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A compound with molecular formula C8H8O3 exhibits the

Chapter 21, Problem 21.8

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QUESTION:

A compound with molecular formula C8H8O3 exhibits the following IR, 1 H NMR, and 13C NMR spectra. Deduce the structure of this compound. Proton NMR Carbon NMR 1 2 2 3 180 160 140 120 100 80 60 40 20 0 12 11 10 9 8 7 6 5 3 4 Chemical Shift (ppm) Chemical Shift (ppm) 172.8 167.9 118.3 64.1 139.4 128.0 Wavenumber (cm1) 4000 3500 3000 2500 2000 1500 1000 % Transmittance 0 20 40 60 80 100

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QUESTION:

A compound with molecular formula C8H8O3 exhibits the following IR, 1 H NMR, and 13C NMR spectra. Deduce the structure of this compound. Proton NMR Carbon NMR 1 2 2 3 180 160 140 120 100 80 60 40 20 0 12 11 10 9 8 7 6 5 3 4 Chemical Shift (ppm) Chemical Shift (ppm) 172.8 167.9 118.3 64.1 139.4 128.0 Wavenumber (cm1) 4000 3500 3000 2500 2000 1500 1000 % Transmittance 0 20 40 60 80 100

ANSWER:

Step 1 of 4

This exercise gives us a compound with molecular formula C8H8O3 along with the compounds IR, 1H NMR and 13C NMR spectra. We’re asked to deduce the structure of the compound. Before deduce structure we have to find the degree of unsaturation.

Degree of unsaturation or hydrogen deficiency index (HDI):

HDI of the compound can be calculated by using the following formula:

Here,

C is number of carbon atoms.

N is number of nitrogen atoms.

H is number of hydrogen atoms.

X is number of halogen atoms.

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