Nome @hualmtulloss Bashici _——seaon 9 ‘Lab Instructor, Dx, be, XK Date_ 06 o4. 200 t PRELABEXERCISE = EXPERIMENT 1 | Melting Point Determination: Purity and Identity of Crystalline Organic Compounds 1. Define the term melting poiat range. emporah Ohure th. A the ple she topertare at hil, the Sample (5 Camplekhy mlb - 2. When determining the melting point ofan unknown substance isa common practice to fit determine a rough melting point by quickly heating the sample flloed bya careful determination ofthe melting poi: by gradually heating the sample atthe ae of 172°Cimin, What the advantage ofthis to stop determination ofthe melting point! 5 aoe i Becamas. by Kis tne thee 3. What two effects do impurities have on the melting point of an organic compound? Copyright © Houghton Miffin Company. All ph reserved 1LAB REPORT EXPERIMENT 1 Melting Point Determination: Purity and Identity of Crystalline Organic Compounds poate Melting ne Flt, Compount start Fini Migpoine Urea [31 E 132. ISLS oe Cinnamic acid ¢ 50-50 mixture 5-25 nihitere Sf ae 1 2 10 ‘ e 190 % 110 e 100 100%. Ure 0 > MikGntifcation ofa: Daknovw:t | ny gumtror ay morn =? a ecipete ame dete oe Teh se ahExperiment 1 Report Sheet Accurate melting pint eae iene ein eee Manipur Renzanstthe , 14 fen +c Melting point mined with Solicglte Ash Cs 18S My unknown compounds Semdewide fe ae 1 Why is itessential to (a) pack the sample tightly in the melting point tube and (b) heat the sample slowly a TRE SETI oy a gg ot ty as Me Lind Sud che walking quake dit ke to AN Nate 4 anes to yenck ase we ae broken wi» ©) Ww orden Yoo oe, acon Waser, S de tk. 2. Whavette Sind ST SN ier a, Mae te re. corfect ore. ( surface sven) will Ge Swlh i : e baahe te iyhek ansfrragch at oll ‘ a Loy or Fine Ril ee ning vi seit point of newly symthesized compounds often ila Booted pliny tube wh «karat idee (of stilar racking pode ge) end we dcarening ti sein poi ofthe wo substances ing th sae apparatus, What pose deste detemmaton of the melting point ofthe known substance serve? To hack the experinubQ setuly mh See lw Se “inshawad, ane. co Snes axdoaa Nok uy woiihes WwW GHrey | Sdpertindy % deat alee ee pee en ae a i devctif bey mbostianera >. a check ter _purity of — sang lag Csubstrene) 5. Three test tubes coniain white crystalline organic solids A, B and C, each of which melts at 149~150°C. A 50-50 mixture of A and B melts at 130-139°C. A $0-50 mixture ofA and C melts at 149-150°C, Inwhet range would a 50-50 mixture of B and C probably melt? L SWha cant pos ray about the identities of A.B aa CV Oganie solik (A= 8) #8 Capen Aank Cate Sitter (ubted) bewes 4 miktare of Seo ats Yn, So, Te & cal on tf te lah ee On Rae dtr Week | oe Bis Aiken Pom A and Toe Jo % etn Han 4 tens Sebidang at lene chara duihiy ‘ iin Company. All ight oe Ks Be ariwne Lhe pak ah oak & Tenor ge hee 4 NaeName_ hudba hth Bashiec Section_O 2. uote Dr fnael Date_13, ©}. 200} PRELAB EXERCISE EXPERIMENT 2 Reerystallization: Purification of Crystalline Organic Compounds Consider the following statement to answer questions Land 2 \— Reerystailization of an impure solid must be carried out using a minimum amount of the required solvens(s) at or near its boiling point 1. Why ist necessary to use only a minimum amount ofthe required solvent for reerytaliztion? 7 obtain a gorol revert of gutidh miei wd ale minimine tre amnst FH nsteal lot wy ickerkion in Me vedbar lignes wl) smth —onmant of selvst is usa Soy rerydellirdion- Why is it necessary to carryout the recrytallizaton ato near the oiling pot ofthe solvent use? In evder 6 remwe seven OG, onl ak 4 beter yolk of prriftyal oryatols « ‘How are insoluble impurities removed during reerystallization? by Atherton welek ahile fa sly. Ge Wt. Citet Fiteration) \ ‘What purpose does the addition of finely divided chercoal serve during the recrystallization of impure solids? : Chascrah is a gerd absorbuxt awh i is abted daring veeryshdlinaion je remem Wat of thay wether oy ue Yeoinay (mguittes. Copyright © Houghton Miia Company. Alrihs reserved 19ode alii tO thé tnaximin amountioF matéialatiat canbe recovered is the weight of the crude sample. In fue, only @ fraction of this «sample is obtined as purified crystals. The efciency aceon (or the percent revovery) és given by **” *rrelape on Saal ua “91008 * ‘weight oferude sample Pocenagereqvey: 0°36) tora , wis ‘Melting pent of crude icbaniide’ . Melting foint f purified aceiailide: Recrystalization pf p-Dibromobenzene, wir Amount St pied prdibroniobendéne reebyered Percentage recovery: “Melting int of énidé ptibromobenzener sts * ee ee Cestions 1. Whatis the purpose of reerystallization? | Wis wed te pprifs oy 2, Haare Sable hifi Temoveddunig bibebystlct noe BY vaccum Sheri eo Re tsciagphehi tte §Wer Rope iawn Ty ke Bross the, selation yd cyahb Ge Wenstemal te the, ant. He te eee Hoag Ha He, “while ce enol Beyiit oo MH oPoee Copyright © Houghion MilNin Company: All rights rere, a+ n Experiment? Report Sheet 3. Crystallization may be iiduced by scratching the vessel beticadh the sirface°of the sOlatich With lass rod. How does sratching the ise of the vessel witha glass rod induce erytalization? Fine, glut partitles prduead aa no nucle ta Be stat me rhllizction, onc aloo silk mks of the selutfon dhvawn onts “tw. aide vf Veosel evap riche; rai diy sebibes Sod aoe ‘ee + MOREE ose atone etiing acy esckcas sk ca Tecken a 2 de nd red