its percentage yield.
Apparatus: Round bottomed flask, beaker, reflux condenser, water bath, vacuum
pump, funnel.
Chemicals: Benzoin, conc. HNO3, ice cold water.
Principle: Oxidation of the alpha-hydroxy ketone with conc. nitric acid yields the
diketone. In benzoin one secondary alcoholic group (-CHOH) is present, which will
be readily oxidized to a keto group and thus benzil is obtained. For this purpose
usual oxidizing agents like nitric acid is used, whereas if sulphuric acid is used it
doesn’t oxidize the benzene ring. Instead of it, it will nitrate the benzene ring.
O O
[O ]
H NO 3
OH O
B en z oin B en z il
Procedure:
1. Weigh accurately 5g of crude benzoin and place in 250ml round bottomed flask.
2. To this add 25ml conc. HNO3 acid, attach the reflux condenser and heat on
a boiling water bath by occasional shaking the flask or until the evolution of
oxides of nitrogen had ceased for about 30-40 min.
3. Pour the reaction mixture into a beaker containing 300-400ml of cold water; stir
well the solution until the oil was crystallized out completely as yellow solid.
4. Filter the product at the pump, wash well with distilled water and recrystallize
from rectified spirit or ethanol.
5. Dry, weigh and calculate the percentage yield.
Precautions:
 Owing to the nitrous fumes forms by the reduction of nitric acid, the experi-
ment should be performed in a fuming cupboard.
 Stirring or vigorous shaking also induces crystallization.
 The mother liquor should not be too concentrated as an explosion may result.
Experiment - 14
SYNTHESIS OF CINNAMIC ACID
Aim: To prepare and submit cinnamic acid from benzaldehyde and report its
percentage yield.
Apparatus: Round bottomed flask, water bath, beaker, glass rod, thermometer.
Chemicals: Benzaldehyde, acetic anhydride, ether, conc. HCl, 10% NaOH,

anhydrous potassium carbonate, distilled water.
Principle: When an aromatic aldehyde is heated with the anhydride form of an

aliphatic acid in the presence of the sodium salt of the same acid (catalyst), α,β-
unsaturated acid results. Thus benzaldehyde on heating with acetic anhydride and
sodium acetate for several hours at 1800C yields cinnamic acid. The condensation
reaction between an aromatic aldehyde and aliphatic anhydride is named as Perkin
reaction (or) Perkin’s condensation. It is a useful synthetic method for the synthesis
of α,β-aryl acrylic acid.
CHO O
CH COOH
180 0C
+ O
HCl
Benzaldehyde O Cinnamic acid
CH3COONa
Procedure:
1. Place 5ml freshly distilled benzaldehyde, 8.2ml of distilled acetic anhydride
and 7g of pure anhydrous potassium carbonate in 250ml round bottomed flask
fitted with a thermometer dropping into the reaction mixture with condenser.
2. Heat the flask in an air bath gradually to about 170-1800C.
3. Heat the reaction mixture for 90 more minutes and allow it to cool.
4. Add 40ml of distilled water followed by 10% NaOH until the mixture became
alkaline.
5. Extract the clear solution with 25ml of ether twice with the help of separating
funnel.
6. To remove any unchanged benzaldehyde the aqueous layer is treating with
conc. HCl.
7. Then, filter the product, wash with 10ml of water and recrystallize from hot water.
39
Experiment - 15
SYNTHESIS OF 1-PHENYLAZO-2-NAPHTHOL
Aim: To prepare and submit 1-phenylazo-2-naphthol from aniline and report its percentage
yield.
Apparatus: Conical flask, water bath, beaker, glass rod, measuring cylinder.
Chemicals: Aniline, NaOH, β-naphthol, HCl, NaNO2.
Principle: When an aromatic primary amine is treated with sodium nitrite in presence of an
acid, a diazonium salt is formed. Such type reaction is called diazotization. The diazonium
salt, thus obtained, react with a phenol or an amine under certain conditions, to form azo dye.
This type of reaction called as coupling. For example when aniline react with HNO2 in the
presence of HCl at 0-50C to yield benzene diazonium chloride. Thus benzene diazonium
chloride reacts with alkaline β- naphthol solution to yield reddish orange coloured phenylazo-
β- naphthol dye.
Diazo coupling is an example of Electrophilic aromatic substitution reaction. The diazonium

ion acts as an electrophile and substitution takes place at C1 position of 2-naphthol, i.e. at the
position of greater electron availability.
+
+
C 6H 5N
H 2 HCl [C 6 H 5 N
H 3] Cl
Aniline Aniline hydrochloride
+
+ +
. HCl
+
HONO
Cl C 6H 5 N N OH Cl H 5C 6 N N Cl H 2O
C 6 H 5 -N-H H 2O
H H Benzene diazonium chloride
O H
. . . ..
+
+
N N N N Cl
+
..
:O ..
:O
H
H
N N
N N
Phenyl azo β-naphthol
Procedure:
1. In a 250ml beaker, dissolve 2.5g of NaOH in 25ml distilled water.
2. To it add 4g of β-naphthol, heat the contents to get a clear solution and then
cool to 50C in an ice bath.
3. In a conical flask, dissolve 2.5ml of aniline in a mixture of 7ml of distilled
water and add 10ml of distilled water.
4. Stir well and cool solution until the temperature falls below 5 0C.
5. In another conical flask, dissolve 2g of NaNO2 into 10 ml of distilled water
and chill it by keeping in an ice-bath.
6. Then add the cold aq. NaNO2 solution, in small portions with constant stirring,
to the well cooled aniline hydrochloride solution and maintain the temperature
below 5 0C by keeping the flask in an ice-bath.
7. Add the benzene diazonium chloride solution to the well-cooled solution of
alkali β-naphthol very slowly, with continuous stirring.
8. When all the solution has been added, allow the mixture to stand in an ice-bath
for about half an hour with occasional stirring.
9. Filter the product, wash with cold water and dry.
10. Recrystallize it from alcohol. Drain well and calculate the percentage yield.
41
Experiment - 16
SYNTHESIS OF DIBENZALACETONE
Aim: To prepare and submit dibenzalacetone from benzaldehyde and report its percentage
yield.
Apparatus: Conical flask, measuring cylinder, water bath, beaker, glass rod, thermometer.
Chemicals: Benzaldehyde, NaOH, alcohol, acetone, distilled water.
Principle: The condensation between an aromatic aldehyde or ketone having no α-hydrogen

atom, and aliphatic aldehyde, ketone or ester having an active hydrogen atom in the α-position
in the presence of dil. alkali to form an α,β-unsaturated compound. This type of reaction is
called as Claisen-Schmidt reaction. Benzaldehyde condenses with acetone in the presence of
aq. alkali to form first benzalacetone and then dibenzalacetone (dibenzylideneacetone).
Procedure:
1. In a 250ml conical flask, dissolve 5g of NaOH in a mixture of 40ml of distilled
water and 50ml of alcohol.
2. Cool the flask in an ice-bath and add a mixture of 5ml of benzaldehyde and
2ml of acetone.
3. Cork the flask and shake vigorously for about half a hr. maintaining the
temperature 20 0C.
4. During shaking, first of all a fine emulsion shall appear, which will readily
solidify to pale yellow crystals.
5. Filter, wash with distilled water. Recrystallize from ethyl acetate. Dry, weigh
and report the percentage yield.
Experiment - 17
SYNTHESIS OF 2,4,6-TRIBROMOANILINE
Aim: To prepare and submit 2,4,6-tribromoaniline from aniline and report its percentage
yield.
Apparatus: Beaker, conical flask, funnel, measuring jar, burette.
Chemicals: Aniline, acetic acid, bromine in CH3COOH.
Principle: Aniline readily undergoes Electrophilic Substitution Reaction by involving the

