bagi apt teal Shanda odall gyhll wacall Magall 4d Practical organic chemistry For Students of first Class Pharmacy department Kadhum japer Zebon Assistant Lecturer Haider Abdul Ghani Moosa Assist Head of ChemistsPUNANVNVNVNVNVV VV VN UN VN EN TA TAEDA DNS < + . + z + + ’ Contents ¢ » + a + iv + ~« + “ + ~ + ~ 1 | Glass ware + x + + N 2 | Filtration a . 3 | Extraction es “ + 4 4 | Crystallization Zz “ + “ 5 | Sublimation + “ + 7. 6 | Simple - and Fractional distillation e 7 | Melting point ¥. 4 ¢ 4 8 | boiling point + 4 - 4 + 4 ¢ 4 + . ¢ 4 é “” + + + 4 + ex + 4 + 4 + 4 + ‘ - 4 + 4 ¢ 4 + IPP EEL EE EL EEE EE ELLE EE EEE e ttt tt ttt tineed NNVNNVAVVNNTANASA DEE EAN ETNA E NYY YN Glass Ware Erienmeger test bes Flask sercelain Sucle ZH wing top | mortar and pestle | | Sp ZA ws mouth bottle | lead dish | | day triangle medicine drops Bas rack | | Benzen burner Preumatic trough er combustion spoon VSS SS SSS SS SSS SSS FSFE FES SEES SESE ESSE SS SFE TSE EES PHF LEL LLL LLL LL ELL ELE LEE ELE EEE tt tt tteLNAANVVAVAN TENANT VD TVET EVN ENE ENN Florence Fiasx — Fevsers Glass plate G— test tube clamp | — Srivring vod &> Graduated cglinder Eo peal Buret clamp | FER ores Fang PIN evopotnd dish | test tube bush c= Trongulay fle OS SAAR AAA QS SSS SESS FEST FEST FEST FESS FFI TSE PETES ESTEE SE SES PPLE PL LILLE LILI LLL ELL LL LIE LESS Ett tt tttSLNNAAVANANANAN UNV ETE ENE ET EEE EN ND ee — | i i HTT OHTA EO) Oooo ooo ooo ooo ooo Poo CeCe CCC CCC CCC CCC CC CCC Ceo e QS SSS SESS SESS SSS FEST EESTI STEFF TTT ESTES SESS ESSE S PELL LLL LLL LL LILES LLL ESSE LSP Et ttt titeDCCC CCPC CCE E EE ESSE EEE EEE ESE Sooo ooo P CPPCC COS LUNE EVEVEVOVEVUEVEVOVOVEV EVV EHV HN Simple distillation eauiement separators funnel Fang filvrpaper inte Funnel i D — > Lighter Lager Caqueous Layer) HO Set __G Benzore ——p-2 te heavier Layer Conganic Layer> 4 chiovolorm ccly oveHels l ep\ aapll {immiscible solution ) Chloroform = + ~—+H,0 Benzoicacid + Salt Organiclayer + aqueous layer CCl, or CHCL; + water (H.0) Benzoic + salt CPPS o PES Peo oe C CLP CEE EEE EPEC CCC CCC CCC Coe E QS SS SSS ESSE SETS ES TESTES TESTES ESTEE SSS SESS SESE SS ES VILLE LLL LES LLL ELLE ILE LISS SE et ttt teRI SAA RAR RRR RRA FNVVVVVVVVVVEVVVEVEVEVETHVE DEDEDE DENN eal ead pladinely Juaill is * A mixture of benzoic acid and salt can be separated by extraction using chloroform (CHCL; ) and water ( H20 ) as solvents The chloroform (CHCLs) layer ( organic layer ) is lower layer and contain benzoic acid , while water ( aqueous layer ) is upper layer and contain salt The two layers are evaporate to dryness to get residue (benzoic acid and salt ) in two beakers, weighting the residue ,then calculate the percentage of each. QPS SPSS SSS ESSE SESS SSS SSS STS TSS STS STS TTS TTT TESS PIPL LLL LLL LE LES EL ELE L EEL ELL Ett ett ttetLNVNVVVNANANAN VV EVEN U LUNE EDU E TT ED EDAD CoP o ooo Ce oC CPPCC CCC CCC CeCe CeCe CCC CCC CCC eee Procedure : ‘Weight benzoic acid (0.2 )gm and (0.5 )gm of salt then mix them Y.Add (30 ml) of distill water ( D.W. ) Y Heat the solution. *.Pour the solution in separatory funnel. ©.Add (5 ml) of chloroform. ‘\ Stopper the separatory funnel and shake vigorously. 