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Organic Chemistry I

by: Columbus Kerluke

Organic Chemistry I CHEM 2010

Columbus Kerluke
GPA 3.83

Yu-Lin Jiang

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Yu-Lin Jiang
Class Notes
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This 59 page Class Notes was uploaded by Columbus Kerluke on Sunday October 11, 2015. The Class Notes belongs to CHEM 2010 at East Tennessee State University taught by Yu-Lin Jiang in Fall. Since its upload, it has received 50 views. For similar materials see /class/221419/chem-2010-east-tennessee-state-university in Chemistry at East Tennessee State University.


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Date Created: 10/11/15
12 Structure Determination Mass Spectrometry and Infrared Spectroscopy Based on McMurry s OrganC Chemisty 6th edition Determining the Structure of an Organic Compound I The analysis of the outcome of a V reaction requires that we know quotthe full structure of the products as well as the reactants In the 19th and early 20th centuries structures were determined by synthesis and chemical degradation that related compounds to each other Determining the Structure of an Organic Compound Physical methods now permit structures to be determined directly We will examine mass spectrometry MS this chapter infrared IR spectroscopy this chapter nuclear magnetic resonance spectroscopy NMR Chapter 13 ultravioletvisible spectroscopy VIS Chapter 14 121 Mass Spectrometry MS Sample vaporized and bombarded by energetic electrons that remove an electron creating a cationradical Bonds in cation radicals begin to break fragment RH XL RH39 e Cation radical Mass Spectrometer k Magnet m CRT L39Hsplay d 5 Slit h V a 39 f iii 2 Inns de ected according to m 1 2 3 K 11szng Slit 3 electron beam Detec tur Heated lament Sample inlet 2004 ThomsnnJElmoks Cole The Mass Spectrum Plot mass of ions mz Xaxis versus the intensity of the signal corresponding to the number of ions yaXis Tallest peak is base peak 100 Other peaks listed as the of that peak Peak that corresponds to the unfragmented radical cation is parent peak or molecular ion M MS Examples Methane l and Propane Methane produces a parent peak mz 16 and fragments of 15 and 14 See Figure 1212 a CH3 H mz 15 mz 16 CH2 2 H Molecular ion M mz 14 Brooks Cole MS Examples Methane and Propane The Mass Spectrum of propane is more complex Figure 122 b since the molecule can break down in several ways a 100 80 60 Relative abundance 1 pp 1 s mz 16 20 4O 60 80 mz z 100 120 S V H er a 03 O G G D O l l m D Relative abundance 92 lt3 44 l 10 2004 MasaiBroom Cole 20 FIJIE lllll I l l 40 60 80 100 m 120 140 122 Interpreting Mass Spectra fMolecular weight from the mass of the molecular Ion Doublefocusmg instruments provide high resolution exact mass 00001 atomic mass units distinguishing specific atoms Example MW 72 is ambiguous C5le and C4H80 but C5H1 720939 amu exact mass C4H80 720575 amu exac mass Result from fractional mass differences of atoms 160 1599491 12C 120000 1H 100783 10 Other Mass Spectral Features If parent ion not present due to electron bombardment causing breakdown softer methods such as