430- Prof.Dr.

Cevher

ORGANIC ALTUG
caltug@gmail.com
room # 130

LABORATO
RY
TECHNIQU
ES
Broadly speaking, equipment can be divided
into two categories-that which is communal
and that which is personal. Cost is usually the
factor which decides the category into which
an item falls, although no hard and fast rules
apply and any distinction is purely arbitrary.

On entering the organic laboratory for the

first time, the first job, of course, is to
familiarize yourself with the laboratory safety
procedures and with the location of fire
extinguishers, safety showers, fire exits and
so on.
Remember the golden rule for working in a
laboratory:
Hint: doubt, ask.
BALANCES
The most commonly encountered balance is a general purpose top-
pan balance (1) which will be able to weigh to the nearest 0.01g.
For more accurate work an analytical balance (2) must be used.
This balance has many similarities with the simple top-ban balance
but it can weigh to the nearest 0.0001g. The doors of the balance
must be closed before taking a reading to prevent any disturbances
in the air effecting the measurement.
 MANOMETERS
A manometer is designed to measure the pressure during a
reduced pressure (vacuum) distillation. The Anshutz manometer
(1) gives a continuous reading of the pressure throughout the
distillation, most often in combination with water pumps.
The Vacustat manometer (2) gives a very accurate 'snap shot'
reading of the vacuum at a particular point and is usually
restricted for use with rotary oil pumps.
A 'Lab Jack' is an adjustable platform that can be used to
raise or lower apparatus by turning the knob at the front. It
is particularly useful for the raising and lowering of heat
sources (e.g. heating mantles) in distillations.
The simplest method of measuring a melting point is by use of an oil
bath (1). A round bottomed flask is partly filled with a mineral oil and
the capillary tube containing the sample is attached to a
thermometer with a rubber band. The oil is carefully heated with a
microburner. The heated block apparatus (2) can be found in many
shapes and sizes but the principle is the same; the sample is heated
placed in an electrically heated block and the observations are made
through a magnified port. The 'hot-stage' apparatus (3) allows the
observer to look at the sample through a microscope while its
temperature is increased.
DESICCATORS
Desiccators are used to dry solids and keep them dry by
containing them in a sealed vessel containing a drying agent.
A vacuum desiccator (2) has a tap, usually on the lid which
allows the desiccator to be evacuated to speed up the drying
process.
ROTARY EVAPORATOR
Rotary evaporators are used to remove large volumes of solvent
from solutions by rotating the solution under vacuum in
combination with a water bath (optional).
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GLASS EQUIPMENT
Glass equipment can be divided into that with ground glass
joints and that
without. For convenience and ease of use, standard-taper
ground glass joint
equipment is strongly recommended.
Standard-taper joints("$"") are designated by numbers
which refer to the diameter and length of the joint (in
mm): for example 14/20, 14/23, 19/22, 19/26 and 24/29.
As the name implies, standard-taper joints are fully
interchangeable with those of the same size.

Standard-taper ground glass joint equipment is expensive,

but with careful
handling is no more fragile than any other glassware.
FLASKS
Round bottomed flasks (1, 2, and 3) are generally used for
reactions carried out under reflux or distillation. Twin necked
flasks and three necked flasks allow the fitting of other
jointed glassware such as dropping funnels and stirrers. Pear
shaped flasks (4 and 5) are the best choice for distillations,
their shape allowing more of the product to be distilled. The
twin necked flask (5) can be used to add a reagent whilst
the product is being removed by distillation.
PIPETTES
Graduated pipettes (1 and 2) are designed for adding approximate
volumes of solutions or reagents. Some pipettes are graduated so
that the 0 reading is at the top (1). These can be filled up to the 0
mark and the appropriate volume added. Others have the full
volume at the top (2). These can be used by drawing the correct
volume into the pipette and then allowing it to discharge its
contents. Volumetric (bulb) pipettes (3) are designed for accurate
work and the volume will be printed or etched onto the pipette
body. Pasteur pipettes are used for the transfer or addition of small
amounts of liquids. These have no volume markings.
CONDENSERS
Water cooled condensers (1, 2, and 3) are the ones
encountered most commonly. The double surfaced condenser
(2) and the coiled condenser (3) are the most efficient and are
often used for reflux of solvents with low boiling points. For
solvents with boiling points in excess of 150 oC an air
condenser (4) should be used. The dry ice condenser (5) is
designed for use with dry ice/acetone mixtures or even liquid
nitrogen as the coolant.
FILTRATIONS
For straightforward filtrations where only the filtrate is required
(e.g. removing unwanted solids or decolourising charcoal) a filter
funnel (1) and fluted filter paper (2) is used. In situations where the
solid is required, a Buchner flask (3) is fitted with a Buchner funnel
(5) using a Buchner collar (4) to form a good seal when under
suction. Flat filter paper (6) of the appropriate diameter is used in
the Buchner funnel.
GLASSWARE USED IN ALL CHEMISTRY COURSES

