CH3 2. An unknown isomer of C4H9Cl has the ¹³C NMR and DEPT-135 spectra shown below: 13C NMR: 90 70 I 50 8 (ppm) CH3CH₂CH₂ CH₂CI A 30 I 1 10 DEPT-135: CH3 CH3-CHCH₂-CI B 90 70 I I 1 Circle the compound that is represented by these spectra. Clearly explain your reasoning. you will need to explain how each of the other three isomers was eliminated from consideration. 50 8 (ppm) C CH3CH₂ CH-CI CH3 30 I 10 CH3 CH3-C-CI CH3 I D

CH3 2. An unknown isomer of C4H9Cl has the ¹³C NMR and DEPT-135 spectra shown below: 13C NMR: 90 70 I 50 8 (ppm) CH3CH₂CH₂ CH₂CI A 30 I 1 10 DEPT-135: CH3 CH3-CHCH₂-CI B 90 70 I I 1 Circle the compound that is represented by these spectra. Clearly explain your reasoning. you will need to explain how each of the other three isomers was eliminated from consideration. 50 8 (ppm) C CH3CH₂ CH-CI CH3 30 I 10 CH3 CH3-C-CI CH3 I D

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.SE: Something Extra

Problem 59GP: The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this...

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The 13C-NMR spectrum of 3-methyl-2-butanol shows signals at 17.88 (CH3), 18.16 (CH3), 20.01 (CH3), 35.04 (carbon-3), and 72.75 (carbon-2). Account for the fact that each methyl group in this molecule gives a different signal.
The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.
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