ORGANIC CHEMISTRY II
ORGANIC CHEMISTRY II CH 318N
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This 3 page Class Notes was uploaded by Brady Spinka on Monday September 7, 2015. The Class Notes belongs to CH 318N at University of Texas at Austin taught by John Colapret in Fall. Since its upload, it has received 7 views. For similar materials see /class/181876/ch-318n-university-of-texas-at-austin in Chemistry at University of Texas at Austin.
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Date Created: 09/07/15
CH 318N Dr John A Colapret Useful Spectroscopic Data Important Infrared Absorptions Type of Absorption CiH stretch CC stretch 7CHCH2 CCH2 others C7H stretch C7H bend 7CHCH2 E F O E to 0 C E E 0 0 0 Em 07H stretch C70 stretch CEC stretch ECiH stretch CC stretch CiH bend overtone CO stretch ordinary x3unsaturated benzaldehydes CiH stretch CO stretch ordinary x3unsaturated aryl ketones Frequency cm39l Intensity Comment Alkanes 285073000 In occurs in all compounds With aliphatic CiH bonds Alkenes 1640 In 1655 In 166071675 w 300073100 m not observed if alkene is symmetrical 9107990 s 890 s 960980 s 6757730 s position is highly variable 8007840 s Alcohols and Phenols 320073400 s 105071250 S also present in other compounds With C70 bonds ethers esters etci Alkynes 210072200 In not present or weak in many internal alkynes 3300 s present only in terminal alkynes Aromatic Compounds 1500 1600 s two absorptions 6507750 s 166072000 W Aldehydes 172071725 s 168071690 s 1700 s 2720 In Ketones 171071715 s 167071680 s 168071690 s increases With decreasing ring size Important Infrared Absorptions continued CO stretch ordinary benzoic acids 07H stretch CO stretch CO stretch CO stretch CO stretch NiH bend NiH stretch CEN stretch NiH stretch 1710 s 168071690 s 240073000 s 1735 s 1800 s 1760 1820 s 165071655 s 1640 s 320073400 m 2007250 In 320073375 m Carboxylic Acids very broad Esters and Lactones increases With decreasing ring size Acid Chlorides second weaker band sometimes observed at 170071750 Acid Anhydrides two bands increases With decreasing ring size in cyclic anhydrides Amides and Lactams increases With decreasing ring size doublet absorption observed for some primary amides Nitriles Amines several absorptions sometimes observed especially for primary amines Characteristic 1H NMR Chemical Shifts Type 0nydr0gen R 2 alkyl Ar myl CH34Si RCH3 RCHZR R3CH R2CCRCHR2 ArC H3 ArC HZR ROH RCHZOH RCHZOR RZNH RCCH3 Chemical Shift cf 0 by definition 0187110 1127114 1147117 1167216 2107310 2127215 2137218 0157610 3144110 3134110 0157510 2117213 Type 0nydr0gen R 2 alkyl Ar myl Chemical Shift LW 0 227216 RCCHZR 377319 RCOCH3 0 414117 RCOCHZR RCHZI 3117313 RCHZBr 3147316 RCHZCI 3167318 RCHZF 4144115 ArOH 4154117 R2CCH2 4167510 R2CCHR 5107517 ArH 6157815 0 957101 RCH 0 II 10713 RCOH Values are relative to TMsi Other nearby functional groups may cause the signal to appear outside of these general ranges Characteristic 1H NMR C0u lin Constants I a lib CC Jab 678 Hz Jab 11718 Hz Ha w Hb Jab 8714 HZ Jab 5710 Hz Characteristic 13C NMR Chemical Shifts Type of Carbon R 2 alkyl Ar atyl CH34Si RCH3 RCHZR R3CH RCHZI RCHZBr RC HzCl R3COH R3COR Chemical Shift J O by definition l 040 l 5755 2 0760 040 25765 35780 40780 40780 Ha IIIa C Hb Hb HbHa I diastereotopic J3b075 Hz J3b075 Hz Inle Hz Ha I a CC C c Hb Hb J3b 075 Hz J3b 8711 Hz J3b 4710 Hz Type of Carbon R 2 alkyl Ar atyl Chemical Shift LW RCECR 65785 R2CCR2 1007150 1107160 c R 0 N 1607180 RCOR 0 N 1657180 RCNRZ 0 N 1657185 RCOH 0 N 1807215 RCH 0 N 1807215 RCR Values are relative to TMSi Other nearby functional groups may cause the signal to appear outside of these general ranges Jab 0715 Hz
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