CHEM LAB component of lower

vapour pressure left in

REVIEWER the container.
 This process is therefore
SEPARATION AND concerned with the
PURIFICATION OF ORGANIC mechanism of
COMPOUNDS evaporation of
molecules or atoms from
SUBLIMATION
the solids and with the
Sublimation- direct mechanisms of crystal
conversion of a substance growth from vapours.
from solid to gas without
passing through the liquid
state. REAGENTS and APPARATUSES

 This is one of the most  Phthalic anhydride

convenient techniques  Sodium sulfate
for the purification of  5% BaCl2 solution
solid organic substances  Distilled water
from a mixture whose  evaporating dish
components differ  watch glass
appreciably in their  wire gauze
vapor pressure.  tripod
 In this method, the solid  weighing scale
mixture is gently heated  alcohol lamp
in a confined container
until particles of the solid
escape into the vapour
phase.
 When the vapours are
condensed on a solid
surface, crystals of the
component with high
vapour pressure can be
collected, with the
HYDROCARBONS mentioned above
will depend upon
the types of
 The most familiar hydrocarbons
hydrocarbons are those present.
contained in gasoline,
kerosene, the motor oils,  The saturated hydro-
and paraffin wax. carbons are inert
towards the common
 For the most part they laboratory reagents and
are mixtures of saturated react only by substitution
hydrocarbons (alkanes) reaction.
resulting from the
different fractions in the  The unsaturated hydro-
distillation of petroleum. carbons react by
addition reaction.
 The rate of reactivity
 Petroleum ether between the members
(sometimes called ligroin of a given series is a
or benzene) is that difference in degree or
fraction which distils over rate of reactivity rather
before gasoline now than a difference in kind
used comes from the of reaction.
“Cracking process”.
 The volatility (tendency
 It contains a certain to vaporize or become
percentage of gaseous)of the mixtures
unsaturated of hydrocarbons
hydrocarbons becomes less as the
(alkenes). carbon content to the
component
hydrocarbons is
 The chemical increased.
properties of the
substances
 The vapors the highly  thermometer
volatile mixtures  test tubes
(Petroleum ether or  graduated
gasoline) ignite readily at cylinder
room temperature.

CLASSIFICATION TEST FOR

 It is necessary to heat the HYDROXYL- AND CARBONYL-
less volatile mixtures CONTAINING COMPOUNDS
before they ignite.

