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LABORATORY MANUAL CHE 103

Organic Chemistry

1. Safety in the Chemical Laboratory:

LMCHE 103: Organic Chemistry In the laboratory due care and caution must be exercised to avoid accidents. Correct handling of apparatus and chemicals is the only insurance against hazards. In particular Always wear Lab coat/apron in the lab. Do not throw away lighted match-sticks without extinguishing them. Do not touch any unknown chemical by hand. Ensure that gas taps are securely closed while putting-off burners. Always dispose off used chemicals in waste container intended for chemical disposal. In the event of any exposure to corrosive chemicals such as strong acids, wash the effected part in flowing water, and contact the instructor for further help. Never try to neutralize the corrosive substance chemically, as this may result in burns. In case of any exposure, move away from the source of exposure (or remove the source). Never use mobile phone/laptop in the lab. 2. Maintenance of Laboratory Records: In any experiment, the results are to be faithfully recorded and analyzed. The maintenance of laboratory records is an essential part of all scientific work. The experimental observations must be taken down in a clean bound note-book and not in loose sheets and certainly not ion the margins of the instructions sheets. There should be no erasure in the observation book. If any entry needs to be corrected, it must be crossed out neatly and a new entry be made. After the days experimental work is over, get the observations initiated by the instructor, if the time is left over, do the necessary calculations and get them checked too. Write up the work in the fair laboratory record with details of the principle and procedure involved, neatly tabulate the data and calculations, and present the report on the next turn regularly.

The maintenance of a day to day observation book, complete in all details, is an essential part of any scientific work at any level, and is a habit that you must cultivate. 3. General Organization of Laboratory: In the few weeks, you will do a set of common experiments involving determination of various organic functional groups and learn (if you are not already familiar with them) the usage of the electronic balance, the techniques of analysis of organic functional groups and general
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LMCHE 103: Organic Chemistry skills of handling glassware. Thereafter, you will do other experiments in rotation and for that arrangement will be displayed. Some experiments or chemicals may be issued to you from counter for every experiment; you must return them faithfully at the end of your experiment so that the next student can use it. Any breakage must be reported to the laboratory assistant and a replacement should be obtained. Read the instructions carefully and apply your mind while doing the experiments. Nothing is gained by mere following the experiments. The purpose of the laboratory work is to understand better the chemical principle involved.

LMCHE 103: Organic Chemistry TABLE OF CONTENT S.No. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. Title Odour Solubility Tests Test for Saturation / Unsaturation Test for Aliphatic / Aromatic Test Test for Elements Lassaigne's Test Test for Amines Test for Amides Test for Aldehydes Test for ketones Qualitative analysis of carboxylic acids- Experiment -1 Qualitative analysis of amines- Experiment -2 Qualitative analysis of amides- Experiment -3 Qualitative analysis of Aldehydes- Experiment -4 Qualitative analysis of ketones- Experiment -5 Qualitative analysis of aromatic compound- Experiment -6 Hazard warning symbols Page No 5 5-8 9-10 11 12 13-14 14-15 15-17 17-19 20-21 22-24 25-26 27-28 29-30 31-32 33

LMCHE 103: Organic Chemistry Common Lab Manual S.No. Experiment 1 Odour (Note the smell of substance) Observation Inference

Pleasant or fruity Phenolic Aniline like Kerosene like Pungent Aromatic

Ester Phenol Aromatic Amine Hydrocarbon Aromatic compounds with halogen in the side chain

Solubility Tests for Carboxylic Acids, Phenols, Amines and Small Molecules The solubility of an organic compound in water depends on both its size and polarity. Compounds with 4 carbons (or less) and at least one polar functional group tend to be water soluble. Larger compounds tend to be insoluble in water unless they have an ionized functional group or several polar functional groups. Thus, an insoluble compound can be made water soluble if one of its functional groups can be ionized. For example, amines are weak bases. If an insoluble amine is reacted with strong acid, the amine will be protonated and become soluble in water. Similarly, carboxylic acids and phenols are weak acids. If an insoluble phenol is reacted with strong base, the phenol will be deprotonated and become soluble in water. Finally, phenols are much weaker acids than carboxylic acids. As such, there are some bases that are strong enough to deprotonate a carboxylic acid but not a phenol. One such base is NaHCO3 (which will make a carboxylic acid soluble in water but not a phenol).