non-bonding electrons present on nitrogen. As -NH2 group is ortho and para directing and
also ring activating group there is an increase in electron density at ortho and para positions.
Therefore aniline on bromination gives 2,4,6-tribromoaniline (i.e) bromination takes place
at 2,4 and 6 positions.
Procedure:
1. Take 5ml of aniline and 19ml of glacial acetic acid in a clean and dry conical
flask.
2. Keep this flask in ice bath and then add 30ml of Br2 in acetic acid drop wise
with constant stirring (using burette) till orange colour of bromine persists.
3. Allow the solution to stand at room temp for 15 minutes, and pour it into the
cold water.
4. 2,4,6-Tribromo aniline precipitates out and filter it off.
5. Recrystallize it from ethanol. Dry, weigh and report the percentage yield.
43
Experiment - 18
SYNTHESIS OF m-DINITROBENZENE
Aim: To prepare and submit m-dinitrobenzene from nitrobenzene and report its percentage
yield.
Apparatus: Round bottomed flask, conical flask, beaker, measuring cylinder.
Chemicals: Nitrobenzene, fuming HNO3, conc. H2SO4.
Principle: Nitro group is deactivating group or electron withdrawing group. It is a meta

directing group and hence it requires drastic conditions when compared to nitration of
benzene. It is an Electrophilic Substitution Reaction.
Procedure:
1. Measure about 2ml of nitrobenzene in 250ml RBF, then separately prepare the
nitration mixture in conical flask by measuring 2.5ml of fuming nitric acid and
add 3.5ml of conc. H2SO4 drop wise by cooling in ice bath.
2. The addition of conc. H2SO4 to fuming HNO3 should be completed within 5-10
min.
3. Add this mixture drop wise to nitrobenzene and shake nearly for 10 min.
4. Fix the water condenser and reflux for 1 hr in hot water bath.
5. Shake the flask and pour these contents into cold water taken in a beaker.
6. A pale yellow m-dinitrobenzene will form and filter it. Recrystallize with
alcohol.
Experiment - 19
SYNTHESIS OF BENZOIC ACID
Aim: To prepare and submit benzoic acid from benzyl chloride and report its percentage
yield.
Apparatus: Round bottomed flask, reflux setup, beaker, measuring cylinder, water bath, glass
rod.
Chemicals: Benzyl chloride, anhydrous sodium carbonate, potassium permanganate,

concentrated hydrochloric acid, sodium sulphate, distilled water.
Principle: In this reaction, a side chain oxidation is performed. In order to achieve this,
benzyl chloride is mixed with sodium carbonate solution and is oxidized with potassium
permanganate solution. The sodium salt of benzoic acid is formed; this is acidified with
concentrated hydrochloric acid when benzoic acid crystallizes out.
Procedure:
1. Add about 2ml of benzyl chloride to a solution of about 2g of anhydrous sodium
carbonate dissolved in 20 ml of distilled water.
2. Place the mixture in a round bottomed flask is fitted with a water reflux
condenser and heat.
3. Add 4g of potassium permanganate in 80ml of distilled water in small quantities
through the water condenser until a permanent pink colour persists even after
continuous boiling.
4. Boil it for about 1 hour. Don’t transfer the mixture in to a beaker.
5. Add about 4g of sodium sulphate to this mixture, and then add concentrated
hydrochloric acid to this solution until the solution is acidic.
6. Cool the solution. Filter and wash the precipitated benzoic acid.
7. Recrystallize the acid from boiling water.
45
Experiment - 20
SYNTHESIS OF BENZOPHENONE OXIME
Aim: To prepare and submit benzophenone oxime from benzophenone and report its
percentage yield.
Apparatus: RBF, reflux condenser, beaker, funnel, measuring cylinder, glass rod.
Chemicals: Benzophenone, hydroxylamine HCl, Con. HCl, NaOH.
Principle: Aldehydes and ketones undergo condensation reactions with amino compounds in
presence of alkaline hydroxides. Oximes are obtained when aldehydes and ketones undergo
condensation with hydroxylamine. Such reactions are called as oximation. Hydroxylamine
reacts with carbonyl compound to yield an oxime. Thus benzophenone condenses with
hydroxylamine hydrochloride in the presence of excess of alkali to yield benzophenone
oxime.
Aldehydes and ketones react with hydroxylamine, in presence of NaOH to give an oxime
of low melting point. Usually they are obtained in two isomeric forms α & β (Beckmann
rearrangement). Amines of ketones undergo rearrangement to amides under the influence of
reagents like sulphuric acid, HF, PCl5.
Procedure:
1. Place a mixture of 25g of benzophenone, 15g of hydroxylamine HCl, 50ml of
rectified spirit and 10ml of water in a 500ml of RBF.
2. Add 28g of NaOH in small portions with occasional shaking [cool the RBF if
reaction mixture is too vigorous].
3. When all the NaOH pellets have been added, attach a reflux condenser and boil
for 5 min.
4. Cool and pour the contents into a solution of conc. HCl in 500ml of water
contained in 1 lit beaker.
5. Filter the precipitate at pump, wash thoroughly with cold water and dry in an
oven at 400C.
6. Find out the yield of benzophenone oxime and recrystallize it from methanol.
7. The oxime is gradually decomposed by oxygen. It should be preserved in
vacuum desiccator filled with CO2 and N2.
47
Experiment - 21
SYNTHESIS OF p- NITROACETANILIDE
Aim: To prepare and submit p-nitroacetanilide from acetanilide and report its percentage
yield.
Apparatus: Beaker, measuring cylinder, glass rod, separating funnel.
Chemicals: Acetanilide, conc. HNO3, conc. H2SO4, glacial acetic acid
Principle: Acetanilide, on treatment with a mixture of conc. HNO3 and conc. H2SO4
gives p-nitro acetanilide together with a little amount of o-isomer. Nitronium ions, obtained
from fuming HNO3 in the presence of conc. H2SO4, attack acetanilide to from p-nitro
acetanilide through the intermediate formation of cyclopentodienyl cation. It is an example
of Electrophilic Aromatic Substitution reaction. The acetamido group (-NHCOCH3) has
ortho and para directing influence. Here glacial acetic acid is used as a solvent to dissolve
acetanilide, conc. H2SO4 is used as a catalyst. Low temperature is maintained so as prevent
polynitration of acetanilide. Moreover this reaction is exothermic. Nitration mixture is added
at cold temperature to stand for 1hr for the reaction to go for completion.
H 3C NO 2
CH3
H 2 SO
fast
+
4 +
+ HONO 2
Slow
+ H
NHCOCH 3 NHCOCH 3
NHCOCH 3
Acetanilide Cyclopentadienyl cation p-Nitroacetanilide

