ACKNOWLEDGEMENT

All praises and thanks are due to the gracious creator for
giving us strength, patience, ability to accomplish this work.
It is a great pleasure for us to express our deepest sense of
gratitude and sincere appreciation to our reverend teacher
Dr. Bilkis Jahan Lumbini, Lecturer, Department of
Chemistry, University of Rajshahi, for her invaluable, erudite
and scholastic guidance, constructive suggestions and kind
encouragement, without which production and presentation
of this work was just impossible.

We are very grateful to Raju vai and Shukur vai for providing
us all necessary books and papers.

Our grateful thanks are due to our parents for their

enthusiastic encouragement and financial help to complete
this work.

It is indispensable to express thanks to all friends for their

co-operation, encouragement and providing us with a
pleasant atmosphere during our assignment work.

MD. ATIQUL ISLAM

SAGAR PANDE
MD. RAKIBUL ISLAM
MD. MOSTAFIZUR RAHAMAN
AIM OF THE WORK

Separation is the first step during the actual analysis of

organic mixture. It is the most important in the sense that if
separation is incomplete the result will not be correct
because the impure compound will give tests of different
functional groups and its melting points will also be very
much different from that of the pure compound obtained from
complete separation. Therefore the aim of work is to learn to
separate the compound of a mixture accurately.
 CONTENTS
Page No.

CHAPTER ONE: INTRODUCTION 1-2

CHAPTER TWO: SEPARATION OF ORGANIC 3-6

COMPOUNDS

2.1 Separation of ethane and ethene 3

2.2 Separation of ethanol, hexane and benzene 4

2.3 Separation of phenol and benzoic acid 5

2.4 Ester separation from esterification mixture 6

REFERENCES 7
 LIST OF FIGURES

Fig 1.1: Simple distillation set-up 1

Fig 1.2: Continuous liquid-liquid extraction apparatus 2

Fig 1.3: Separatory funnel 2

Fig. 2.2.1: Separation of benzene and hexane 4

INTRODUCTION

One of the main concerns of experimental organic chemistry

is the separation of mixture and the isolation of compounds
in as pure a form as needed for subsequent use. A pure
substance contains only one kind of molecule; an impure
substance is a mixture of molecules. When the various kinds
of molecules of a mixture can be made to behave differently
under the conditions of some procedure, the procedure may
form the basis for a separation.
Several general methods are used for separation in organic
mixture such as distillation, extraction, filtration, sublimation,
chromatography and crystallization. Here some methods are
discussed:

DISTILLATION
The most commonly used method for purification of liquids is
distillation, a process by which one liquid can be separated
from another liquid or a liquid from a nonvolatile solid. This
process consists of heating a liquid to a temperature at
which it is converted to a vapor and then condensing the
vapor back to a liquid in another part of the apparatus.

The basic elements of a distillation apparatus are a boiling

flask, a column through which the vapor raises a
thermometer, a condenser and a receiver.

1
Purification of a mixture by distillation depends upon the fact
that substance can differ in the degree to which they can be
vaporized under the experimental conditions.

EXTRACTION
Extraction is one of the separation methods in organic
chemistry. It is a general term for the recovery of a
substance from a mixture by bringing it into contact with a
solvent which preferentially dissolves the desired material.
The initial mixture may be a solid or liquid and various
techniques and apparatus are required for different
situations.

2
2.1 SEPERATION OF A MIXTURE OF ETHANE AND
ETHENE

In order to separate the mixture of ethane and ethene, it is treated

with bromine in carbon tetrachloride solution. When bromine in
carbon tetrachloride solution is added to a mixture of
‫ܪܥ‬ଷ ‫ܪܥ‬ଷ and ‫ܪܥ‬ଶ = ‫ܪܥ‬ଶ , ethene reacts with bromine solution to
form colorless vis-bromide but ethane does not.

REACTIONS
CH3-CH3 + Br2 = No reaction

Solution of CCl4 Zn dust

CH2=CH2 + Br2 CH2(Br)- CH2(Br) CH2=CH2

FLOW CHART OF SEPARATION OF ETHANE AND

ETHENE

Ethane & ethene

(both in gaseous form)

Br2 in CCl4

Dibromoethane Ethane gas

(oily liquid)
Zn dust +∆
Ethene
Fig.1. Separation of mixture
3
2.2 SEPARATION OF A MIXTURE OF ETHANOL
HEXANE AND BENZENE

The boiling point of ethanol, hexane and benzene are 78, 68.7
and 80 C ̊ respectively. After fractional distillation hexane is
separated from the mixture, then by reflux the rest of mixture is
separated.

FLOW CHART OF SEPARATION OF ETHANOL

HEXANE & BENZENE

ETHANOL, HEXANE AND BENZENE

Fractional distillation at 68-69

ETHANOL+BENZENE HEXANE

Stark reflux

ETHANOL BENZENE

Fig.1 Separation of mixture Fig.2 Fractional distillation column

4
2.3 SEPERATION OF A MIXTURE OF PHENOL AND
BENZOIC ACID

5% NaHCO3 is a reagent that reacts with benzoic acid to form a

soluble salt of benzoic acid but phenol doesn’t react then the
mixture can be separated by a separating funnel. Free benzoic
acid will be reformed by treating dil. HCl.

REACTIONS
C6H5COOH+NaHCO3 = C6H5COONa+CO2+H2O
C6H5COONa+HCl = C6H5COOH+NaCl

FLOW CHART OF SEPARATION OF BENZOIC ACID

AND PHENOL
Benzoic acid + Phenol
Ether soluble
Mix & extract NaHCO3 (aqueous)

Na salt of benzoic acid +Phenol

Water soluble

Separate layers

Na salt of benzoic acid Phenol in ether

aq. HCl
Evaporate solvent

Benzoic acid Phenol

5
2.4 ESTER SEPARATION FROM ESTERIFICATION
MIXTURE

When a mono carboxylic acid is heated with an alcohol in the

presence of a small amount of mineral acid as catalyst, it yields
an ester and water. This reaction is known as esterification. It is a
reversible process. When SOCl2 is added to the mixture C6H5-COCl
will be obtained. After adding 5% NaHCO3 to the mixture of
C6H5COEt + C6H5-COOH free ester will be obtained.

REACTIONS

Esterification
C6H5-COOH + EtOH = C6H5COOEt + H2O reaction.(It is a
reversible process)

C6H5-COOH + EtOH = C6H5COOEt + H2O

C6H5-COOH+ SOCl2 = C6H5-COCl + (SO2+HCL)(gas)

C6H5-COCl + EtOH = C6H5COOEt + HCl

5% NaHCO3 C6H5COOEt
C6H5COOEt + C6H5-COOH
+C6H5-COONa

6
REFERENCES

1. ADVANCED PRACTIAL ORGANIC CHEMISTRY

O.P. Agarwal

2. Experimental Methods in Organic Chemistry

MOORE AND DALRYMPLE

3. ORGANIC EXPERIMENTS
LOUIS F. FIESER
KENNITH L. WILLIAMSON

4. Techniques and experiments for organic chemistry

ADDISON AULT