[_fluffychicken]

An aromatic amine with a molecular formula of C12H17NO gives the following IR and NMR data. Predict and draw the structure of this compound. You can ignore the fingerprint region and the impurity identified in this IR. The 4H multiplet (peak f and g) in the 1H NMR is two overlapping peaks and each peak has an integration of 2H.


What I have deduced is that this is a phenol with the remaining 6 carbons and the amine group at the para position. I am having a hard time elucidating the structure especially the proton NMR peaks at around 2.7, 1.5, and 1.2. I also know that there is 1 methyl group at the end because of the 3H with peak at 0.9 ppm. Maybe there is also an alkene group in the carbon chain para to the phenol since the degree of unsaturation is 5. Please help me deduce the structure, thanks.

Edit: I realized that this cannot be a phenol, an -NH2 may be attached to the benzene ring and para to that, there is maybe a carbonyl group with the remaining carbons.

[Babcock_Hall]

If you think you have a carbonyl group, can you rule out any carbonyl-containing functional groups?

[wildfyr]

The two peaks above 3200 cm^-1 are indicative of an amine.