Question

The proton NMR spectral information shown in this problem is for a compound with formula $\mathrm{C}_9 \mathrm{H}_8 \mathrm{~F}_4 \mathrm{O}$. Expansions are shown for all of the protons. The aromatic ring is disubstituted. In the region from 7.10 to $6.95 \mathrm{ppm}$, there are two doublets $(1 \mathrm{H}$ each). One of the doublets is partially overlapped with a singlet $(1 \mathrm{H})$. The interesting part of the spectrum is the one proton pattern found in the region from 6.05 to $5.68 \mathrm{ppm}$. Draw the structure of the compound and draw a tree diagram for this pattern (see Appendix 5 and Problem 25 for proton-to-fluorine coupling constants). DIAGRAM CANT COPY

   The proton NMR spectral information shown in this problem is for a compound with formula $\mathrm{C}_9 \mathrm{H}_8 \mathrm{~F}_4 \mathrm{O}$. Expansions are shown for all of the protons. The aromatic ring is disubstituted. In the region from 7.10 to $6.95 \mathrm{ppm}$, there are two doublets $(1 \mathrm{H}$ each). One of the doublets is partially overlapped with a singlet $(1 \mathrm{H})$. The interesting part of the spectrum is the one proton pattern found in the region from 6.05 to $5.68 \mathrm{ppm}$. Draw the structure of the compound and draw a tree diagram for this pattern (see Appendix 5 and Problem 25 for proton-to-fluorine coupling constants).
DIAGRAM CANT COPY

Introduction to Spectroscopy

Donald L. Pavia,… 4th Edition

Chapter 5, Problem 26

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Step 1

This indicates that the compound contains 9 carbon atoms, 8 hydrogen atoms, 4 fluorine atoms, and 1 oxygen atom. The presence of fluorine suggests that there may be some electronegative effects influencing the chemical shifts in the NMR spectrum. Show more…

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The proton NMR spectral information shown in this problem is for a compound with formula $\mathrm{C}_9 \mathrm{H}_8 \mathrm{~F}_4 \mathrm{O}$. Expansions are shown for all of the protons. The aromatic ring is disubstituted. In the region from 7.10 to $6.95 \mathrm{ppm}$, there are two doublets $(1 \mathrm{H}$ each). One of the doublets is partially overlapped with a singlet $(1 \mathrm{H})$. The interesting part of the spectrum is the one proton pattern found in the region from 6.05 to $5.68 \mathrm{ppm}$. Draw the structure of the compound and draw a tree diagram for this pattern (see Appendix 5 and Problem 25 for proton-to-fluorine coupling constants). DIAGRAM CANT COPY

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