Organic Practical Experiment

Date 28-2-23Expt. No. 1Page No. 1Experiment 1object: To Prepare O-chlorobenzoic acid fromphthalic anhydride (3 step process)Step1: To Prepare phthalamide from phthalicanhydrideTheory: Phthalic anhydride on fusion with ureayields phthalamide with the evolutionof CO2 and ammonia.Reagent: Phthalic anhydride (10gm) + urea (2gm)Procedure: Take a mixture of logm phthalicanhydride and 2 gm urea in a roundbottom flask and heat the well mixedmixture on a sand bath upto 130°Cto 135°c when the solid mixturehas melted the reaction will takeplace vigorously with the evolution ofCarbon dioxide and ammonia within10 min The mixture froath up andbecome solid and allow it to coalat room temp. and add 20ml ofth2 To stirr the content well andTeacher's Signature : IOCii -Fusion+ NH 2-C-NH2NH+CO2C+NH40Phthalic Anhydridephth alimide DateExpt. No.Page No.shake it. Filter the product wash withlittle ice cold H2O and dryResult:Yield8gmM.P to236°CColour+ WhiteStep2: To prep are anthranilic acid fromPhthalimide.Theory: The ring in phth alamide can be often byalkaline hydrolytis to yield the productphth alimide product. The later undergoesHofmann Bromide reaction to formanthranilic acid.Requirements: Phthalimide (5gm), NaoH (11.5gm),Bromine (1.8ml), Conc. Hcl (sufficientquantity) , glacial acetic acid (rufficientquantity)Procedure: In a conical flask dissolve 6.5gmof NaOH in 25ml of H2O and coolinan ice bath. Now add 108mlbromine gradually with continuousshaking of stirr. The Content till theTeacher's Signature NH2CoCONH2NaoHNHCOOHCOOHCophth alimidePhthalimidicAnthraniacid DateExpt. No.Page No.bromine has reacted cool it again to 0°cand add 5gm of phth alamide andshake the content well. Add a solutionof 5gm NaoH in 20ml of H2O andagain shake the content carefullyHeat the mixture to about 80°Cfor 3-4 min. Filter while not ifnecessary and cool the filter ate Ininc. ice. Neutralise solution byadding slowly conc. Hcl (12-1 13 ml) withstirring then add gradually glacialacetic acid (15ml) to precipidateanthranilic acid completely Filter theproduct wash with little cold H2Oand recrystalise 1gm from bollingH2O.ResultsYield2.6gmM.P146°Ccolour+colourless crystals.step III; To prepare - chlorobenzoic acidfrom anthronilic acid.Theory The diazo group in a diazoniumsalt solution can t be replaced by aTeacher's Signature DateExpt. No.Page No.halogen atom when it is treated withcuprous halide in the presence ofcorresponding halogen acid. It is thehalogen that join to the copper thatenters the nucleus Hence anthranilicacid is first diazotive than undergoessandmeyer reaction to yield O- Chloro-benzoic acid.Reagent: Anthranilic acid (2.5 gm), sodiumNitrite (1.7gm) Copper sulphate (4.5 gm),sodium Chloride (4.2gm), Conc. HCl,copper tuming (14.4gm)Procedure:APreparation of cuprous chloridesolution-In a round bottom flask dissolve 4.5gmof copper sulphate and 4.2gm ofsodium Chloride in 13ml of H2O.Heat the solution upto boiling andthen add about 14ml conc. Hd followedby 2.5 gm copper turning Boil (reflux)the content till the colourless clearSolution is obtained Filter it(if necessary) and cooled in icebath.Teacher's Signature COOHCOOHNH2N=N-clCOOHNaNo2HclCuacl3clHClAnthranilicDiazoniumacidO-ChlorobenzoicSaltacidpast DateExpt. No.Page No.BPreparation of diazonium salt solution ofanthranilic acidIn a beaker disolve 2.5gm of anthranilicacid in a mixture of 3.5ml conc.Hcl and 15ml of H2O warm it ifnecessary to get a clear solutionand cool it in ice bath withvigrous shaking to it. Add dropby drop a cold solution