LMCHE 103: Organic Chemistry 2 REAGENT AND TEST CLASS Soluble in cold or hot water. (If the unknown is soluble do NOT perform solubility tests below) Soluble in dil. HCl Soluble in dil. NaOH Soluble in NaHCO3 Insoluble in water, acid and alkali SOLUBILITY TABLE GROUP OF COMPOUNDS

Neutral, acidic or Lower members of series. Neutral, e.g. basic. (Test with alcohols; Acidic, e.g. acids, phenols; litmus or universal Basic, e.g. amines indicator paper) Basic Acidic Strongly acidic Neutral Most amines (except III amines with only aromatic groups Most acids, most phenols. Most carboxylic acids. Hydrocarbons, nitrohydro-carbons, alkyl or aryl halides, esters and ethers. Higher molecular weight alcohols, aldehydes and ketones

0.2 g ( 4 drops ) sub +2 ml 10 % NaHCO3 solution

Dissolves with brisk effervesence of CO2

Acid

LMCHE 103: Organic Chemistry

0.2 g ( 4 drops ) sub +2 ml dil. HCl. Shake well Dissolves in HCl. Reappears on adding 10 % NaOH dropwise

Basic Substance (Amine)

0.2 g ( 4 drops ) sub +2 ml dil. NaOH. Shake well

Dissolves in NaOH, reprecipitates on adding conc. HCl

Phenol (Aromatic acids)

LMCHE 103: Organic Chemistry

Solution turns yellow or brown when boiled. Oily globules obtained having aniline like smell when boiled Oily layer disappears on boiling white ppt. obtained on cooling and acidification with conc. HCl Substance unaffected in cold and on boiling

Carbohydrate

Anilide

Ester or amide of aromatic acid

Nitro compound, aldehyde or ketone, hydrocarbon

LMCHE 103: Organic Chemistry 3 Test for Saturation and Unsaturaion: Bromine (in Methylene Chloride) Test for Multiple Bonds Alkene

Alkyne

Standards Cyclohexane, Cyclohexene, and Bromobenzene Procedure In a hood, 0.02 g or 1 drop of the unknown is added to 0.5 mL of methylene chloride. Add a dilute solution of bromine in methylene chloride dropwise, with shaking, until the bromine color persists. The bromine solution must be fresh. Positive Test Discharging of the bromine color without the evolution of hydrogen bromide gas is a positive test. Complications Should be employed in conjunction with Baeyer test (dilute KMnO 4). Electron-withdrawing groups in the vinylic position can slow down bromine addition to the point that a negative test is erroneously produced. Tertiary amines (like pyridine) form perbromides upon treatment with bromine and lead to false positive tests. Aliphatic and aromatic amines can discharge the bromine color without the evolution of HBr gas.
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LMCHE 103: Organic Chemistry Y ellow colour decolourized , ppt formed Unsaturated compound easily brominated Saturated compounds