1. Graduated
Cylinder
2. Wash Bottle
3. Erlenmeyer Flask
with Side Arm
4. Erlenmeyer Flask
5. Beaker
6. Funnels (Plastic
and Glass)
7. Test Tubes
8. Petri Dishes
GLASSWARE COMMONLY USED IN ORGANIC
CHEMISTRY FOR CONDUCTING REACTIONS
AND PURIFICATIONS:
1. Cork ring
2. Fractionating

column
3. West condenser

4. Separatory funnel

5. Stopper

6. Round bottomed

flask
7. Three-way adapter

(distilling head)
8. Claisen adapter

9. Vacuum adapter

10. Thermometer

adapter
11. Plastic clip (Keck

clip)
12. Rubber fitting for

thermometer
adapte
ADDITION FUNNELS

Addition funnels (or dropping funnels) are used to add

reagents to reactions. Self equalising dropping funnels (2)
are used stoppered to add reagents that might be air
sensitive, or for the addition of reagents under reduced
pressure.
RECEIVER ADAPTERS
Receiver adapters are used to allow collection of distillates emerging
from a condenser. The simple receiver adapter (1) can be used to direct
the distillate into a conical flask. The jointed adapter (2) would be used
with a round bottomed flask, the vented side arm preventing a closed
system which would otherwise form an explosion hazard. Adapter 3 is
designed for vacuum distillations. The 'pig' adapter (4) allows collection
of three different fractions without interrupting the distillation. The
receiving flask can be swapped by rotating the 'pig' about its joint.
Separating funnels are used to separate immiscible
solvents such as water from organic solvents and are most
commonly used in solvent extraction. Their tapered shapes
allows for efficient separation of the two layers. There are
two types of funnel, those fitted with a ground glass tap (1)
and those with a PTFE (‘Rotaflow’) screw type tap (2).
COLUMN CHROMATOGRAPHY
Column chromatography is a technique used for the separation of
mixtures. Chromatography columns are designed to be filled with a
'stationary phase' (usually silica gel) and the mixture to be
separated is passed through the column with a solvent system. A
simple column (1) has to be plugged with a small amount of glass
wool to retain the stationary phase, whereas this is unnecessary in
a column fitted with a sintered glass support (2).
The Dean-Stark apparatus is designed to collect water produced in
synthetic reactions carried out under reflux. The reactions are
normally done in solvents (for example toluene) that remove water
formed in a reaction as an azeotrope. The condensed mixture of
toluene and water collects in the burette and the denser water
separates and falls to the bottom. The tap allows the water to be
removed.
FRACTIONATING COLUMNS
There are several types of fractionating column but the most
common is the Vigreux column (1) which has indentations
designed to force condensing liquid into the rising vapour.
This is necessary to achieve the equilibrium needed for
efficient fractionation. The Vigreux column is often
incorporated into a still head (2). Alternative columns are
packed with glass beads (3) or open columns (4).
STILL HEADS
Still heads are designed to connect a flask to a condenser in
distillations. The simplest (1) allows a thermometer to be
attached to follow the temperature of the distillate. The
Claisen still head (2) has an additional socket to allow a
dropping funnel or mechanical stirrer to be fitted. The splash
head (3) is used to prevent the 'raw' distilling liquid from
carrying over into the vapour. This type of still head is often
used in steam distillations.
A Soxhlet extractor is a piece of apparatus designed to
extract substances with a low solubility in the extracting
solvent. It does this by allowing condensed solvent to wash
through a paper thimble (1) placed in the extractor (2) which
is designed to return the washings to the boiling flask by
siphon action.
1. Ground glass stopper.2. Screw capped adapter, used for
thermometers or air bleeds in vacuum distillations.3. Gas inlet
adapter, used to allow delivery of a gas (e.g. a protective layer of
nitrogen) to a reaction. 4. Step down adapter, used to connect
ground glass joints of different diameters.5. Step up adapter,
used to connect ground glass joints of different diameters.6.
Guard tube, when filled with a drying agent, such as calcium
chloride, it can be used to protect reactions from moisture.
GLASS EQUIPMENTHOW TO
REMOVE STUCKED GLASSWARE?

