An unknown with the formula $C_8H_{10}O_2$ has the spectra on the next page. Please answer
these questions for this compound.
1. How many degrees of unsaturation does this compound have?
2. Does this compound have a carbonyl group?
3. How did you come up with your answer to b?
4. Does this molecule have symmetry?
5. In the $^{13}C$ NMR, what does the chemical shift of the signal at about 24 tell you? Please
be specific as to what the chemical shift tells you.
6. In the $^{13}C$ NMR, what does the splitting pattern from the ORD of the signal at
about 24 tell you? Please be specific as to what the splitting pattern tells you.
7. In the $^1H$ NMR, what does the chemical shift of the signal at about 2.1 tell you?
Please be specific as to what the chemical shift tells you.
8. In the $^1H$ NMR, what does the integration of the signal at about 2.1 tell you?
Please be specific as to what the integration tells you.
9. In the $^1H$ NMR, what does the splitting pattern of the signal at about 2.1 tell
you? Please be specific as to what the splitting pattern tells you.
10. Please draw the molecule in the box.
Chem 322 - Graded Problem Set 6
Here are spectra for the unknown $C_8H_{10}O_2$. Please answer the questions on the
previous page.