Y elow colour persists ( i.e. no decolourization

Baeyer Test for Multiple Bonds (Potassium Permanganate Solution) Alkene

Alkyne

Standards Cyclohexane, Cyclohexene and Bromobenzene. Procedure Dissolve 1 drop or 0.02 grams of the unknown in 0.5 mL reagent grade acetone. Add a 1% aqueous solution of potassium permanganate dropwise with shaking. If more than one drop of reagent is required to give a purple color to the solution, unsaturation or an easily oxidized functional group is present. Run parallel tests on pure acetone and, as usual, the standards listed above. Positive Test The disappearance of the KMnO4's purple color and the appearance of a brown suspension of MnO2 is a positive test. Complications Water insoluble compounds should be dissolved in ethanol, methanol, or acetone. Often, the brown precipitate fails to form and the solution turns reddish-brown. Easily oxidized compounds give a positive test: a) Most aldehydes give a positive test. b) Formic acid and its esters give a positive test. Alcohols with trace impurities give a positive test. Phenols and aryl amines give a positive test. Carbonyl compounds which decolorize bromine/methylene chloride usually give a negative test.
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LMCHE 103: Organic Chemistry Pink colour decolourizes immediately Unsaturated compounds

Slow decolourization

Easily oxidizable compound, aldehyde and phenol

No decolourization 4 (i) Test for Aliphatic / Aromatic Nature: Ignite 0.1 g ( 2 drops) substance in nickel spatula

Saturated compounds

Burns with Sooty flame Burns, non luminous flame

Aromatic compound

Aliphatic compound

(ii)

0.2 g (4 drop) sub +a mix of 1 ml conc. HNO3 and 1 ml of conc. H2SO4. Shake well. Heat for 10-15 minutes on boiling in water bath. Pour it into 20 ml of cold water.

Y ellow colour solution or ppt No yellow ppt

Aromatic compound

Aliphatic compound

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LMCHE 103: Organic Chemistry 5 Test for Elements Lassaigne's Test: It is a general test for the detection of halogens, nitrogen and sulphur in an organic compound. These elements are bonded covalently in the organic compounds. In order to detect them, these have to be converted into their ionic forms. This is done by fusing the organic compound with sodium metal. The ionic compounds formed during the fusion are extracted in aqueous solution and can be detected by simple chemical tests. The extract is called sodium fusion extract or Lassaigne's extract. Test for nitrogen: The carbon and nitrogen present in the organic compound on fusion with sodium metal give sodium cyanide (NaCN) soluble in water. This is converted in to sodium ferrocyanide by the addition of sufficient quantity of ferrous sulphate. Ferric ions generated during the process reacts with ferrocyanide to form blue precipitate of ferric ferrocyanide.

soduim ferrocyanide

Ferric ferocyanide Test for chlorine: Chlorine present in the organic compound forms sodium chloride on fusion with sodium metal. Sodium chloride extracted with water can be easily identified by adding silver nitrate solution after acidifying with dil. Nitric acid.

Test for sulphur: If sulphur is present in the organic compound, sodium fusion will convert it into sodium sulphide. Sulphide ions are readily identified by sodium nirtoprusside.

sodium nitroprusside

violet color

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LMCHE 103: Organic Chemistry 6 (i) Test for Amines: (a) Reaction with nitrous acid Dissolve the amine (0.5 mL) in concentrated acid (2.0 mL) and water (3 mL) and cool the solution to 0 - 5 in an ice-bath for 5 minutes. Add a cold solution (ice-bath) of sodium nitrite (0.5 g) in water (2.0 mL) from a dropper, with swirling of the test tube, still keeping the mixture in the ice-bath. AMINE I aliphatic OBSERVATION N2 evolved. FUNCTIONAL GROUP TEST

I aromatic

Diazonium salt is formed

0 - 5oC

Aryldiazonium Chloride

Add the cold diazonium solution and with swirling to a cold solution of 2-naphthol (0.2 g) in 5% NaOH solution (2 mL). An orange-red azo dye is formed. Azo dye formation for aromatic primary amines: Aryldiazonium salts react with aromatic rings of phenols to form highly coloured azo compounds. These reactions are called coupling reactions.

