MOD ORGANIC CHEM I
MOD ORGANIC CHEM I CHEM 2211
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This 28 page Class Notes was uploaded by Thurman Wilderman on Saturday September 12, 2015. The Class Notes belongs to CHEM 2211 at University of Georgia taught by Morrison in Fall. Since its upload, it has received 27 views. For similar materials see /class/202577/chem-2211-university-of-georgia in Chemistry at University of Georgia.
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Date Created: 09/12/15
spin state A A I no applied magnetic field magnetic field is applied Energy uspin state 3 l cammm 7046 Applied magnetic field EU in tesla Milena NMR spectrum sample in tube radlofrequ nny generator pumranmmmuuunmmmammi superconduning gnet these protons sense 3 these protons sense a larger effective magnetic smaller effective magnetic field so come into resonance field so come into resonance ai a higher frequency at a lower frequency gt 3 u E d E deshielded nuclei shielded nuclei quotdownfieldquot 4 quotupfieldquot Frequency mexhyl 5 Proton R W CH3CH2Br CH k 7 A s A i 5 ppm A39mqurncy 4 5mm equency CI CHCl chemical shift of the signal for the methyl protons if there were no protons on the adjacent carbon direction of the applied field if the magnetic field of the methine proton is in the same direction as the applied magnetic field it will add to the applied magnetic field so the adjacent methyl protons will show a signal at a slightly higherfrequency if the magnetic field of the methine proton is lined up against the applied magnetic field it will subtract from the applied magnetic field so the adjacent methyl protons will show a signal at a slightly lower frequency 4 frequency n LHSUHLIZ chemical shift of the methine proton if there were no protons on the adjacent carbon signal for the methine proton j is split into a qua t frequency all a all with 1 395 p m qucncy 4 frequcncy Examples of Infrared Spectra An Infrared Spectrum The functional group The fingerprint region 4000 1400 cm391 region 1400 600 cm391 J mu 1 l l l l l c 39 a w Tmnsmumm l l mm mm mm you 00 mm 2mm mm 1400 Him 1 l l 1 U mm Mon mm mm 2m hm l M u39 High energy Low energy The functional group or diagnostic region is used to determine the functional group present The fingerprint region is used for structure elucidation by spectral comparison Examine the absorption bands in the vicinity of 3000 cm jL 1x I mnsmumw OCH CiH Wavenunlhenmnquot 2011 Fenian E ucmmn In anenmuhcr Curl 2011 Parson Eauaauan Inc Vmeiunglii tum 55 n CIH i 400 Ml ROI 3400 i301 1001 INK 300 1401i 1200 1000 W11 IN MW 1100 ION MK M Wiwnumhcr imF L6 201 i Pearson Education In wavenumber cm 1 assignment 3075 sp2 CH 2950 sp3 CH 1650 and 890 a terminal alkene with two substituents absence of bands has less than four adjacent CH2 groups 1500 1430 and 720 IT N 943 JrPENrYNE s 7 T9 5 San 65 532 54 55 497 56 7 7 m u as at CH3 CH2 C 751 a llsuasrmn szus rmmrb 1 Lmum mm 75 424 as 3979 72 33 CHgi Hzigci Hzi l i i i I i mm won moo um um moo Mm 360 1x00 00 won son hnn 2mi m Benzene inplane and out Benzene ring ofplane C H bends Sharp absorption bands at quot1600 cm 1 and 1500 1430 cm l Overtones at 1700 1900 cm 1 for the inplane and outofplane benzene C H bends The benzene overtones in the diagnostic region are readily recognized 25 m 27 28 20 4 45 l l quotr Tnmmnmnu CH3CHCI13Cl 12CH3 l mm mm mm mm anu mm mm I r l l i l mun Wuvcmuui39el murh Functionalgroup regions Both Fingerprint regions Compounds are compounds are alcohols different alcohols Wmdunglli mm 2h 15 45 55 f 7 2 n H ll 3 N Is 16 m L l l l l r4 39rmmmumm CH3CH2CHCHZCH3 w I l wlllll WILD Ml 1H1 HUI lleU Xllll film W sznumbe rumquot 2m1 Pearsun Edunannm Inc F H CH3CH2CHZCOCH2CH3 t 1 i I 0 I I mm HUD 39 anmmmbcr Wmquot L I 1200 Esters have a carbonyl and 3 C 0 stretch Ketones have only a carbonyl stretch 1 4 a 1 m mam Df anuuumlwr uur v 20H Pearsun Enucanam Inc Tnmm umce Acids are readily distinguished from alcohols 1 Waveicnglli Hum 315 n w Immmhmnce CiO 7 i CH3CH2CH2CH2COH C O Wuwnunmu cur39v 1 2 Pearson Edumnan Inc a 0 1 y 3 4 5 7 M We on r e 1 t t A r 1 w av r U aldehyde group 1 CiH CH3CHZCHZCHZCH 1 1 7 Co l r 1 l 1 1 I 2mm Mn Mon Mm 100 mm a 0m Wuwnumhurmn v The stretch of the C H bond of an aldehyde shows one absorption band at quot2820 cm 1 and another one at quot2720 cm 1 Identifying a functional group by the bending vibrations win1mm iwm 4 4 a lt 5 5 n 1 i i 1 N4 PJgiiJ 39 quot quot stretch bend i i i i i i man mm 1500 um 300 moo ann 1500 2100 2 man Pearson Educahon int 0 Primary amine two N H stretches at 3350 cm l Amine N H bend quotlsopropyl split at 1380 cm 1 indicates the presence of an isopropyl group Wmclunglh pm 55 V r Wm Vavmmmhm 1cmquot 39 137 Jani39zgnOW 3mquotquotxim Agrilliriank39xim39izgmfi39bmini11 zzbni39ii lg 2011 Pearsan Eauca am Inc wavenumber cm 1 3050 2810 and 2730 1600 and 1460 1700 Vilnnn 39vv NM 111 mm m n00 assignment 5p2 CH an aldehyde benzene ring a partial singlebond character carbonyl 12 HCECCHZOH G Tmnsmilluncc i 2800 2600 24 00 2100 2000 IN 1600 annumher muquot um 1200 um son mm 4000 3800 3600 3400 3200 3000 2011 Pearson Education W wavenumber cm 1 assignment 3300 OH group 2950 p3 CH 2100 alkyne 13 I 1 CH3CNHCH3 v x 39 V 4000 1800 3600 I400 1200 W000 2800 264 0 1400 2100 1000 1800 1600 400 IZOD 1000 300 6 D0 Wm cmlmlwr mmquot 20 1 Pearsan Eaucaxlon Inc wavenumber cm 1 assignment 3300 N H 2950 sp3 CH 1660 amide carbonyl 1560 N H Bend 14
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