Proposing a compound structure consistent with an observed NMR spectra
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Compound A_1 C_8H_10O_1 has the IR and ^1H NMR spectra shown. Propose a structure consistent with the observed spectra, and assign each peak in the NMR spectrum. Note that the absorption at 5.5 disappears when the D_2O is added.
(See attachment for diagram).
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The solution provides a detailed written explanation of how to propose a compound structure consistent with an observed NMR spectra.
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Since you asked for either Question A or Question B, I have chosen to do Question B. I think it will be easier for you to follow.
We know the compound is C5H8Cl2.
If we did not have the chlorine atoms, then we'd have C5H10. This indicates 1 degree of unsaturation. Therefore, we should expect a double bond or a ring structure.
Now let's look at the spectrum. We see that the 8 protons are split in two separate groups, each one containing four protons. Therefore, the compound is made ...
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