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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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A compound with molecular formula C9H18 exhibits a 1 H NMR

Chapter 16, Problem 16.43

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QUESTION:

A compound with molecular formula C9H18 exhibits a 1 H NMR spectrum with only one signal and a 13C NMR spectrum with two signals. Deduce the structure of this compound.

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QUESTION:

A compound with molecular formula C9H18 exhibits a 1 H NMR spectrum with only one signal and a 13C NMR spectrum with two signals. Deduce the structure of this compound.

ANSWER:

Step 1 of 2

There are 18 protons in this compound but only one \({ }^{1} \mathrm{H}\) NMR signal, there must be an incredible amount of symmetry present, probably in the form of lots of methyl groups. So, we need 6 methyl groups ( 3 protons each) to account for all 18 protons. That would leave three carbons left, along with an index of unsaturation. A three membered ring would take care of these leftover features and would also account for the additional \({ }^{13} \mathrm{C}\) signal. Hence, the structure of the unknown compound is shown as follows:

 

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