chemical ionization are used Peaks above the molecular weight appear as a result of naturally occurring heavier isotopes in the sample M1 from 13C that is randomly present 123 Interpreting Mass Spectral Fragmentation Patterns The way molecular ions break down can roduce characteristic fragments that help in identification Serves as a fingerprint for comparison With known materials in analysis used in forensics Positive charge goes to fragments that best can stabilize it 22Dimethylpropane MM 72 C5H12 Relative abundance CH El 20414 Thomsnna39Emoks Cola Mass Spectral Fragmentation of Hexane Hexane mz 86 for parent has peaks at mz 71 57 43 29 CchHQCHZCIIZCHZCHB Hexane E CHSCHZCHZCHZCHZCH3F I Z1 CCquotU1 1Lquot it I 222 2 3113 VA CH30H20HZCHZCH2 CH30H20H20H2 CH3CHZCH2 CH3CH2 71 57 29 abundance 10 100 base peak Thomson Brooks Cole Hexane SI ig BID 3 FD t39u 4 OJ 2 41 21 a 391 ln ll llll n n I I iquot I I I I I I I JILD 21 40 60 80 1 00 120 140 6 Thomson Brooks Cole Practice Problem 122 methylcyclohexane or ethylcyclopentane Sample B Mass Spectral Cleavage Reactions of Alcohols Alcohols undergo occleavage at the bond next to the C OH as well as loss of H IOjH to gNeCC amp C OH RCH239 RCH2 Ij OH cleavage I 11 Dehyd at01 CZC Mass Spectral Cleavage of Amines Amines undergo occleavage generating radicals Fragmentation of Ketones and Aldehydes u A CH that is three atoms away leads to an internal transfer of a proton to the CO called the McLa erly rearrangement Carbonyl compounds can also undergo 0L cleavage Fragmentation of Ketones and Aldehydes 030 I l 39 McLafferty CN rearrangement quot C R rooks Thomson B Cole 0 Alh 1 a RCH2 II gt RCH2 i C R cleavage Thomson Brooks 20 125 The Electromagnetic S ectrum Frequency v in Hz 102 1018 1016 1014 1012 101 l I quoty rays X rays 1 39 I Infrared Microwaves Radio waves 1 I 10 12 10quotl 10 8 106 10 4 10quot2 Wavelength A in m f I quot m H Wavelength M in In x Visible xu 380 nm 500 nm 600 nm 700 nm 780 nm 38 x 107 m 78 x 107 m Thomson Brooks Cole Wavelength and Frequency e Wavelength 4 400 nm lt 800 um gt Violet light y 3 3 j u 750 x 1014 5 1 v 375 x 1014 5 1 Q 2004 Thomsunl moks Cole Absorption Spectra Organic compounds exposed to electromagnetic radiation can absorb photons of specific energies wavelengths or frequencies Changing wavelengths to determine which are absorbed and which are transmitted produces an absorption spectrum Energy absorbed is distributed internally in a distinct and reproducible way See Figure 1211 23 Infrared Absorption Spectrum of Ethanol Wavelength hum 80 Transmittance W MJU U 350C IJUUU 2600 2200 200 1800 150039 1MB 12W lU U 800 600 4U Wan39e11u1nber f L39m l 2004 TmmsnnfElmoks Cole 126 Infrared Spectroscopy of Organic Molecules I IR region is lower in photon energy than visible light below red produces heating as with a heat lamp I 25 x 106 m to 25 x 105 m region used by organic chemists for structural analysis I IR energy in a spectrum is usually measured as wavenumber cm1the inverse of wavelength and proportional to frequency I Wavenumbercm391 1tcm I Specific IR absorbed by organic molecule is related to its structure IR region and vicinity 4 Visible N 538139 1 39 Elicmwaws infrared