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Problem 2

Formula: C7H14O

Spectroscopy Reference

IR spectrum NMR spectrum

Rule 2, omit O, gives C7H14
7 - 14/2 + 1 = 1 degree of unsaturation.
Look for 1 pi bond or aliphatic ring.

The band at 1718 indicates a carbonyl, probably a ketone. The bands at 3000-2850 indicate C-H alkane stretches.

Structure answer

This is the structure. See if you can assign the peaks on your own.

NMR answer

Note that D and E are chemically similar enough that their peaks overlap.

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