wR oh Lets sea 2) that he cally Henne eh gtekad 99 Shhh dirslve impuiter a & et nt bh. Stns sap Givetwo reasons why vacuum filtration is someties preferable to ordinary gravity filtration Them: frase) To Increase Nha veh oR Rithevelion bean ch in facter tL te de iy» 9% foman see inpttin od Wa fom Ne eprhlo ™ pbb Wey ape poodle hea aetpaontoe a 1a standard chomiyOS handbook for the See ‘in hot and cold, Beeman. acckenilide glabhe i) ht ode. ond bak are play t : cote . tan H,2- "Retin “seme & Ne yey oh PAS atom i RE er oa he Ge” je 5 fe dee AO qui) xed act i ee lat chareal and sugar are the Rain impurities in sample of enue sestaild, explain ow rerystalization from water would remove each. Bes is ee Reuss Come 4 ‘ghia 2p ond is Vstounn Riheecion: be : ae ey ae ce ta Meek + bast An Wate ‘the recrystallization se hed the edu eee a was used as Agee tba re wa Yo « Heed is schbl ie ete it eet a the i Soka ees oe are ee ee , ee ages Beane” cx hexere Kees a byes oak ig ‘nd * Seconncy Hilde Qa heen > does net ‘ abide! in Gabe. Wins oe 0 vigil Mx Gelade amg dase Ryname Dhwel tittle B adh’ Scction_09, Labtnatrictors D7. Jona db Dae_do 09 loo? PRELABEXERCISE EXPERIMENT 3, Distillation; Separation and Purification of Organic Liquids 1. High boiling liquids are often disilled under reduced pressure by applying vacuum to the distillation set up. What practical benefit does one obtain by cacrying out the dstilation under reduced pressure? Stace mang substances — ceconpee either A+ bbw, Y Meg bali. pork under adisors auapheric. ptrasun, it is necessary dane He boing gan iy reducing praure- 2. Why is it necessary to add a boiling chip or two during the distillation ofa liquid? TH preicute bunping of Lge while histhhhion chih is ew 6 Seperbeatics anc elie ath. Cee a ae Ca e er hi pene Vapor pressvn is Tae pressure, exetat by a Vapor che ib is iy enyilibtiom ith Woe Vigad or slid Gm, or bithy of Ue sume subshua- a TIE boilig post ofc Weyad YAY Regpartin ab hid he og Prasate -f Hoe View Laces equ 4b The grasunn. exerhol by Hh sural, 5 4. Does the vapor pressure of a liquid change with temperature and if so, why’? Yes, the veper prasure of Liguid ts divally rede te the Yep eachure Prthe Legyid The Vopr prs. 4 liguich incrates Ne increng’ / tenpecthin. Te Wier te Tewperctar 4) a Vig Hee opeher fhe \ avefege aC eneigy of the wiles . When Wich wethur dhs mb A ‘sa eaeigy, the wlecdis wore Gite ene RL wd Wortain Fe sepercke fin woh ther anh dese wore wibredlis bred, rig pnp itn Compe Atsgyerewa Stn Wve. Voy kee ico Vi hd Poin. ‘hy Se tae is PHL vpn prenere-wane Qhucolr tbh eabic Section 02, Labtasivcsor__Dr. mal Date oF. Ano LAB REPORT EXPERIMENT 3 Distillation: Separation and Purification of Organic Liquids Disaton of Hexane Quanity Disled, mt 1 3 s 7 9 u ‘Temperature = Stpanaion of aiivary Mintore Quantity, Das, 1 me de 0 Sea te aT a Temperature Par Pee 620 R¥b _K20 We Wi'c Anic tet 'e ‘without Column : Ore i ee “Temperature Poo Foe we Re PHL 109 404e dna c 109C with Column . ‘Questions 1. Plot the boiling point against the volume of distillate forthe cistilltion of the hexane-toluene mixture both with and without a column, Label each curve. 15 110 = 105 Het fs Z IL celamn boing point °C & pee AP ala 0 an Be pe 4 6 10 12 14 16 18 20 wy volume of stilt, ml. Copyright © Houghion Miflin Company, Allright reserved, 31Experiment3 Report Shoot 2. Fromthedstiaion curves, estimate the volume of quid boiling below 85°C with and without column withoxt lawn ae 6) vel ca icles! mt Zio nk ee 2 jaro mmeetse pete bina ce feparain Usieg Frachanckeg Colum ik mor ehicied. BeOwoe ibbigs anes me le a en ech cahigh ae the sofice up dich the Netor, Wes, Cmeliese. Bb chal in CO i. bin St A Fi necessarily pure. Explain, Beaune ct He a 2bstryhic print to Bay ida Om fae < cnatcut bibliog pont a llhorfk Hy ai. ref pre - es. elohf md aude "ct hape fay fre Some by, 5. Whee: does reduton nthe amosphet presse have on te haling fons 0s hau LE atl{ ceerera the boilay pint bhi’ ll lenol + meta} Saves. Abe some compnne devon evaily at high mnpersfr so Peek Pressure ty led nis down RR Ut rt vc cee ET rp eat Beime tach mAeiahe fn a clfferank heshe eneray« Mh» rt Mb declan hove gees the het of Vaponirahion at Be some thine & 8efe Be Mid surfer and Wepatbe 7. Why Bt cen toa el aut ‘ina distilling apparatus that is closed tightly at every joint and ala “Bette” very high vopa prsiire Mey be fm od 05 rete of me venflhen bh Ametphere om mor Gn He olistilling Plesk 4 erp hele 4 ey wipro unl ng PTA SLAC cs i Sv ir a S aege ce heb L fsssfcr and there will be edeoys 4 Peah all Surfece for the opt Cmelacse th His , ng oa prorch the Sope of Vopos ferme oo esis biel lett tie ase tit pci aie toxiniog of “ep deinen pce? ; Ce Tore Gill be ont look of thy Legend Som PS Hermah capensin lieth. Ae Shak. Aho oe pie aa © fy he Agel — veg geablbrinen Ake flee 2 On He ofker hywel eet er viene eD Ask Veprr Prasure privbscel firm mire Ligpeck tri SePRELAB EXERCISE EXPERIMENT 4 Extraction: A Separation and Isolation Technique |. Whar ae he ingrgat eneia cp hy cose gekecting shen for extacton Mush Teadil issdve Whe substance. Fea SE Pobd sparingly Soluble. a ns Bam Wich Ae Lv detind subitome 45 Pas a Sl, “soe a Gere ZL shuld ost, ot Ge oe eth the Soluihe in om wndertible wis, nae Sele nat Monde mee ie be separated y extracting with aqens sodium bicarbonate anda sable orgie