Laboratory Worshees Experiment 6: Sy2 and E2 Mechanisms Flow Diagram Draw flow diagram forthe experimental procedure ofthe experiment. Chemisty 2 Laboratory Mal periment 6 oi iets EDcot vr) Foe diagram - 5 Smb 2 -branbeph| © Bont Fok ((ornl-buk er (Bane Bu @ Disil @ 105% | at 4 Iris Suomikoratory Worksheets Experiment 6 Pre-Lab Questions: 4, Why sit important to mix naphthol with sodium hydroxide before adding 1-iodobutane? Red e .alliertiny,... nse 2, Why is it important to fully precipitate the product in an ice bath prior to isolation by suction fitration? Why do you rinse your product with ice-cold water rather than room temperature water? ARC palack is. sede. slic eles ge ep eon, eal dispel, stig he schon talent sn. ec... dais. de hee £2.28. sel, diysspee pel fam 3, Whats the boiling point of 2-heptene? xe ear eter) “ 4 Give the fl chemical equation forthe rescton in art2, Se sureto clue any si products, Use structural omulae hte -o es ° ae. OD 4B AAA od) oy 2 ew 5. Chemwstch practice question; Use the Chemical Rik Assessment Sheet to find what precautions youneedt take when handing hyérbromc al Whatisthe Chemwatehhatard tating forthe body contact of Hr sotions? Peecnatitt weer PPE he x0. coabect eat Chessy 2 aboratory Maru 2018ere wae Experiment 6 Results 4. _ Synthesis ofan ether from a naphthalene alcohol Ah. O3..g (Molarmass «144.17 mo PM 110 ceed (Puch seetr ot. 5.D. ug [Molar mass = 20028 g mot} mass of naphthol use Moles of2-naphthol used Theoretical mass: Mass of2-butoxynaphthalene: Percentage veld DE — (Report toa whole number) _Sooyour oes yale) 2 bb Tcof qiuld a Wy ae (2b - eroet at RO ne? a(rmeds) + A(t-berynatlee) Thaehal ner | 2 0: 29% Ce-mpbal baits)", F,Mevo 2200-29 {iWqy = 25% ‘Thin Layer Chromatography Photograph your developed TLC plate, entity and submit this with your report. showing all measurements, Label all components with their (eps indeed ab fa ck of ecunend) fs 2-nspisl At a Be Co-opeh Arale@ t-bem Dvdues @ 26 L Ahem ; Sepetethg 7 dees tie Oe as ep Me Fm @ tbl Mew Evil he istry 2 laboretary Manual 1 a0l8artery erst Eperinent 6 Jate, comment on whether the reaction had gone to completion, (hint: how many resent in the reaction mixture? Has al of the limiting reagent been consumed?) he filly cope eof THE lee voate Mabon rth ies Tht nd by di, gem Bee ets tt kd Tb. PEE hla deli effe. Fekete she. AML tet A We, pee, s ee kesee EG vale ge te reache wiht nitinol TLE pi Using your TCP ‘components are “ie eli la Bec bi which i ste by ven thse observations how might the percentage yd be maxmisedn future experiments? Se ne eeideedts) RY Tiled alec MeO Zettel. ence. tectsh, aoh.jte Healy of Zemphbel to qertipte ia te rod 45 fe pipet jon (nncheoprile) wilt intro aide Ce yon) 2, _ Synthesis of alkenes from an alkyl halide Wat was the limiting reagent inthis reaction? SE cee Cbsened ction temperature: Sot Mass cf iting reagent sed Sieg (2 ee) Moles of iting reagent used: pOO82h eral Theoretical mass: (peek?) 8 as ofheptene: .