Spectroscopy Data Tables infrared Tables (short summary of common absorption frequencies) ‘The values given in the tables that follow are typical values, Specific bands may fall over a range of ‘wavenumbers, cm”. Specific substituents may cause variations in absorption frequencies. Absorption intensities may be stronger or weaker than expected, often depending on dipole moments. Additional bands may confuse the interpretation. In very symmetrical compounds there may be fewer than the expected number of absorption bands (it is even possible that all bands of a functional group may disappear, i.e. a symmetrically substituted alkyne!). Infrared spectra are generally informative about what functional groups are present, but not always. The 'H and SC NMR’s are often just as informative about functional groups, and sometimes even more so in this regard. Information obtained from one spectroscopic technique should be verified or expanded by consulting the other spectroscopic techniques. IR Summary - All numerical values in the tables below are given in wavenumbers, cm” Bonds to Carbon (stretching wave numbers) ingle bonds pL SLO NL ed { FyN YN | not very useful alkoxy C- not very useful 1250 acyl and phenyl C-O ads, \ riple bonds: \_/ PT\ TP Louk votes revo apres aio02250 2202260 Tonge dipoles pode ae nese brs weaker dips dies ee Tas oe Bonds to Hydrogen (stretching wave number ye ; . 7| \ 30003100 4 sp CHT 3300 2700-2760 2830-3000 (ooo? cH ane sp'CH patterns below) (sp C-H bend = 620) (two bands) 7 \_ f/f \_/ \ a FN :—o—+ R—S—H 7A. STA a /™ J / { s100%so0 3100500 . pia Nts sconn r 20-80 sma soe e bands) Lone band) alcoho] O-H acid O-H thiol S-H rongYamines = weak Z.fles\classes\spectroscopy\typical spectra charts DOCspectroscopy Data Tables 2 Carbonyl! Highlights (stretching wave numbers} Altchyaes Keone es Tes i — i aN, | ! Re No ® H aR ao R 07 saturated = 1725 conjugated = 1690 aromatic = 1700 saturated = 1715 conjugated = 1680 aromatic = 1690 6 atom ring = 1715 saturated = 1735 conjugated = 1720 aromatic = 1720 6 atom ring 5 atom ring = 1775 4 atom ring = 1840, saturated = 1715 conjugated ~ 1690 aromatic = 1690 Somme = 1748 4 soming= 1780 3 naming = 1850 Anes “Aniyades if I ZN Jk ana, R 0" R . Saturated ~ 1760, 120 Sonjugated = 1660 conjugated = 1735, 1785 conjugated = 16 rove = 1725, 1788 aromatic 1660 G atom ing 1750, 1800 Stam rng Som ang = 1785 1863 44 atom ting = 1745 Sometim. sp? C-H bend patterns for alkenes Acid Chlorides nitro i —_— ° €. J, a oi mA saturated = 1800 be conjugated = 1770 5 Sromaties 1770. £ asymmetric = 1500-1600 symmetric = 1300-1390 Very often there ia very weak C-O overtone at approximately 2 x7 («3400 em this ic mistaken for an OH or NH peak sp? C-H bend patterns for aromatics steron — alkene substitution deseriptve frequencies (emr') | aromatic substitution descriptive frequencies (em) . SF monttiaed 9851000 mentite NL eau — gsr \ = disinned yoyo . \_/ x Mea disubstinted OTIS rs fo suas00 ometine) i SOR \—/ ube pera disubtinsed / “\ alkene 790-840 x ‘aromatic 790-840 NL eae ttasion a towenn iso event) Sons vs pele / \ na een none pictures for comparison (not here). A strong C=O peak willSp oscopy Data Tables 3 wo 39m | 0, 30 2010 To 550 40 1500 1900100 10 990 900 —_ alkene sp? CH am thiol SH bend ‘mono * St = a GN ime " wed to — im phenol C-0 - — cites a wero fos _ " loa showy CD Carton fea OF | SCeectch senate CH rea | Nite ze sect onto Pea mm Sm eae st i pom Sho won ato To 20 200 Too" 1509140000 00 1100 90 800 700.0 50 E pou a yi VPP — es alkene sp? C-H = — bend cae aromatic sp? — — bend = 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 ot -0 in sant ngs seston dea between C and 0. ‘aiyariaes i 760 & 1820 (satrted) [725-178 (ansterate) LN twostong bands aol Zo 150-1350 (aoy, stone) .ctroscopy\typical spectra che onal groups ina compound (ll values TR Spectrum 2250 sharp stronger than alkyne, a ite lower when coajpated alkynes . 