Procedure:
1. Dissolve 2.5g of acetanilide in 2.5ml of glacial acetic acid, taken in a 100ml beaker.
2. Add 10ml of conc. H2SO4 gradually with vigorous stirring. Cool the flask in an
ice-bath to 0-50C.
3. Add a cold nitrating mixture of 1.1ml of conc. HNO3 and 7.1ml of conc. H2SO4
from a separating funnel drop wise into the reaction mixture maintaining the
temperature below 20C.
4. When all the acid has been added, allow the mixture to stand at room temperature
for half an hour and then pour the contents on 50g of crushed ice, where by
crude p-nitro acetanilide is precipitated. Allow standing for 10 minutes.
5. o-Nitroacetanilide goes into the solution while p-nitroacetanilide remains insoluble.
6. Filter, wash thoroughly with cold water and dry. Recrystallize it from alcohol.
Experiment - 22
SYNTHESIS OF p-NITROANILINE
Aim: To prepare and submit p-nitroaniline from p-nitroacetanilide and report its percentage
yield.
Apparatus: RBF, condenser, beaker, measuring cylinder, funnel, glass rod.
Chemicals: p-Nitroacetanilide, H2SO4, 10% NaOH, distilled water.
Principle: Direct hydrolysis of amide compounds to get nitro amines is not possible as they
get oxidized in the presence of HNO3. The most convenient way is to protect first the amino
group by acetylation and then nitrating the acetylated product by usual method. Here 70%
H2SO4 is used to hydrolyze p-nitroacetanilide and 10% NaOH is added to convert the
sulphate salt into free p-nitroaniline. The rate of reaction can be increased by refluxing the
mixture for 30 min.
Procedure:
1. Place the mixture of 1.5g of p-nitroacetanilide and 7.5ml of 70% w/w H2SO4
[4.3ml H2SO4 + 3.2ml distilled water] in RBF
2. Boil under a reflux condenser for 20 min or until a test sample is remain clear
upon diluting with 2-3 times its volume with water.
3. The p-nitro aniline is present in the liquid as its sulphate salt.
4. Pour the clear hot solution into 50ml of cold water and the p-nitroaniline
is precipitated by adding excess of 10% NaOH solution or of conc. NH3
solution.
5. Then, cool the mixture in ice cold water. Filter the product at pump, wash well
with distil water and recrystallize from a mixture of equal volume of rectified
spirit and water.
49
Experiment - 23
SYNTHESIS OF p- BROMOANILINE
Aim: To prepare and submit p-bromoaniline from p-bromoacetanilide and report its
percentage yield.
Apparatus: RBF, condenser, beaker, measuring cylinder, funnel, dropper, glass rod.
Chemicals: p-Bromoacetanilide, conc. HCl, 5% NaOH, ethanol, distilled water.
Principle: Hydrolysis of p-bromoacetanilide can be easily carried out with the help of water.
The breaking of amide group upon hydrolysis is called amide hydrolysis. Many amides will
not undergo hydrolysis easily in the presence of water. They require either acid or base as
a catalyst. Here conc. HCl is used to bring complete hydrolysis and the reaction mixture is
heated for 40 minutes. The product p-bromoaniline is present as its chloride, 10% NaOH is
added to convert it into free p-bromoaniline; acid hydrolysis is employed here since alkaline
hydrolysis is slow.
HN CH3 NH2
1. C on c. H C l
2. N aO H
Br Br
p-B ro m o aceta nilide p-B rom o aniline

Procedure:
1. Dissolve 1.8g of p-bromoacetanilide in 5ml of hot boiling ethanol contained in
a 250ml of round bottom flask.
2. To this, add 2.2ml of conc. HCl drop wise with constant shaking.
3. Attach reflux condenser and boil the solution for 40 minutes or until a test
portion is remained colourless when it is diluted with distilled water.
4. Pour the reaction mixture into 100ml ice cold water.
5. Add 5% NaOH solution with constant vigorous shaking until the solution is
just alkaline to litmus.
6. The p-bromoaniline is separates as oil, which is soon crystallizes.
7. Filter the crystals at pump and wash with 100ml ice cold water and dry in the
air.
Experiment - 24
SYNTHESIS OF SALICYLIC ACID
Aim: To prepare and submit salicylic acid from methyl salicylate and report its percentage
yield.
Apparatus: RBF, measuring cylinder, beaker, water bath, glass rod.

Chemicals: Methyl salicylate, H2SO4, NaOH.
Principle: Alkaline hydrolysis of esters is called saponification and is an irreversible process.
Here one mole of methyl salicylates (oil of wintergreen) reacts with two moles of NaOH to
form sodium salicylates with methanol and water, each of one mole. Sodium salicylate is
reacted with H2SO4 or HCl to remove the sodium ion and forms salicylic acid with sodium
sulphate as a by-product.
Procedure:
1. Measure 3ml of methyl salicylate in clean and dry RBF.
2. Add 50ml of 6M NaOH and some boiling chips.
3. Heat the reaction for 30-40 min after boiling started. Turn off the burner when
mixture is clear.
4. Remove condenser when it was cool enough to touch, and then wait till room
temperature.
5. Transfer the mixture in to a beaker, and then slowly add H2SO4 until pH 2.
6. Cool the reaction mixture in ice-water for 5 minutes. Let the mixture settle and
then filter at vacuum pump.
7. Dissolve the solid by using a minimal amount of boiling hot water.
8. Then cool the solution to room temperature, and then cool in ice bath for 10 min.
9. Vacuum filter and rinse with ice cold water. Recrystallize from hot water,
measure the yield of dry product.
51
Experiment - 25
SYNTHESIS OF 5-NITROSALICYLIC ACID
Aim: To prepare and submit 5-nitrosalicylic acid from salicylic acid and report its percentage
yield.
Apparatus: Conical flask, measuring cylinder, beaker, glass rod.
Chemicals: Salicylic acid, calcium nitrate tetrahydrate, acetic acid.
Principle: Nitration of salicylic acid occurs by placing a nitro group on the aromatic ring
system via an Electrophilic aromatic substitution reaction. Here calcium nitrate is used as
the nitrating agent in presence of acetic acid. Two groups –CO2H and –OH in salicylic acid
complement each other since they both direct the entering nitro group to the 5th position. The
5th position and the 3rd position, are both electronically favoured since the –CO2H group is
meta directing and the –OH group is ortho-para directing. The nitro group is attached at the
5th position, and not at the 3rd position, due to steric effects. We can also use anhydrous nitric
acid or concentrated nitric acid and concentrated sulphuric acid as nitrating reagent.
Procedure:
1. Weigh accurately and dissolve 3g of calcium nitrate tetrahydrate in 10ml of
acetic acid with in a 100ml clean and dry conical flask by gently heating on a
water bath.
2. Add 2g of salicylic acid and heat the reaction mixture on a boiling water bath
(below 80 0C) for few minutes until a dark red solution will form.
3. Pour the dark-red coloured reaction mixture into a 100ml beaker containing
20ml ice cold water, will get dark-red coloured solution forms, which keep in a
refrigerator after 4-5 hrs yellow crystals of 5-nitrosalicylic acid separates out.
4. Filter the crude product at suction pump, wash with cold water and dry.
Experiment - 26
SYNTHESIS OF BENZOIC ACID
Aim: To prepare and submit benzoic acid from ethyl benzoate and report its percentage
yield.
Apparatus: RBF, measuring cylinder, beaker, funnel, glass rod.
Chemicals: Ethyl benzoate, NaOH, HCl.
Principle: Esters are hydrolysed either by an acid or a base. Alkaline hydrolysis of ester
is irreversible which is also called saponification. Acid hydrolysis of ester is a reversible
reaction. Acid hydrolysis of esters can occur by more than one type of mechanism, the
common mechanism is, the alkaline hydrolysis, which occur through a Nucleophilic acyl
substitution. Here ethyl benzoate on hydrolysis with NaOH gives benzoic acid and ethyl
alcohol where OH- ion of NaOH acts as a nucleophile.
53
Procedure:
1. Weigh accurately 5g of ethyl benzoate and 20ml of 2M NaOH solution in a
clean and dry RBF.
2. Reflux the reaction mixture for 45-60 min until all oily drops of the ester have
disappeared.
3. Allow it to cool and then transfer the reaction mixture to a 250ml beaker.
4. Add 30ml of 5M HCl slowly with stirring to precipitate out the benzoic acid.
Continue adding the acid until no more precipitation takes place and mixture
turns acidic.
5. Allow it to cool to room temperature and filter off the precipitate.
6. Wash the crude compound with small volume of distilled water. And recrystallize
from distilled water.
Experiment - 27
SYNTHESIS OF NITROBENZENE
Aim: To prepare and submit nitrobenzene from benzene and report its percentage yield.
Apparatus: RBF, measuring cylinder, beaker, funnel, separating funnel, glass rod,
thermometer.
Chemicals: Benzene, conc. HNO3, conc. H2SO4, anhydrous CaCl2.
Principle: Nitration is a substitution reaction in which –NO2 group is substituted on aromatic

