4000 100 80 60 8 8 40 IR Spectrum (liquid film) 20 % of base peak 3000 59 2000 115 87 11 80 40 13C NMR Spectrum (500 MHz. CDCI, solution) DEPT CH₂ CH₂ CH proton decoupled 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) 1 10 9 8 1737 v (cm') M** 146 120 160 m/e 160 1600 7 wy 1200 6 120 800 Mass Spectrum 200 240 280 C6H1004 solvent 80 5 4 1 Problem 46 No significant UV absorption above 220 nm L 40 3 2 0 1 8 (ppm) TMS L 0 8 (ppm) 135

4000 100 80 60 8 8 40 IR Spectrum (liquid film) 20 % of base peak 3000 59 2000 115 87 11 80 40 13C NMR Spectrum (500 MHz. CDCI, solution) DEPT CH₂ CH₂ CH proton decoupled 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) 1 10 9 8 1737 v (cm') M** 146 120 160 m/e 160 1600 7 wy 1200 6 120 800 Mass Spectrum 200 240 280 C6H1004 solvent 80 5 4 1 Problem 46 No significant UV absorption above 220 nm L 40 3 2 0 1 8 (ppm) TMS L 0 8 (ppm) 135

Principles of Instrumental Analysis

7th Edition

ISBN:9781305577213

Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Chapter20: Molecular Mass Spectrometry