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LMCHE 103: Organic Chemistry

II aliphatic and II aromatic III aliphatic III aromatic

Yellow oily nitrosamines are generally formed. No visible reaction. Dialkylanilines yield green solid p-nitroso compounds (if p-position unsubstituted). R2NH + HNO2 -> R2N-NO

(b) Reaction with benzenesulphonyl chloride: Benzenesulphonyl chloride reacts with primary and secondary but not with tertiary amines to yield substituted sulphonamides. (i) C6H5SO2Cl + H-NHR + NaOH C6H5SO2NHR + NaCl + H2O (ii) C6H5SO2Cl + H-NR2 + NaOH C6H5SO2NR2 + NaCl + H2O The substituted sulphonamide formed from a primary amine dissolves in the alkali medium whilst that produced from a secondary amine is insoluble in alkali. Place 0.5 mL (or 0.5 g) of the compound, 15 - 10 mL of 5% NaOH and 1 mL of benzenesulphonyl chloride in a test tube, stopper the tube and shake until the odour of the sulphonyl chloride has disappeared. The solution must be kept alkaline (if no reaction has occurred, the substance is probably a tertiary amine). If a precipitate appears in the alkaline solution, dilute with about 10 mL of water and shake; if the precipitate does not dissolve, a secondary amine is indicated. If there is no precipitate, acidify it cautiously to congo red with concentrated hydrochloric acid (added dropwise): a precipitate is indicative of a primary amine. (ii) Test for Amides: NaOH Test 0.2 g sub + 2 ml of 10 % NaOH solution. Heat strongly for 5 minutes. Cool and add 10 drops conc. HCl CH3-CO-NH2 + NaOH -> CH3-CO2- Na+ + NH3 On heating NH3 is evolved On addition of HCl white ppt is obtained Amide

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LMCHE 103: Organic Chemistry Urea Nitrate Test White ppt 0.1 g sub + 3 ml saturated oxalic acid. Shake well Urea Oxalate Test White ppt 0.1 g sub + 3 ml saturated oxalic acid. Shake well (iii) Test for Aldehydes: Schiff's Test 0.1 g (2 drops) sub + 3-4 d r o p chiff's reagent. Shake well.(don't heat) (The Schiff reagent is the reaction product of Fuchsine (rosaniline hydrochloride) and sodium bisulfite) Violet or red coloration within two minutes Aldehyde present Diamide (like urea) Amide

Fuchsin itself is colored due to its quinoid structure (see also for example viologen) but is decolorized by sulfonation at the central carbon atom which disrupts the favourable resonance in the molecule. More bisulphite (depending on stoichiometry ) reacts with available amine groups to so-called N-sulfinic acid groups. The reaction of the Schiff reagent with aldehydes is complex. In it the aldehyde groups react with the sulfinic acid groups forming a sulfonamide.

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LMCHE 103: Organic Chemistry Tollen's Test Bright silver 0.2g (4 drops) + 1 ml of Tollen's reagent i.e. colour or black Ammonical silver nitrate. Heat the test tube in water ppt -silver bath for 10 minutes mirror Aldehyde

Aldehydes reacts with silveroxide to form white precipitate of metallic silver while ketones cannot, due to absence of reducing hydrogen atom.

Fehling's Test Red ppt 0.1 g (2 drops) sub + 1ml each of Fehling's solution A and B, Heat to boil. Aliphatic aldehyde or aldose

There are two solutions which contains cupric oxide as oxidising agent, when reacts with aldehydes it forms red precipitate of cuprous oxide.

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LMCHE 103: Organic Chemistry Action of sodium bisulphite solution: Saturated solution of sodium bisulphite in water, when mixed with aldehydes gives a white crystalline bisulphite addition

compounds. Benedict's Solution Similar chemical reaction and cupric oxide are present in benedict's solution but presence of citrate gives differant complex. It reacts with aldehydes to form red precipitate of Cu2O. It cannot reacts with benzaldehyde and its aromatic derivatives.

