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EXTRACTIONS : SEPARATIONS BASED

UPON SALT FORMATION

The separation of aniline from


toluene
– is effected by extraction with
dilute hydrochloric acid.
– The aniline goes into the
aqueous layer as its salt, aniline
hydrochloride.
– Whereas aniline is very soluble
in toluene and virtually insoluble
in water, its hydrochloride salt,
because of its polar nature, is
soluble in water and insoluble in
toluene.
Phenol from Toluene
 Mixture contains than 2 compounds????
 combinations methods of separations.

 The condition for successful separation

is that :
 the components be such that a wide

polarity difference exists or


 can be induced between any two of

them.
Extraction of Water Insoluble
Mixtures
 These procedures are
used after the water
solubility test
 Assumption:
 all possible fractions are
obtained
Extraction of Water Soluble
Mixtures
 If all components of the
mixture are water soluble,
steam distillation is the best
method for the separation.
 However, it may prove to be
unsatisfactory if the mixture is
not chosen carefully the
components of the mixture
undergo reaction with each
other or with boiling aqueous
acid or alkali during steam
distillation.
 Extraction, which does not
involve heating of the mixture,
would be preferable.
• Sample:
– mixture of acetic
acid, butanol, butyl
acetate, water
 Is the separation of the components of a mixture by the
selective distribution of the components between a mobile
phase and a stationary phase.
 Chroma meaning "color" and graphy meaning "written“(Greek).
 The mobile phase
– Is a liquid or a gas and carries the compounds along a
column.
 The stationary phase
– may be composed of various types of materials,
– for example, silica gel in column chromatography.
 The ability to separate is based on selective and preferential
absorption of these components in the mobile phase by the
stationary phase.
 Organic chemists are interested in :
– gas chromatography (GC) and liquid chromatography (LC).
 Gas chromatography is useful for relatively volatile and thermally stable organic
compounds.
– This method involves a gaseous mobile phase, which is usually helium or,
less frequently, nitrogen.
– The stationary phase is either a liquid adsorbed on a solid support, an
organic compound bonded to a solid support, a solid, or a nonvolatile liquid.
 Liquid chromatography uses a liquid mobile phase, which is usually a common
organic solvent.
– The stationary phase may consist of a liqUid adsorbed onto a solid support,
an organic species spread over a solid support, a solid, or a resin.
– Examples of liquid chromatography are
 column chromatography,
 high-performance liquid chromatography (HPLC), and
 thin layer chromatography (TLC).
 Gas Chromatography
– 1. The sample should be volatile and reasonably stable to heat.
– 2. Simple gas chromatographs are inexpensive, are easy to operate, and
give results rapidly.
 Liquid Chromatography
– 1. Duration: With the simple gravity flow columns, the separation of the
components is time consuming.
Rapid analyses are carried out with HPLC and flash chromatography.
– 2. Stability: A small percentage of organic compounds may react with the
stationary phase of some columns.
Proper choice of conditions, in order to prevent undesirable side reactions,
allows virtually any organic compound to be analyzed by LC.
– 3. Cost: Flash and other types of column chromatography are fairly cheap;
HPLC has a much higher initial cost, because of the high-quality pumps and
column packings that are necessary.
 the most rapid, easiest, and
most often applied method
for accessing Organic
compounds.
 the immobile phase is a thin
layer of adsorbent spread
over a sheet of glass or
plastic
 Compounds can be detected
on TLC sheets in various
ways. The simplest is to use
a low-power hand-held UV
light.
Developing Solvent

 Increasing
polarity Determination of solvent for
TLC

Good – over– under developed


Preparation for TLC
Development
Result

Rf ?
Chromatography
Chromatographic column theory of packed columns
•The effect of column efficiency and column selectivity on resolution

Poor resolution because of poor


column efficiency

Good resolution because of good


column efficiency, although
column selectivity is not
great
Good resolution because of good
column selectivity, although
column efficiency is poor
Poor resolution because of poor
column selectivity, although
column efficiency is good
Column Chromatography
Types of Columns
Packed chromatography
column
 Slurry Packed
Columns
 The solvent is used
to pack the column.
 The column is prepared dry without the use of
solvent and developed just once with a Single
volume of solvent, in contrast to the slurry method
and multiple volumes of solvent in traditional column
chromatography.
 Using the dry column technique, columns as long as
6 ft have been packed and mixtures of mass of up to
50 g have been separated.
Flash Chromatography
 In flash chromatography, the
column is pressurized with a
flow control adaptor
attached to the top of the
column to pressure the
column
 The flow control adaptor is
attached to an air line at a
medium pressure.
 Fast separation
Microscale Column
Chromatography
High-Performance Liquid
Chromatography (HPLC)
Chemical Tests for Functional Groups

 Homework
Spectroscopy

 UV
 IR
 MS
 NMR