100 80 60 40 20 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 V (cm³) % of base peak 27 107/109 M+ 186/188/190 ل Problem 5 Mass Spectrum C2H4 Br2 No significant UV absorption above 220 nm 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (50.0 MHz, CDC13 solution) proton coupled proton decoupled solvent 200 160 120 80 40 0 8 (ppm) 13C NMR Spectrum (50.0 MHz, CDC13 solution) proton coupled proton decoupled solvent 200 160 120 80 40 0 8 (ppm) 1H NMR Spectrum (200 MHz, CDCl 3 solution) 10 9 8 7 6 5 сл 94 4 3 21 1 TMS 0 8 (ppm)

100 80 60 40 20 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 V (cm³) % of base peak 27 107/109 M+ 186/188/190 ل Problem 5 Mass Spectrum C2H4 Br2 No significant UV absorption above 220 nm 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (50.0 MHz, CDC13 solution) proton coupled proton decoupled solvent 200 160 120 80 40 0 8 (ppm) 13C NMR Spectrum (50.0 MHz, CDC13 solution) proton coupled proton decoupled solvent 200 160 120 80 40 0 8 (ppm) 1H NMR Spectrum (200 MHz, CDCl 3 solution) 10 9 8 7 6 5 сл 94 4 3 21 1 TMS 0 8 (ppm)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

ChapterL3: Carbon (13c) Nmr Spectroscopy

Section: Chapter Questions

Problem 9CTQ

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13C NMR Analysis of Aspirin Chemical Shift (Observed ppm) Assignment(s) (A'-J') Expected Chemical Shift Range (ppm) B' D' E' JOH Acetylsalicylic Acid (Aspirin) 169 & 170 152 125 135 (4 peaks) - 122 20 160 140 120 100 Figure 14.13 125.7-MHz 13C-NMR spectrum of aspirin in CDCl3. solvent 80 60 40 20 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
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
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)
MASS % of Base Peak IR 100 5045 % Transmittance 100 T 50 4000 1540 ¹H NMR 300 MHz t 557 5.0 Hz 60 alla illle 677 69 1140 4.5 70 4.0 13C/DEPT NMR 75.5 MHz 3000 130 120 110 100 الد الله da 110 113 100 110 mm 817 Hz 500 90 80 m/z Wavenumber (cm-¹) 3.5 ми линия 80 90 480 Hz 957 3.0 70 2000 440 2.5 Hz 1450 2.0 -1126 120 1000 60 50 40 30 1287 130 1.5 ppm 20 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)
3296 IR Spectrum (quid film) ....... wwwddd 4000 100 80 60 40F 8 -28 20 40 proton decoupled 10 13C NMR Spectrum (100 MHz, CDC, solution) 2H - 3000 ¹H NMR Spectrum (400 MHz, CDC, solution) 55 200 2.5 9 80 82 2114 8 2000 M = 83 120 V (cm-¹) 2H L 160 expansion 1600 1200 C₂H₂N 160 200 240 280 m/e DEPT CH, I CH₂ 1 CH 1 2.0 I 7 1H 6 L 120 Mass Spectrum 2H 1.5 800 5 solvent I 80 exchanges with DO 4 2H L 3 No significant UV absorption above 220 nm ||| L 40 2 113 08 (ppm) 1 1 TMS 0 8 (ppm) IR: List bands and possible/probable structural units responsible Band (cm³) Possible stretches/functional groups MS: Molecular Formula 13C NMR: 1 2 3 4 5 6 ¹H NMR: 1 Chem. Shift (8) Type of C (sp, sp2², carbonyl, etc.) 2 Chem. Shift (8) Multiplicity (singlet, doublet, etc.) IHD(DU)= 3 4 5 6 If you need more space, add any additional signal info here: (Show calculation) of attached c # of attached H's # of identical C's in signal Probable Type of H (methyl, aromatic, etc.) # of identical H's in signal
43 184 IR Spectrum (Iquid film) 4000 3000 100 80 60 40 20 40 13C NMR Spectrum (100.0 MHz, CDCI, solution) 9 80 DEPT CH₂ CH₂4 CHA proton decoupled 200 ¹H NMR Spectrum (400 MHz CDCI, solution) expansion 7.5 7.3 ppm 8 P 10 SAMSUNG Galaxy A53 5G 2000 1600 V (cm) 105 M+- 134 120 160 m/e 160 09b0f2ca-eac1-4... 1200 T L 120 2.8 2.7 ppm 7 6 ww 800 Mass Spectrum C10H14 200 240 280 T 1 5 solvent " 80 expansions 1.8 1.7 ppm 1 4 3:54 م 0 *1 470 صفحة Problem 96 UV Spectrum max 260 nm (log10=2.5) PE 40 1.45 1.35 ppm 3 2 Problem 97 08 (ppm) expansion 1.05 0.95 TMS I 0 8 (ppm) 1 202 تمشح بـ 100 جيجابايت تخزين على OneDrive cloud لمدة 6 أشهر 185.
use software to make 1H-NMR and 13C-NMR from the data in the paper and make a table with the following data 1H: chemical shift , multiplet structure, integration, assignment 13C: chemical shift
4000 100 80 60 IR Spectrum (liquid film) 40 20 $ 2 2960 3000 41 77 79 40 13C NMR Spectrum (50.0 MHz. CDCI, solution) proton decoupled 200 ¹H NMR Spectrum (200 MHz, CDCI, solution) T 40 10 9 80 2000 107/109 1 8 120 v (cm¹) m/e 1600 M** 156/158/160 160 160 3.5 1200 120 200 240 766 800 Mass Spectrum expansions ppm 2.5 1 7 6 5 650 C3H6Br Cl 280 T 2.0 ppm solvent 80 4 H-C-H Problem 18 No significant UV absorption above 220 nm H-C-H 1 3 40 H-C-H 0 1 2 1 124 8 (ppm) TMS 0 8 (ppm) 107
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…
NMR data Summary NMR solvent: DMSO-d6 'H NMR: Splitting (Multiplicity) Integration Chemical Shift 9.67 singlet 1H singlet doublet 9.17 7.37 6.72 2.00 1H 2H doublet singlet 2H 3H 1"C NMR: Chemical Shift 167.8 153.3 131.1 121.1 115.1 23.8 15N NMR: Chemical Shift 132.3 Instructions: Step 0: Look at the structure of Tylenol. Determine integration, and splitting you are expecting in the 'H NMR. Step 1: Look at the integration and splitting of the signals in the H NMR spectrum - assign the chemical shift of the protons of the methyl group; make a note which signals in the 'H NMR are due aromatic protons, NH and/or OH. Step 2: Look at the 'HSN HSQC spectrum - Use this spectrum to assign the chemical shifts of the NH proton and the OH proton. Step 3: Look at the 'H1SN HMBC spectrum - Use this spectrum to assign the chemical shifts of the aromatic protons in the 'H NMR. Step 4: Look at the 13C NMR spectrum - Make a note which carbon atoms are aromatic and/or alkyl. Assign the chemical shift of…