(iv)

Test for Ketone: Action of Borsches Reagent: Ketones reacts with 2, 4 dinitrophenyl hydrazine solution to give a orange/red precipitate of ketone 2,4 dintrophenylhydrazone derivative

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LMCHE 103: Organic Chemistry Action of sodium nitroprusside solution: The nitroprusside ion, which may be regarded as a special carrier of the nitrosonium ion, forms a coloured complex with methyl ketones. In presence of alkali eg acetone is converted to CH3COCH2- ion which reacts with nitroprusside ion [Fe(CN)5NO]2- to give highly coloured ion [Fe(CN)5NOCH2COCH3]2-.

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LMCHE 103: Organic Chemistry

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LMCHE 103: Organic Chemistry Experiment No. 1 Experiment: To analyze to organic compound (Carboxylic Acids) Equipments required: Melting point apparatus, Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods etc. Material required: Some common Carboxylic acids, Sodium Bicarbonate, Sodium Hydroxide, Potassium permangnate etc. Learning Objectives: (i) The purpose of this experiment is to detection of carboxylic acid functional groups in organic compound. (ii) Students get awareness that how acids undergo chemical reactions. (iii) They will get an idea of chemicals used for their detection. Outline of procedure: Preliminary examination Physical State Odour Solubility Test for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: No Elements Present Functional Group Test: Take a pinch of substance and add 5 ml of cold saturated NaHCO 3. Brisk effervescence of CO2 is evolved which indicates the presence of COOH group. RCOOH + NaHCO3 RCOONa + H2O + CO2 Refer to Common Lab Manual (page 5-19)

Confirmatory Test for some acids (A) Oxalic Acid (COOH)2 . H2O Warm a mixture of 2 ml of aq. solution of acid and dilute H2SO4 and few drops of KMnO4 solution. Colour of KMnO4 is decolourized. Oxalic acid is confirmed. M.P. 101 (B) Benzoic Acid (C6H5 COOH) Take a little substance and add 2 ml of nitrating mixture (equal amount of conc. HNO 3 and conc. H2SO4). Heat carefully for 5-10 minutes, cool and pour in beaker containing water. A pale yellow solid separates out. ( m- nitrobenzoic acid). Benzoic acid is confirmed. M.P. 121

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LMCHE 103: Organic Chemistry


Required Results: Parameters: NA Relationships: NA Graphs/Plots: NA Error Analysis: NA

Caution: Add the compound in Sodium hydrogen carbonate solution slowly so that effervescence is visible clearly. Hazards:

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LMCHE 103: Organic Chemistry Experiment No. 2 Experiment: To analyse to organic compound (Amines) Equipments required: Melting point apparatus, Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods etc. Material required: Some common Amines, Sodium Bicarbonate, Sodium Hydroxide, Potassium permangnate etc Learning Objectives: (i) The purpose of this experiment is to detection of amino functional group in organic compound. (ii) Students will learn to detect the element other than C, H and O. Outline of procedure: Preliminary examination Physical State Odour Solubility Test for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: Test for Nitrogen atom: To 2 ml of the sodium extract add 2 ml of freshly prepared solution of FeSO4. Dirty green precipitate is obtained. If no green colour ppt is obtained then add NaOH solution till green colour ppt. Fe(OH) 2 persists and boil the mixture. Cool and then add dil. HCl or H2SO4. Prussian blue colour is obtained and nitrogen is confirmed. Na + C+ N FeSO4 + 2NaOH Fe(OH)2 + 2NaCN Fe(CN)2 + 4NaCN 3Na4(FeCN)6 + 4Fe3+ NaCN Fe(OH)2 + Na2SO4 Fe(CN)2 + 2NaOH Na4(FeCN)6 ( sodium ferrocyanide) Fe4[Fe(CN)6]3 + 12Na+ (Ferric ferrocyanide) (prussian blue) Refer to common lab manual (page 5-19)

Functional Group Test:

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LMCHE 103: Organic Chemistry

