Organic Chemistry II
Organic Chemistry II CHEM 2320
Weber State University
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This 14 page Class Notes was uploaded by Alfonso Reynolds on Wednesday October 28, 2015. The Class Notes belongs to CHEM 2320 at Weber State University taught by Don Davies in Fall. Since its upload, it has received 39 views. For similar materials see /class/230797/chem-2320-weber-state-university in Chemistry at Weber State University.
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Date Created: 10/28/15
Pagelers Nomenclature 1 Pmmde an example ofeach of the followmg mammal gangs 6 pom amine oxide hemiacetal nitmsnamine 2 Pmmde a common name fox each the followmg slmclmes 4 pmms AH Idennry the eenea systemmmname fox each the followmg smuclmes 6 9m N HackKV CHJ cm 3 pmms HO CH3 rm Mk b lrformylr pheny1e1haml k m d 227hydmxyphenylpmpanal ezehydmxyezepheny1pmpana1 WNW M r b Srdimethylammoylmethylrzrpemanone M a m d 3NNemme1hymeexeelepemanamme e Aeexesmmemmmhylel rpemanarmne Page 2 of 6 11 Theory 1 Natural products that contain nitrogen are called 2 points 2 If a basic substance has a pr of 15 the pKa of its conjugate acid is 2 points 3 Circle all of the following carbonyl compounds that could be formed from the 13 dithiane of formaldehyde 3 points a benzophenone b MVK c acetaldehyde d lphenyl 2propanone 4 Circle all of the following reagents that will yield a hydrazone when reacted with an aldehyde or ketone 3 points a NH20H b NHzNHPh c NHzNHCONH2 d CH3NH2 5 Given a mixture of benzoic acid benzylamine and naphthalene provide a scheme similar to the one in your text p847 showing how benzylamine can be separated from the other two components by an extraction method 5 points 6 Which sul lr functional group is contained in all sulfa drugs 2 points a sulfoxide b sulfone c disulfide d sulfonamide e thiol 7 Which compound would react most rapidly with sodium methoxide and heat 2 points a chlorobenzene b 2 L1 i pyridine c 3 L1 i pyridine d 2 L1 A whole PageS of a 8 Cncle all ofthe following ammes that can be Iesolved mm pure enmuomxs a poms HzC 09 10 Ab K Wlnch sequence mks me following caxbonyl geups m older ofmcxeasmg mommy Leasueamve hsted mg 3 poms H30 02 1 0 we H1 01723 11027371 0 32 d 3271 e23 017372 10 Tnphenylphosphme 1s txadmonallyused as me swung mammal fox Wang 1 Co ldmb of ole nanon xeae mus 1phosphme be used m place mphenylphosphmev Justify your answex 3 poms below 3 pom vT vlj a NaBHd bL1AllltL c DIBAL d H 1 d e FCC PageA of a 111 Reac nns Pmdml the pmdncls enhe followmg mo reachons a pom 1 paravunmuehwg ca sto heal 1 ca CH 2 DMS 3 Nsz KOH heat Complete each synthem below by f hng m the rmssmg reagents 13 pmms I ESgE lt1 We K Hac N CHu 0 What reagents are necessary convert phthahrmde m allyl ammev a pmnls sm eummauun 3 ANHZ Page 5 of 5 IV Mechanisms Usmg eenea anew pushing pmmde a dela ed meehamsm fax the msmen shown below Include all mlennedmle structures and formal charges 8 paints HCN cat Neon HO CN XH heat V Synthesis structures 13 palms socx2 2 LOH YNH Page 5 of 5 2 F111 m the mssmg reagents that are needed for the followmg tmnsfemanen 4 pmnls ML v1 Extra Credit 5 pmnls posslble 1 Stamng mth phenylacelylene show how the Drarmnoalcohol pmduet may be formed 1 2 H 3 t H ct We CH HH2 t 5 You xecewed pmnls out of mu pmnls posslble Fox an update ofymn overall lecture gade go to h pcomseswebexedu Page 1 of 8 Theory 1 pmnls a mole llghl b lnfmled xadlallon Cuole all ofth fonnulas that are equal lo frequency 3 palms a hv b oA c h2 d hcA e y h2ul3a Whlch ofthe bonds below would absorb at the hlghesl frequency ln 12R specimscopy7 3 now a crc b 00 0 OF d OH 9 ON De ne speouosoopy 2 pmnls Whal does an odd value fax a molecular lon