-g[Molarmass=36.19 gma Percentage vied: ee UH % (Report toa whole number) ‘Show your calculations: Te well fin tt t Phecebel mine of proliact me Mn Density = 0 sallin relat) # 0.035L nel LIND mt As. Sat t Ptheples) © 46 1 Sbynel (5.5) (11423) = m0 1 5s (dep) = 0.03 8t= AES Fbliy 4 ay 44e a sine Sites 2 3.459 174-ginl = 9.0364nd a. 2 tabertoy Marval soleapocatry Worksheets Experiment 6 Post-Lab Questions 1. Ethanol isnot normally used as a solvent for x2 mechanisms, Why? (Hint: Ethanol is an H-Bond donor and acceptor!) Can you also predict an undesirable side reaction that might occur using ‘ethanol a a sohent that would not occur if diethylether were used asthe solvent? on Set ethanol ethyether Cb teh alan Rel bcag.cOEis, GONEN, ih sang bee ale. 2... H chee be rysdeoehle®...rerol tin).e..ale72, eebiee abbattien cn inst woth ta elfen ly. ‘hei 2hleg n...peli.ptOl..2tletc a sdlush eeorot 1 Hct alliage. tae albehes... ua batnbi BE. 2, What would happen if inthis experiment, you used 2-‘odo-2-methylpropane as the electropile in Patt 1? Draw a mechanism and give the mechanistic descriptor (name of the mechanism). coe ter (C HP > oe Hr Asie -bas...,eattion, 13. The reaction of DBU with 2-bromoheptane gives two alkene products, what are they? Which of these would you expect to be the major product? Explain your answer. Weg Ante, Ae ual E) chant Batten dbs Detatnnetlda M fe tan... prada. REAAS..i2. an Ade raloe.5thititadt a. ablaetensit ia reali. fasacdhey 18... RDM EHS. ales christy 2 Laboratory Maru selsporto Worksheets Experiment jon of bases very important in elimination reactions. Why inthis case was DBU chosen over 4, Select Give an example of an undesirable reaction that might take something Ike sodium hydroxide? place if sodium hydroxide was chosen asa base. op wee. ce Hy, fae. £4etacp yreaal Ha. sid. Ae. coeste Ae 6. nek hate eli lbs. ft pills alae ah DBv.. dake. Al. 8% diay steric shield {for structural determination, in proton NMR diferent hydrogen chemical environments are observed. This is reflected in the diferent cheval shits ofthe hydrogens. On the structure (shown below), indicat (2) The tts) siumber of diferent hydrogen environments (b) the relative intensity of each signal we would tapect in the 'H NMR spectrum, and (c) the mutipity we would expect from each hydrogen environment due to simple 3-bond coupling (name of the signal) 55. Proton ('H) NMR spectroscopy isa useful method spectroscopy, Environment Integration (insensita™) A 2 Tripler 8 G Tyee c ete Tepe Pt D yl Donwset c z “egret Dablet . z Tot G BL Top X 3 Sendepiet Tepe a auctor 4 otal = fH eoviontmets cot Chemise 2 aberator Manualcanaraon Woke: Expeiment toxynaphthalene is provided. Identity the chemical regions (a), (b) ‘the 3H NMR spectrum of 2-ut re bvlabelngthe structure of 2-butonnepthalene below. ey xl ourasignent° {a), (b) and (c} using: tatetin Cases) i) Sspliting ? (ii) Chemical shift (#here i> ¥0 4p Ca Railetial ar. wn cts nth {2 a inbie, ale Beied: (oss ay Teale tit dat kat herr ettlpbiek. cabbest bee Bnd nn QL foUber!..aucte. rth... én. ed Gebmeg ts aptly. beatin ote LEC aul fhacenal. si ele t gletems ti A litany pbb Bose ‘pha ab wf fi ° x ts wR coast cool ( yer Cherise labortry Mana yorortry Wortsbeets Marking Scheme experiment 6 Question R Question? i Question3 a Question 4 ‘ Questions A TOTAL ho Flow diagram R Reais Part 1: Sample (appearance/lbel/vield) B Yield calelation correct i. es. ee) R TiC plate ond Rt values B Has uncompleted? R How to masse yiels? A art 2: Sample eppearance/label/ield) B ‘Yield calelation coroct ig gs. te) R oral hs Post iab Questions ‘veston A ‘Question? Bl Questions R Question ¢ a Questions “ Question 6 hs Torat ps ‘oeker check 7 Formatting B Sienificant Figures nl aoe 7 aot Chest 2 Laboratory Maral