The only laboratory operations which

require the use of grease on the ground
glass joints of the apparatus are vacuum
distillations using oil pumps for
pressures lower than about 5 mmHg,
and reactions involving hot sodium or
potassium hydroxide solutions which will
attack the glass. If grease is used it
should be applied sparingly; a very thin
smear around the joint is all that is
required.
GLASS EQUIPMENTHOW TO
REMOVE STUCKED GLASSWARE?
The misuse of grease can cause ground glass
joints to become stuck or 'frozen'. Occasionally
this happens anyway, and, of course, unless
the joint can be unfrozen and the pieces of
apparatus separated, the equipment becomes
useless.
As with many things, prevention is better than
cure, and the best way to prevent frozen
ground glass joints is to disassemble the
apparatus as soon as it is finished with. Wipe
the joints clean, checking that they are
completely free of chemicals. Never leave
assembled dirty apparatus lying around the
GLASS EQUIPMENTHOW TO
REMOVE STUCKED GLASSWARE?

If, despite precautions, ground glass joints do

become tightly frozen, it may be possible to
loosen them by squirting a few drops of
acetone (or other solvent) around the top of the
joint.
Capillary action may be enough to suck some
solvent into the joint and loosen it. If this
simple trick does not work, the joint may be
loosened by gentle tapping, or failing that, by
heating it in a flame.
VOLUMETRIC ANALYSIS
1. Volumetric flask, used to prepare accurately diluted solutions.2.
Analytical pipette, used to deliver an accurate volume (aliquot) of
solution.3. Pipette filler.4. Burette (black graduations), used for
titrations where the solution is clear or of a pale colour.5. Burette
(white graduations), used for titrations with dark, highly coloured
solutions.
ASSEMBLING APPARATUS
There are many different ways to assemble apparatus and it
is important that you carefully follow the guidelines that
might be in the practical script. This section illustrates the
basic principles and good practice involved in putting
together equipment.
ASSEMBLING APPARATUS
Jointed glassware makes the setting up of glassware convenient
and easy but care must be taken to prevent damage of the joints.
ASSEMBLING APPARATUS
Clamps
Clamping is one of the most common of operations in chemical
practicals. Good practice when clamping is vital for proper setting up
of apparatus as well as for safety.
ASSEMBLING APPARATUS

