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Solution: Propose a structure for a compound with molecular

Chapter 14, Problem 14.53

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QUESTION:

Propose a structure for a compound with molecular formula C8H18O that exhibits the following 1 H NMR and 13C NMR spectra: 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 Proton NMR Carbon NMR 3 2 2 2 70 60 50 40 30 20 10 0 Chemical shift (ppm) Chemical shift (ppm)

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QUESTION:

Propose a structure for a compound with molecular formula C8H18O that exhibits the following 1 H NMR and 13C NMR spectra: 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 Proton NMR Carbon NMR 3 2 2 2 70 60 50 40 30 20 10 0 Chemical shift (ppm) Chemical shift (ppm)

ANSWER:

Step 1 of 3

This exercise shows us both   spectrum as well as    spectrum and tells us that they originate from a compound with molecular formula C8H8O. We're asked to determine the structure of the compound that's giving rise to the displayed spectra.

First, examine the   spectrum. The total integration number is 9; we know there are 18 protons present in the molecule, so we'll need to multiply each signal's integration by 2 in order to obtain the true number of protons that the signal represents. There are four signals in  .

 

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