solvent, What cifeence in the chemical properties ofthe carboxslic acid andthe phenol makes this eoparation ppsible? Aguesus geek lien: Licthck. is atkabne -emagh tb covert cotbrigli, ccd te tha saths bit act phensls There , Gist age sedhan Witarloonete is Use + Temetie. ant athe iene the mirhre one How gronds ar Rewored ith oy Soin bye. 3. What safety precaution should one take when using chlorinated solvents for extraction? We shall awoiel brethiry tes Vaprs becouse dey 4 Ore Todic. ancl Some ave Cle ie We Cm te Phew sikh (fe cory at oprercdirs iy tm Ph ive, foool » ‘Whats the practical advantage of sing dichloromethane (density = 1.325 wm.) over diethyl ether (Gensity~ 0.706 gm) for extracting organic compounds from an aqueous solution using a separatory ; funnel? Dietlyd ether & hyhly flommble awh gon stendiy, tn axe / fa me devckep owgeeres cnwtrhons t expla peroricles. \® Dichlos methane ts mere Hus Ferma Ha Santer byer which. Cx be “ Venerol Frew He Copyright © Houghton Min Company, Allright reserved 41vom Dhue tah. BadIdee Rete e Ogre aes See rationing Dre: ‘Cuaul Dae_2? 04 gnF LAB REPORT EXPERIMENT 4 Extraction: A Separation and Isolation Technique Separation of Three-Component Mixture Weight 4 ‘Compound recovere mp, °C found mp, °C (lit) ‘m-Niroeiline fog lil C Tee Benmcaid =f 9 AZ, kes Naphthalene SO EEO a 2 Aoees Questions 1. Whatare the advantages and the disadvantages of using ether as an extraction solvent? \ BAe Advertages : Rondkly remsned Wy evegsr tian « Ve wastes eee by Femming a Tiyerr in Hae Sepe et wo ch iy om ora Se ‘ oi i uuradhive. CAnpniac sin ore nds ove of lb ther i. Se ro a a os We ef i Cyc het My hapa eens Rp cibo usar tn Gale vic cacid extracting an organic oo from an aqueous solution in creas funnel? Ta tts te Iywe Fore Magers tin Hla Seporrtoos fanned ah chick coll be encilg Saparited ie ele fa ee ak fe pen bape en be BANS, 3, Why ee ‘the stopper at the top of the separatory funnel be removed before liquid can be withdrawn ee A ; eee ie elec twth m ether is inode ta ertintton ithe eaae F the equilibtien, Vapor presume of Th sarect aill are ty The nnile he, oe Se tidy found Re teow i is bat veleswed by tains . wo gle ae ‘a > sane i gi peo ane ie FOR ST FORE a toy trvadl bg cdewaers PhineasExperiment 4 Report Sheet 4, Complete the following flow diagram for this extraction experiment, showing names and siructures of the materials present at ench stage se Colt a. a 1 Ether solution of m-nitroaniline, benzoic acid, and naphthalene dilute HCL lower upper layer layer Got o Benesic ceth 10% NaOH y Rewnic aeih 44 Copyright © Houghton Mifin Company. All ight reservedthle We cur wt aes tr The » Sependsy Pam earl Call ddsdve A xperimers 4 Report sheet ‘5. Write four equations (showing structures) for the reactions used in this experiment to separate and recover ‘n-nitroaniline, benzoic acid, and naphthalene. oot Kos iat ; Z Oo 4NaotH > Let 4t,o 2 OP Nt cool Z See at G abet og ts wo, “A = i ae : ee L A a. ek a Oe aes 6. Verify the conclusion (drawn in See. 1) that two extractions of A with $0-mL portions of ether yield 57.8 mg of A, whereas one exiraction with 100 mL of ether yields only 53.5 mg of A. hoe her Jietd = Xp4%. 2 I+ 436 SA.Bmg. eae 7. The solubility of suberic acid is 0.14 g/100 mL of water or 0.56 g/100 mL of ether. Calculate the volume of ther needed to remove 90% of the suberic acid from 100 mL of a saturated aqueous solution in a single exraction G&_. 25 ea -1y 0-4 es Ne ee od l \oo oN = aas me. Copyright© Houghton Miftin Company. Allrighsreverved 45name Phucbtety Wah Ralwied Sem OQ Lab nsructor_ Dx Tywoch Dae_O 40 QooF PRELAB EXERCISE = EXPERIMENT 5 Isolation of Natural Products: Caffeine and Eugenol 1 eve docs sodium carbonate serve during Une extraction of caffeine from tea eaves? ible aad Sediaw Galen ae eee ak ee eR aA Conve 3s hes ak ate te aca in Adler mda. tbc are Sete eo ieee -obaacine rage Na ond ST eltatm bane oak teangitn Ment th Mee bers Sinus Quen, Sra veaske exes Map Om Tow onvartcl bles SSS MiB Gils Oubseke W. Senden, Meine & wmore sll ty chilean” aud Go" be Sepuntan ‘What ppeee docs can layer of anyros som suite in he apex of he Ral serve while" rwni tiie in SG Ee i even ts Cighine ein Sule wll obo the small mah of RO Beck iy dussolved (athe chillerometlena smok = aaah a) os the cgemn ager het wy Wwe gala ih te fhek dy, oculad | eae 1S emablsion fn Ye Ecleamesee Aol piedinn sible Teles bred evaubin- Beira wie saad ty sepredteSayewe wetend trom ce : 2. Mise ahs ed apo og pk lig a4 ta iiohblet A dUstltcien in. ce Wageieohin a Swain. Coat 7s \iged white trkes oo \wer we by We ihadicte Show C any wh te eed Mat As oer ban pe BL Qian ik ta Wedel Ae the ely pA Gt WA ey be _Sepoake ead woe effedbne 4. The Te ap ee PE water test. wes alanced equation forthe reaction invalved in tis test. tty LON Oe ; ow &, wy” ‘i ° : aes oC eg e~ : ~Xe on Hl \ Poe CCopyrait © Houghion Mifin Company. All rights reserved 53Name Dhclmb Ml, Budabc Seaton 9 tabinsiutor Dt, med ae tO LAB REPORT EXPERIMENT 5. Isolation of Natural Products: Caffeine and Eugenol PART A. CAFFEINE (SUBLIMATION) ~~ Isolation of Caffeine from Tea Observed mp of caffeine: Sublim a rasa PReerstallize, ‘The literature mp value is 235-236°C. ‘Questions 1. Explain the chemical meaning of sublimation. i, > J < A qhtor iy Ghidh © Sik gee Ailey ty Aa gett Ashe aitlot Ah an istermabich Wsh chhe. Veo aot co 4 prihiodos Fede eioue tmpurthies de ach subline * PATRAS GSR RRR neath. v be Lbinchin kes plac. dabtes (ow! aKreg. ie SC PART 8 EUGENOL (STEAM DISTILLATION) ie bree Isolation of Eugenol from Cloves (Odor ofthe steam distillate: Odor of oil of cloves: ‘Copysignt © Houston Mimi Company. Al sights reserved 55Experiment 5 Report Sheet Questions |. Explain why the distillate from the stoam distllaion was turbid, especially early inthe distillation 2. Ifyou performed the chemical tests or determined the spectra of your eugenol sample, describe the results bere 56 Copyright © Houston monn Conpany. Ai sgh reservedLab instrctor_ sr, ned Date__&5. 