Chemical apparatus should always be securely

clamped and fixed to a stable support.
ASSEMBLING APPARATUS
Joint Clips
Plastic joint clips are used to hold jointed glassware together
firmly when assembling apparatus.
 STORING SAMPLES
(PARAFILM/TEFLON TAPE)
Teflon tape is less permeable to solvents than Parafilm, and
volatile samples wrapped in Parafilm may still evaporate over
a period of weeks. If a sample is to be stored in a round
bottomed flask for some time, it should be stoppered with a
cork stopper or plastic cap. A rubber stopper should not be
used as it will tend to swell when exposed to organic vapors,
and a glass stopper may freeze.
 STORING SAMPLES
(PARAFILM/TEFLON TAPE)
When samples must be stored for a period of time, they
are best stored upright in screw-capped vials. Samples
may evaporate through the joint over time, and if a
highly volatile sample is used, the joint should be
wrapped in Teflon tape (semi-stretchy white film) or
Parafilm, (stretchy plastic film) to create a better seal.
 ASSEMBLING APPARATUS
Assembling Jointed Glassware
The correct assembly of jointed glassware is essential in any laboratory practical.
Although the exact clamping arrangements may vary from laboratory to laboratory
there are some general principles that need to be learned.
 ASSEMBLING APPARATUS
Assembling Jointed Glassware
The correct assembly of jointed glassware is essential in any laboratory practical.
Although the exact clamping arrangements may vary from laboratory to laboratory
there are some general principles that need to be learned.
GREASING JOINTS
Ground glass joints are manufactured to fit quite well with one
another, and yet they are not perfectly airtight. In some situations
(e.g. when using reduced pressure inside an apparatus), grease
must be applied to each joint to ensure a good seal. Grease is also
used whenever the joint may be in contact with a highly basic
solution, as basic solutions can form sodium silicates and etch
glass.
 GREASING JOINTS
Grease can be applied with a syringe full of grease, wood splint, or toothpick.
Grease should be lightly applied in portions around the male joint, closer to
the glass end than the end which will be in contact with reagents. If grease is
allowed near the end which will contact the reagents, there is a possibility the
reagent will dissolve the grease and become contaminated. The female joint
should then be connected, and the joints twisted to spread the grease in a thin
layer. The joint should become transparent all the way around the joint, but to
a depth of only one-third to one-half of the joint. If the entire joint becomes
transparent or if grease is seen spilling out of the joint, too much grease has
been used. Excess grease should be wiped off with a KimWipe .
CLEANING AND DRYING
GLASSWARE