ring. Aromatic hydrocarbons may be nitrated, where hydrogen atoms replaced by nitro group,
with conc. HNO3 in the presence of conc. H2SO4. The function of sulphuric acid is to convert
nitric acid into the highly reactive nitronium ion (NO2+), which is real nitrating agent.
Procedure:
1. Place 17.5ml of conc. HNO3 in 250ml clean and dry RBF. And add 20ml conc.
H2SO4.
2. Keep the RBF in ice bath and maintain the temperature between 55-60==C
using a thermometer.
3. Place 15ml of benzene in portions of 1-2ml. Shake well to ensure thorough
mixing after each addition of benzene.
4. Do not allow the temperature to rise above 55-600C.
5. After complete addition of benzene, keep reflux and maintain 600C for 10-15 min.
6. Pour the contents to the flask into 250ml of cold water in a beaker.
7. Stir well and allow it to stand. When nitrobenzene has settled to the bottom,
pour the liquid as completely as possible.
8. Transfer the residual liquid into separating funnel and add 25ml of water.
Shake well and allow it to stand.
9. Separate the nitrobenzene and add into conical flask containing about 205g of
anhydrous CaCl2.
10. Filter off the crude product and dry. Weigh and report the percentage yield.
55
Experiment - 28
SYNTHESIS OF 2-IODOBENZOIC ACID
Aim: To prepare and submit 2-iodobenzoic acid from 2-aminobenzoic acid and report its
percentage yield.
Apparatus: Measuring cylinder, beaker, funnel, dropper, glass rod.
Chemicals: 2-Aminobenzoic acid, H2SO4, NaNO2, KI, solid Na2CO3.
Principle: The procedure consists of diazotization of 2-aminobenzoic acid followed by

reaction with KI (in H2SO4). 2-Iodobenzoic acid/o-Iodobenzoic acid is an organic compound,
ant it can be synthesized via the diazotization of anthranilic acid or 2-amino benzoic acid. 2-
Iodobenzoic acid can be synthesized via a Sandmeyer reaction consisting of the diazotization
of anthranilic acid followed by a diazo replacement. First anthranilic acid is treated with
nitrous acid in order to convert the amino group into the diazo group. The diazo group is
ejected, yielding a carbocation which is then attacked by highly nucleophilic I− anion.
Procedure:
1. Transfer 2g of solid 2-aminobenzoic acid into a 100ml beaker placed in the
ice-bath.
2. Add 7.2ml of H2SO4 (2.6 M) and mix the contents thoroughly for 1 min with
the help of a glass rod.
3. Cool the solution for 5 minutes. Measure out 4.4ml of cooled NaNO2 solution
from the vial placed in the ice-bath.
4. With the help of a dropper, slowly add the cooled NaNO2 solution to the acid
solution with constant gentle stirring using a glass rod to obtain an almost clear
solution (3-5 minutes).
5. Remove the beaker from the ice bath and then slowly add 9.4ml of KI solution
with stirring.
6. Keep the beaker in hot water for 5 minutes.
7. Filter the crude product and wash it thoroughly with 10ml distilled water.
Collect the washings along with the main filtrate.
8. Neutralize the combined filtrate by gradually adding the given solid Na2CO3
until effervescence ceases. Dispose of the filtrate.
Purification:
 Place the funnel containing the precipitate on a 100ml conical flask.
 Pour about 15 to 20ml of the sNaHCO3 solution (using test tube) over the filter
paper so as to dissolve the precipitate completely.
 Add the pinch of charcoal powder to the filtrate and mix it thoroughly. Filter
the solution to remove charcoal.
 Add dilute H2SO4 gradually to the filtrate till effervescence ceases. Filter off
the purified product.
 Use 10-15ml distilled water to wash the precipitate. Keep the filter paper with
the product on a watch glass.
 Cover the product with the same funnel and keep it for drying (for a minimum
of one hour).
57
Experiment - 29
SYNTHESIS OF CYCLOHEXANONE
Aim: To prepare and submit cyclohexanone from cyclohexanol and report its percentage
yield.
Apparatus: RBF, measuring cylinder, beaker, funnel, separating funnel, glass rod.
Chemicals: Cyclohexanol, sodium dichromate dihydrate, concentrated sulfuric acid, ethyl

acetate, distilled water.
Principle: This preparation shows that a ketone can be prepared by the oxidation of a
secondary alcohol. In a similar way, an aldehyde can be prepared from a primary alcohol,
but since aldehydes are easily oxidized further to carboxylic acids, they must be distilled off
from the reaction mixture as formed.
Procedure:
1. Dissolve sodium dichromate dihydrate (12.5g) in distilled water (60ml) in
a 100ml beaker and with continuous stirring with a glass rod carefully and
slowly add concentrated sulfuric acid (11g, 6ml).
2. Allow the mixture to cool. Place cyclohexanol (6g) in a 100ml conical flask
and add the dichromate solution to it in one portion, with swirling to ensure
thorough mixing.
3. When the temperature rises to 55 0C, cool the flask in cold water; sufficient
external cooling should be applied to keep the temperature between 55 and 60
0C.
4. When the mixture no longer heats up, allow to stand, with occasional swirling,
for 1 hour.
5. Pour the mixture into a 250ml round bottom flask; add distilled water (60ml).
6. Set up a distillation apparatus (but with a stopper instead of a thermometer and
a 100ml graduated cylinder to collect the distillate).
7. Distil the mixture using a Bunsen burner until about 30ml of distillate (two
layers) has been collected.
8. Transfer to an Erlenmeyer flask and saturate with salt (about 7g).
9. Separate the layer of cyclohexanone in a separatory funnel. Extract the aqueous
layer twice with ethyl acetate (10ml).
10. Combine the ethyl acetate extracts with the cyclohexanone layer.
11. Dry with anhydrous magnesium sulfate (5 min) and filter into a pre-weighed
dry 50ml RBF.
12. Distil off the ethyl acetate, using a distillation apparatus set up on a steam
bath.
59
Experiment - 30
SYNTHESIS OF PICRIC ACID
Aim: To prepare and submit picric acid from phenol and report its percentage yield.
Apparatus: RBF, measuring cylinder, beaker, Buchner funnel, water bath, dropper.
Chemicals: Phenol, conc. H2SO4, conc. HNO3, distilled water.
Principle: The principle involved in this reaction is Aromatic Electrophilic Substitution

Reaction. When phenol is treated with nitric acid in the presence of sulphuric acid, nitration
occurs immediately at ortho and para positions producing picric acid. Phenol is first reacted
with sulphuric acid, a mixture of ortho and para phenol sulphonic acid is obtained. The
mixture is treated with nitric acid, nitration happened at two positions meta to the sulphonic
acid in each compound and finally the sulphonic acid group is replaced by the third nitro
group producing picric acid (2,4,6-Trinitrophenol).
Procedure:
1. Place 7.5g of phenol and 20ml of conc. H2SO4 in a clean and dry RBF.
2. Shake the mixture and heat on a water bath for 30 min, during the period a
clear solution is obtained.
3. Cool the flask in an ice bath. Now, add 22ml of conc. HNO3 drop wise with
constant shaking.
4. An exothermic reaction takes place and red fumes are evolved and the liquid
becomes deep red in colour.
5. Heat the flask in a water bath and pour in carefully in to about 100ml of cold
water.
6. Filter the crude solid using Buchner funnel and wash thoroughly with cold
water.
Experiment - 31
SYNTHESIS OF HIPPURIC ACID
Aim: To prepare and submit hippuric acid from glycine and report its percentage yield.
Apparatus: Beaker, conical flask, funnel, glass rod, cork, measuring cylinder.
Chemicals: Glycine, 10% NaOH, benzoyl chloride, distilled water.
Principle: Electrophilic substitution of benzoyl group on nitrogen atom of glycine gives N-

Benzoyl glycine, commonly known as Hippuric acid.
Procedure:
1. Dissolve 2.5g of glycine in 2.5ml of 10% NaOH solution taken in a conical
flask (if not dissolved add few more ml of 10% NaOH).
2. Add 4.5ml of benzoyl chloride in two portions to the solution. Stopper the
flask and shake vigorously after each addition.
3. Transfer the solution into a beaker containing water and filter it. If product is
not formed, add crushed ice.
4. Recrystallize it using boiling water.
61
Experiment - 32
MICROWAVE ASSISTED HYDROLYSIS