70. 200 PRELABEXERCISE EXPERIMENT 8 Preparation of Alkenes from Cyclohexanol or 2-Methyl-2-butanol, and Tests for Unsaturation | Consider the dehydration of the following alcohols using a strong mineral acid as the catalyst and (a) place a circle around the alcokois that will dehydrate according to E1 mechanism, (b) place a box around the alcohols that will dehydrate according to E2 mechanism, and (c) place a triangle around the alcohols that DH Son , Yo (cy) pes . ; eh 2. Explain why alcohols generally have a higher boiling point than the alkenes derived from them through dehydration reaction. Becrure alcohals —fitm hydrogen berbing and ame or mor stayer Wen Cac oe Kerf dehy em Wafer tubing eet Ahan Ahem SU Wares ica pat tye err podicu inood eee orterepclsbazan is ee w Os Oe | Les aie a ate oO if ER ther 1~ methyl -1-cyeleherene —“matislene. Cycldvexenc C neon) ls <157 oh se Gan the radon qunon 3 be ilsebed fm cach eter using any ts fr usuraion eal in the procedure? If yes, how? If not, why not? oh a ie becuse, KM tea beefed ott wedtilene acter Copyright © Housizon Mimin Company. AU rights reserved, ws cid lesen fee Fe in. \w As O84 ec al ee, Geed wave Qluchabi tte Bevshic’ Section 02. Lab Instructor, De. Jmneok pate_ 25. 10, JeoF LAB REPORT EXPERIMENT 8 Preparation of Alkenes from Cyclohexanol or 2-Methyl-2-butanol, and Tests for Unsaturation Alkenes from Cyctoheranol or 2-Methy12-butanol Write a balanced equation for the preparation of cyclohexene (or 2-methy|-2-butene) fiom cyclohexanol (or 2 methyl-2-butanal).* Cet,oe PMG ONS =O Use the balanced equation to calculate your yield ae Name of alcohol Molecular weight of alcohol urclohexand 400. Ab068 3fuul 2 Moles used= OA534 moi cnet ag Ce a f6yx 0-46 woh Name of alkene Molecular weight of alkene —Gyloloerpuy su an Moles expected = _©-A5.24 mol vein Ye, Grams expected = fa EB COs ‘theoretical ysid) VE Yio Grams obtained = 4 hemad = les A opeldetaun -thear fide (actual yield) eae xim=__& Percentage yield = anu Hales Composition of Alkene Mixture (GC Analysis, Part B only) Name of Alkene Percent in Mixture 1 2. “Even though two alkenes are formed, the theoretical yield ofthe minture can be calculated by assuming that only one alkene is formed. Copyright © Houghton Mifflin Company. Al rights reserved 119 luExperiment Report Sheet . ‘Tests for Unsaturation Bromine test alkene: Reel bauen Color ofS rominn. —cliseggrenrs attane: Geka bemacn cal —ef — biirmine is Aeliheel ty Yeblone ax Bp. Nie age cha of Bingpent sod —lesnen eo bans Akane! i \ 4 Sulfuric avid test Alene Dissdve or = mame __Nusdebe pp) Ger Pra degen Colubete Questions 1. Write equations for the mechanistic steps in the dehydration of cyclohexanol (or 2-methyl2-butanol).* Assume an EI mechanism. ° set cet A, « an +h Sy 1 eee epee ee ulyeateas ge ‘ J RAL, Hpplicstion ebay 9 Be Gros arisiey fam the perm claig te experineit: (Hume ff) 2 Pat f the eleolol Orprat athat Gig thragh ony tathoo FET eR A gl lel seenmipely rirpat SRe (ote Dee ae W netnhre wy Baas of ee nee HS + le,Co, 5 NaSOy 4. co, awe I 4, Would the dehydration of -mathyleyclohexanol yield single alkene? Explain, using equations. oto, deky drvtion of R—mebligheyclhexanol yields a muxtum of alkeusy. My : oH On Wb oy det Femthyl — Smeebhy I~ clhstene 4 Get? ‘tty did Part your mech etl Dov fog ett nes of Clo een YAM He Cydbohasancl Oat nat ASR sok Some slime Ay 12¢ {Uti col Copyright © Houghion Mifflin Company, All rights reseeved.Experiment § Report Sheet 5. Acid-catalyzed dehydration of unsymmetrically substituted alcohols usually favors formation of the most stable alkene. Based on your results, which of the two alkenes formed in Part B is more stable? 6. Write a balanced equation for the reaction of cyclohexene or each of the two alkenes from Part B with bromine, with potassium permanganate, and with cold concentrated sulfuric acid. (Attach a sheet of paper to this report sheet if you need more spice.) Da methyl a. bideme. to more stable them Jimeagt [bua ie beowse it is dest Wnindorest. (Copyeight © Houghos MilNin Compan. All sights reserved, 121* Ofer Ch: ae eyclehexéne Dibyowo * Shea fabroreacgho ton, fom - A > OK ae ee : : “ a> nave Qhudrakublels B ashied Section 02 ee Lab Instructor Dr. ded Date_o4 aot PRELABEXERCISE EXPERIMENT 9 Cis-Trans Isomerism in Alkenes: Models and Experiments |. Using the structural formulas ofthe following substances, explain which ones can exist as cis-trane isomers: I-chloropropene, 2-chloropropere, I-pentere, 2-pentene vee aes { daa( nyse awk qigechoe ORION Fas “a Cés-traws pee i es “Gn Be exist on Cs ch, Bs Wo oe camsrs - =e ee aac HO steamy, SONS oc So. Define the term diastereomers Sage OS Diaderermons cs 4 Stervisamer f camp rund Vowiss or mon. cba couters