7.Allow the two liquids to separate into clear layers and separate the aqueous layer from organic layer. ‘Pour the organic layer in small beaker( » 9.Add (5 ml ) of chloroform to aqueous layer and stopper the separatory funnel and shake. 10.Allow the two liquids to separate clear layer. 11.Pour the organic layer in first beaker which contain the organic layer then pour the aqueous layer in another small beaker ( Jof known weight and evaporate till dryness. )Y.Weight the two beakers . ‘Y Calculate the weight of benzoic acid and salt. ) £ Calculate the percentage of each The properties of solvents: ) tt must be volatile ( has low boiling point ). .Immiscible with water. * Solubility of solute in the solvent must be high. VELLLL LLL LLL LLL LL LE LILLIE ILLS LS LS ILS SS BSS SSS SSS SESS SESE ESSE EET E SESE STE SEF SSS SESS STSSNANVVVNANAN UNV EV EVEN UN EN EN EN ENTE LT ND v Bally By pens Lge Ad Say Slelerdanall Cuda gb BS GSS Ul Gang Salall obs ALE Apluaiily Repeat the same experiment by using another solvents like ether or ccl,? Why ? explain that ? Bg pec yh ae (Aly Ala Adal ge Ce gl CS 13) Legh a stat (pil all Sg tall Lali (te ain fal Aah EB ads cll Gee Ct eb iL og yell ual Qk Gy tial ee SL GL Jab aldinall gh pial Jptaall Ge igi ney Smee Vs Epa «Ava BEPC EPEC CEE E ECC C CCCP CPPCC CCCP CCPC PCC CCC CCC CES VSS SSS SSS SESS SESE ESSE ESSE TESTS FSS TTT TFT SF TESS SELLS L ELI LIL LLL ILLES LLL EL EL ELE tet titeSNAVNNVEVVVVEVVVEV OTLEY EVEN VET N TY ONY eee eee eteeedeeeecececececceececeeeeceeeeeeeee (Crystallization)Experiment No. 3 This method involves the process of preparing a saturation solution by dissolving substances (solute ) in desirable solvent at an elevated temperature and filtering while hot. The substances should separate in crystalline form upon cooling. Byghy Alas Bugis] Aiba YS Sad AS ya All dy pal SAL ts 1} Ag Lanial Sees all tall a pall A gb Ady al hl al MA ht oda ys Isp AU ole Bobadhahs ol cats eal gS yey Aa pally Cask NS ap ay Galle Gade LES le aed Cass sl gl 1S. a aly Ua util Aha glued ae; Adiga) Sold) gail Xp yo 38.555 0 US phy Cl yo Bae 6 y sll ale] Aube sya Jlje fe Yi be 4) Si ae lgnall Zap ca i) a BLT USS ga Glee 98 Jeri (gill uel pal go jy AY Haake al Uh a all aL) as Gl Gan.) gb BALD 4b 955 gill Guhl Ulead Syay V4) 3} ally Uh kal gigi ob pall ot pall ge elit Y gill Cy dell Ulan! Gans, Dai ht ey ll oad OS ol eas Ay pill aie plain JSS Cild.y dacial y Col yg Ugalans gill Chall JLaciaal Sains € co hy Lag AAS al gl) GF AGREI a yall OLS AMAT 4 GSS ll abl Lanta any. AGB S y pues Ball Guat UW ity LELLPSL ILE LE LILLE ILL ELI LL LL SL SESS LETS QPS SSS SSS SSS SSS SSS FSS SSS SSF SSF FFF FFE FEES FEESCoCo ooo eee eee eC ECC CCP P PCC CC CCC CCPC CCC CCC ee E PNVVVVEVVEVEVEVEVEVOVOEVEDEDEDVED EDEN “ ‘lt consists in first finding a solvent which will dissolve the crude material ( ) Readily when hot but to a small extent when cold. The crude substance is then dissolved in a minimum of the boiling solvent , the solution filtered to remove an insoluble impurities and then cooled, when the solute will crystallize out, leaving at room temp. ,the crystals are then filtered off. lizatic i 1. Dissolves the solute readily at an elevated temperature. Y Dissolve the solute only sparingly at lower temperature. ¥ Give no chemical reaction with solute 4.