Can someone tell what the structure is?

[Brazen]

 

Chem: can someone tell what the structure is?

I see from IR spectrum that I have OH, C-H sp2, C-H sp3, C=C aromatic, C-O groups.

I see that I have 91, 134, and 149 fragments. I know that 91 is benzene-ch2+ fragment. I don't know what the 134 or 149 fragments are. I know that 149 is actually the whole structure.

 

Looking at proton and C13 NMR i see that i have OH, benzene, CH3, CH2, CH groups, not sure if i got all of those groups right.

 

I can't seem to get what the structure is.

Here is spectra:

http://i39.tinypic.com/zmjypd.png

http://i44.tinypic.com/wkst91.jpg

[hypervalent_iodine]

The mass spec should be a big help to you. Have you ever heard of the rule of 13? It's certainly not a fail safe, but it can be very helpful in determining your molecular formula. In this case you should be able to determine what it is fairly easily. You know you have at least one oxygen in your compound and figuring out if there is more than that should come to you quite quickly given the other information you have about the structure.

 

Have a look at the integration of your ¹H NMRand work out your ratios. From there it should become obvious what your groups are and how many of them you have and from there it's simply a matter of figuring out how they're connected. The way it fragments in the MS should give you some clue as to which isomer is more likely.

[Brazen]

Nope, never heard of the rule of 13, and ty for telling me about it helped. according to the rule of 13, if i did it correctly I have C10H13O, i calculated degree of unsaturation and i got 4.5, don't know what to make of the number. since it is not the whole number.

 

as for the integration if i did it correctly, i think that peak after seven have five H, peak before four have two H, peak before three have one hydrogen, peak right after one have two hydrogen, then the next three hydrogen and the last one H from OH.

 

Does this look right?

[hypervalent_iodine]

Remember that the m/z at 149, is the mass of your compound +1. You should get C10H14O, which then gives you a much more reasonable DBE.

 

Alright, so you can start to look at what fragments you can make and try to put them together. If you have a phenyl ring, what kind of substitution pattern do you think you have? Have a look at the splitting of your CH group and see what that tells you about adjacent carbon centres. You might also want to look at your carbon spectra to see what that's telling you.