Hat is of «iter image ft anithsy Aereacsonir f Fhe Some Campanas ‘Successful intersonversion of fumaric acid and maleic acid depends on momentary breaking and remaking. of the pi bond. Why is it easy to break pi bonds and not sigma bonds? Sim Gai ere med by eat to heck overp cheren ; pi beds Arm by sile 6 wth yifersbioy ond xr neh ecaLet in ome Altech prtiition Povan iach tonic fe Gk ot bara te sym od, ~ 4. What Purpose does the addition of bromine serve in the procedure describe forthe isomerization of ‘methy! Inaleate to methyl fumarate? Provide a mechanistic explanation, br Neds HU, Conttls Ht st Ze Ns zZ i] Welt, 47 —> i - c NOL Ae H 7 Ny at Ns —Figes St W eas 4 Gg onyight © Hoxghon Mittin Company. Al sige weed \\ 129Name Qhudref Ue l —Bushia’ Section _9 Lab Instructor_D Jad Date. 1. it. 200F LAB REPORT EXPERIMENT 9 Cis-Trans Isomerism in Alkenes: Models and Experiments PART A. CIS-TRANS ISOMERISM ILLUSTRATED WITH MODELS Models of 1,2-Dichloroethene 1 jae a Nessie Ss B Cs 2. dih\orectene 4 trart—_.2.- dichlors ethene 5 enh , te fer sitet, sitar it. 6. 4 am lack He staple bana 7. Some /¢o, Sapertinpasshl. nay 8 —chlnstaene Ning Work) 0 BA dp tty. 4 wre yep amncchet te the Simm she nee Aik ee ha al ee, ge = d 12, | * (mleic, ao ee me oot W 2B. ol PAM reitass Gv. 4 enc offer. ‘Experiment 9 Report Sheet Conversion of Maleie to Fumarie Acid Mp of maleic acid:__13 Fo — 32.6 ‘¢. . The literature mp value is 130.5°. ‘Mp of fiumaric acid: ee a OP mp valuc is 287°C. 2 Conversion of Methyl Maleate to Methyl Fumarate Mp of methyl fumarate: __. The literature mp value is 102°C, 1. Write equations that show a plausible reaction mechanism for the acid-catalyzed isomerization of maleic acid o imate aid® H a one” u r on a ee ee wpa mete of me maleate to methyl famarate oe a! 9 Br’ on A Ae eo Nee . {Aes fms o=< Ke Bess OFS Bh Ree ied. cay ts OCH, OCMg rosa ots be ae Nee Nady rl = = % o-( bi . sats u Q@ PAs HH Nes e by, ae’ Set SS 7 Nes Sue, ice ses FE eee eGo ony Wyre ole i se Aa eo Aig, 1 of ecu, *For an interesting discussion of dis mechanism and pertinent expesimeats, se J 8. Meek, “The Determination (of a Mechanism of Isomesization of Malic Acid to Furnatic Acid," Chom, Edu. 1975, 52,541 132 ‘Copysght © Houghten Mirtin Company. All ight reservedPree Qhutiitsle Suit 8° 9 cao = Visio, Decsleth oe I PRELABEXERCISE — EXPERIMENT 11 Electrophilic Aromatic Substitution |. Procedures for the nitration of bromobenzene and methyl benzoate use a mixture of conc. nitric acid and cone. sulfuric acid to generate the required nittonium ion, Whet is the role of sulirie acid in this mixture? Sy probinekin ond tenet of Wacker fine mihi oth qitenivin ion is Primed, Sebfuic awd in Ye withre acts 09g tly chong ritedion of Girmr ben tee ancl welll bevdocbe.. 2, Students are advised to dispose of the 959% othanol mother liquor from the recrystallization step in the nitration of bromobenzene in a waste battie for halogented wastes while the same solvent used for the recrystallization step in the nitration of methyl benzoate is disposed of in a non-halogenated waste bot. Explain this apparent contradiction, Beciiye Bnerd whhar Viner usel fr ritahow af wwdligt Lentadhe prrcbtes « proilece Gh Wer wo Waitin aaitlr Gta dispar ef in o ron bobegenbel oote lttle Whereas, ace Ptidack from WAtGWan 4 Wamdgeatine — Gribais \elagen Awdk (5 Lstomiag., 3, What is the ole of the AICI; and FeBrs catalysis used in the procedures for Friedel-Craits alkylation and aromatic halogenation reactions described in this expeciment? AIC, : Gace Chlaine is very Tein, Ny Denese OY fats a ave Vobsniaw don RBiys it fs very Teactin vith beaten Fy mad forms r a ve Voloniun (On. WA ptassium trom nd not semen brain ede ogee fr reine in the bromation experiments? \ % ile s { Vy doyee es ve Cause bromine Coudes “Severe baits . Therefore , prbaasiun, a ame, is use “ey tbe Soule st bowie We Wyominsin hich is godmad win Tha, Terchinn- Copyright © Houghvow Min Company. All sights reserved. 161reve Diusclisbl lL, Gaal ce Section _O%. Lab Insnctor_S1. Jiwech Date_ 9-11. gout LAB REPORT EXPERIMENT 11 Electrophilic Aromatic Substitution PART A, ELECTROPHILIC AROMATIC SUBSTITUTION: DIRECTING EFFECTS Nitration Molecular Weight Militers Grams Moles Boe Wg FEW GPR Bromobenzene/ ret + E55] Tan eels : ; et) (circle) 136 fg A nol 2G 4 0.015 HINO; (gp. gr. ~ 1.42) C5 nd Biomol 4.26 4 0-068 180, (op. gr.— 1.84) 13 fe _3 mb SHIg 05S The compound that limits the yieldis__ Meth ben anecto. Theoretical yield of product: _ 0 0136 moi _. Qs B24) —— = Actual yk: _Q.42 (Get _g Percentage yield: ___% Observed melting point of product:_G@— Fa °C Name of product ce Table 11. 