2150 (variable intensity) not presen or weak when symmetcally subsitted, litle lower whea conjugated sp CH seth 3300 sharp, stoag sp Call bend «0 ‘AILIR values are approximate and bave a range ‘ot possiblities depending on he roleclar ‘vironment in which the functional group resides ‘Resonance often mudifes peak postion because of electron delocalization (C-0 lower a6)1 C20 ger, et). IR peaks are ot 100% felable, Peaks tend tobe stronger (tore stese) ‘whea tere isa lage dipae assocatd with ‘iain i the funcional group and weaker in less poer bonds (othe pont of disappearing seme conpleely symmetrical bond) Alkene sp? bending patterns ‘monosbstitted alkene (985-1000, 900-920) seminal disubstituted (960-990) cis dsubstinted (675-730) tras disubstituted (80-900) visubstiute (790.840) texrasubstiated (one, no sp? CH) Aromatic sp? Gl bending patterns monosubstined (730-770, 690-710) ‘onto dsubstiuted (735-770) ma disubstated (880-900 sometimes, 750-810, 680-725) pa disubstituted (790-840) There are also weak overtone band between 680 ad 2000, Sut are not show here "You an consult pcttes of peal patter in ater Feference books, I tere ea srg C-O bet, they may be partially covered up sD0C CO hand alkanes sp) CHL seteh 2850-3000 sp CHbend 460 & 1380 c ot wef “ener sp? CHseteh 3000-3100 650-1000 (Geotable for so CH bend ° spectral pliers) 00-1660 weak or not present 3050-3150 590.900 (ee tale), sp? Carte st cattend “overeat * verwecn 16 0 1 & 1480 « canbe wea aicools seohol 600.3500 ateory Jooe.2a = oer Wi ‘al =2550 (wee e (cy ero) er / 3300-3500, wo bande fue anes on nd Wii fe2* amines, wanker Nell bend, 1550-1640, stronger in edes than anes —c 1000-1380 (ancerain) cihere ‘tkoxy 1120 tpi) CRS 1040.8 1250 aromatic) Titre compounds JJ_g. 1322-2600 symmetric rons) Heo 1300-1390, symmetne (median) Noe ‘carborchalogen bonds tnsally not | ‘very usefulSpectroscopy Data Tables Adeshelding side less electron rich eding side = ‘Typical 1H and 3 NMR chemical shift values. 5 sheng side ~ more eecton ish “ypial proton chemical sis Cafdon andor htroaronswitost hydrogen do =x, tol pear er ul nfacne any ner pons i i tty beacon nthe emit sis othe proen siti -0—H ; i 1 5 5 is cartoryic wid OF 3 2 sta = ero Cat es sina coca ies _, ane 7 z tS i os 1 LS 1 9 + TM 6 54 3 2 16 ‘epieal carboa-13 chemical si puss i $ ’ ae “e I A cates Es — a \ an 0 ste avid chlorides —, i i wih evita on 7 ingle pcb with A ‘with & without H TI ott oo 02M py 120mg Z.fles\classes\spectroscopy\typical spectra charts DOCSpectroscopy Data Tables Caleulation of chemical shits for protons at sp? i carbons [Eximation ofsp" C-H chemical shill with muliple substituent parameters for protons within 3 Cs of consideration —Gi-Cy-C,— | a = divctty atached substituent, use these values when the hydrogen and substituent are attached tothe same carbon rey ce removed substituent, use these values when the hydrogen and substituent are on adjacent (vicinal) carbons twice removed substituent, use these values when the hydrogen and substituent havea 1,3 substitution patern X = mbstieeat Starting value and equations for CH's Re Galks)) — ny) BCH, = 