\tis sufficiently volatile so that it may be removed easily from purified crystals. ACrystallization is effected by the following factors : ) Type of solute Type of solvent used Y Time of growth of crystals ‘Temperature Ag Aa phy Conall Casall Ls ey LSE ace gey LS aT 8 Ug ey ll BLN Gp a yl at WS LS salad cul anny Le bay All cose Cy Fil fil J paS 6 ele at Ques cube BA pall he eh 85 pL La clay Y pede 25l3 pty Guba gd vill go 5 ul ule chai SS SSS SSS SESS S SEES ESE EE EEE EEE EEE SES SEES SESE SESS LILES SILL IEF L ISLES LLL L LE LL EEL ESS Ett tttPNANNVVVTVVVEVVV TEV V TEV D VETTE ETE HEIN Choice of solvent: Benzene will dissolve hydrocarbon The solvent will dissolve most readily compounds similar in constitutionto. its self, thus alcohol usually dissolve the hydroxyl compounds . The final choice should depend on inflammable of solvent and also on its. Apparatus : COPPELL LEPC CECE CECE PEEP C CCC C CCCP CCPC CCC ESS Acetanilide , charcoal cost. gh Ba glll Aalee 6B aria (lly MetLtl) hall solvent [__Boiling point solvent Boiling point water 100° Acetic acid 1180 methanol | _64.7C° | _ acetone 56.50 Carbon tetra | ° chloroform 0 chloral (CCL) — CHCL; amd 4°%ethanol BC benzene 800° Dichloromethane ac Petroleum 35-36 C2 ether Toluene 110c° Reagents : Watch glass, beaker, glass rod, Buchner flask, Buchner funnel, filter paper. PPLE L ELL LEIS SELLS LLL LE LL SEE ESP Ett ttt S PSSSSSSSS SS SSS SESS SESS EFSF FFF SEES EEE SESE HFSSSNVVVNVNENVUN EUV EVEN UNV UN ATTN ENED TY DAY CPPS EEE EPEC EPEC PoC CCPC CCC CoCo CCC Coe S Procedure : Place a sample of impure acetanilide (10 )gm in beaker containing water or weight ( 1)gm of benzoic acid . Y Heat the contents with stirring. Y Add about ( 0.5 )gm of charcoal and continue heating with stirring. * Filter the hot saturated solution. ©.Transfer the filtrated in to (2) separate beaker. 6.Leave beaker (1) in ice bath and water ,and beaker (2) at room temperature . 7.Compare the shape of crystals form at low temp. and form at room temp. Filter the solution of beakers (1)and(2). ‘Record the yield. ) Calculate the percentage of yield . we of pure substance we of impure substance pio Percentage of pure crystals % = PELL L LL LLL LLL LLL LILLIE LIL L SSS LSS SS tet S SPS SSE SSS SESS SSS SS SFSF SSF FSF SF FFF FFF FFF FFF FS SSSSNVVVNANVNAN ANTENA EVEN ENE U TUTTE EAD Y Saturoted Soluation rg ____— Pure. Substacte. Crastras to diy nae ithe pihevpafe” by Quen ond 3 aleulae the Weigle n CoP PPP PC PPP PCE CECE CCCP EPC E PCCP CCPC CCC CCC CCC CCE VSS SS SSS SSS SSS SSS SESS ESSE SESS SESS ESSE STS SST SS VIELE ELLIS LLL ILLES ELLE LLL ELIS ES tet tttSNAVVNAVVVVNVVVVVVVVVVV EVV UVVVVV NYY ONY CPPCC LEPC EL PLES PE EEE LEE Ee oe Ee CEES CCE EC CCCP CoS dipill ye cildiade paay elall ga ball ball 5 9 (benzoic acid ) hs jill Ganala Sale Lia! aie) 22 (1) Gaalall g5y Ldes de (1+) ss ol ll eal hen 6 AB LA ANG