of 1.7 gmlodium nitrite in 4ml H2O keepingthe temp. below 5'c Add this diazoniumChloride solution in the cold andwell starred cuprous proceed rapidlywith foaming Allowing the reaction mixtureto stand for about 1/2 hr at roomtemp. Recrys tallise 1gm of solutionContaining a little alcoholResult:-Yield1.6gmM.P +140°Ccolour colourless crystal.Precautions:IDuring diazotisation the temp.should be maintained below 5°c.2The diazonium salt soln should be addfrequently to the cuprous chloride sal?Teacher's Signature DateExpt. No.Page No.insmall fraction without delaying thediazonium compound decompose onstanding. Datept. No. 02Page No. 6/3/2023Experiment - 2object :-> To determine the weight of thesulphur in a given organic Compound bymessenger's method.Theory: when oxidised with alkaline potavium ispermagnate sulphur of the organic Comp.quantitatively Converted into sulphuric acid.Sulphuric acid thus obtained is estimatedby ppt as Basoy.Reagent::->KMnoy (AR)1.5 gmKOH (AR)0.7 gm(=30ml) conc. Hdsufficient quantity till solbecome colourlessBael2dissolve about logm of Bacl2 of ARquantity in 100ml distilled H2O.Procedure:Take 25ml sol? of organic sulphurComp. in 500ml round bottom flask fitted withwith an air condensor / quick fit apparatus)1.5 gm of KMOO4 with 0.7 gm KOH and till30 ml distill H2O EP shake the contentthe air Condensor and reflex the mixturefor about 4hr. Add a few piece of glassbeads [China dish] to cool the content atroom temp. E then add (is 30ml) conc. Hclgraduatly through the condensor withTeacher's Signature: Q KMnoy + 2KOH2K2MnO4 + H2O + [o]S t 3 [o] + H2OH2SO4H2SO4 + Bacl2Bason + 2Hdl andmasserandingniscussDateExpt. No.Page No.occassionally the shaking the completely decolourisedfilter colourless soln. Transfer theContent to corning beaker & Concentrateto half of its Add Bacl2 soln to thehot soin obtained above with stirringtill complete ppt occur. Allow the ppttric filter paper with the hot distilledto settle , filter , wash through gravime-water. Place the filter paper afterfolding it so as to completely enclosethe ppt in a dry EP weighed silicaCrussible Heat the crussible firstgently then strongly to ignite theppt till red hotCool the crussible in a dericator of finallyweight Repeat the heating ef coolingtill Constant weight is achieved.Ash Treatmentsome of the Basoy ppt in the reactionmay be reduced by Carbon of the filterpaper into Barium sulphideBa soy + CBas + 4COIt can be reconverted into Basoy byadding / drop of conc. Hcl & 1drop ofTeacher's Signature : Bas + 2HdlBadz + H2SBas + H2SO4Basoul + Hcl DateExpt. No.Page Noconc H2SO4 of heating the crusible firstgently untill the unused acid hasbeen completely driven off Then itis cooled & weight agained Mostof by simply heating converted the crusible into to Basoy redthe Bas ishot Ash treatment should be avoidedIculationas far as possibleobservation:.42 gm of Basoy contains 32.06 gm ofweight of crussible :-14.5532phurweight of crusible + PPt :- 15.3286weight of ppt :- 0.77540.7754 gm of Basoy = 233.42 32.06 x 0.7754Result: The given organic comp. contains=0.1064 gmlow= 0.1064 gmPrecautions:1.To avoid bumping few Lilica piercersshould be added in the reaction flask.2.use of excen of Bacl2 soln shouldbe avoided Expt. No.Page No.Experiment -3object To determine the strength of given anilinesolution by bromination method.Principle:- Aniline undergoes bromination with standardbrominating solution (bromide t bromate) togiven qualitative yield of tribromo anilineunreacted Bromine liberates Iodine fromKI solution quantitatively