 Solubility of Alcohols in
 The temperature at
Water- most organic
which oil vaporizes
compounds are not
sufficiently to form a
soluble in water, EXCEPT
mixture with air which
for low molecular –
can be ignited and
weight amines and
continues to support
oxygen- containing
combustion is known as
compounds like
the flash point.
alcohols, carboxylic
acids, aldehydes, and
ketones.
REAGENTS and
APPARATUSES
o Low molecular-
 Kerosene weight compounds
 Paraffin wax are generally
 Conc. HNO3 limited to those with
 Conc. H2SO4 fewer than five
 25% NaOH carbon atoms.
 Petroleum ether
 1% bromine in  Lucas Test- coordination
CCl4 of the zinc chloride with
 Amylene the hydroxyl results in the
 Dilute Na2CO3 formation of a sufficiently
solution good leaving group.
 evaporating dish
o The carbon- possess additional
oxygen cleavage functional groups
can occur when a that enhance
reasonably stable solubility in the
carbocation is reagent.
produced.
 Chromic Acid Test (Jones
o If R is 3º, benzylic or Oxidation)- primary and
allylic, the reaction secondary alcohols are
takes place rapidly oxidized by
immediately; 2º chromium trioxide in
alcohols require 2-3 acidic ,aqueous acetone
min to undergo whereas tertiary alcohols
reaction, whereas are stable to oxidation .
simple 1º alcohols o Oxidation- readily
do not react over a detected by the
period of 10-15 min. appearance of the
green Cr3+ ion.
o The test results in o Aldehydes can also
the information of be differentiated
an insoluble alkyl from ketones using
chloride as a this test.
cloudy suspension  2, 4- Di-
that later separates nitrophenylhydrazone
into a distinct upper (or 2,4-DNP) Test-
layer. Aldehydes and ketones
may be differentiated
o This requires that from most other
the test alcohol be functional groups by
soluble in the test their formation of a
reagent, thus characteristic yellow to
restricting the test orange-red 2,4-
to water –soluble dinitrophenylhydrazone
alcohols and other precipitate with an
alcohols which may acidic, alcoholic solution
 of 2,4- (blue) and
dinitrophenylhydrazine. carbohydrates do.
o Non- conjugated
carbonyl compounds
usually form yellow
hydrazones while
 Tollen’s Silver Mirror Test-
conjugated carbonyl
Tollen’s reagent is an
compounds form
ammoniacal solution of
orange- red hydrazones.
silver ion prepared by
dissolving silver oxide in
ammonia.
o The reagent is
 Fehling’s Test- the reduced to metallic
reagent in this test is silver by aldehydes
cupric ion, Cu2+, in an which, in turn are
alkaline solution. oxidized into
o To keep the copper corresponding
from precipitating acids.
as hydroxide, it is o Ketones are not
complexed with oxidized by the
tartrate ion. reagent.
o Aldehydes reduce
copper, the solution
usually turns from
deep blue to
muddy green, and
gradually a brick-
red precipitate of
 Iodoform Test- in the
cuprous oxide,
presence of a base,
Cu2O, is formed.
most methyl ketones are
o Most simple ketones
converted to an enolate
(blue) do not react,
ion by the removal of
although certain
one of the protons
hydroxyketones
adjacent to the carbonyl characteristic
group. medicinal odor.
o In the presence of
a halogen like
iodine, the enolate
anion and halogen
react to form a
monohaloketone o Methyl ketones are
which forms an not the only
anion more readily compounds that
than the original result in a positive
ketone because of iodoform test.
the electro- o Secondary alcohols
negativity of the having an adjacent
halogen. methyl group are
o The process is oxidized into methyl
rapidly repeated ketones by the
until the methyl iodoform test
group has become reagent. These
a trihaolmethyl methyl ketones
group. then give a positive
o Cleavage of the iodoform test.
trihalo compound
by a base then
produces the salt of
a carboxylic acid
and a haloform.
o In the case of
iodine, the water-
insoluble iodoform
is formed.
o It is bright yellow
solid that melts at
119-121º and has a
COMPARATIVE INVESTIGATION o Functional groups
OF ORGANIC COMPOUNDS present in an organic
compound can be
 Generally, organic determined by using
compounds can be infrared spectroscopy.
classified into
hydrocarbons and  Organic compounds
hydrocarbon derivatives have different physical
(organic halides, ethers, properties, which are
thioethers, alcohols, intristic (or characteristic
thiols, etc.), based on of the class) such as
the replacement of odor.
hydrogen by another
element or by a group of  The physical state of an
different elements organic compound at
(functional group). room temperature may
o Specifically, organic- indicate the strength of
compounds are interactive forces that
conveniently classified exist between in
as different classes of molecules.
hydrocarbon  The dissolution of organic
derivatives based on compounds in certain
the substituent solvents may involve
element or group of physical or chemical
highest priority to the interaction.
hydro-carbon
derivatives based on  Water solubility of these
the substituent compounds may differ
element or group of due to their varying
highest priority to the polarities.
hydrocarbon
  Solubility in acids or SOLVENTS:
bases leads to more
 5% HCl Solution
specific information
 5% NaOH solution
about the compound,
i.e., as having either PROCEDURE:
acidic or basic property.
Physical State, Color, Odor
 Ignition of the organic
compound brings about 1. Observe the physical
a chemical change. state and appearance
 Some organic of the sample at room
compounds decompose temperature
and blacken (charring) 2. Note the color. With a
while others burst into wafting motion, describe
flames. the odor

Solubility Properties

MATERIALS NEEDED 1. Introduce the sample

into a clean and dry test
 DISTILLED WATER
tube. If the sample is a
 LITMUS PAPER
liquid, use 4 drops; if the
 TEST TUBES
sample is a solid, use
 TEST TUBE HOLDER AND
0.1g. Grind solid samples
RACK
to increase the surface
 SMALL EVAPORATING
area. Add the solvent
DISH
dropwise, counting the
number of drops of
SAMPLE COMPOUNDS:
solvent added to a total
of 3 mL. Use a dry and
 cyclohexane
calibrated dropper (X
 DCM
number of drops=1 mL).
 ethanol
Do not heat the mixture.
 phenol
 benzoic acid
 ethyl acetate
 ethylamine
2. Note any color changes, Ignition Test
warning, or
1. Place 3-5 drops of the
effervescence. Describe
liquid sample in a small
the solubility of the
evaporating dish and
sample in the solvent
light with a match. If the
used as soluble (miscible)
sample is solid, use a
or insoluble (immiscible).
pinch amount
2. Observe if the sample is
flammable or not and
Reaction with Litmus paper
observe the formation of
 If the sample is soluble soot. Note the color of
in water, test its the flame produced
aqueous solution with
OPTIONAL: if flammable,
the red and blue
observe burning time. Note
litmus papers.
down your observations
o Note the color
changes in both
litmus paper.
Infrared (IR) Analysis

 Identify the type of

principal bond
present in the sample
compound that may
be observed in the IR
spectra and give its
wave number range.
o Use the
appendix notes
as your guide.