09 +a ‘alkyayi) (aromatic) Tuo ‘Be (bromo J iodo) “pode RjC=CRO- (alkenyl ther) Nitto) HS hil tin, RCO- (ketone) ACO. (aromatic ketone) XC tats) 90- (suloxie) R BCH = 09+ 3G +9 Eis the summation symbol forall substituents considered — Starting value and equation for CHh's Ina similar manner we can calculate chemical shifts for methylenes (CH) using the following formula SCH, = 12 Ta B+) Rood HCCC — is she summation symbol forall substituents considered ‘Starting value and equation for CH's Ina similar manner we can calculate chemical shifts for methines (CH) using the following forma SCH= 15+ 3a ey Eis the summation syeabol forall substituents considered ‘meine 9 ‘ethylene wr of, Cia Crh c, methy] methyl Ny” i HOP IC im -metbytene Emenyiene (02),~54 ppm a. methine = 15 +(9q+23)e methyl b, methylene = 1.2 +(15)q + (0p +(0.3)p=3.4 ppm sctual = 3.0 and 3.2 emethy e-methyl=09 + (15) =24 ppm actual = 2.6 Z.fles\classes\spectroscopy\typical spectra charts DOC Calculations are generally elose to actual chemical shifts fora single substituent, but are less reliable as the numberof substituent factors goes up. Multiple substituent factors tend to overestimate an actual chemical shi. 9+ (O.1)y = 1.0 ppm actual = 1.0 ne=12+(03)_= LS ppm actual = 1.7 £ methylene 1.2.+(1.7q=2.9 ppm actual 2.9ectroscopy Data Tables 7 Estimated chemical shifts for protons at alkene sp* carbons Substituent onic Geis owas ‘Substitution relative to calculated "H’ He 00 00 00 Hydrogen R 0s 02 “03 sm kyl tedns ght CoHsCH- OF “02 02 B(ppm) = 5.246. ge Osis + & xans Benzyl X-CHe 0. a 00 Halomethy! Example Calculation (HYROCHy- 06 cr} 00 alkoxymethy! gem ()yRINCH- or “1 Or H aminomethy! trans cy LH RCOCH- a7 “OT BI Tes a-keto H NOCH; oF 01 “01 CHO" R,C=CR- 12 00 on Alkenyl 8 2+14=66 Cob Ta aa “Or actual = 66 Phenyl F 1S aa “To Strans=5.2-0.1 Fluoro ‘actual ¢ u 02 ot Beis -5.2404-5.7 oe —____—_, actual = 5.6 Br 1 oa 06 " Bromo rE TT ox 0 Jodo. RO- 12 7 akoxy (ether RC 2 “08 actual= 6.4 (J= 18, 1.4 Hz) Z.fles\classes\spectroscopy\typical spectra charts DOCSpectroscopy Data Tables 8 Estimated chemical shifts for protons at aromatic sp* carbons Substitution relative to calculated Substinunt ortho meta para meta ortho A 00 00 00 _ Liydroxen CH 02 aI az paa—\ Methyl Tics a0 a0 a mdr Sho CholromethyL Chc- 38 on oH S(ppm) = 73-4 gan? meat Op Halomethyl HOCH: “OI “1 Hydroxvmethyl R2C-CR- or 00 “0 Alkenyl Cals i oF “Or Phenyl F “03 on} wz Fluoro. a } oo Chloro Br 02 “Ot a Bromo —_ rE om 02 oF Todo 06 “01 “05 RS rr as oo “OT (_RN- “08 D2 N-amino RCONH- or “1 “03 N-amide ON To 03 oF Nitro Ri 02 thiol/sulfide ‘OHC- ws a2 oF Aldehyde ROC- or or wz Ketone 09 02 0s 7 or o2 06 Or 02 oF 02 03 Z.fles\classes\spectroscopy\typical spectra charts DOC Example Calculation 2 1 i Pos cro. Z we H6 Qh asp H 4 H ; | 1, 6 (CH) =0.9 +28 2.8Q) actual 3. 8 B)=7.3 + (40.2) tho + 60:4) pars= 6.7 actual 4, 8 (CH) =12+@8)a+(.4)a=34 actual =3:3 5. 6(5)=5.2+(0.1) gum =5.9 actual = 5.9 6. 8O)=52+(02) pray =5.0 actual = 5.1 7. B(N=5.2+ (02) ce = 5.0 actual = 5.1 1Spectroscopy Data Tables ° Real Examples of Combination Effects on Chemical Shifts anisotropy 08 Shielded ‘bond example toa (CH) 08, shielded it shielding cone a from o bond 26 H_ deshielded 2 <— 15, hydrogen H Ht) bonded enol HO ro HC cH, hydrogen hoo Goes N= bondin eisai Saat and tae om protons pepe bf ' 36 1513 1309 30 13 10 09 ‘multiple substituents CH CHCl cut t 4 4 4 0.2 4=28—e 3.0 = 4a23—e 534 AR 1972 <— A=72 —* 2(o0ps) substituents at methyl (CHs), methylene (CH) and methine (CH) q g CHCl ony 1 (CH).CHCL yc“ Ph HACH,C~ Ph (CCH Ph 3.0 35 41 26 3.0 35 alkene substituent resonance and inductive effects 09 14 2.0 38 Hon Os so P64 Lt ect, 750 Sho’ cK cad Ne H H i cS H H H a sk a9 6158 aiomnaii esonance and inductive ics 1 TS 66 nt 2075 4 oO x H an = PK 19 “%q = HN hw N H \9/ \ / Jf eh ra é bond anisotropy io Yo wok dot produces deshielding Extra electron density via resonance produces Withdrawal of electron density via resonance effect on aromatic shielding effect on aromatic protons, especially _ Produces deshielding effect on aromatic protons, protons. atortho/para positions. especially at ortho/para positions. alcohol H=1-5 | R3N-H_ amineH= 1-5 |enollI=10-17 H~Q phenolH=410 | 0 sg PK thilH=125 | Rec amide 8}, aromatic thiol H= 3-4! ‘NH RN it acid H= 10-13 Z.fles\classes\spectroscopy\typical spectra charts DOCSpectroscopy Data Tables 0 1. One nearest neighbor proton a “SF ea aE etrbation() by to populations ‘eighbor prtan(s) 4s about S050 (or II) AE; (observed) on Protons in this environmen havea xmall cancelation % ? @P Protons inthis cvironment have small ‘observed proton A, (observed) Fie external gate sd pode lina ieranent aed he eal Shute en tanitony Baty at EL mate td By and produce higher t coca tansy hy amt. = coupling constant f \ I ls Nt nule (= #nighbon) alld ergy de icing ST oon ei jl teats vats Lane Spm) 2, Two nearest neighbor protons (both on same earbon or one each on separate carbons) GQ 2 @ poe the rato of there fo populations Ht about observed pH proton " 2, Sie ha ‘two equal energy ' 2 ' ® two neighbor proton ae ike [ ectal enerzy DP wermtsaonotacace |), Prince rye arranged four possible ways | N+ 1 mule (N= # neighbors) Gime t ppg coin twie) | 4 jrieeriesetay speaks =N'+1=241=3 pas ee con el et ee soem) 3. Three nearest neghbor protons (on same carbon, or wo on one and one on another, or one each on separate carbons) Qo @ mc sone PO = the ratio ofthese ight populations i about 1:33:1 os on nF tw @M _tiencghbor protons ae ike tie WW t range ig ste way rer populntons ach poss (similarto flipping a coin thrice) it Ww " ‘of mde transitions N+ I rle (N= neighbors) eg wr rm sural ey it peaks N+ 341-4 peaks 8 (ppm) Z.fles\classes\spectroscopy\typical spectra charts DOCin, troscopy Data Tables atterns when the N+1 rule works group without any coupled protn(s) N-o ° 4 N 1 g 4 N Pw ete | ec —c—0] ec» 4 ‘ sJenone aer mn TlH ne Nol 3 “ealeorexp ommon, but not alwai if je—c- ty “T* NL “ “se @ ou, ye Hee. CH sept Ne a Bit e llln ull i 3-cakeorep amealeorene N-8 Pascal’ triangle = covfficients of variable terms in binomial expansion (x y)" n= integer Moltiplts when CH fm singlet = doublet = wplet a= quartet gt quintet sep seplet theN. works (all values are equal sae peak = 100 1A pl peak = 50% 1 peaie= 25% 1 i 1 peak relative sizes of 3 peak = 6% Peaks in multiplets ar | peak 8 Goede peak shows) 14 6 6 1 pak ‘eed nsak shows) eS Mee tak wan ae se ay gt an Enek=08% d= wiplet of doublets; et. Z.fles\classes\spectroscopy\typical spectra charts DOC (ble of doublet of doublets «Add = doublet of doublet of doublet of doublets; dt = doublet of tripletsTypical Coupling Constants O30He 16s 03H, TKe ratte ste kere io Talat im we ae eeu 7 oats 1H in oe Vs pts ton act stony, et oneal coping TT tae ae mid < ge Oe q ee Gitte THe ‘. sstie woh mr deen ha angle, see plot of sy? vicinal coupling i Karplus equation (different x bonds) Range ‘Typical Range — Typical hoe cane one ake te Tr rotons op ir chlo ark ee age tas 0-3 Hz 2He Ha S-8 Hz Hz . «peo soil