1: te thepl— r= ts ben onthe —__ Smucmect product “F0~e=o Must = 181 9/9 Friedel-Crafts Alkylation 0, Molecular Weight Militers Grams Moles Reagent tert Butyl chloride . Phenol eet al AICls “The compound that limits the yield is ‘Theovetical yield ofproduct___ mot CCopsrieht © Houphion Mittin Company. All gh reserved 163Experiment 11 Report Sheet ‘Actual yield g Percentage yiekl: ‘Observed melting point of product: x Name of product (see Table 11.1) Structure of product Questions 1, Based on your experimental resulis and those of your classmates, indicate whether cach of the following substituents is an 0 p-director or an m-director. NS oo, * HO -N=0 4 HOS Seo ae, 4 OSH me a 2, Weitean equation for the mechanism ofthe nitration (or alkylation) of your assigned compound. Inclugeing oC ‘your mechanism the formation of the electrophite. Sac 0G eee 9, \—-0CHy eo, ey HNO, *. one ee ( See ow 3. For your assigned compound (bromobenzene, methyl benzoate, or phenol), draw the intermediate arenium 9¢ for nitration (or alkylatio ‘met an - 08 le oe TT pg vet ara HH, ot —OH subs z a e—- i—> No No, OL - not ble. 4, Use the structures in your answer to Question 3 to explain the observed directing effect (see Question 1) of the substiuent in your compound. ie O=Ci och, 12, St r Nop + NI, es ey No, Mthorsic wil is a aides ging and mato he avomnhie Vy Lom octine amd op hivecteel los CCopyipht © Houston Min Company. Al ight reservedExperiment 11 Report Sheot 5. Answer Questions 5 end for one ofthe two compounds not assigned o you that hes the opposite directing Boon es ake ihe ving los give Pemmer ais «a cata ome * Se iF 15 am op diverted. 6. Examine the o,p-directing substituent(s) in this experiment (@) What structural feature favors o,p-substitution? Te Subtttheat Sump Comedbed| 4. the benrere rig must Corbin a Lae pie 4 ebchins,. (b) Which 0,p-directors listed on page 150 have this structural feature? 0- Brame nitobenrtene 7. Examine the m-directing substituent(s) inthis experiment. (@) What structural feature favors m-substitution’ Te subshhuect grap Shall be cithelrasaing te ptedaw patil wwe Oita om tif So mde ill de me (©) Which medirecrrs listed on page 150 have this structural feature? i CW, sm wo. -c~ 8. Basedon your analysis, predict whethe: each of the following groups will be o,p~ or n-diectors in ‘electrophilic aromatic substitution reactions. =8CHy Yh divertor —N==0 — madiceoly 9 i] oO poe meee “on traolincl o 9, Inthe case of op-ditectors, two regioisomers can be formed. Write the siruetures ofthe two possible products for one of the o,p-directing compounds in this experiment. What factor favors formation of the bserved regivisomer? bs $7 ee NANO Wo, aX i ° ° WS%y aS Noy Copyright © Heughton Miflin Company. Allright reserved 165Experiment 11 Report Sheet PART B. ELECTROPHILIC AROMATIC SUBSTITUTION ACTIVATING EFFECTS Molecular Weight Milliters, Grams Moles Reagent Acetanilide/ Aniline/anisole (circle) KBrO; 480% HBr (9. gr.= 1.49) aes ie ae (6p. gr.~ 1.05) ‘The compound that limits the yield is* Theoretical yield of prodvet: mol 8 Actual yield g Percentage yield Observed melting point of product: Name of product (see Table 11.2): Structure of product Questions 1, Based on your observed product, write « balanced reaction equation for the bromination of your assigned. compound. "To determine this, write a halarced reaction equation forthe formation ofthe product you abserve for your assigned compound, See Question I 166 CCopyriatt © Houghton Mittin Company. Allright reserved,pee BhnclenDldL Babs seetog of Lab introctor Des dnsch Dae__O8> Wo 9nsf PRELABEXERCISE — EXPERIMENT 12 Stereoisomerism: Principles Illustrated with Molecular Models, Computer Modeling and Experiments Wht is optical actvty? Tt 6s the ability te ret a plone wor chiral mbccnbs onl hen they an, active. zs Othen Soca stern. warner fhe, plive viet maT (cds ot . tats ‘What is: coors light? (Hint: Refer to your course textbook) Tt sa strom 4 Nght thab poses Aiea), Pe ge ansh allows ome dMeawn te Ras ae me oth polar ation canstert pow 3, Detecting the odor of chemicals by sniffing chemicals is nota safe practice in an organic chemistry lab, Yer, you are advised to sniff (S)-carvone and ()-carvone in this experiment to detect their odors. Why is it safe to carefully sniff these compounds to detect their odors? Grouse tise cwikin corm ih & ~ nxtund protact ancl sniffiig 6 soft. Als, Very Small cunt ot ef gets tase g_Dthig whic jy maligibie. 4, Spevific rotation of « chiral compound is a physical property of that compound whereas observed rotation ‘snot. Explain, Te observed vob a Semple clifon m Be Ligh pg i Sig Bos ah, Dee one blak: dard thie [= ay t be eas TKanfne, Sptesfic, saben oMfadvesk yf conveg th, oleae ttt. Copyright © Howpiton Min Company. All sights reserved 187vane Dhclndlli, dashed Section_O3, Lab Instotor_cOT-_Swracel Date_OR. \y Genk LAB REPORT EXPERIMENT 12 Stereoisomerism: Principles Illustrated with Molecular Models, Computer Modeling and Experiments PART A. PRINCIPLES ILLUSTRATED WITH MODELS A Stereogenie Center e 1 glo Neue of c 2 in 4 _Summaly 3 el on a :) romobutane chy a tc. a. Ce hog hw 1.3-dibromobutane a 1 } ics & eeu Won ed : ee re Bahia S.aromoditane © yews 2 hee AL u e es wt Le, ae 44 8 4 Re a Sr WOW Br Copyright © Houghton Mifflin Company All eighie reserve. 189Eiapodtied (2: —toport Slice Chirality and Enantiomers o sek ah be M t 2. Thy am _tileshe A males. aac 3. Jee i 14 ae — The oe dome, — a ate * 6 Diastereomers and Meso Forms 1s ee a u Coren, Beck sud Vole sa Bro subst gime d Yash atin. : Pee Yellen & ges SE =< ee | Jon {thor ates rf 27. tA elbow 28. 