We have to identify an unknown compund (C9H12) and I want to believe it\'s Cumen

Question

We have to identify an unknown compund (C9H12) and I want to believe it's Cumene but the IR and NMR don't really look like anything for C9H12. I am really confused and the professor said that the readings both looked like the compound, so what could it be if it is not Cumene?? The 4 numbers from L-R are 2963, 1764, 1680,1605 before the fingerprint region. NMR is below, I believe you can see that. Thank you!

We have to identify an unknown compound (C9H12) and I want to believe it's Cumene but the IR and NMR don't really look like anything for C9H12. I am really confused and the professor said that the readings both looked like the compound, so what could it be if it is not Cumene?? The 4 numbers from L-R are 2963, 1764, 1680, 1605 before the fingerprint region.

Explanation / Answer

The given compound is not C9H12.

Look at the IR, there is a peak at 1764, it is characteristic of CO (carbonyl) peak, so the compound contains a keto group or aldehyde group.

Next look at the proton NMR. it has doublet and then another two singlet, one multiplet. if cumene is present then you wont see two doublets, you can see one doublet and one heptet. but here it showed clear doublets, and two singelts, and one multiplet so hundred precent the given spectra is not cumene.

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