l l l J A 10 5 10quotquot 10quot 10 3 10 cm A 39 25 10quotquot cm A 25 gtlt 10 31mm 2 25 p111 2 25 Hm Iquot i 4000 0111 1 17 i 400 till I Hr H 1 Mint L 9 2004 Thnmsuni moks Bale Infrared Energy Modes IR energy absorption corresponds to specific modes corresponding to combinations of atomic movements such as bending and stretching of bonds between groups of atoms called normal modes Energy is characteristic of the atoms in the group and their bonding Corresponds to molecular vibrations Infrared Energy Modes Symmetric Antisymmetric Inplane Outofplane stretching stretching bending bending Thomsan Brooks Cole 28 127 Interpreting Infrared Spectra Most functional groups absorb at about the same energy and intensity independent of the molecule they are in Characteristic IR absorptions in Table 121 can be used to confirm the existence of the presence of a functional group in a molecule IR spectrum has lower energy region characteristic of molecule as a whole fingerprint region 29 TAB LE 121 ChiW racteristi IR Absnrptinns of Same Fu nttionall Emu p5 Func limml 3mm 1111212 and pusiliun mm fl Intensityr uf ahwrptim Allinmm n my gm up 4 quot H Allienes l 39 r E quot121L Allnmes EK M quot7 l ng halides l lquot1 394 I quot 1 Manholg H H rf r 39I Ammatica 3 a It H E g 3 12 3 11M 1 rm 1 BED 3300 HUD 2260 6130 504 5 If 4510 SKID Sd SEED 1 H5114 15E 303E Medium ta strung Medium Medium St mng hxladi11n1 Strong SI Pang Strung Emmi Strung We a quota mm mm Week ll 1quot a j 1quot 1450516110 Medium 1 Amines f E i 3 3an Medium L39 Iquotxf NEH 133 Medium Carbonyl camp unds 7 r u 4 IBM 1750 Strung Carbuwylin ncicla w Iv 11 ELEM 3 NU Stmngg vex bread Nitriles A If E 7 ELEM22m M rlium Nitm 1201111101de M g 1543 Shung 39Car ibmlir acids atlas aldehydg and ken181 it Trun millmacu Trmamimuxcu 1 CHNCHRWHJ I 7 a 7 T r 39 I 39 39 a LINJU 115011 CM39HJU ZED 1201 2mm IHEH IEit JU MUU 1200 1qu HBO EUO Wm unumbur icm 39 I Wuvulength pm 6 w quot3900 3000 i 9200 204M 3 E500 HBO 1200 IOfl 39W v nurn hpr l t39Tn 1 W uvelenmh mm HvaHgIJC UFI v I HEKJU 1250 2200 ZU JIJ HEN MUD 14W 12039 Wamnumber um 4sz 1501 mun 2004 Thomson BrooksCole Regions of the Infrared Spectrum 40002500 cm391 NH CH OH stretching 33003600 NH OH 3000 C H 25002000 cm391 CEC and C a N stretching 20001500 cm391 double bonds stretching CO 16801750 CC 16401680 cm391 Below 1500 cm391 fingerprint region 33 Regions of the Infrared Spectrum WaveIength Ime 25 3 4L 5 6 7 8 9 10 12 14 16 100 I MI E I I I I I I I I I 3933 80 I I I I NH I I 00 I E 60 5 BEN I I E 0 11 H I I C N I Fingerprint region a In I 030 39 I E 0 H I I 0 0 I 0 I I I I I I 4000 3500 3000 2600 2200 2000 1800 1000 1400 1200 1000 800 Wavenumber four I I Thamson Breaks CoIe Differences in Infrared Absorptions I Molecules vibrate and rotate in normal modes which are combinations of motions relates to force constants Bond stretching dominates higher energy frequency modes Differences in Infrared Absorptions Light objects connected to heavy objects vibrate fastest at higher frequencies CH NH OH For two heavy atoms stronger bond requires more energy higher frequency C E C C E N gt CC CO CN gt CC CO CN Chalogen 128 Infrared Spectra of Hydrocarbons CH CC CC C E C