2 ee ola, tt ig Put of oe of he Geog (on & 190 (Copyright © Houshton Mitin Company. All rights reservedDa end a : “The R$ Convention 2 aM mba etn Bereapate Cote 3. dy Chorin, mothy ydbeagis om eff! an, goose Chott ecsorsentse tiers eM hanger cso a Ey h >Methyt ” al Cie Sy? ae 38 Fateny Connfrr Clochesisa anata = cof gurl 40 i = catia ae t ra oe : 43, vi age eee Osis je pena whe a. eave EB Copyright © Houghton Mifis Company Alright sree, ee. Experiment 12 Report SheetExperiment 12 Report Sheet PART B, PRINCIPLES ILLUSTRATED WITH COMPUTER MODELS A Stereogenic Center ie eee 2, 3 4, ne 5 6 L-bromobutane 2-dromoburane 1,2-dibromobutane 1 3-dibromobutane 1,4-dibromobutane 23-dibcomobutane (Chirality and Enantiomers 192 Copyright© Houghton Miffin Company. ll ight reserveda ma Name Phudnd ltd Bothie’ Section _02. Lab instructor_ Dy. teal Date_15* foot PRELABEXERCISE — EXPERIMENT 13 Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions 1, Inthe separation of butyl chloride from the reaction mixture, what is the purpose ofthe following wash th Yin. a Goldwaes Ay tule Stavtin 4 il, fe grodach bach Uptime 6 sodumbiontonts: 75 Neubtabine a vernal ceed c. Water: Sy peanane Water ch Sanpete ah ay Wet CO 2, Inthe separation of n-butyl chloride from the reaction mixture, what isthe purpose of the following washes? 8 Concentrated sulfuric acid: 75° Pema. n-butyl aleshol- b Water: 75° Pears. Imperiher (oda aot chcota) Sodium hydroxide fr remot of frases of Ny Soy 3. The addition of anhydrous calcium chloride to the crude product obtained from the separation procedure ‘often results in the product becoming clear (transparent). What causes this clearing? Removed of Hrateo fF elecbel cud factor From the ‘ Golding Couns op Secon. h. ( are Oy Dene coi = 2 primary halide, readily forms a precipitate when treated wih 2% ethanolic silver ie Een Bem the benry hic Carbreahion Famed os sill Wun Nie ee - fase by he agin oad), Therefore, Gb tenths GH ethand Peis cae ees Copyright © Houghton Mifhis Conary. Al rights reserve, 209Name oh alint, Oe L. Ke. ahuvy Section_O2. Lab instructor_ Dr. fy al Dare_{5'- fl. Lov’ Lege LAB REPORT EXPERIMENT 13 Gee Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions PART A. PREPARATION OF ALKYL HALIDES FROM ALCOHOLS, Preparation of Butyl Chbride (an Sy1 Reaction) Reactant Molecular Weight Grams Moles Butyl aleohel PE 54 2-067 2 Hydrochloric acid BE4E 2-263 ‘The compound that limits the yield is bx beth alcssl rec yer concn ae eS Sie Beret = sey inlet AEB rennp yall cre Ulli Pesferna e Tp nese EG Raton res Mecaie Wee en vis seat ee slain es cet) 48% HBr (micro) sue i ‘The compound that limits the yield is ‘Theoretical yield of n-butyl chloride: ‘mol ‘Actual yield: eee Percentage yield: _______% (Copyright Houghion Mifflin Company. All ighs reserved a A vehiExperiment 13 Report Sheet Question 1. Explain why more elimination occurs in competition with substitution in the preparation of rbutyl chloride than in the preparation of n-butyl bromide. Gece in pmpowtion ot t= bath chloride SH, mechonirn. one. Fiat te athotin * is Prk whan deter prot to Ae hycln chlo. cork vat a9 bed~ mck Rewivey ptm fina fue Webi) Glin dn gee om olen On He ether wel ne bufybamite goer tnlie "Sn? ruchoming re ne aio cy Formed GK Ns ge feelin Werbre Wes Waterons yet n-bed) ioe t-biby@ Woah edoulson + wow@ oo. > ® wet e ne v =O AON Mw MW. Rea wy a> » \ So % tO) 5 ees Mog eas Lc, 5 Oe % v as * O& W-bebd Sronibe « at w Ry Cw. i SSDS A Map a BEAN 212 CCopyisht © Houghton Min Company, Al rights reserved.Experiment 13 Report Sheet PARTS B AND C. STRUCTURE AND REACTIVITY OF ALKYL HALIDES. Reactivity of Halides Toward Silver Nitrate and Sodium Iodide ‘Time for Precipitate R Group in RX “Structure: ‘Ag’ in Fthanol Tin Acetone Ck ( \ apuyi 2-tWardrbon A * 3 tye’) A 2-Methyl-2-propyl A ea: 3, 4 (den Aly aly chlyig LeBuy) Orbit AV > reeks! > a-chlew 5 tockln 5 cCWenbe 2. Give an explanation forthe order of reactivity observed forthe three saturated alkyl halides with Ag” Resdruchy A ollagh Witkes bas me Ae ably fin Awe mat selic Gale Chon: 3. Explain the unusual position of ally! chloride in view of the fact that it is a primary halide. Myke ts conjeg bet Merk wre ARC We pin die 5 Soe Sara: age Ga ae WE went Raina! Shien oh Fern Aton A Vere Wyo gy Yew reachvi e ty 4 aerated oe Drone Red F ipecetone 2h Wyl > Len allen > det = > Bevde fas ah (Copyrgtt © Houghton Mitin Company. Al rights esecved. 213Experiment 13 Report Sheet 6. 9. 214 OT ee Te TNs ok nh Sel Nhe yh rec Gilad yy SAGE Whshs Big ade Aact Sie: Explain the position of allyl bromide and benzyl bromide in thi: co Aye bide his dale Unk cA WS, AKAN A. Loo Ulnerens, henry chlande vod nd anck Becta 4 99> Megbridh tation: Account for the behavior of bromobenzene toward I. Bertne is sgh Wigbildlital wed wah Wun Veh iryy onkig Anwhon, Uk ill wk Reade IO 6 Why must the acetone be anhydrous and: mama dry for the test with sodium iodide? We otder 4, preted NACL — Crone Sisduhsy Miso if acute ci ndf antydins chem adled to Selim fadide it oil fin Pree ed oe de'e went this, Copysight © Houghton Mifin Company. All sights reservedhi > Y So AMERICAN University 0 SHARJAH ga taiass COLLEGE OF ARTS AND SCIENCES DEPARTMENT OF CHEMISTRY ORGANIC CHEMISTRY LABORATORY - I (CHM - 217) Thin Layer Chromatography NAME: Qhudicblal beshie ) WH: 417401Data and Calculations The behavior of a specific compound in a specific chromatographic system is, frequently described by the Re value, This number is the ratio of the distance traveled by the compound to the distance traveled by the solvent, Distanceink compound traveled Re Distance solvent traveled Developing solvent: __WieWwexsel - Color of in Bue Codes E Ink Spor) Spor) Spots) Distance (Solvent Front) | @,5 cm \ \ Xo Distance (Spot) LF \ \ - —_ Re] 0. 