OF BENZAMIDE
Aim: To perform hydrolysis of benzamide by using Microwave Irradiation Technique.
Apparatus: Glass beaker, glass rod, measuring jar.
Chemicals: Benzamide, 20% sulphuric acid.
Principle: Microwave normally has wavelength between1cm and 1m, Frequency of 30 to

300 GHz. Microwave irradiation induces specific interactions between materials and waves
of electromagnetic nature assimilated to dielectric heating. In Electromagnetic spectrum the
Microwave radiation is located between IR & Radiowave radiation. Telecommunication and
MW radar equipment occurs in many of the band frequencies in this region. In order to avoid
interference with these systems, the household and Industrial MW ovens operate at a fixed
frequency of 2.4GHz. The energy = 0.3cal/Mole (from E=hν).
Procedure:
1. Place a mixture of benzamide and 20% sulphuric acid in a 150 ml glass beaker
(clean and dry), and then place in a microwave oven and heat for 10min.
2. Cool the reaction mixture. After cooling, make the reaction mixture basic with
dil. NaOH solution.
3. A white colour product of crude benzoic acid will form.
4. Check the formed benzoic acid by its solubility tests and melting point (Melting
Point: 121-123 0C).
Experiment - 33
SYNTHESIS OF TETRAHYDROCARBAZOLE
Aim: To prepare and submit tetrahydrocarbazole from phenyl hydrazine and report its
percentage yield.
Apparatus: R.B.flask, condenser, beaker, funnel, glass rod.
Chemicals: Glacial acetic acid, cyclohexanone, phenyl hydrazine.
Principle: Fischer Indolization (Fischer Indole Synthesis) occurs when phenyl hydrazine
reacts with saturated cyclic aldehyde or ketone. Cyclization takes place with loss of NH3
under the influence of reagents like glacial acetic acid. Phenylhydrazine of saturated cyclic
ketone like cyclohexanone undergoes cyclization very rapidly when boiled with glacial
acetic acid.
Procedure:
1. Dissolve 2.5ml of cyclohexanone in 18ml of glacial acetic acid in a clean and
dry R.B. flask.
2. Add 2.2ml of phenyl hydrazine to the above reaction mixture.
3. Boil the mixture under reflux for 5 minutes and cool the solution whereby
tetrahydrocarbazole will crystallize out.
4. Filter off the product at vacuum pump.
5. Recrystallize it using aq. ethanol/aq. CH3COOH.
63
Experiment - 34
SYNTHESIS OF BENZOIN
Aim: To prepare and submit benzoin from benzaldehyde and report its percentage yield.
Apparatus: R.B.flask, condenser, beaker, funnel, glass rod.
Chemicals: Benzaldehyde, ethanol, distilled water, KCN
Principle: Many aromatic aldehydes undergo condensation when treated with a solution
of alkali metal cyanide (KCN or NaCN) in aqueous ethanol to the alpha hydroxyl ketone.
Thus, Benzaldehyde gives benzoin. The reaction is called as benzoin condensation. This
is probably due to the KCN undergoing partial hydrolysis generating HCN, which then
added onto the benzaldehyde giving cyanohydrins. The later then reacts with unchanged
benzaldehyde giving benzoin. Thus the reaction depends upon the catalytic influence of the
cyanide ion and the mechanism may be represented in the following way.
Procedure:
1. Weigh accurately 5ml water and 10ml ethanol and place in 250ml conical
flask.
2. To this, add 1g of KCN (or NaCN) and mix it thoroughly.
3. Then, add 5ml of freshly distilled benzaldehyde to this solution.
4. Boil the reaction mixture gently on a water bath for 30 min with the reflux
condenser attached to the flask. As a result a clear solution was obtained.
5. Then cool the reaction mixture in an ice-water bath. Pour this solution into a
beaker containing 100ml of ice-cold water. Precipitate out benzoin as a pale
yellow mass.
6. Filter the product at the pump, wash well with water.
7. Rrecrystallize from rectified spirit.
Precautions
 The reaction is sometimes vigorous and some of the material may be lost
through the condenser. Hence large container should be used while refluxing.
 KCN or NaCN should be used carefully since it is poisonous. Residual solution
containing alkali cyanides should be rendered innocuous by the addition of an
excess of sodium hypochlorite before being discharged.
 The filtrate contains sodium cyanide, and should be washed down with a lib-
eral quantity of water.
 They should never treat with acid.
65
Experiment - 35
SYNTHESIS OF PHTHALIMIDE
Aim: To prepare and submit phthalimide from of phthalic anhydride and report its
percentage yield.
Apparatus: Round bottomed flask, sand bath, measuring cylinder.
Chemicals: Phthalic anhydride, urea, methanol, distilled water.
Principle: Nucleophile is amino group of urea, both amine groups of urea acts as
nucleophile, attracts 2 moles of phthalic anhydride resulting in the formation of 2
moles of phthalimide (Nucleophilic Substitution Reaction).
Procedure:
1. Mix 2g of phthalic anhydride and 0.4g of urea and place the mixture in dry round
bottomed flask.
2. Heat the flask on low flame on sand bath. When the contents melt effervescence
commences and gradually increases after 10-20 min, the mixture suddenly froths up to
about 3 times the original volume and becomes almost solid.
3. Remove it from the flame and allow it to cool and add 5ml of water to it.
4. Filter at the pump. Recrystallize from methanol.
Experiment - 36
SYSTEMATIC QUANTITATIVE ANALYSIS OF

ORGANIC COMPOUNDS
Chemists frequently use qualitative patterns of reactivity to identify the functional groups
of unknown compounds. This technique, called qualitative analysis, was an especially
important tool for structure determination in the early days of organic chemistry. An alkene,
for example, can be identified by its reaction with bromine disappearance of the red-brown
colour of the bromine provides clear visual evidence that a reaction has occurred.
The analysis and identification of unknown organic compounds constitutes a very important
aspect of experimental organic chemistry. Often, a common first step in the identification of
an unknown substance is to determine what elements are present in the sample. Although
it is often possible to establish the structure of a compound on the basis of spectra alone
(IR, NMR, etc.), the spectra typically must be supplemented with other information about
the compound: physical state and properties (melting point, boiling point, solubility, odour,
colour, etc.), elemental analysis, and confirmatory tests for functional groups.
In this experiment you will carry out several qualitative tests that will allow you to identify
functional groups in organic molecules. You will then apply what you have learned by
characterizing unknown organic compounds in terms of their functional group and solubility
behavior. There is no definite set procedure that can be generally applied to organic qualitative
analysis. Various books have different approaches, but a systematic approach based on the
scheme given below will give good results. Each functional group has a particular set of
chemical properties that allow it to be identified. Some of these properties can be demonstrated
by observing solubility behaviour, while others can be seen in chemical reactions that are
accompanied by colour changes, precipitate formation, or other visible effects.
A combination of physical and chemical tests will be used to determine what functional
groups are present. Each of these tests should give an easily visible result. The different tests
are explained in detail and the procedures are described below. The section that follows the
individual tests will guide you through the process of putting it all together and developing a
scheme that you can use to identify each of the compounds. If you work this out before you
come to lab, the experiment should be go very quickly and you’ll be out early; if you don’t
you’re unlikely to finish before the end of the period.
By the end of this laboratory, you should have developed the skills to determine the functional
67
group of an unknown compound by using classification tests.
In carrying out identification of an organic compound following tests and observations are
carried out:
I. Preliminary Tests and Physical Examination

II. Determination of Physical Constants (M.P/B.P)
III. Detection of Elements
IV. Determination of Solubility Group
V. Detection of Functional Group
VI. Special Tests, if any.
Preliminary test and physical examination
Test Observation Inference

