Question 3: Below are the spectral data (IR, MS, 1H NMR, and 13C NMR) for an unknown organic compound. Examine the data carefully and answer the questions that follow. 3a) What functional group do you observe in the IR spectrum? 100 80 60 40 20 3376 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 V (cm-1) سليليليييييل % of base peak 59 73 3b) How many signals from 13 Mass Spectrum sp carbons in C-NMR 3c) How many signals 2 from sp carbons in 13 C-NMR M+88 (<1%) 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (150 MHz, CDCl solution) DEPT CH2CH₂ ↑ CH ↑ proton decoupled solvent 200 160 120 80 1H NMR Spectrum (600 MHz, CDCl solution) 10 expansions 1.6 1.5 1.4 1.0 0.9 ppm 9 8 T 3d) What is the formula of this molecule (you may need to solve structure first)? 40 0 5 (ppm) 3e) Proposed structure exchanges with D₂O L 7 6 5 4 3 2 1 TMS L 0 ō (ppm)

Question 3: Below are the spectral data (IR, MS, 1H NMR, and 13C NMR) for an unknown organic compound. Examine the data carefully and answer the questions that follow. 3a) What functional group do you observe in the IR spectrum? 100 80 60 40 20 3376 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 V (cm-1) سليليليييييل % of base peak 59 73 3b) How many signals from 13 Mass Spectrum sp carbons in C-NMR 3c) How many signals 2 from sp carbons in 13 C-NMR M+88 (<1%) 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (150 MHz, CDCl solution) DEPT CH2CH₂ ↑ CH ↑ proton decoupled solvent 200 160 120 80 1H NMR Spectrum (600 MHz, CDCl solution) 10 expansions 1.6 1.5 1.4 1.0 0.9 ppm 9 8 T 3d) What is the formula of this molecule (you may need to solve structure first)? 40 0 5 (ppm) 3e) Proposed structure exchanges with D₂O L 7 6 5 4 3 2 1 TMS L 0 ō (ppm)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter17: Carboxylic Acids

Section: Chapter Questions

Problem 17.17P

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