B.Sc.(Hons)Chemistry part-2 Course:Chem 221F Organic Chemistry Group no.

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Submitted by: Submitted To:

Name: y Mst. RiktaKhatun

Dr. BILKIS JAHAN LUMBINI LECTURER DEPARTMENT OF CHEMISTRY UNIVERSITY OF RAJSHAHI

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Date of Submission: 19th June 2011

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. BilkisJahanLumbini, 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. WeareverygratefultoRakibvaiaforprovidingusallnecessarybooksan dpapers. 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 cooperation, encouragement and providing us with a pleasant atmosphere during our assignment work. Md. RokunuzzamanKhondokar (09064545) Md. Roniul Islam (09044553) Mst. RiktaKhatun (09204563) HafizaRawshon Jamal Hira (09204574)

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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.

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CONTENTS
CHAPTER SUBJECT

One
Two
2.1 2.2 2.3 2.4

Introduction Separations of organic compounds

Separation of ethanol, acetone and acetic acid Separation of toluene, ether and acetylene Separation of benzoic acid and benzene sulphonic acid Separation of enol from keto-enol equilibrium

PAGE NO. 05-06 07-10 07 08 09 10 11

Three

References

LIST OF FIGURES
Fig 1.1: Fig 1.2: Fig 1.3: Simple distillation set-up Continuous liquid-liquid extraction apparatus Separatory funnel 5 6 6

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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.

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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.

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2.1 Separation of Ethanol, Acetone and Acetic acid

NaOH solution is added to the mixture until the phenolphthalein end point is reached. The mixture is distilled when sodium acetate (CH3-COONa) is left as residue. The distillate (alcohol & acetone) is fretted with saturated NaHSO3 solution and crystalline derivative is removed (no salt of acetone). The remaining liquid consists of alcohol and water which is separated by fractional distillation. Sodium acetate (CH3-COONa) when distilled with concentrated H2SO4 yields acetic acid. Acetone is removed from bisulphite compound by treating with diluted HCl.

REACTIONS:
(C2H5OH + CH3-CO-CH3 + CH3COOH) + NaOH
CH3COONa + (C2H5OH+ CH3COCH3)(C2H5OH + CH3COCH3 + CH3COONa)
P.P.T. con. H2SO4 NaHSO3 dil. HCl

(CH3)2C(OH)(SO3Na) + (C2H5OH+ H2O)

Fractional C2 distillationH5OH

CH3COOH

dil. HCl

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CH3COCH3+ NaCl + H2SO4

2.2 SEPARATION OF TOLUINE ETHER AND ACETYLINE

The mixture is treated with ammonical AgNO3(Silver nitrate) solution which precipatesacetyline as silver acetylide. The remaining liquid mixture of toluene and ether is treated with cold con.H2SO4 in which ether is soluble.Toluene is separated from acid layer. On distilling acid layer ether distills over.

REACTIONS:
CH3

+ C2H5-O-C2H5+ C2H4) + 2Ag(NH3)2NO3

CH3

Ag2C2 (white ppt) + (

+ C2H5-O-C2H5)

Ag2C2 + 2HCl CH3 (

C2H2+ 2 AgCl

CH3

Cold& con. + C2H5-O-C2H5) Separating funnel H2SO4

C2H5-O-C2H5(soluble) Distillation

C2H5-O-C2H5
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2.3 SEPARATION OF BENZOIC ACID AND BENZENE SULPHONIC ACID

The mixture is treated Ca(OH)2 (calcium hydroxide) or CaCO3 (calcium carbonate)orNH3 (ammonia). Then benzene sulphonic acid alone reacts with NH3. But insoluble benzoic acid stays in NH3 as solid. Benzoic acid is then easily removed by separating benzene sulphonamide is then hydrolyzed in presence of acid to get benzene sulphonic acid.

REACTIONS:
COOH SO3H
COOH

(Solid)

NH3

separating funnel
SO3NH3

H2O/H+

SO3H

BENZENE SULPHONIC ACID

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2.4 SEPARATION OF ENOL FROM KITO-ENOL EQUILIBRIUM

When the reagent tri methyl sylylchloride is added to keto-enol equilibrium then a complex compound produces. The product compounds are treated with tri-butylammonium chloride (Bu4NH4F) to get enol.

REACTIONS
OH CH3-CO-CH2COOC2H5
CH3-C=CHCOOC2H5 OSi(CH3)2 CH3-C=CHCOOC2H5
Bu4NH4+F-

(CH3)3SiCl

OH NH4+F- + Bu3SiF + CH3-C=CH-COOC2H5 (Enol)

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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

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