peak lndlcale7 2 pmnls In thls lype ofNMR speouosoopy the magneuo eld 15 held oonslanl whlle the equencyls gadually mueased 3 pmnls In a mass speouum whal value would correspond lo the slmolme shown below7 3 11011115 020 9 H300 0 A In H NMR speclmscopy how can an OH 01 NH peak be poslllvelyldenh ed7 2 pmnls Pagez of x 9 Ifa quartet havang a eenphng constant of 8 Hz has a wadth of 110th of ppm an a H NMR speetnarn what as the total frequency efthe NMR that paedneed the spectmrn 3 11011115 11221114 H amp 11 amt 11 Shown below as a combmahon of alpha and beta nuclear spans paedneed fmm neagabonng pmtons that contnbntes to a splattang pattem of a gven pmton t t peants up 4 pmnls W 12 What We facloxs asseeaated wath the BC naae1eaas de1ayed the devehapment ofBC NMR spectroscopy 4 11011115 Page 3 of 8 II Spectra interpretation and prediction 1 Predict the R absorption frequencies of the following functional groups within 10 cm39l 4 points a nitrile CN b carbonyl of an ester 2 Compound I has amolecular formula of C7H1 40 In a 13C NMR spectrum compound I gave 5 peaks and a 1H NMR spectrum showed 3 peaks a singlet a triplet and a quartet Provide a structure for compound I 4 points 3 Based on the following 1H NMR and mass spectrum provide a possible structure for unknown compound II Justify your answer by correlating key peaks or fragments in the spectra with your structure 8 points MS Nm5157 Relative Intensity 1mmvale Page 4 of 8 4 Elucidate the structure of compound III C7H1602 shown in the 1H NMR below Justify your answer by correlating your structure with the spectrum 6 points 5 Compound IV having a molecular formula of C HloOz gave the IR and 13C NMR spectra below The off resonance splitting is indicated above each peak in the 13C NMR spectrum Identify the structure of compound IV and justify your answer by correlating your structure with each spectrum 8 points I I Innn am I I I m snnn ma I I I I I I I 100 80 50 4O 20 0 ppm l l 39 l 39 l 20 180 160 140 120 EDSuAIEH Page 5 of 8 6 Label the different 1H environments in the structure below a b c Then complete the table for each different type of proton Note there may be fewer than 7 different proton environments 12 points H H W H H ZC C N39C ire H H n I environments I a I b I c I d I e I f I g I I spin spin splitting I I I I I I I I The labels on two containers of organic substances were missing Elemental analysis revealed they were both isomers of C4H100 and each gave 4 peaks in there13C NMR spectra Identify the structures of each substance based on the follow1ng mass spectra 6 p01nts 100 80 3 392 B 60 E m 2 5 407 m K 20 l l l I i til i l t l l l l l l l l l l l l l 1 15 20 25 30 35 40 45 50 55 60 65 70 75 mz 100 WW1 80 z 399 g 60 S w 2 4 2 4r m K 20 M illil illl W W W W H a W H a 1 l 2 25 30 3 40 45 50 55 60 55 70 7S Page 6 of 8 Unknown compound V was found to have a molecular formula of CMHW and gave the following H NMR spectrum Identify unknown V and justify your answer by correlating each proton with each peak 6 points Page 7 of 8 9 Use the following 1H and 13C NMR to predict the structure for compound VI which has a molecular formula of C7H1203 Justify your answer by correlating your structure with each spectra 7 points 1 l 1 l l I 200 180 160 140 120 100 80 60 40 20 0 Cusrnar4zs ppm Page 8 of 8 111 Extra Credit 5 points 1 Unknown VII CWHM gave the following 13C NMR spectrum with the off resonance splitting indicated above each peak ldentifythe unknown compound and justify your answer l l l l l l l l l l 2 O 180 160 140 120 100 80 60 4O 20 O was ppm You received points out of 100 points possible To check your overall performance in lecture see htpdvistaweberedu
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