a vin ey cong re i1Me 101% te pane one /oN\ an sextant ete aes o opal cmting ‘smaller than the trans ison ‘notice through 4 bonds ia ia ia ha 119Hz 17H 23He sp? trans coupling (always Dis-propargylie coupling Zonorisches mie he rn ia Taal |= eT] . rrr se % 410Hz — 7Hz_ | ‘is proton ortho 6-10 Hz OMe / Hy meta 2-3Hz 2He A Hun poe Ole Oe sp? sp" vicinal coupling Hye When I values are less than 1 Hz it often dificult wo resol ZAMles\closes\spectroseopy\Wynical spectra ch sD0C ve them and a peak may merely appear wider and shornSpectroscopy Data Tables ‘Methyls = q, methylenes =t, methines Similar chemical shift information presented in a different format. Remember, proton decoupled carbons appear as singlets, When carbons are coupled to their hydrogens, carbons follow the N+1 rule} 4, and carbons without hydrogen appear as singlets = s, DEPT provides the same information. Carbon chemical shifts are spread out over a larger range than proton chemical shifts (they are more dispersed), so itis less likely that two different carbon shifts will fall on top of one another. The relative positions of various types of proton and carbon shifis have many parallel trends (shielded protons tend to be on shielded carbons, etc.) - | Hy on al Simple alkane CHy t Is f" carbons x2 0-30ppm dx 20-40 ppm s0-soppm 4e30-60ppm @ © @ © sp* carbon cHro gure fH ° j ReXtLO OXYEEN 4 50.60 ppm @ @, d <= 55-80 ppm 4 60-80 ppm d = 70-90 ppm ) © CHeN sp® carbon CHyrN next tonitrogen 4. 19.59 ppm d &3 35-55 ppm @ © ~Fres -fN 4 50-70 ppm d & 50-70 ppm @ (s) sp? carbon next to bromine or chlorine 4 25-50 ppm ex = (X= Cl, Br) 60-80 ppm dS 60 - 80 ppm © @ ®) sp carbon (alkynes) —e sp carbon (nitriles) —¢ 8 70-90 ppm 8S 110-125 ppm ‘bon (alkenes and aromatics) = \ Orn 4 8 & 100-140 ppm simple sp? carbon resonance donation moves 6 lower, resonance withdrawal moves 6 higher x cx 8 = 140-160" ppm sp” carbon attached to an electronegative atom (X = oxygen, nitrogen, halogen) or Cp carbon conjugated with a carbonyl group 2 x 8 & 160-180 ppm carboxyl carbons (acids, esters, amides) (s) @ 8 & 180-210 ppm aldehyde carbons, lower values when conjugated 8 & 180-220 ppm ketone carbons, lower values when conjugated @ Z.fles\classes\spectroscopy\typical spectra charts DOCSpectroscopy Data Tables 4 Calculations of alkane “C chemical shifts not listed above, sp’ Carbon Chemical Shift Calculations Calculations for sp* carbon '°C chemical shifts of functionalized carbon skeletons can be performed starting from the actual shifts found in the corresponding alkane skeleton, and introducing corrections factors based on the functionality present in the molecule, This assumes that the alkane '"C shifts are available, which is why several examples are provided below. Examples of C, alkanes as possible starting points for calculation '°C shifts in ppm. ‘Steric Corrections Approximate C shift calculation from serateh, canes ———_, Be = -) + 9x(He+ HB) -2x(by + steric corrections 1 sey | somlay | sery | gteraty - . = ~ ci -2516)-20)+€)-29 al -283) ine : E 4 2-2 49142)-20)+ BAEISHEIS}= 28 (cal= 340) a 2 28 rs 9315)-02) + BSHEISON=45 (tal =479) se 2 a 25 is 94012)-32)+(95)=27ecal=27 6 3-6 cis (ecmal—85) 5G shifts for various carbon alkane skeletons - useful starting points for calculating sp3 carbon chemical shifts | Zz A ‘ os ee So Z.fles\classes\spectroscopy\typical spectra charts DOCoscopy Data Tables x X is attached to a terminal carbon atom (ppm) J X is attached to an internal carbon atom (ppm) Substituent =X C, correction! Cy