Propose a structure for a compound with molecular formula C3H180 that exhibits the following 'H NMR and 13C NMR spectra: Proton NMR 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 Chemical shift (ppm) Carbon NMR -70.5 31.6 19.3 13.7 70 60 50 40 30 20 10 Chemical shift (ppm)

Propose a structure for a compound with molecular formula C3H180 that exhibits the following 'H NMR and 13C NMR spectra: Proton NMR 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 Chemical shift (ppm) Carbon NMR -70.5 31.6 19.3 13.7 70 60 50 40 30 20 10 Chemical shift (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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.18P: Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a)...

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Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

Propose a structure for a compound with molecular formula C3H180 that exhibits the following 'H NMR and 13C NMR spectra:
Proton NMR
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
Chemical shift (ppm)
Carbon NMR
-70.5
31.6
19.3
13.7
70
60
50
40
30
20
10
Chemical shift (ppm)

Expert Solution

Step 1

As given Compound has molecular formula C₈H₁₈O.

There is one hetero atom Oxygen. Oxygen being more electronegative element has -I effect , so de-shielded the proton of carbon atom.

Strength of De-shielding is more for hydrogen of carbon atom that is directly attached to Oxygen, and less for the hydrogen of carbon atom that are at some distance.

Splitting Of H is given by n+1 rule, where n is the no of hydrogen atom on adjacent carbon atom

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