which is titratedagainst standard hypo sol? using starchas an indicator from volume of hypoused we can calculate amount of bromineused to brominate aniline and hencequantity of aniline present may becalculated.Reagent Required:1.Brominating sol'= Dissolve 0.75gm of an by drouspotassium Bromate (KBrO3) of 2.8 gm ofPotassium Bromide (KBr) in 250 ml ofdistill H2O.2.Hypo solution :- Dissolve 1.5gm of sodiumthio sulphate in 250 ml of H2O.Teacher's Signature 5KBr+ KBrO3 + 6Hcl3Br2 +3H2O + 6kdNH2NH2Br0t 3 Br2Br + 3HBr.Br2KI+ Br22KBr + I2.2Na2S2O3 + I2Na2S406 + - 2NaI.SodiumthioSulphate Note: Attempt sion carries 10 main of cationicDateExpt. No.Page No.3.Standard Aniline soln. Dissolve accuratelyweight 0.16 gm of aniline in minimum ofdil Hcl sol? and make up the vol. to100 ml in 100 ml measuring flack4.Potassium Iodide sol?:+ Dissolve logm of KIin 100ml of distilled H2O.5.Starch soln: Prepare a paste of 1 gm solubleStarch in little quantity of H2O & addthis suspension to 100ml of boiling H2OConstant stirring Boil. the Content toget a clear sou if still insolublestarch is filter it. of use filterate asindicator.Procedure:-(i)Standarisation of hypo solution : Pipette outsoln 20 ml brominating soln in throughlyclean titration flask of 250ml capacityAdd to it 25 ml of distilled H2Ofollowed by the add? of lome conc? Mclshake the contents well. Now add 20ml of KI sal to it and again Shaketo liberate the iodine which is indicatedby the transformation of dark yellowTeacher's Signature (ii) Kange Polymer structure andfollowingNote: (iii) Attemptany carries three 10 questions marks. antinnic Answer out polymerisation of is the requiredExpt. No.DatePage No.colour. Content to brown then add hypo soln towith continous of titration flask drop drop thisshaking till a Creamish byyellow starch colour appear. Add few dropsof soen and shake starchturns colour of soln dropwise , continuousfrom end greenish blue to light Green. This isMaking till last drop change colourof repeat the titration till concurrentpoint of titration Note this readingreading are obtained(ii)Titration with Brown aniline sol?:- Fillburette, pipette out 20ml of knownbrominating soln of hypo in separatinganiline soin in 250 ml . Conical titrationflask having stopper of add to it 20 mlof distilled H2O add to it 10ml of conc.Hcl also and shake the constants willrun the brominating sol? is smallproportions with constant shaking tillpermanent yellow colour persists. Nowadd 8ml of KI seen of again shakewill titrate the Podine Liberated usingstarch as an indicator.Teacher's Signature : 8.(i) Random and phy-Vulcame degradianofwer anes as is reducing agent agents in in organic organicrequiredHowdizingNote: (ii) (iii)Polymers Attempt question the concept 10 ~ation? of cationic dies Elastomers: is What more isof isstomersDateExpt. No.Page No.(iii)Titrate with unknown aniline sol?:- Procedureis same as with known sel?Observation:(i)Preparation of known aniline soleweight of weighing bottle-weight of weighing bottle + aniline- -weight of aniline soln dissolve in W2-W1-100 ml sol?(ii)Standardisation of Hypo sotS.Novol. of brominating Burette ReadingHypoSoLn (ml) Initial Final(ml)1.2.3.