have characteristic peaks 2850 2960 cmquot C C 800 1300 cml 2004 Thomson BrooksCole 37 TILLmImjtumcu Iquot39quotcal iiquot i l HTSH iEIZIKMJ EELIG39 EIFIJD 39lHIIH EMU 1 lUElI 121M VFu39II39uu umbtm 1mm 39 393 2 C HEEL HE rial3H1quot HIM Alkenes 3020 3100 cm 1640 1680 cm 1 910 and 990 cm 890 cmquot1 2004 Thomson BrooksCole 39 1Hexene Trmuu niilmmu I ski391 Wm39 Elanwh I Inn LE El I 5 I5 7 9 U 1393 H W EU 34 131 I 7 I v 7 l V l IV I I I l 39 a i lt 397 I If I m I I i It r lquot39 WVIIII a fl I 4 1quot MIquot quotWan I I II II II 39l I I ll I III I II I I I 1quot f I I I I I l39 l H 39l l 39 J I l iII lull I I I I I I I n I I II quotquot3 i a II II I l w I I I I I I II 1 1 quotU i II ll li LuHLJ l iu lIEI L L 1391 lip I I39 I I I I I I 4WD SEI39J D SKI30 E E EIJE I EMU IHEHZI IEE L I l l l 1W III39WJI39I HEP lm 4C4 raven urn her um quot 1339 2004 Thomson BrooksCole 25 3 4 5 IE 7 E 9 if 12 H l EU 24 1 I l l I I I I I I w quot 39II Fry quotquotquot rquot 39ihquotquotquot sk Ifquot quot3quotquot quotquot39Tquotquot quotL I fquot a u iI 39 39 I H I r 39 39 39 39 II39 39I39 39 5 rm I I I I II E II II Ir I l 4 IL r I I l I I I in I IJ l I I 391 d I H I 3939I I1 I u g y I I III I I I l I FEIT i I J E In I M 1 39 139 39 4 II I 2U J Ll CHEIC12I3IC EI I I I I39IJ if H 39 ll I I i LIJILTILI TLFJU LJ LIELII IIIIIIJ EEUU39 2mm IEUIJ mun 14LII1I 1qu 1mm LIIL39I mu W veumnber 1cm 129 Infrared Spectra of Some Common Functional Groups Spectroscopic behavior of functional groups is discussed in later chapters Brief summaries presented here IR Alcohols Alcohol 7 g 3400 3650 cm 1br0ad intense Thomson A Brooks ole Wavelength lpml f pN Transmittance WM I 1 l D l I 4000 3500 3000 2600 2200 2000 1800 1600 1100 1200 1000 600 Wavcnumbur cm 1 l E 2004 ThomsonEruoks Cole 3300 3500 cm 1 sharp medium intensity 3 Wave eng th 11m 25 3 4 6 7 8 9 10 12 14 16 20 24 I I I I rumm mJ W FWH 11 1quot I f1 A I39 I I II I II I 80 1 1 I 0 IIFINWII 1 WI 57 I JI l II I I I I I J7 II n Iquot U s I I I IIIII 39II 390 I I g 50 IIII I 7 II I WI lily Ir I I I I I I r I U I 391 Ilr lI39lII E 40 39 l wall II39 l 1 H g NH2 lquot Xxx NH2 U U L a 20 III j I 0 XVquot I I I I I I 4000 3500 3000 2600 2200 2000 1000 1600 1400 1200 1000 800 600 400 Waven umber cm 1 IR Aromatic Compounds Weak C H stretch at 3030 cm 1 Weak absorptions 1660 2000 cm 1 range Mediumintensity absorptions 1450 to 1600 cm 1 Aromatic compounds 3030cm391weak 16602000 3111391 weak 1450 1600 cm 1 medium Ix J1r1omson i Brooks Colo Phenylacetylene WaveTength pm I 25 3 4 5 6 7 8 9 10 12 14 16 20 24 100 I I I I I I I I I l l l V m ww m I a W 80 I II Nf 1 L 39 I I I I c 3960 E 40 I CECH II 7 I I I I I I I I l I I mm 3500 IIIIIII 25qu 2200 2000 law 1mm llt1III 12m IIIIIU 5mm EIII In WaxDnumber cm 39 I 2004 Thomnnu moks Cole IR Carbonyl Compounds Strong sharp CO peak 1670 to 1780 cm1 Exact absorption characteristic of type of carbonyl compound 1730 cm 1 in saturated aldehydes 1705 cm1 in aldehydes next to double bond or aromatic ring H O 1730 cmquot1 1705 cm 1 1705 CID 1 Practice problem 127 Wavelength um 25 3 4 5 6 7 8 9 10 12 14 16 20 24 80 3W I I r f W 60 W m WWI 40 r i v I 1U A I 0 I l I I I I I I i I I 4000 55500 3000 2600 2200 