heal Lal yo GS acl 5 yd 6 il lel OGLE Gd pal wvadall eure Gee AY! Wall i gad ll aie Gadall ly sly Gana 5 gia gleall ells Sul Lue Sly a at sayy Sef ghd Uy Lk phy Aa yo atl lal pees AAS cle dy al (Buchner funnel) axing 135 ca5 sll 45 yy cle Upland i git ol yall Sl! an Gal gl hot saturation solution (Jl 95 qual J slaall ant ji) de pur eat ill ol yay FB py che My pteall S3La ue 38 Gf GALAN Uglaall ent aie Ula! Crass os al 5 les la al pally gcael Sell ISS & aL oa iad ge Gala Usloll aw 5d ol Op ad ll BBA ata (16% —¥+) cn abel Go BS AS Gas BEA Ge Aes Ly Ge AE yy Jad Guhl Ge Different filtration apparatus LLL LL LLL LLL LLL LLL LES E LL LLL LES SS St tet QPS PSS PSS SSS SSE SS FSS FSET FEST FST F ESTES EFF EES ESSSNVANVAAVAVVVVVV TVET UA VETTE EN LT ONG “ Experiment No. 4 (Sublimation) Yr Coe eo ooo PCCP CC CCPC CCC CPPCC CCPC CCC CCC CCC CCC Eee QS SESS SSS SSS SSS SS ES FSFE T STS SS TTS TFS TFS FFT TSS PLLLLLL LLL LILLE LLL LLL ELE PLES Pet tt titeNUEVO TETHVVUVVVVEVED EHH HEHEHE HN number of soli is beingtransformed directly to vapor state (display the characteristics properly of condensing to solid state)without passing through the intermediate liquid state Reagents : Benzoic acid + Salt Apparatus used : N99 me tt Gy) Saal Cemad Aya Y) cig pl! Canad Aline Salil Cis Nila Cae Aga Atta opt) od gh Gee bis Gai ised a Lay sic gual Atal) cyan Agha) oda Aaleal! Aa! CoC P CPPCC PEP CEE EEE CCE CeCe ee eee Eee eee ee eee Eee ee QS SSS SSSSSSSSSSS SSF SSS FSET TFET TSF FEST F STS FE SES LILES LLL LLL LILLIE LLL LLL LILI SLES ttt tetttSNNVVVVVVVVEVVVOVVVEVEDVEVEVEVEDEDVE ION Cee CEE eee Pee EC EP E LEE e EEC eee eC o CCC Cee C CCC CES Procedure : 1 Place a (benzoic acid + salt ) mixture in beaker (400)ml , place (200)m! round bottom flask filled with cold water on beaker which contain mixture. The beaker is placed on a sand bath or over low flame. Heating as required from (15)minute to (1)hour , depending on the intensity of heat applied. 3.The material capable of subliming will collect on bottom of cold flask and on the side walls inside the beaker the pure crystalline form. *.Determine the melting point of pure crystals. m. p. of benzoic acid = 121 + 2 Co m. p. of salt = 800-850 C° ) intensity of heat Y pressure Cold. water ao Benzoie acid Beaker Send. Both da fier mixture of CBenzoic +5aK> vesidue 256i soul Benzene Berner (ak Care roTr or ger CONTEC Experiment No. 5 ve PLLELLL ISLE LLL EL ELL LE LLL EE EEL EL Ete eet SSS SSS ESSE SEF FFF FTES TTT FFT T TTT S TTT S SST SSSSNNVVVVVEVVVV EVV UV OVE VV VE VVV NYY ONY COPPELL PEPE CELE PEEPS ELE E SES eS eo SCS Sooo ESS (Simple andFractional — distillation) The boiling point : may be defined as that temperature at which vapor pressure (the pressure exerted by substances equals the pressure of atmosphere above liquid. The purification of liquid organic compounds by conversion to vapor state with heat and condensation of vapors to the liquid state in known as distillation a definite value at give pressure for every pure organic compound and is known as boiling point. cp $l) aca) a 5Hlal) laiy dai Osi og glaaly pil) Lyall Aa jal li Fell sala) ipa