Good laboratory practice requires that

organic reactions are carried out in clean
glassware. Unless the reaction is being
carried out in aqueous solution, the
glassware should also be dry, since many
organic chemistry experiments are ruined
by the presence of water.
CLEANING AND DRYING
GLASSWARE
Glassware can usually be cleaned with water
and either industrial detergent or a mild
scouring powder using an appropriate brush.
Make sure that you clean all the inside of the
piece, and that you rinse it thoroughly with
water afterwards. The final rinse should be with
distilled or deionized water, and the glassware
should be left upside down on a drying rack or
on absorbent paper to dry.
Use oven at 125°C for at least 12h.
CLEANING AND DRYING
GLASSWARE
The drying process can also be speeded
up by rinsing the wet glassware with
acetone.
Acetone is freely miscible with water,
and rinsing a wet flask with 5- 10 mL of
washing acetone (not reagent grade
acetone) removes the water. The
acetone should be drained into the
waste acetone bottle, not thrown down
the sink. The remaining acetone in the
flask evaporates quickly in the air, but
the drying can be speeded up by
CLEANING AND DRYING
GLASSWARE
Alternatively the flask can be dried with
hot air using a hot-air blower of the 'hair
dryer' type, but remember that
acetone is flammable.
Indeed many laboratories do not permit
the use of acetone for cleaning purposes
because of the additional fire hazard,
possible toxicity problems associated
with long-term exposure and, of course,
expense.
CLEANING AND DRYING
GLASSWARE
To clean glassware, use the following
procedures:
Use 2-3 mL solvent to rinse residual organic
compounds from the glassware into a waste
beaker. The compounds should be highly soluble
in the solvent. The default solvent is often
acetone as it is inexpensive, relatively nontoxic,
and dissolves most organic compounds. Some
institutions reuse their acetone ("wash acetone")
as the solvation ability is not spent after a few
uses.
CLEANING AND DRYING
GLASSWARE
As it will soon become second-nature for
most students to use acetone as part of
their cleaning ritual, it is worth reminding
that the purpose of acetone rinse is to
dissolve organic residue in a flask.
Not everything dissolves in acetone, for
example ionic salts are insoluble in
acetone and are more successfully rinsed
out with water.
After a preliminary rinse, glassware
should then be washed with soap and
water at the bench.
CLEANING AND DRYING
GLASSWARE
Residual acetone will likely evaporate
from the flask, but it is acceptable for
small quantities of residual acetone to be
washed down the drain. Acetone is a
normal biological byproduct of some
metabolic processes,11 and has low
toxicity as it can be easily excreted by
most organisms.
DRYING TUBES
A drying tube is used when moderately but not meticulously dry
conditions are desired in an apparatus. If meticulously dry
conditions are necessary, glassware should be oven or flame
dried, then the air displaced with a dry, inert gas.
TRANSFERRING METHODS
A solid can be dispensed from its reagent jar directly into a
vessel or onto a weighing boat or creased piece of paper. If a
solid is to be transferred into a vessel containing a narrow mouth
(such as a round bottomed flask), a "powder funnel" or wide-
mouth funnel can be used. Alternatively, the solid can be nudged
off a creased piece of paper in portions using a spatula
POURING LIQUIDS
When transferring liquids with volumes greater than 5mL5mL,
they can be poured directly into vessels. Graduated cylinders
and beakers have an indentation in their mouth, so they can be
poured controllably as long as the two pieces of glass touch one
another (Figure 1.17a). If pouring from an Erlenmeyer flask, or
transferring a liquid into a vessel containing a narrow mouth
(e.g. a round bottomed flask), a funnel should be used. Funnels
can be securely held with a ring clamp or held with one hand
while pouring with the other.
Using Pasteur Pipettes
Pasteur pipettes (or pipets) are the most commonly used
tool for transferring small volumes of liquids (< 5mL)
from one container to another. They are considered
disposable, although some institutions may clean and
reuse them if they have a method for preventing the
fragile tips from breaking.
 INERT
ATMOSPHER
IC METHODS
Meticulously dry or oxygen-
free conditions are
sometimes necessary when
using reagents that react
with water or oxygen in the
air. To safely and effectively
use these reagents,
glassware should be oven or
flame dried, then the air
displaced with a dry, inert
gas (often nitrogen or argon).
This creates an "inert
atmosphere" inside an
apparatus, one that will not
react with the reagents.
Inert gases can be delivered to a flask through gas lines and a
gas manifold (in a research setting), or through a balloon of
inert gas (more common in teaching labs).
DRYING TUBES
Drying tubes are pieces of glassware that can be filled with a
drying agent (often anhydrous CaCl2 or CaSO4 in the pellet
form) and connected to an apparatus either through a
thermometer adapter or rubber tubing. Air passing through the
tube is removed of water when it comes in contact with the
drying agent. Since it is important that air can flow through the
drying tube, especially so the apparatus is not a closed system,