State Solid Generally high molecular weight, usually
having more than 6 carbon atoms chain.
Eg: Acids, Sugars, Amides, etc.
Liquid Generally low molecular weight.
Eg: Alcohols, Ethers, Esters, Aliphatic amines,
Aldehydes, Ketones, Hydrocarbons, etc.
Colour Pale Yellow Nitro compounds, nitrobenzene, dinitrobenzene,
nitrophenol, quinones, iodoform
Yellow Orange Nitro-aniline
Pink α-Naphthol, β-Naphthol, resorcinol
Red Azo compounds, methyl orange
Green Nitroso compounds
Greenish yellow o/m-nitrobenzaldehyde
Brown-dark Phenols, Amines, (darken due to oxidation)
Colourless Compounds not containing strong
chromophore.
Eg: Acids, Hydrocarbons, ketones, esters, urea,
thiourea, acetamide, acetanilide, benzamide,
naphalene, etc.
Odour Pleasant Alcohols (low mol. wt.), Aromatic hydrocarbons,
ethers, alkyl halides, chloroform, chlorobenzene.
Deep Sweet Chloroform
Fruity Esters
Phenolic / Phenols and cresols

Carbolic
Fishy Aromatic amines
Kerosene Hydrocarbons
Moth ball Naphthalene
Bitter Almond Benzaldehyde, nitrobenzene
Pungent/ Aliphatic acids, Acid chlorides, formaldehyde,
Irritating and side chain halo hydrocarbons
Ignition test: i.Non-sooty Aliphatic compounds
Flame test: Take Flame
a small quantity
of compound ii.Sooty Flame Aromatic compounds
and put it on a
metallic spatula
or in a porcelain
dish and ignite
it directly on the
flame.
Test for Decolourization Unsaturated compounds may be present
Unsaturation: of KMnO4
Action of KMnO4 No Saturated compounds may be present
(Baeyer’s test): decolourization
Sub (solid/ of KMnO
4
Liquid) + Sodium
carbonate
solution + few
drops of 2%
KMnO4 solution
and shake
vigorously.
Action of bromine Decolourization Unsaturated compounds may be present
water (for freely No Saturated compounds may be present
or sparingly decolourization
water soluble
compounds): Sub
(solid/liquid) +
bromine water drop
wise, and shake
vigorously.
69
Detection of Extra Elements (Lassaigne’s Test):
Preparation of sodium fusion extract: Transfer a small, clean, dry piece of sodium metal
(made free from kerosene using a filter paper) into a fusion tube and heat gently till the
sodium metal melts and fuses. Introduce a little amount (about 5-10mg) of the organic
compound into the fusion tube. In case of volatile liquid a larger amount should be added to
fusion tube. Heat the tube gently over flame then heat strongly till it becomes red-hot. Break
this red-hot tube into a mortar containing 10-15 ml of distilled water, crush with a pestle or
glass rod. Transfer the contents into a porcelain dish, boil and concentrate the extract. Filter,
cool the filtrate and carry out the following tests using the filtrate, which is called as Sodium
Fusion Extract.
Test for the presence of Nitrogen, Sulphur and Halogens in the given compound by
Lassaigne’s test using sodium fusion extract. Detailed procedure is as follows.

Test for Nitrogen: Prussian Blue test: To 2ml of Prussian blue/green Presence of
the extract, add a pinch of solid ferrous sulphate colour nitrogen
and heat it to boiling. Add carefully 3 or 4 drops
of dil. H2SO4.
Test for Sulphur: Sodium nitroprusside test: To Purple or violet red Presence of
1ml of the extract add 1 ml of freshly prepared colour sulphur
sodium nitroprusside.
Lead acetate test: Stock solution + acetic acid + Black precipitate Presence of
2 ml lead acetate (5%) sulphur
Test for Nitrogen & Sulphur: To 2ml of the Blood red/wine red Presence of
fusion extract neutralize with HCl, add a few colour solution nitrogen and
drops of FeCl3. sulphur
Note: if the Lassaigne extract containing excess of sodium metal, sodium cyanide and
sulphides are formed instead of sodium thiocyanate.
Test for Halogens: Silver Nitrate test: To 1ml White ppt, which Indicates the
fusion extract, add about 2ml of dil. HNO3 and freely dissolves in presence of
boil for 2-5 min. Then cool it and add few ml of 2 ml of ammonia chlorine
AgNO3 solution. solution
Pale yellow ppt, Indicates the
which is difficult to presence of
dissolve in 2 ml of bromine
ammonia solution
Yellow ppt, which is Indicates the
insoluble in 2 ml of presence of
ammonia solution iodine
Functional Group Analysis:
Identify the functional groups present in the compound by qualitative tests, wherever possible
two confirmative tests should be carried out. The details are given in the following tables.
Carboxylic acids:
Solubility in sodium Bicarbonate solution: To The compound Presence of
50mg of the compound add 1 ml of 10% sodium dissolves with carboxylic acid
bicarbonate solution. effervescence group
To the clear solution add a few drops of conc. HCl. The compound Compound is a
is regenerated carboxylic acid
Esterification: To 50mg of the compound add 1 ml Fruity odour Confirmation of
of ethyl alcohol or methanol and add 1 ml of conc. carboxylic acid
H2SO4 and heat the mixture in hot water bath for
5 min. Pour the contents into cold 10% sodium
bicarbonate solution.
Ferric chloride colouration: To 50mg of the A brownish Confirmation of
compound add few drops of ammonium hydroxide violet or carboxylic acid
until alkaline to litmus. Add 1 ml of neutral Ferric reddish brown
chloride solution. precipitate
Phenols:
Neutral FeCl3 test: Take 5 drops of the compound Green/brown/ Compound may
and add a few drops of freshly prepared neutral violet/blue be a phenol
FeCl3 solution. colour develops
Phthalein fusion test: To 100mg of the compound in i.Pink colour Compound is
a test tube add equal amounts of phthalic anhydride develops phenol
and heat. Add 2 drops of conc. H2SO4. Stir the ii.Red/blue/ Compound is
mixture, cool and add 2-3 drops of this mixture into fluorescent a substituted
a beaker containing 5ml of 10% NaOH. colour develops phenol
Reaction with bromine water: To 1 drop of phenol Formation of an Phenolic nature
add bromine water until orange colour persists. Pour yellowish white is confirmed
it in a beaker containing ice cold water. precipitate
Libermann reaction: Take 1 or 2 crystals of NaNO2 Deep green or Phenolic nature
in a dry test tube, add 0.5g of phenol and heat for deep blue colour is confirmed
1 ml. Allow it to cool and add twice the volume of develops which
conc. H2SO4. on dilution
changes to red
colour
71
Diazotisation: Take 2 or 3 drops of aniline in a test Formation of Confirms phenol