lal) 0 Stein Li) Lid 9 i pull Audit) My po arid "i shin Lyla if impurities in liquid are non-volatile the liquid may be purified by direct or simple distillation the impurities remaining in the distilling flask. Renae etl assole et os nes all tl on dae Ai Lge Banas Gol eV Lael Uarindy p'5I fi (0+) Littell eid See renee nme ren Vis of cigs 8 ball Sst) pe GBS gS oye Lat GE GL SK | SAS) Bakal Si pall hue aye Aen gt Leal desea oS ate iad gil al gall po Ley Glapaull yl) Aly lo Alaaal gy Aad Sey sill gy jall g gi Le Uw (miscible solution) Las) tail! Aa! 5: Glad YSq de jied! il pall $ Yule n LLP EL ELSEIF LILLE LL EEL EEE LE ESS tte tt tt te S F999 FFF 9999995559995 995499495945NUVVVETVVVOVEVEVEVEVEVEDEDVDVEV HEH EVN “ CoCo CCPC CCPC CCC E CECE CCC E CECE ECE CECE EC EEC ELSE Apparatus used : ? cre dar om ame aera Simple distillation Procedure : L.Prepare a distillation set — up using (250 )ml of distilling flask fitted with a thermometer and water, cooled condenser. 2.Add two small pieces of porous plates. 3.Place (100 )ml of ethanol in the flask and start the water (note the water inlet is at lower end of the condenser. 4,Heat the flask with a hot flame until the contents being to boil and adjust the temperature so that distillation precedes at 2 or 3 drops per-second. 5.Discard the first 2 or 3 ml of distillate and di collected. i until 60 mi has been “\.Record the observed boiling range of alcohol . w LPL L LLL LLL LLL LLL LLL LL LS EELS tt ttt ttt VSS SSS SSE SSS FSS SS FESS SESE STFS TF FETT ESOS SFE SES ESSNNN TTVVVUTHVVV VE HE VV H EVV distillation. 2.Fractional distillation : api Seill pla) If impurities are them-selves volatile liquid then separation of these mixture from bulk of the required substance is achieved by fractional Lapse Ap 59 one Sl Sy Cay Gan jee uliles eel Lingh pi jail pala Jann a (2+) os ul _ < i Fractional distillation Solvent Boiling point water 100c° inflammability CEP C CEE EEE EEE CELE EEE EEE EEE EEE EEE EE CEE EEL EES “A PILL LPE LLL LL LLL LLL LLL ELSES ES Et bet ttte S SPSS FFE PFS SESS SSE SEES SFT FSF SESE SESS SSS SSS SLNVNANVVNVVNVTNVVN VEU EV UVV VET VEN YET NY v methanol 4°%Alcohol inflammable Acetone Chloroform _ Benzene 11s CLs | ae [inflammable | (Melting point)Experiment No. 6 Theory: Cee tee eee deeee cece eceeeeceeeeeeeeeeeeeeeeeeeeee QS SESS SS SSS SESS SEES SESE TSS E SSS F SFT FST SFT SF TSS PLL LL LLL LLL LLL LL SLL SLE LES LS ES tt tt tttCoCo eee E LeeLee eee CEE CPC e Coe C CCE CCC CCC CC ee SNVVVVVNANANAN EVE VN EEN ENED EN UTED T ET AY Melting point : for solid is that the temperature which the solid and its liquid in equilibrium without changing in the temperature at one atom pressure . it can be determined by introducing amount of substance into small capillary tube , attaching this to the temperature centered in heat bath (oil bath ), heating the bath slowly and observing the temperature at which melting beginning and it complete. Pure substance usually have sharp M.P. for example (145.5 — 146 ) ‘Impure substance of the same compound melts at lower temp. and over a wide range (ex. 140-144) Th LP. Method : ) Place a small quantity of sample on a filter paper . 