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Solved: Draw the structure of the compound with molecular

Chapter 23, Problem 23.84

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QUESTION:

Draw the structure of the compound with molecular formula C8H11N that exhibits the following 1 H NMR and 13C NMR spectra: Proton NMR Carbon NMR 5 138.8 128.4 126.1 43.5 40.0 128.8 2 2 2 Chemical Shift (ppm) Chemical Shift (ppm) 7 140 130 120 110 100 90 80 70 60 50 40 6 5 4 3 2 1

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QUESTION:

Draw the structure of the compound with molecular formula C8H11N that exhibits the following 1 H NMR and 13C NMR spectra: Proton NMR Carbon NMR 5 138.8 128.4 126.1 43.5 40.0 128.8 2 2 2 Chemical Shift (ppm) Chemical Shift (ppm) 7 140 130 120 110 100 90 80 70 60 50 40 6 5 4 3 2 1

ANSWER:

Step 1 of 2

This exercise asks us to decipher the identity of an unknown compound. We’re told that it has the molecular formula \(\mathrm{C}_{8} \mathrm{H}_{11} \mathrm{~N}\) and that it exhibits the displayed \({ }^{1} \mathrm{H} \text { NMR and }{ }^{13} \mathrm{C} \text { NMR }\) spectra.

The 1H NMR contains a multiplet at 7.2 ppm worth 5 hydrogens, a triplet at 3.0 pp, worth 2 hydrogens, another triplet at 2.8 ppm worth 2 hydrogens, and a broad singlet at 1.4 ppm worth 2 hydrogens. The \({ }^{13} \mathrm{C} \text { NMR }\) has four peaks in the aromatic region (138.8, 128.8, 128.4, and 126.1 ppm) as well as a peak at 43.5 ppm and a peak at 40.0 ppm.

 

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