tube add conc. HCl until aniline dissolves and add red orange dye
3 ml of cold water. Cool the test tube in ice to 00C.
Add few drops of 20% NaNO2 solution (which is
also cooled to 00C) to the aniline solution. Add this
diazonium solution to a cold solution of phenol in 10
ml of 10% NaOH solution. Maintain the temperature
at 00C.
Amines:
Solubilityindil.HCl:Take10mg The compound dissolves The compound may be
(5 drops) of the compound and and a clear solution is primary/secondary/tertiary
add 15 ml of dil. HCl. obtained amine
Nitrous acid test: Dissolve 1. If liberation of brown gas Indicates the formation of
50mg of the substance in 1 ml with the formation of an diazonium ion. Primary
of Conc. HCl and dilute with orangish brown solution amine is confirmed
3 ml of water. Cool in ice and 2. If yellow oily drops Indicates the formation of
add few drops of cold NaNO2 separates outs N-Nitrosoamine. Secondary
solution. amine is confirmed
3. Dark red colour solution Indicates the formation of
is obtained; to this add 1 p- Nitroso amine. Tertiary
ml of 5% NaOH. Dark amine is confirmed
green solid separates out
Reaction with bromine water: Formation of an Primary amine is confirmed
To 1 drop/10mg of amine add yellowish white
bromine water until orange precipitate
colour persists. Pour it in a beaker
containing ice cold water.
Diazotisation of primary amine: Azo dye is formed Primary amine is confirmed
Take 2 or 3 drops of amine in a test
tube, add conc. HCl until aniline
dissolvesandadd3mlofcoldwater.
Cool the test tube in ice to 00C.Add
few drops of 20% NaNO2 solution
(which is also cooled to 00C) to the
aniline solution.Add this diazonium
solution to a cold solution of phenol
in 10 ml of 10% NaOH solution.
Maintain the temperature at 00C.
Carbonyl compounds:
2,4–DNP test: To 2-3 drops of comp. Add 1 An orange C a r b o n y l
ml of 2,4-DNP reagent (if compound is solid precipitate compound is
dissolve it in few drops of methanol). Keep it in present
hot water bath for few minutes if no precipitate
is formed.
Bisuphite addition reaction: To 1 ml of comp. Formation of white May be Aldehyde
add 1 ml of saturated sodium bisulphite addition product or ketone
solution.
Tollen’s test: To 1 ml of comp. add 5 ml of A silver mirror is Aldehyde group is
tollen’s reagent and heat. deposited (or black confirmed
ppt)
Fehling’s test: To 1 ml of comp add 1 ml of Red coloured ppt. Aldehyde is
Na2CO3 solution and 1 ml of Fehling’s is formed (aromatic confirmed
solution A and 1 ml of Fehling’s solution B. aldehydes react
Boil the mixture for 2-3 min. very slowly)
Note: If all the tests are negative except 2,4-DNP test then the compound may be ketone.
Amides:
Hydrolysis: Take 5mg of compound Ammonia gas is liberated. Amide is confirmed
in a test tube and add 2 ml of NaOH Turns red litmus to blue
and heat for 2 min on a burner. (Test White ppt. of carboxylic Amide is confirmed
with litmus). Add HCl to the above acid is formed
alkaline solution.
Esters:
Hydroxamic acid test: To a drop of the Deep violet or deep reddish Confirmation
compound add 100mg of solid hydroxyl amine colour develops due to the of ester
hydrochloride and 5 m of 10% NaOH solution. formation of hydroxamic
Boil the mixture on a bunsen flame for 2-3min. acid
Cool and acidify with dil. HCl. To this solution
add few drops of neutral FeCl3 solution.
Hydrolysis: Take 2 ml of ester in a 50 ml Ester undergoes hydrolysis Confirmation
round bottomed flask and add 20 ml of 30% to give an alcohol and acid. of ester
NaOH solution and reflux using a water The alcohol being liquid
condenser for half an hour. Cool the mixture floats on the mixture and
and neutralize with conc. HCl. acid gets precipitated by
neutralisation
73
Carbohydrates:
Molisch’s test: Aq. solution of sample A reddish violet ring Carbohydrates
+ 2/3 drops of α-naphthol, mix + 2 ml at the junction of two are present (The
conc. H2SO4along the side of the test layers test is specific for
tube carefully. carbohydrates. They
undergo dehydration
when treated with conc.
H2SO4 to form furfural.
This condenses with
α-naphthol to form
coloured compound).
Solubility test: Pinch of powder and a If soluble Monosaccharides are
few drops of water. present
If insoluble Polysaccharides are
present
Fehling’s test: 1 ml of Fehling’s A + Yellow or brick red Reducing sugars are
Fehling’s B + sugar solution + boil. ppt present
Benedict’s test: 5 ml Benedict’s Yellow or brick red Reducing sugars are
reagent + 3ml sugar solution + boil ppt present
for 2min and cool.
Tommer’s test: 2 ml of Tommer’s Yellow or red ppt Reducing sugars are
reagent + 3 ml of sugar solution + boil present
for 2 min and cool.
Barfoed’s test: 2 ml of sugar solution Brick red ppt at the Monosaccharides are
+ 2 ml of Barfoed’s reagent + boil on bottom of test tube present
water bath.
Seliwanoff’s test: 3 ml of Seliwanoff’s Red ppt Ketoses like fructose and
reagent + 1 ml of sugar solution and sucrose are present
boil for 2 min.
Rapid furfural test: 1ml of sugar Deep purple colour Ketoses like fructose and
solution + 1 ml of alcoholic naphthol sucrose are present
solution + 5 ml of conc. HCl + boil.
Osazone test: 0.2g of sugar + 0.4g a. Greenish yellow a. Glucose is present

of phenyl hydrazine HCl + 0.6g of needle like crystals
sodium acetate + water. Boil on a arranged like a fan
water bath for 20 min. Crystals are b. Thin small needle b. Lactosazone is present
formed which are observed under like crystals arranged
microscope. like a ball of cripples
c. If plate like c. Maltosazone is present
crystals appear like a
sunflower
Iodine test: Suspension of solution a. Blue or violet colour a. Starch is present
of polysaccharides + 1 or 2 drops of b. Brown or violet b. Glycogen is present
iodine solution. colour
Urea:
Biuret test: Place 20mg of urea in a dry test tube Copper sulphate Confirmation
and heat it gently for a min. The comp melts with colour changes to of urea
liberation of NH3 and resolidifies to form biuret. purple colour
Dissolve this in 1 ml of hot NaOH solution and heat
it. Cool and add a drop of CuSO4 solution.
Thiourea:
Test with FeCl3: Take 10mg of the compound and Blood red colour Confirmation
heat it on a burner till it melts. Then add 2-3 drops of develops due of Thiourea
CH3COOH followed by a few drops of potassium to ammonium
ferricyanide. thiocyanate
Melt 10mg of thiourea in a dry test tube and add few Green colour Confirmation
drops of dil.CH3COOH, followed by few drops of appears and slowly of Thiourea
potassium ferricyanide changes to blue
Hydrocarbons:
Test with AlCl3: To a few mg of the compound Orange colour Compound
or 0.2 ml of liquid add 3 ml CHCl3 and shake develops on the may be halo
well. Then transfer a pinch of AlCl3 into a dry sides of test tube. hydrocarbon
test tube and sublime. Then add CHCl3 to the Purple or blue Compound
sublimed AlCl3 such that the CHCl3 layer or green colour may be poly
touches the AlCl3. develops. hydrocarbon
75
Halogen hydrocarbons:
ElementalAnalysis (Lassaigne’s Halogen present Halogen hydrocarbon
test).
Sub + alcoholic AgNO3 solution White ppt Halogen present in side chain
– warm. No white ppt Halogen present in nucleus
Anilides:
To 50mg of the compound, add Carboxylic part of anilides separates Confirmation
5 ml of conc. H2SO4 and warm as solid of benzanilide
carefully.
To 50mg of the compound add Formation of oily droplets indicates Confirmation
5 ml of conc. H2SO4, warm the amine part which is extracted of acetanilide
carefully and neutralize with dil. with ether. Evaporate ether and test
NaOH. for primary amine (any 10 test)
Nitro group:
Mulliken’s test: 0.2g of the compound + 2 ml of ethyl Black or grey Presence of
alcohol + 0.1 gm of solid NH4Cl + 0.1g of Zn dust. Boil precipitate nitro group
for 5 min and filter. Filter + Tollen’s reagent.
Azo-Dye test (If primary amino group absent, then only Orange red Presence of
perform this test): 0.5g of the compound + 0.5g of Tin dye nitro group
metal + 2 ml of conc. HCl. Boil or 3 min, cool filter and
dilute with about 5 ml of water + few drops of NaNO2.
Add this sol to a cold solution of alkaline ß-naphthol.
Test for Dinitro compound: 0.5g of the compound + 1-2 Dark purple or Presence of
ml of acetone, shake well to dissolve the com pound+ violet colour dinitro group
1-2 drops of dilute NaOH solution. No purple Mononitro
colour compound
Alcohols:
Sub + 2,4-dinitrophenyl hydrazine solution No red precipitate Alcohol may
(excess) – warm if necessary be present
Sodium metal test: Sub + freshly cut shiny sodium Vigorous reaction A l c o h o l
metal (in a dry test tube) (brisk effervescence present
of hydrogen gas)
Esterification reaction: Sub + benzoic acid + Fruity odour Confirmation

conc. H2SO4 (in a dry test tube) boil for some of alcohol
time and pour in a china dish containing water or
Na2CO3 solution.
Report:
From the above step by step analysis of given organic compound shows that, it is
State:
Colour:
Odour:
Aromatic/Aliphatic:
Saturated /unsaturated:
Solubility:
Extra elements:
Functional group:
M.P. / B.P.:
77
Experiment - 37
SEPARATION OF ORGANIC BINARY MIXTURE
Following procedure separates the organic binary mixture:
Physical state of the mixture: Solid-Solid / Solid-Liquid / Liquid-Liquid.
Solubility of the mixture: One of the components in a binary mixture may be soluble in any
one of the reagents NaHCO3/NaOH/dil. HCl. Based on its solubility the mixture is separated
into individual components. If one of the components is insoluble in ether, then ether will be
the separating reagent.
S. No. Ether 10% 10% Dil. HCl Inference

