[caliheat]

Hi everyone, I have a molecular formula C₁₁H₁₄O₂ and the following ¹H NMR data:
1.0 (3H)
1.5 (2H)
1.7 (2H)
4.4 (2H)
7.4-8.1 (5H)

I was thinking it should be something like this: (butyl-benzoate)
because the structure fits, except for the benzyl group with 3 equivalent H groups. My question is, how can you get a 5 equivalent proton (5H) group? I can't think of any structure and I can't find it online. Thanks!

[Corribus]

The range of values for the 5H peak suggest they're not all equivalent and that it's multiple peaks overlapping.

[caliheat]

Oh ok, so then that group should be the benzene ring since there are 5 protons (non-equivalent)and the signals lie in the 6.0-9.0 Aromatic hydrogen range?

[Corribus]

Yes

[caliheat]

Great thanks, I was just confused because I thought that the (nH) (where n is an integer) group meant that they were all equivalent, but now I will check if there are multiple values within the range.

There is one more I am having trouble with. The molecular formula is C₆H₁₄O. The ¹³C NMR data is given:
3 peaks, one at ~10ppm, one at ~20ppm and one at ~70ppm.

I know that means there are 3 non-equivalent carbon groups but I can't find the proper structure. The degree of unsaturation is ((2*6+2)-14)/2 = 0 which means it only has single bonds. The closest I have gotten is this: (diisopropyl ether), but due to symmetry I believe it only has 2 non-equivalent C groups. I have also found structures with 4 non-equivalent C groups, but not 3 .

[Corribus]

Great thanks, I was just confused because I thought that the (nH) (where n is an integer) group meant that they were all equivalent, but now I will check if there are multiple values within the range.

The n refers to the integration value.  If it's a single peak, this will usually mean the number of equivalent protons.  However if the integration is over a collection of overlapping peaks, then they aren't necessarily equivalent.

I know that means there are 3 non-equivalent carbon groups but I can't find the proper structure. The degree of unsaturation is ((2*6+2)-14)/2 = 0 which means it only has single bonds. The closest I have gotten is this: (diisopropyl ether), but due to symmetry I believe it only has 2 non-equivalent C groups. I have also found structures with 4 non-equivalent C groups, but not 3 .

I think ether might be the right direction.  Can you think of another simple one that fits the formula?