2.Crush the sample to powder with spatula . ¥ Place tiny amount of sample in capillary tube. £ Attach the capillary tube thermometer by rubber hand. °.Place the thermometer in oil bath. ‘Heat the bath slowly and note the temp. at which the substance states. V.Record the melting point . PIPES ELLE LLL ELE LL ELL LES E ELE te tt tt tee S PSPSPS SS SES SSS SSF SSE SSE SSF SF FSF FFF FF SFE SF SSH FS FSSLNNAANVANVA VAN UN VNU EV EVENT T ED END CPP e eee eee eee eee ee CCPC CCCP CCPC CPC CCC CCC CCC Cee! Take M.P. of impure mixture of salicylic acid ‘A. Impure mixture of benzoic acid consist of (0.3 gm salicylic acid + 0.9 gm benzoic acid ) B. Impure mixture of salicylic acid consist of ( 0.3 gm of benzoic acid + 0.9 gm of salicylic acid) Then take their melting point Experiment No. 7 (boiling point) theory : oiling point ; it is that temperature at which the vapor pressure(the pressure exerted by the substance ) equals the pressure of atmosphere above the liquid. The apparatus consists of a boil tube which contains liquid for B.P. determination and inverted capillary attached to a thermometer which immersed in liquid bath, heat liquid bath gradually ,when the bubbling becomes rapid, discontinue heating and the temp. is allowed to drop (1-°2) and stream of bubbles which indicate the B.P. of liquid is noted. Method : ) Place ( 2-3 )ml of liquid in the boiler tube by using capillary tube. Y.Immerse the capillary tube in the boiler tube. Attach the boiler tube to the thermometer . 4.Immerse the thermometer in liquid bath. © Heat the bath slowly. PIPE LE ILE ELL LLL LL ELL SLES ELL Et ttt ttt QV SSS SSS SESS SSS SS ESSE TESTS FTES SFT T FFT T STF SES OSSCPPCC PPPoE PEPE CELE CEP E ECC PEEP CCC CC oC CCE eS SNVENVTEVEVVV TEV VETTE HEHEHE HED HH ON 6.Note the temp. at which the stream of bubbles begin; then remove the source of heat and the temp. is allowed to drop ( 1-°2) which is mean cool the bath oil take the temperature at which the liquid recodes into inverted tube ( capillary ). Apparatus for determination of boiling point VSS SSS SSS SSS ESSE SESE ESSE ESET TSF TTT TTT EEE TEESE SES FELL LLL LLL LLL LILLE LIL LLL SSP SS ttt tt testPNNVVVVVVVVVEVEVEVVVVEVOVEVOVEV EVE EON substance Boiling point \ Acetone 560° ¥ ‘Methanol 650° r Ethanol 3C € Benzene 81C° ° Water 100 C x Chloroform 620 theemomerer capillary sube boiler tube Pareb$ing orl (beth oD heat churned ‘Apparatus for determination of boiling point re PELL LE LILLE LLL SEL LLL LLL EDEL PEt ttt tite COPPELL PLCC CELL E SELLE EEE EEE LES ELE LESH E LSE o HOS SSS SESS SS SS TESS SSE S SESS SSS SSE SESS SSE SESE SS SEESSNUUNVUEVVVVVVDEVVVOVEVEVED VED EDEDEDDN substance Boiling point y Acetone 56C° Y Methanol z 50 * Ethanol BO i Benzene | aC ou Water | 100 <7 Cchioroform [62 thermometer botlertube —___| Pavabféne off = ———J (both ofl) heat cbwnerd Apparatus for determination of bolling point re 4 v ¥ v ¥ v ¥ ¥ 4 ¥ ¥ v v v v v ¥ ¥ v ¥ ¥ ¥ ¥ v ¥ ¥ v ¥ v v ¥ v v 4 ¥ v v ¥ v ¥ v ¥ ¥ 4 v LEPLPPP LPL IP PLES SEE EL ESSE SESE t et btte DESL CLES ESL ESE SLES EL ESSE SPEC ECE C PCP LES ELE LESS