NaHCO3 NaOH
1 + + + - Separating
reagent is 10%
NaHCO3
2 + - + - Separating
reagent is 10%
NaOH
3 + - - + Separating
reagent is dil.
HCl
4 - Separating
reagent is ether
Solubility Procedure:
Take about 100mg of the given mixture in a test tube and then add 10% NaHCO3 solution
shake well and filter. Then neutralize the filtrate with conc. HCl. On neutralization if one
of the components separates that indicates the mixture solubility as 10% NaHCO3 and if
nothing separates on neutralization that indicates the mixture is insoluble in 10% NaHCO3.
Then the procedure is to be continued with 10% NaOH. If NaOH is also negative then repeat
the same procedure with dil. HCl and neutralize with NaOH.
Table 1: Solubility chart
Separation Procedure:
1. If physical state of the mixture is Solid-Solid: Transfer the entire mixture into a conical flask
and repeatedly extract with the reagent in which the mixture is soluble (NaHCO3/NaOH/dil.
HCl) and filter. The completion of the mixture separation is checked by neutralization of the
last drops of the filtrate. If no solid separates that indicates the completion of separation and
if solid separates the process is to be repeated until no precipitation occurs on neutralization.
After the separation, combine all the filtrates, neutralize and filter. The solid obtained is
component-I.
2. The solid insoluble in the reagent is component-II which is washed thoroughly with water
and dried.
3. If physical state of the mixture is Solid-Liquid or Liquid-Liquid: Transfer the mixture into
a beaker, add ether and stir well. If one of the component is insoluble in ether, then ether is
the reagent for separation. If both components are soluble in ether transfer the mixture into a
separating funnel and check the solubility in NaHCO3/ NaOH/ dil. HCl. Separate the mixture
based on its solubility.
The flow chart for the binary mixture is as follows:

79
Solid-solid mixture:
Solid-liquid or liquid-liquid:
The possible combination of binary mixtures:
1. Strong acid + Neutral including hydrocarbons.

2. Strong acid + Weak acid.
3. Weak acid + Neutral including hydrocarbons.
4. Base + Hydrocarbon.
5. Carbohydrate + Weak acid.
6. Carbohydrate + Strong acid (other than p-nitrobenzoic acid)
81
REFERENCES
1. Laboratory Manual of Organic Chemistry by Raj K Bansal.
2. Analytical Chemistry by GL David Krupadanam, D. Vijaya Prasad, K.

Varaprasad Rao, KLN Reddy and C. Sudhakar.
3. Comprehensive Organic Chemistry by VK Ahluwalia and Renu Aggarwal.
4. Text book of Practical Organic Chemistry by Vogel.
5. Elementary Practical Organic Chemistry by Arthur Vogel.
6. Experimental Organic Chemistry by David Todd.
7. Laboratory Method of Organic Chemistry by L Gattermann.
8. Practical Organic Chemistry by FG Mann and BC Saunders.
9. Practical Pharmaceutical Chemistry by Sharma.
10. Advanced Practical Organic Chemistry by NK Vishnoi.
11. A Practical book of Practical Organic Chemistry by Dr. KS Jain, Dr. PB

Miniyar, Dr. LVG Nargund.
12. Practical Handbook of Pharmaceutical Organic Chemistry by Dr. MN Deodhar,

JR Jagtap.
13. Advanced Practical Organic Chemistry by John Leonard, Barry Lygo, Garry
Procter.
View publication stats

Advanced Pharmaceutical Organic Chemistry Practical Text

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Advanced Pharmaceutical Organic Chemistry Practical Text

Uploaded by

Copyright:

Available Formats

See discussions, stats, and author profiles for this publication at: https://www.researchgate.

A Practical Handbook of Advanced Pharmaceutical Organic Chemistry

Book · January 2021

Jithendar Reddy Narender Boggula

SEE PROFILE SEE PROFILE

The user has requested enhancement of the downloaded file.

Dr. M. Ram Mohan

Jithendar Reddy Mandhadi

© 2020, by Publisher, all rights reserved

I feel immense pleasure to introducing “Practical Handbook of Advanced

The importance of a laboratory course attached to a theory course is undisputable

I honestly acknowledge and warm gratitude to my parents, fellow colleagues and

S. No. Experiment Name Page No.

Pharmaceutical Chemistry is concerned primarily with modification of structures

Laboratory glassware refers to a variety of equipment used in scientific work,

Round bottom flask (single neck)

Round bottom flask (triple neck)

Round bottom flask (four neck)

Round bottom flask (double neck)

Flat bottom flask

Copper water bath

Water pipes for condenser

Test tube holder

Test tube stand

Bunsen burner and tripod stand with mesh

Electric water bath

Hot air oven

Melting point apparatus

DIFFERENT TECHNIQUES INVOLVING IN THE

1. Flute filter paper if necessary. Fluting is desirable when a rapid filtration is

Figure 2.1: Beaker containing funnel

Figure 2.2: A Buchner funnel in a filtration flask

Since the procedures of simple distillation are so similar to those involved in

Figure 2.3: Distillation apparatus. A distillation flask with a thermometer is placed

DETERMINATION OF MELTING POINT

Requirements: Thiele’s tube containing liquid paraffin, capillary tube, thermometer,

Figure 3.1: Melting point determination

Figure 3.2: Melting point determination using Thiele’s tube

DETERMINATION OF BOILING POINT

Figure 4.1: Boiling point determination using Thiele’s tube

DETERMINATION OF ACID VALUE

Aim: To determine the acid value of given oil.

Chemicals: KOH, oxalic acid, alcohol, solvent ether, phenolphthalein indicator.

Principle: Acid value is the number of mg of potassium hydroxide or sodium

Each ml of 0.1N KOH ≡ 5.61 g of fatty acid

DETERMINATION OF SAPONIFICATION VALUE

Aim: To determine the saponification value of given oil.

Chemicals: HCl, KOH, sodium carbonate, phenolphthalein indicator, methyl orange

Principle: The number of milligram of potassium hydroxide or sodium hydroxide

Each ml of 0.5N HCl ≡ 28.05g of KOH

DETERMINATION OF IODINE VALUE

Chemicals: Conc. HCl, KI, Na2S2O3, potassium dichromate, iodine monochloride,

Significance: Iodine value mainly gives the indication of proportion of unsaturation

Each ml of 0.1N Na2S2O3 ≡ 0.01269g of iodine

Apparatus: Conical flask, pipette, measuring cylinder, stirrer, beaker, funnel.

Principle: Acetanilide is also known as N-phenyl acetamide. It is prepared by

If heating is prolonged and excess of acetic anhydride is employed variable amounts

Ar N H CO CH3 + (CH 3 CO) 2 O Ar-NH-(CO-CH 3)2 + CH 3 COOH

Chemicals: Salicylic acid, acetic anhydride, conc. H¬2SO4.

Chemicals: Aniline, benzoyl chloride, sodium hydroxide, distilled water.

Principle: Insertion of benzoyl moiety instead of an active hydrogen atom present in

Benzanilide is obtained by benzoylation of aniline in the presence of dilute NaOH

SYNTHESIS OF PHENYL BENZOATE

Chemicals: Phenol, benzoyl chloride, sodium hydroxide, distilled water.