[jenny]

I have an 1H NMR Spectrum for my solid unknown. in CDCL3 solvent. I have figured it to be aromatic per tests  in lab. There is sextet connected to a doublet, maybe they are a multiplet, but they almost seem separate. the doublet is from 7.1-7.2 and the sextet 7.1-7.37.  I've assumed  a benzing ring. then I have a singlet slightly under 5.6  This is what throws me off. This category is vinyl, or poss. phenol.  I was assuming a phenol yet my m.p. is 93 degrees.  and it was insoluble to NaOH. *delete me* Just head me in the right direction because I am stuck. I was a fishlike odor, crystallike/dense. Any My IR spectrum has a peak at 3000

[Mitch]

Get a mass spec. Then you can try IR and you can still get a carbon.

[dexangeles]

an IR would help a lot

[jenny]

Thank you.  I do actually have an IR spectrum but I'm having a hard time understanding it. I went to a website link from a prev. message that you provided for IR spec. that helped.  I appreciate your effort, I will just keep trying.  Thx.  

[movies]

The IR peak around 3000 cm-1 probably corresponds to alkyl C-H stretch, but that doesn't tell you too much.  Do you have a weak/medium intensity IR peak around 3300?

Have you done any tests to tell if you have a nitrogen in your compound?

[jenny]

in lab we followed a flow chart and after all of the tests, I concluded that my solid is  aromatic. We were provided with IR spec (thin film) NMR 1H and 13C NMR.  I'm not sure what tests could have been performed for nitrogen.  I have an IR peak at 1600, 1500 and 1300. I just have to study this more to understand it. Sure is complicating. Thanks!!

[movies]

Those IR stretches sound like aromatics to me, they are at least in the right range for it.

How many carbons do you see in the ¹³C spectrum?  Do you have just a regular ¹³C or do you have DEPT as well?

[jenny]

In the 13C spec I have a carbon at 144, a triplet at 128.6, 128.4, and 126.4  and my solvent CDCl3 as a triplet at about 77ppm. I'm believe it is aromatic but I have to figure out the actual compound. The stretch on the 1H NMR at 5.58 is throwing me off.  I do appreciate your time in helping me. I have a huge test tomorrow trying to figure this out and learn the substitution and elimination reaction mechanisms has me overwhelmed. Thanks.

[movies]

Are those all of the peaks in the 13C and 1H NMRs?  The 1H NMR signal at ~5 is probably from a benzylic proton or something, although it is a little bit off for that even.

[jenny]

I finally figured it to be triphenylmethane. I had to figure out the ratio of carbons and protons. The singlet at 5.6ppm indicates the proton not attached to the benzene rings. I think. Thanks for helping me brainstorm.

[dexangeles]

I love figuring out compounds

1 suggestion: if u wanna know if there is a benzene ring, look for the overtone around 1600-2000, and their confirm it with the peaks at 600-1000.  This will tell u the type ob substitution of the ring, if any is present.