Question

Need some guidance on this spectroscopy problem from my MCAT book

Answer 1

https://chemistry.stackexchange.com/

Answer 2

(sorry if it's hard to read, the compound formula is C5H10O2)

my attempt: judging by the IR spectrum there's an -OH group and a C=O double bond, judging by the 1H NMR there's a few singlets that are split into triplets, not sure how to integrate this information

Answer 3

thanks hero, will try there too

Answer 4

Ugh why don't they just tell you how many hydrogens per peak in the HNMR

But the compound has one element of unsaturation and it does seem to be a carbonyl group.
Also since there are 2 oxygen's, I think we have an ether
carbonyl with an ether so could possibly be an ester, but would have to see the possibilities

But I was too lazy to learn how to integrate HNMR since they always told us how many hydrogens per peak so unless I know that I guess that's all I can help for now

I feel like that the multiplets and how they're deshielded (and 1100 band), we probably have an ether with an ethyl group and then a carbon bonded to another carbon which is the carbonyl and has a methyl substituent
This is what I was thinking so far



Anyway I hope some of what I said helps you figure it out and I'm too lazy to make my response seem neat

Actually just realized that it can't be an ether, since it has to be an alcohol and since it's at 3000 that means it's a carboxylic acid so that means COOH on one side and then we have to figure out the carbon chain



But wait if it was a carboxylic acid then how come we don't have a peak at 12 on the HNMR?? And if it was an alcohol then it can't be at 3000. It would have been at 3300 cm^-1

I hope I didn't confuse you more and if you find out anything more do let me know :b