the drying agent should be fresh as used drying agents can
sometimes harden into a plug that restricts air flow. Drying tubes
can also be filled with basic solids such as Na2CO3 to neutralize
acidic gases.
WHAT WOULD YOU DO IF YOUR
GLASSWARE IS CONTAMINATED
WITH ‘’BLACK TAR’’?
Large amounts of tar material can
often be scraped out with a spatula,
but the remaining material usually has
to be dissolved out with an organic
solvent. Acetone is usually used since
it is a good solvent for most organic
materials, although vigorous scrubbing
and/or prolonged soaking may be
necessary in stubborn cases.
WHAT WOULD YOU DO IF YOUR
GLASSWARE IS CONTAMINATED
WITH ‘’BLACK TAR’’?
Some books recommend the use of
powerful oxidizing mixtures, such as
sulfuric/nitric acids and chromic acid,
as a last resort technique for cleaning
dirty glassware. This practice should
be strongly discouraged from the
safety point of view as the
mixtures used are all highly
corrosive and some are potentially
explosive.
WHEN YOU START TO
CLEAN UP YOUR
GLASSWARE?
Cleaning and drying glassware is an
unavoidable chore in the organic
laboratory, but it is part of the job.
However, it can be made much easier
by following one simple rule: clean up
as you go along. By cleaning
glassware as soon as you have finished
with it, you know exactly what was in it
and how to deal with it, and freshly
dirtied glass is much easier to clean
than dried out tars and gums.
WHEN YOU START TO
CLEAN UP YOUR
GLASSWARE?
There are plenty of periods during
the laboratory class when you are
waiting for a reaction to warm up
or cool down, for a crystallization
to finish and so on. Make use of
such times to clean, rinse and dry
your freshly dirtied glassware.
DISPOSAL OF
HAZARDOUS WASTE
Waste disposal is one of the major
environmental problems of modern
society and the safe disposal of
potentially hazardous chemical
waste places a great burden of
responsibility on those in charge of
laboratories.
DISPOSAL OF
HAZARDOUS WASTE
It is important that everyone who works in the organic
laboratory appreciates the problems and exercises their
individual responsibility to their fellow citizens and to the
environment by not disposing of chemical waste in a
thoughtless manner.
DISPOSAL OF
HAZARDOUS WASTE
Solid waste
Solid waste from a typical organic laboratory comprises
such things as spent drying agents and
chromatographic supports, used filter papers,
discarded capillaries from the melting point
apparatus and broken glass.
Common sense is the guiding principle in deciding how
to dispose of such waste. Unless the solid is toxic or
finely divided it can be placed in an appropriate
container for non-hazardous waste.
DISPOSAL OF
HAZARDOUS WASTE
Solid waste
Filter papers can be disposed of in an appropriate
container unless of course they are contaminated
with toxic chemicals. Toxic waste should be placed in
special appropriately labelled containers.
It is the responsibility of your laboratory staff and
your instructor to provide these containers and see
that they are clearly labelled: it is your responsibility
to use them. Some toxic chemicals need special
treatment to render them less toxic before disposal.
This often involves oxidation.
DISPOSAL OF
HAZARDOUS WASTE
Solid waste
Broken glass, discarded capillaries and other 'sharp'
items should be kept separate from general waste
and should be placed in an appropriately labelled
glass or sharps bin.
Chromatography silica should be transferredto
polyethylene bags in a fume hood after removal of
excess solvent, moistened with water and the bags
sealed for later disposal.
DISPOSAL OF
HAZARDOUS WASTE
Water-soluble waste
It is very tempting to pour water-soluble laboratory
waste down the sink and into the public sewer system. It
then becomes a problem for someone else, namely the
water authority. This is bad practice.
The only waste that can safely be poured down the sink
is non-toxic, neutral, non-odorous, water-soluble material
such as discarded water layers from aqueous-organic
extractions.
DISPOSAL OF
HAZARDOUS WASTE
Water-soluble waste
The waste should be washed down with plenty of water,
and strongly acidic or alkaline solutions should be
neutralized before disposal. Any chemical that might
react even with dilute acid or alkali should never be
disposed of down the sink.
For safety's sake, if there is any doubt, do not dispose of
material down the sink.
DISPOSAL OF
HAZARDOUS WASTE
Organic solvents
Organic solvents are the major disposal problem in the
organic laboratory. They are usually water immiscible
and highly flammable, and often accumulate very
quickly in a busy laboratory. Waste solvent should be
poured into appropriately labelled containers, never
down the sink. The containers are then removed from
the laboratory for subsequent disposal of the solvents by
burning.
DISPOSAL OF
HAZARDOUS WASTE
Organic solvents
There should be two waste solvent containers one for
hydrocarbons and other non-chlorinated solvents and
one for chlorinated solvents. Chlorinated solvents
have to be handled differently during the combustion
process since they generate hydrogen chloride. It is
therefore very important that you do not mix the two
types of waste solvent. If the waste container is full, ask
the laboratory staff or your instructor for an empty one;
do not be tempted to use the sink as an easily available
receptacle.