What's a stable structure for C9H10O3 given the IR and NMR data below?

Question

IR: 2300-3200, 1710, 1600;
H1-NMR: 2.9--2H--triplet, 4.1--2H triplet, 6.9--3H--(crazy quartet looking), 7.1--2H--(crazy triplet looking), 11.7--1H--singlet/broad.

I think that is a 1,4-disubstituted benzene ring (C6H4) based on the two triplets at 2.9 and 4.1 and that there's a COOH group somewhere, given the IR. The crazies around 7 are screwing with my head. I've been doing fairly well with this NMR stuff otherwise :(

Please help with the rest of the problem!

Anonymous · Accepted Answer

It's a monosubstituted benzene ring, with C6H5-O-CH2-CH2-COOH.

The two triplets are the CH2 groups, and the craziness is from the coupling on the benzene ring. Their values are more consistent with ring-H, whereas the 2.9 and 4.1 values are more consistent with CH2 groups that are heavily deshielded by electronegative atoms (the oxygens).

Hope that helps!

tostado · Answer

Monosubstituted Benzene Nmr

? · Answer

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RE:
What&#39;s a stable structure for C9H10O3 given the IR and NMR data below?
IR: 2300-3200, 1710, 1600;
H1-NMR: 2.9--2H--triplet, 4.1--2H triplet, 6.9--3H--(crazy quartet looking), 7.1--2H--(crazy triplet looking), 11.7--1H--singlet/broad.

I think that is a 1,4-disubstituted benzene ring (C6H4) based on the two triplets at 2.9 and 4.1 and that there&#39;s a COOH group...

Anonymous · Answer

For the best answers, search on this site https://shorturl.im/avGau

This looks like 2-bromo-2-pentene. Can't tell from the information given whether it's E or Z.

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What's a stable structure for C9H10O3 given the IR and NMR data below?

4 Answers