Section: Chapter Questions

Problem 20.11QAP

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4000 100 80 60 20 % of base peak 3376 40 10 3000 59 13C NMR Spectrum (50.0 MHz, CDCI, solution) 173 proton decoupled 200 I 9 80 ¹H NMR Spectrum (200 MHz, CDCI, solution) DEPT CH₂ CH₂ CH4 IR Spectrum (liquid film) 2000 M+88 (<1%) 120 1600 v (cm¹) m/e 160 160 I I 8 7 mmm 1 120 200 240 6 1200 . Mass Spectrum L 800 1 5 C5H₁20 280 solvent L 80 4 problem 78 3 No significant UV absorption above 220 nm 40 Il 08 (ppm) 1 2 1 TMS 0 8 (ppm)
опанит 1715 1600 IR Spectrum 100 4000 (liquid film) 43 80 75 60 M 40 20 % of base peak 10 3000 40 C 13C NMR Spectrum (20.0 MHz, CDCI solution) proton decoupled 9 80 200 ¹H NMR Spectrum (100 MHz, CDCI, solution) 101 8 2000 v (cm¹) M** 132 120 160 m/e 160 7 6 1200 120 Mass Spectrum 200 240 280 800 C-H 5 C6H1203 solvent L 80 4 -CH3 No significant UV absorption above 220 nm 3 H-C-H u -CH3 40 2 59 TMS 0 1 8 (ppm) TMS 0 8 (ppm)
Resolves into 13C NMR Spectrum (50.0 MHz, CDCI, solution) two signals at higher field DEPT CgH11Br Resolves into two signals at higher field expansions proton decoupled solvent 35.0 34.0 ppm 200 160 120 80 40 O 8 (ppm) 1H NMR Spectrum (200 MHz, CDCI, solution) expansion 3.0 2.5 ppm TMS 10 9 8 7 6 5 4 3 2 1 8 (ppm) Determine the structure of the compound based on the above information
4000 IR Spectrum quid film) 100 80 60 40 YI 2248 41 10 3000 43 40 proton decoupled "C NMR Spectrum (150 MHz CDC, solution) 68 DEPT CH, CH, 1 CHT 9 200 ¹H NMR Spectrum (600 MHz, CDC, solution) M83 (<1%) 80 120 2000 v (cm) 8 m/e 160 160 2.3 L 7 1600 2.2 200 ryper 1200 6 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 120 Mass Spectrum 240 21 2.0 expansions (not to scale) 800 I CsH₂N 280 5 expansion 80 4 270 255 256 255 expansion No significant UV absorption above 220 nm 27.0 245 250 255 1.0 3 40 L 2 0 8 (ppm) 1 1 TMS L 1 0 8 (ppm) 10 ¹H-¹C me-HSQC Spectrum (600 MHz, CDC, solution) Black cross-peaks CH and CH Red cross-peaks CH₂ ppm 20 ¹H-"C HMBC Spectrum (600 MHz, CDC), solution) -22 -24 -26 -28 116 118 120 122 124 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm ppm 20 22 -24 26 28 -116 118 -120 122 -124 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm IR: List bands and possible/probable structural units responsible Band (cm³) Possible…
Myriam 1718 1. 4000 3000 1600 1200 800 V (cm¹) 100 Mass Spectrum 43 119 80 60 JIK M+* 40 176 20 161 C12 H16 O 40 80 200 280 120 160 m/e 13C NMR Spectrum (50.0 MHz, CDCI, solution) expansion 188 IR Spectrum (liquid film) % of base peak DEPT CH₂ CH₂ CH proton decoupled L 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) J 1 9 10 I 8 2000 160 the 1 7 6 240 120 130 130 125 ppm 125 ppm L 5 expansion 1 80 1 4 solvent Problem 99 UV Spectrum max 262 nm (log₁0 € 2.5) solvent methanol 40 t I 3 1 2 4 08 (ppm) TMS 1 0 8 (ppm) 1 1 205
IR Spectrum (CCl4 solution) U 4000 3000 100 80 60 40 20 JL 40 80 13C NMR Spectrum (100.0 MHz, CDCI, solution) % of base peak DEPT CH₂ CH₂ CH proton decoupled 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) 10 9 8 2000 1693 v (cm¹) 155/157 120 160 m/e 160 7 1600 183/185 7.8 6 your 1200 120 800 Mass Spectrum C8H7OBr 280 solvent 80 M+= 198/200 200 240 expansion سلا 5 7.2 ppm 4 3 Problem 100 UV Spectrum max 258 nm (log₁0€ 4.2) solvent: ethanol 40 2 0 1 206 8 (ppm) TMS L 0 8 (ppm) 189
7.) From the following sets of data, please propose a reasonable structure for the unknown organic compound. This molecule is entirely composed of C, H, and N only. Please show all of your work and feel free to write on the spectra any clues as to the structure. 4000 3000 2000 1000 S DO Infrared spectrum of unknown. KBr salt plate sample. 100 MS-NU-6396 80 60 40 20 - 10 20 30 40 50 60 70 80 90 100 110 m/z Mass spectrum of unknown. Molecular ion = 83.1 Relative Intensity
(f) C10H13NO2 4000 100 80 60 20 % of base peak 3284 43 3000 40 10 IR Spectrum (KBr disc) proton decoupled 13C NMR Spectrum (50.0 MHz, CDCI, solution) DEPT CH₂ CH₁ CH 200 9 80 ¹H NMR Spectrum (200 MHz, CDCI, solution) exchanges with D₂O on warming 108 le 137 M+* 179 120 160 2000 8 1658 v (cm¹) 1600 m/e 1 160 if L 7 120 expansion 1200 6 200 240 280 7.6 800 Mass Spectrum C10H13 NO₂ 5 solvent 80 l 7.0 4 ppm UV Spectrum max 250 nm (log₁0€ 3.1) A max 287 nm (log₁0 2.2) solvent: chloroform 3 40 2 0 1 8 (ppm) TMS 0 8 (ppm)
13C NMR Spectrum (50.0 MHz, CDCI, solution) DEPT proton decoupled 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) C₂H₂ NO ₂ expansion 3.0 160 2.0 120 1.0 ppm 10 9 8 7 6 Determine the structure of the compound 5 solvent 80 4 40 3 2 08 (ppm) 1 TMS 0 8 (ppm)
Interpret the NMR spectrum 11 1 10 69 9 8 00 4 7 6 5 ppm 4 C,H,O,N M. Wt = 139 3 N 1 0
A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below.. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH;CH,O°N 1. BHTHF N-bromosuccnimide A CH;CH,OH B 2. H,O,/OH- D hv reflux Compound A NMR (relative integrated areas below peaks) PPM 5 Compound B IR INFRARED SPECTRUM PPM 5 1 6 0.8 Compound A IR INFRARED SPECTRUM 0.6 0.8 0.4 0.4 0.2- 3000 2000 Wavenumber (cm-1) 1000 The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 2000 Wavenumber (cm-1) 3000 1000 Transmitance Relative Transmittance
3000 15MHz carbon-13 NMR spectrum CDCi, solution off-resonance decoupled proton decoupled 200 In spectrum (nujol mull) 135 28 2000 100MHz proton NMR spectrum CDCi, solution 1600 V (cm-1) wayang 147 40 60 80 100 120 140 160 180 200 220 240 260 260 300 320 340 m/e 10% expansion at 130ppm 1670 mt 150. 2H 1200 800 mass spectrum 209 3H 124 180 160 140 120 100 80 60 40 UV spectrum a 14.999mg/10ml hexane 0.150mg/10ml hexane 1cm b 0.5cm cells 250 300 200 problem 3H 2 (nm) 20 0 350 6 (ppm) 8 (ppm)