1H NMR & IR : unknown structure determination

[dead actor]

Hi all,

I was struggling in solving this question which is a part of a practice exam, and I need you to be patient with me and teach me step by step how to figure out the structure and how to read and analyze the spectra.

I attached the two 1H NMR & IR spectra so you will be able to know what structure I'm talking about.

I started with finding the saturation number which is 5 so I know that at least I have aromatic ring and double bond(s)
I predicted the compound to have an ester but I'm not sur.

please help me to know what is this structure.
The molecular formula is C8H8O2

and all the peaks and ppm readings are in the attached figures.

http://img257.imageshack....mg257/3670/scan0004t.jpg

http://img405.imageshack....g405/4821/scan0003aa.jpg

http://img213.imageshack....mg213/8636/scan0005j.jpg


thanks all.

[chemisttree]

Hi all,

I was struggling in solving this question which is a part of a practice exam, and I need you to be patient with me and teach me step by step how to figure out the structure and how to read and analyze the spectra.

I attached the two 1H NMR & IR spectra so you will be able to know what structure I'm talking about.

I started with finding the saturation number which is 5 so I know that at least I have aromatic ring and double bond(s)
I predicted the compound to have an ester but I'm not sur.

Right. You note that there is the carbonyl stretch in the IR but no corresponding OH group in either the NMR or the IR spectrum.

What might the 'R' group be in that ester? Any hint from the NMR spectrum? What group gives a singlet at ~3.7-3.8ppm that integrates to 3H? (your spectrum is integrated to peak height... it should be by integrated by area in the future)
All of the aromatic protons are accounted for. What type of substitution do the integration and splitting patterns indicate? Mono-substitution? Di-substitution?

[dead actor]

Right. You note that there is the carbonyl stretch in the IR but no corresponding OH group in either the NMR or the IR spectrum.

What might the 'R' group be in that ester? Any hint from the NMR spectrum? What group gives a singlet at ~3.7-3.8ppm that integrates to 3H? (your spectrum is integrated to peak height... it should be by integrated by area in the future)
All of the aromatic protons are accounted for. What type of substitution do the integration and splitting patterns indicate? Mono-substitution? Di-substitution?
I have three signals in the aromatic region that accounts for 5 hydrogens. There is only one more signal of three hydrogens. It must be a CH3 group. so this gives me
C6H5 + CO2 + CH3?
so I'm only thinking of C6H5-COOCH3 which is a methyle benzoate
http://images.absoluteastronomy.com/images/encyclopediaimages/m/me/methyl_benzoate.png

right?

I don't know what type of subsitiution I have, may be a di ?

[chemisttree]

Right. It is a mono-substituted aromatic ring. There are three types of protons in that ring, 2 ortho, 2 meta and and a single para (think of the symmetry). The three signals in the NMR should integrate 2:2:1 (edit: or was that 2:1:2?) by area (not peak ht as they are split like crazy).

[nimmysnv]

Right. It is a mono-substituted aromatic ring. There are three types of protons in that ring, 2 ortho, 2 meta and and a single para (think of the symmetry). The three signals in the NMR should integrate 2:2:1 (edit: or was that 2:1:2?) by area (not peak ht as they are split like crazy).

I was actually little bit confused about this but you cleared my confussion by letting this know to me as, I will search about this little more for my further knowledge.

Thanks!