615 ea \ R Distance Solvent Front) | 6.5 cm, m1 oly, Distance Spot) LF in \ otis” || - ;. Disenee Gobet Fond |G 5 og Lah |X Distance (Spot) 5G tm Re} 0. 8615 Xi Distance (Spot) LF cm . o Shik Raha 65 com % Cones Gadus ion . a x, is the Sime 2g Fu. unhvenn senple &) Hoax : TAY a ciley cams ftom Joi. 2Questions: 1. Why it is necessary to elute thin layer plates inside a sealed container? win otlar te gre eumparctin A sndbans. Te Weve a Sauce envionment deal wdkur in arder th bee Goi New ten) A cangonds oo chamchgrphy gehe 2. Arrange the following solvents in order of increasing polarity: CHCh, CHOH, 1:0, CC, CHyCO,CHCHs, CH;CO:H CoH > Wo > CHOW POO CANE Agcl, > Cy highest polarity lowest polarity 3. What is meant by the term R:? RA RC a Gn) ie te fg smovernet As Compared wih noped a the thYR narmah fh Ae chek. 4, Should the sample spotting on a TLC plate be done above or below the level of the eluting solvent in the chromatographic chamber? Why? a Semple spitig, on A TE ge dah be abne he ~ 4 Cae Are dhitiog stk Becante te dewsal conpands hin Ne, amit will dissdve im the sdvert wl ond Ub Gai ch gp upwerds On the aes nnd dey he shad the choad Coporls io the ihr. ail ale itech wih the shred sar mck ofeck the play, :5. Indicate whether the Ry value depends on the following: a. The length of the plate. Becwe de Compend and Yer siMech Ware Webde vorensho 4 __cle b. The solvent used. Because he compen aot alse Werad dopedinn on a hats, | % c. The type of the adsorbent used, Du Gag x Me chich “ee pala diaeasa., uy Tay\v _— September 13, 2007 A 3, AMERICAN, EES ofp ANE JAH COLLEGE OF ARTS AND SCIENCES DEPARTMENT OF CHEMISTRY Quiz #1 ID NUMBER FIRST NAME. FAMILY NAME Three test tubes contain white erystalline solids X, Y, and Z cach of which melts at Lae A.50-50 mixture of Y and X melts at 130-139 °C, A mixture of and@yelts at 149-150 °C. In what range would a 50-50 mixture of X and Z probably melt? What can you say about the identities of X, Y, and Z? Rage Se Case wide ah KA Bo 130 13H'c Yee gt CCmpomh Yad & on Wedrad) , What two effects do impurities have on the melting point of an organic compound? a Nk \nwevs “Wee sone hiba gsi oh ue Compenn ah, e b. Branches he indissn git Sane. 3. What is the effect of adding small amount of sand to the sample when determining a melting point? eo: 4. Whats the name and the structure ofthe compound that you will crystallize in today’s experiment? if re, H al a ® heckerilide ork a O iy, WE. TyW,ON ® pm Dibrew wane oop Luck? a Dr. IMAD ABU-YOUSEF Byes M-217 September 20, 2007 AMERICAN U versttyQ7S, Mea barista COLLEGE OF ARTS AND SCIENCES DEPARTMENT OF CHEMISTRY Quiz #2 ID NUMBER FIRST NAME FAMILY NAME 1. Why can we use a water-ethanol mixture but not water-hexane mixture as a recrystallizing solvent? eam. thane! i Shille in arter thertan hexmre YE doo neh olissdlee tn anky AM: Keo tidber and hexane ore not wiscille. = fun 7 2. Assuming the sand and sodium cholride are the main impurities in a sample of crude acetanilide, explain how recrystallization from water would remove each. Sond Gn be Yemeverl ty. Wty ee filet ef He \\, cone Leua ef chy nf lider ip HON Sodtiowa Wlaide loo her or eck wm Xe oo ch ex Ns allt goa ee anh Cen Ye romana Tay WS Bthhion maa e edie; EK the WK 3. What is the title of today’s experiment? Diki\hevon + Seach, oe perificahion of \ouids VL GOOD LUCK ° Dr. Imad Abu-Yousef—~ CHM-217 September 27, 2007 » ORE g Mimi a ) COLLEGE OF ARTS AND SCIENCES DEPARTMENT OF CHEMISTRY Quiz #3 Dbudvsbulebn 1D NUMBER FIRST NAME FAMILY NAME 1. Briefly account (2-3 sentences) for the following: a. A fluted filter paper is used in the gravity filtration. In erelen A Uatreice Be sufi aren over hick the stim to be flere is syteacd nach geligy Ha SWrembe quel by RAR OMe ReQue b. It is important to use a boiling stone when a liquid is boiled. Jes, decruse then hedtiry = Veutd a ghensmenn cldach fs, due te Siger hobo \s Cre. Ae ath die 4h wel Me heb ol wk be disWhuteck eve Aainghoud ae ttn. 2. Draw the structure of benzoic acid. a a \ x Loan ota CW GOOD LUCK? Dr. IMAD ABU-YOUSEFCHM-217 October 04, 2007 AMERICAN a) UNI RsITy O, /Suarjan EA aa 3E OF ARTS AND SCIENCI CHEMISTRY DEPARTMENT Quizax ‘t Qhudirab tts. _ Basic 1D NUMBER FIRST NAME. FAMILY NAME 1. Complete the following flow diagram for this extraction experiment, NH; cl co, Oo, ‘organic layer 40h NaOH | 10% Neon a Cy aqueousiayer organic layer wt coop Luck® Dr. IMAD ABU-YOUSEFi oe 217 November 01, 2007 (0 } AMERICAN, U Ofs | Ga ES Gf ons y COLLEGE OF ARTS AND SCIENCES DEPARTMENT OF CHEMISTRY Quiz #5 asia 1D NUMBER FIRST NAME, FAMILY NAME, 1. Describe with equations a simple chemical test that you could use to distinguish between cyclotixene and cyclohexane. What the visible result would be? ® Cowine West: ofclhetene » tad-bremn Gla of bromioe deepen c gpclohedone 2 SR. tek-binm cher A ttomnn dil ot ae = sehr Yee Re Cyclhenee (dle? Od been) Golawlore) oe CO &, Fig ay, WR. Cycbhexene 2. What is the purpose of today’s experiment? Gs— trom Comers FF ekeves 5 Tos Wey inpabnt t kon (frat ot) whdley 9 npened Gm erite as ca tape rut, Beane tn Het Om tee Pep erties 1 - Arrange the above halides in order of decreasing reactivity toward AgNO (Sy1) M+ DT > 2. Consider the following alkyl halides: n-Butyl Chloride, -Butyl Bromide, n-Butyl Iodide I ats ur Amrange the above halides in order of decreasing reactivity toward Nal in acetone (Sy2) to> @ > aX tN GOOD LucK® Dr. IMAD ABU-YOUSEF