Test for tertiary- amine To a small amount of substance add 2 mL of 2% NaOH and then add dilute HCl to it, if a green yellow or green yellow colour is produced which turns dark greenish on adding an alkali to the solution the t-amine is present. Carbylamine Test: To a small extent of substance add 2 ml of alcoholic KOH solution 4 drops of CHCl3 and heat the mixture. Highly offensive odour of carbylamine or isocyanide is produced. RNH2 + CHCl3 + 3KOH RNC + 3KCl+ 3H2O

Azo dye test: Take substance in 2 ml dil. HCl if substance is insoluble add 3-4 ml of water and cool the mixture to 0. To this add precooled 2% NaNO2 solution in very small amounts that no brown fumes escape from the solution. Add 1 ml of this solution to a solution of -napthol in alkali when an orange red dye is obtained to t- amine.

Confirmatory Test for some amines (A) Aniline (C6H5NH2) B.P. = 183 C (i) Dissolve the drop of substance in 2 ml of ether and to it add 10 ml H 2O. Add 1 ml dil. solution of bleaching powder and shake. Purple colour is obtained. Aniline is confirmed. (A) Pyridine (C5H5N) B. P. = 115 C Add a drop of substance to 2 ml of HgCl2 solution. White ppt. of pyridine mercuric chloride is obtained. Pyridine is confirmed. (ii) To a solution of substance in dil. HCl and add few drops of Meyer's reagent (sol. of HgCl2 and KI in water) Pale yellow ppt. is obtained which dissolves on heating but reappears on cooing.
Required Results: Parameters: NA Relationships: NA Graphs/Plots: NA Error Analysis: NA

Caution: (a) Do not expose yourself to the vapours while performing carbylamine test because isocyanide is highly poisonous. Destroy it immediately as described above. (b) Maintain the temperature of the reaction mixture below 5C during diazotisation, as diazonium chloride is unstable at higher temperatures. (c) Always add diazonium chloride solution into the alkaline solution of -naphthol and not vice-versa.

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LMCHE 103: Organic Chemistry Hazards:

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LMCHE 103: Organic Chemistry Experiment No. 3 Experiment: To analyse to organic compound (Amides) Equipments required: Melting point apparatus, Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods etc. Material required: Some common Amides, Sodium Bicarbonate, Sodium Hydroxide, Potassium permangnate etc Learning Objectives: The purpose of this experiment is the detection of amide functional group in organic compound Outline of Procedure: Preliminary examination Physical State Odour Solubility Testt for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: Test for Nitrogen atom: To 2 ml of the Na extract add 2 ml of freshly prepared solution of FeSO 4. Dirty green precipitate is obtained, then add NaOH solution till green colour ppt. Fe(OH)2 persists and boil the mixture. Cool and then add dil. HCl or H2SO4. Prussian blue colour is obtained and nitrogen is confirmed. Chemical equations: FeSO4 + 2NaOH Fe(OH)2 + 2NaCN Fe(CN)2 + 4NaCN 3Na4(FeCN)6 + 4Fe3+ Fe(OH)2 + Na2SO4 Fe(CN)2 + 2NaOH Na4(FeCN)6 ( sodium ferrocyanide) Fe4[Fe(CN)6]3 + 12Na+ (Ferric ferrocyanide- prussian blue) Refer to Common Lab Manual (page 5-19) Refer to common lab manual (page 5-19)

Functional Group Test:

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LMCHE 103: Organic Chemistry Confirmatory Tests for some amides (A) Acetamide ( CH3CONH2) M.Pt. 82 Add conc. H2SO4 in substance and heat till strong smell of vinegar due to the formation of acetic acid is observed. Acetamide is confirmed. B.P. 182 C (B) Urea (NH2CONH2) M.Pt. 132 C (i) Biuret Test: Heat a small amount of substance in a dry test tube. The solid melts and ammonia is evolved. Cool the tube when white residue is left in it. Dissolve it in 2 ml water, add a drop of CuSO4 solution and then add 2 ml NaOH solution.When violet colour is obtained, urea is confirmed. (ii) Add 2-3 ml of conc. HNO3 to very small amount of substance and boil on cooling, white crystals of urea nitrate are obtained. (C) Benzamide (C6H5CONH2) M.Pt 129 C Take small amount of substance and add dil. NaOH. Boil for 5 minutes allow to cool and acidify with dil. HCl. White ppt. of benzoic acid is obtained Benzamide is confirmed.
Required Results: Parameters: NA Relationships to be determined: NA Graphs/Plots: NA Error Analysis: NA

Cautions: Use concentrated acids like sulphuric acid and nitric acids very carefully they can cause burns Hazards:

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LMCHE 103: Organic Chemistry Experiment No. 4 Experiment: To analyse to organic compound (Aldehydes) Equipments required: Melting point apparatus, Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods etc. Material required: Some common aldehyes, Sodium Bicarbonate, Sodium Hydroxide, Potassium permangnate, Shiff's reagent, Tollen's reagent etc. Learning Objectives: (i) The purpose of this experiment is to detection of aldehydic group in organic compound Outline of procedure: Preliminary examination Physical State Odour Solubility Test for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: No Elements Present Functional Group Test: Schiffs Test: Take 2 ml of the cold aqueous solution of the compound and add 2 ml of Schiffs reagent. Shake vigorously and allow standing for two minutes. A deep violet-red or red colour is obtained which indicates the presence of aldehydic group. Confirmatory Test for some common aldehydes: a) Acetaldehyde (CH3CHO) M.Pt. = 20 C Take 2 ml of aqueous solution of the substance and add 2 ml of freshly prepared sodium nitroprusside solution. Dilute the solution with NaOH solution (drop by drop). A deep wine colour is obtained, Acetaldehyde is confirmed. b) Benzaldehyde (C6H5CHO) B.P. = 179 C Take a little substance in a test tube and add 2 ml of KMnO4 solution. Heat the contents for five minutes. Filter and acidify the filterate with dil. HCl. A white ppt. of benzoic acid is obtained. Benzaldehyde is confirmed. c) Take substance and add Tollens reagent very slowly. A grey ppt. is obtained, Benzaldehyde is confirmed. Refer to Common Lab Manual (page 5-19)

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LMCHE 103: Organic Chemistry


Required Results: Parameters: NA Relationships to be determined: NA Graphs/Plots: NA Error Analysis: NA

Cautions: (a) Always use freshly prepared reagents to perform the tests. (b) Do not heat the reaction mixture directly on a flame. (c) After performing the test, destroy the silver mirror by adding dilute nitric acid and drain off the solution with excess of water. Hazards: Acetaldehyde is harmful by inhalation, ingestion and through skin absorption. Some experiments with animals suggest that this substance may be anticipated to be a carcinogen. Formaldehyde 37% solution causes burns. Very toxic by inhalation, ingestion and through skin absorption. Readily absorbed through skin. Probable human carcinogen. Mutagen. May cause damage to kidneys, allergic reactions, sensitisation and heritable genetic damage. Sulfuric acid is harmful if swallowed. Corrosive - causes burns. Skin or eye contact will lead to severe irritation or burns. Ethanol is highly flammable.