2000 1800 1600 1100 1200 1000 800 600 Wavcnumbcr cm I II 2004 Thomna39Emoks Coie Phenylacetaldehyde Phenylacetaldehyd 2004 Thomson BrooksJ39Cole CO in Ketones 1 g 1715 cm1 in sixmembered ring and acyclic ketones 1750 cm1 in 5membered ring ketones 1690 cm1 in ketones next to a double bond or an aromatic ring 0 1 CH300H3 0 CH30HCHGCH3 1715 curl 1750 cm 1 1690 cmquot1 LE Thomson Brooks Cole 1690 cm 1 CO in Esters 1735 cm 1 in saturated esters I 1715 cm 1 in esters next to aromatic ring or a double bond 0 H H CH3000H3 CH30HCHCOCH3 1735 cm391 1715 cm391 1715 cm391 Thomson Bmuks Cole Chromatography Purifying Organic Compounds Chromatography a process that separates compounds using adsorption and elution Mixture is dissolved in a solvent mobile phase and placed into a glass column of adsorbent material stationary phase Solvent or mixtures of solvents passed through Compounds adsorb to different extents and desorb differently in response to appropriate solvent elation Purified sample in solvent is collected from end of column Can be done in liquid or gas mobile phase Principles of Liquid Chromatography Stationary phase is alumina Al203 or silica gel hydrated SiOZ Solvents of increasing polarity are used to elute more and more strongly adsorbed species Polar species adsorb most strongly to stationary phase For examples alcohols adsorb more strongly than alkenes 53 HighPressure or HighPerformance Liquid Chromatography HPLC More efficient and complete separation than ordinary LC Coated silica microspheres 1025 pm diameter in stationary phase Highpressure pumps force solvent through tig tly packed HPLC column Detector monitors eluting material I Figure 1217 HPLC analysis of a mixture of 14 Besticides using acetonitrilewater as the mo ile phase HPLC of Pesticide Mixture Oxamyl Methumyl Carbcfuran Propoxur Fluometuron Diuron Warfal39in Sidurun Methincarb Linumn Mexacarbate 1 2 4 5 6 7 8 9 10 i H L39t I 9 10 11 12 13 14 Minutes 2004 TimmsunfBroolG Cole Prob 1239 Cyclohexane or Cyclohexene Transmittance 22 4000 3500 Transmittance 70 4000 3500 3000 2004 Thomson BrooksCole 3000 2600 2200 2000 1800 1600 1400 1200 1000 Wavenumber cm 1 Wavelength Inn 6 2600 2200 2000 1800 1600 1400 1200 1000 Wavenumber cm 1 Problem 1248 Unknown hd roca rbon 80 60 40 20 Relative abundance Wr g llll AIL J B I 1 l f I 3 10 20 40 60 80 100 120 140 b Wavelength gm 6 397 16 20 24 l l l 4 5 8 9 10 12 80 T me J mwv wvw Transmittance WM 14 1 I 1 w 4 w 1 I v I 1 4000 3500 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 40 Wavenumber cm 1 2004 Thomson BrooksCole Problem 1249 Unknown hyd roca rbon2 100 4 m 00 o o o J l I N o 1 Relative abundance l n O Wavelength 111 4 5 6 7 8 9 10 m 0 039 WWM I 0 Wm WM 5 O 4 o Transmittance 72 N O I I 1 l l I Y 4000 3500 3000 2600 2200 2000 1800 1600 1400 1200 1000 Wavenumber mm 1 2004 Thomson A BrooksCob Some Useful Websites Interpretation of IR spectra CSU Stanislaus httpwwwchemcsustaneduTutorialsINFRARED IR Spectroscopy Tutorial CU Boulder httporcchemcooradoeduhndbksuoportirtutort utoriahtm NIST Chemistry WebBook httpwebbooknistciovchemistrv SDBS Data Base httpwwwaistCloiDRIODBSDBSmenu ehtm


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