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Propose a structure for an ether with molecular formula

Chapter 14, Problem 14.52

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QUESTION:

Propose a structure for an ether with molecular formula C7H8O that exhibits the following 13C NMR spectrum: Chemical shift (ppm) Carbon NMR 160 140 120 100 80 60 40

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QUESTION:

Propose a structure for an ether with molecular formula C7H8O that exhibits the following 13C NMR spectrum: Chemical shift (ppm) Carbon NMR 160 140 120 100 80 60 40

ANSWER:

Step 1 of 2

This exercise shows us a    spectrum and tells us that it originates from ether with molecular formula  .  We're asked to determine the structure of the compound that's giving rise to the displayed spectrum.

There are five signals in the    (given in values of ppm): 159.7, 129.5, 120.7, 114.0, and 55.1. From the molecular formula we can determine that there are 4 degrees of unsaturation in the molecule. This fits the definition of a benzene ring, as each pi bond is one degree of unsaturation and we add on one degree of unsaturation for the ring.

 

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