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LMCHE 103: Organic Chemistry Experiment No. 5 Experiment: To analyse to organic compound (Ketones) Equipments required: Melting point apparatus, Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods etc. Material required: Some common Ketones, Sodium Bicarbonate, Sodium Hydroxide, Potassium permangnate etc Learning Objectives: (i) The purpose of this experiment is to detection of ketone group in organic compound Outline of Procedure: Preliminary examination Physical State Odour Solubility Test for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: No Elements Present Functional Group Test: Schiffs Test: Take 2 ml of the cold aqueous solution of the compound and add 2 ml of Schiffs reagent. Shake vigorously and allow standing for two minutes. A deep violet-red or red colour is obtained which indicates the presence of aldehydic group. 2,4-Dinitrophenylhydrazine test (2,4-DNP test): Take 2-3 drops of the liquid compound in a test tube or in case of solid compound, dissolve a few crystals of it in 2-3 mL alcohol. Add a few drops of an alcoholic solution of 2,4 dinitrophenylhydrazine. Appearance of yellow, orange or orange-red precipitate confirms the presence of carbonyl group. If precipitate does not appear at room temperature, warm the mixture in a water bath for a few minutes and cool. Confirmatory Test for some common ketones: (A) Acetone (CH3COCH3) B.P. = 56 Iodoform Test: Take 2 ml of the substance and add 3-4 drops of iodine solution and add NaOH solution drop by drop. Warm the solution. Brown colour of iodine disappears and a yellow ppt of iodoform having characteristic hospital like smell is formed. Acetone is confirmed. (B) Acetophenone (C6H5COCH3) B. P. = 202 Take a little substance and add conc. H2SO4. Orange colour is produced. Acetophenone is confirmed.
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Refer to Common Lab Manual (page 5-19)

LMCHE 103: Organic Chemistry (C) Take 2 ml of substance and add 2 ml of alk. KMnO4. Heat the contents for 5 minutes. Cool, filter and acidify the filtrate with dil. HCl and white ppt. of benzoic acid is obtained. Acetophenone is confirmed.
Required Results: Parameters: NA Relationships to be determined: NA Graphs/Plots: NA Error Analysis: NA

Caution: Do not inhale the vapours of iodine its potentially carcinogenic Hazards:

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LMCHE 103: Organic Chemistry Experiment No. 6 Experiment: To analyse to organic compound (aromatic compound) Equipments Required: Beakers, Test Tubes, Funnel, Tripod stand, Bunsen Burner, Stirring rods, nickel spatula, steam bath etc. Material Required: Some common aromatic compounds, concentrated H2SO4, Potassium permangnate etc. Learning Objectives: (i) The purpose of this experiment is to detection of aromaticity in organic compounds. (ii) Students learn that which chemicals could be used to detect the aromaticity Outline of Procedure: Preliminary examination Physical State Odour Solubility Test for saturation / unsaturation Ignition Test: Aliphatic/ Aromatic Element Detection: No Elements Present Functional Group Test: Confirmatory Tests for some aromatic compounds (A) Benzoic Acid (C6H5 COOH) M.P. 121 C i) Compound on nickel spatula Burns with Sooty flame. ii) Take a little substance and add 2 ml of nitrating mixture (equal amount of conc. HNO 3 and conc. H2SO4). Heat carefully for 5-10 minutes, cool and pour in beaker containing water. A pale yellow solid separates out. (m- nitrobenzoic acid). Benzoic acid is confirmed. (B) Toluene Aluminium Chloride test: Place 1 ml of chloroform in a dry test tube; add 0.1 ml of the liquid sample and mix thoroughly. Weigh 0.25 g of anhydrous aluminum chloride in the hood using the aluminum weighing boats provided. Tilt the test tube to moisten the wall of the tube. Then add the anhydrous aluminum chloride so that the powder strikes the wetted side of the test tube. Orange to red colour formation. Refer to Common Lab Manual (page 5-19)

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LMCHE 103: Organic Chemistry


Required Results: Parameters: NA Relationships to be determined: NA Graphs/Plots: NA Error Analysis: NA

Caution: Aluminum chloride is highly reactive. In contact with moist air, it releases strongly acidic and irritating hydrogen chloride gas.

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LMCHE 103: Organic Chemistry HAZARD WARNING SYMBOLS (signs or labels) A brief description of what the hazard might be. (You can identify these symbols on the chemical bottles which are being used during the experiment USE THE CHEMICALS ACCORDINGLY)

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