(iii)Titration with unknown aniline sel +S.No.Aniline soin Brominatingsol' Burette Reading HypoBrominatingBrominatake (ml) added (B) Initial final (D-c) eq"tohypo sain ting(c) (D)usedanilineE=D-CX20 (B-E)V,2Teacher's Signature DateExpt. No.Page No.Experiment -4objectTo analyse the given organicmixturePreliminary observationStateCrystallinecolourBrown whiteodourCharacteristicSolubilityPartially soluble in water.Functional Group testExperimentObservationInference1.Compt saturatedBrisk effervercence-CHOOHsoen of NaHCO3grd confined2.Aq. sol? of Comp +White oppaleecencePhenolic grpFectconfirmed3.Two drops of Fecl3Green colourPhenolic grpto alcoholic seen ofappearconfirmedComp.Teacher's Signature : DatePage No.Expt. No.Separation method of Mixture - Mixture ispartially soluble in method H2O hence it isfirst separationResidue (wash with H2O)Mixture shake+ H2O filterFilterate ( evaporate dryness upto)(Comp A)Test for residue(A)Element detection - No element present(B)Functional group testExperimentObservationInference2 drop of Fecl3 toGreen colourPhenolic grp1)obtainedConfirmeddecohalic soln ofComp.whitephenolic2)Aqueous soln ofappalescencegup ConfirmedComp.Separation of residue - Since residue is soluble HenceH2O and contain phenolic groupin it is separated by NOOH methodResidue (comp C) wash with NaOH and than H2OResidue Shake+ NaoH filterFilterate (Comp.B) Regenerate with conc. HdFilter.Teacher's Signature: DateExpt. No.Page No.Identification of Comp A- -Preliminary ObservationState- - CrystallineColour - Dark greenodour- - odourlesSolubility- Soluble in waterElement detection - No element presentFunctional group test -ExperimentobservationInference1)Comp t saturated soin Brisk effericenceTOOH grpof NaHCO3of CO2confirmed2)Ignision TestPlace mixture on aComp. burnsAliphaticSpatula and ignitewith non-smookyComp.on flameflame3)Melting point - observed - 102°CExact101°C4)Possible Comp. - oxalic acid.5)Confirmatory Test-Neutral comp. selwhite ppt solubleOxalic+ Cachin dil Hd butacidnot in CH3COOHConfirmedTeacher's Signature : DateExpt. No.Page No.Identification of Comp. BPreliminary observation -State - Crystalline solidColour - whiteodour- - Characterstic smellsolubility- in soluble in waterbut soluble in NOOH.Element detection - No element presentFunctional group test1)2 drops of Fecl3 + alcoholic Green colourPhenolic grpsoln of compconfirmed2)Aqucous soln of CompWhitephenolic grp+ Fecl3appales anceconfirmed.Melting point - observed- 124°CExact - 122°CPossible Comp. - B- NaphtholConfirmatory Test-Comp. + conc KOH + Chloroformdeep blueB-naphthelt warm slowlycolourconfirmedTeacher's Signature : DateExpt. No.Page No.Derivative - Picrate - In a test tube prepare asaturated lotn of compound in alcohol. Inanother of picric acidtest tube laturated doesin same soluent mix the two soluent tostand far few min.Identification of Comp. C-Preliminary observation-State - Solidcolour - whiteOdour -Characteristic lmellSolubility- - Insoluble in waterElement analysis-Compit /ml conc. HNO3+White curdycl presentcoal then add AgN03ppt solubleinNHYOHFunctional Group test -1)2 drops of Fecl3 + alcoholicgreenphenolic grpset of comp.ColourConfirmed2)Aquous soln of Comp + Feelwhitephenolic grpappalesceneconfirmedMelting point observed 54°CExact53°CTeacher's Signature : DatePage No.Expt. No.Possible Comp - p - dichlarobeneneConfirmatory Test-ObservationExperimentInferenceTake organic comp. 1gmtwhite crystallinep-dichloro-types ofbeazeneIce cold water, addnitrating mixture withsubstanceconfirmedoccassional shaking. Nowformedheat the water flaskfor about 20min cooland pour the contentin ice cold water tfilterResult - The given Organic mixture Comp. -Compound AName - Oxalic acidStructure -O=C -OH2H20O= C -OHCompoundBName- B- NaphthalOHStructure -derrivative - Picrate [orange Colour)melting point - 156°cCompound CName- P- dich loro benzeneclStructure -0omelting point. - 54aTeacher's Signature :