correction | C, correction —cr, 9 6 8 2 —eH.cHs 18 9 6 2 HICH)» 26 14 3 2 —c1CHs) 32 20 1 2 —c—=cn, 2 5 5 : ij 20 1 5 1 SH 5 2 6 4 2B 7 7 2 ittached to a terminal carbon atom (ppm) _[f X is attached to an internal carbon atom (ppm) —— OH i a 44 4 —or 6 37 6 5 of 6 ‘9 ‘ \, nn, 5 2 5 —navor) 32 4 ——NICHs), 5 37 4 3 at 5 21 5 \. —no, 38 is Z.fles\classes\spectroscopy\typical spectra charts DOCoscopy Data Tables 6 X is attached to a terminal carbon atom (ppm) JX is attached to an internal carbon atom (ppm) Substituent =X. C, correction } Cy correction C, correction || C, correction ‘Cy correction ! C, correction — 0 8 a 61 3 a al uf Es “ios tS er 20 10 4 28 10 “4 — - n 2 7 fou ba 3 —f ‘0 o ia x i a ia \, ‘ 1 Le / / —é 31 3 % f o } 3 Nv | | 0 1 1 _f 22 2 3 18, 1 3 Noe i 1 X is attached to Substituent=% | C, correction 5 | : df ‘0 foe bos \vcit i 0 _f 2s 2 3 Nw ty —c=N 3 3 3 P —f 33 2 3 \, —sH nit Rot 8 —sr 2 ; 8 3 wo | 6 Ff Z.fles\classes\spectroscopy\typical spectra charts DOCAdditonal surting point for caleulaing YC chemical shits (om) of substinted benzene tings (ust afew possblies. atom in relative postion tothe Subwttuent Start with 128 ppm, 26 us 3 SQ Substiuent 2, 0 7 “OH eT ZA 4 ee BE RT ALS — Re bo f rvidine ° 7 7 150 -CH,COCH, 6 9 0 0 4 / \ furan “CHy-CHly 1B > 1 0 4 0% 18 a ey 8 123 + conection factors ao coucICH 158 increments for drcetly attached carbon atoms See 2 Toca, acl “CiCHiay AS OxCCHy Bes cond we N(CH Ja 2% 2 Terie 1s NOs zo 4 cit “4 cn isu foreach pa oftis-a.a"sbstiuents =I -cHOH 48 men 3s 1 for each pair of geminal-a,a substituents -5 -CHECH, 47 CHO ise forsach pairofgeminalata ‘substituents 3 sect + 5 coc, woos iene or mace Plsustivens are present 2 “Cais no Co, 510 ‘cot 8 18 .ctroscopy\typlcal spectra charts DOCSpes troscopy Data Tables 8 Common fragmentation patterns in mass spectroscopy 1. Branch next to am bond o fet FYY radical cation Piloctron partially filin loss of electrons at [Characteristic carboncation tabiliy alo applic = bond ofan alkene fegmentaton raencsantarmaice | ex® > 2098 > i® > cu® fran aromatic 2. Branch next to an atom with a lone pair of electrons - yn . -D aT @., RS — Sch ee y N radicalcaton Tone parelectons partially il in loss of electrons at carbocation sit via resonance. This {sa common fragmentation for any ator that has a lone pair of electrons (oxygen ~ alcohol, ether, ester; nitrogen = amine, amide, sulfur = thiol or sulfide, ete.) Aleohols often lose water (0M 18) and primary amines can lose ammonia (M-17), 3. Branch next to a carbonyl (C=O) bond. ..and possible subsequent loss of carbon monoxide, CO ° jdt ff | aR u @ radical cation Ro-chb: <> R-CEOr RF ° ® Ry or Ry can be lost fom An oxygen lone par partially fill inthe loss of electrons a the subsequent loss of CO is possible aléchydes, ketones, acids, carbocation sit via resonance. Thisis a common fragmentation after & fragmentation so not only can testers, amides.. CHCH) Loss of small molecules via elimination reactions H,0H,8 CH,OH C,1j0H NH) CHyCO,H HF HCI HBr musk Me om SD McLafferty Possibilities 4 i eo °) Ch Notice! Motafferty He ext etes Aen oS Non I. cf nas = 44 81) man 26 R=1) Ssh) Die-cty nikon) Se(ke CHC) 70 (R= C3H;) 86 (R= Cyt) ~ H DCF ) ty col v oo Le % 7 oun a oy 4 on ne a e' Lo) “ip i a Son, 4, No mass 42 (R=) mass 92 (R=H) mass ~ 40 (R= H) mass ) 56 (R=CHy) 106 (R=CHy) 54(R= CH) 55(R=CH) 70 (R= CH;CHs) 120 (Re CH,CH,) 68 (R= CH,CH;) 69 (R= CHsCHy) 84(R=Cilh) 134 R= CF) s2(R= Cit) a3 (R= Cult) Z.fles\classes\spectroscopy\typical spectra charts DOC