Any organic chemists want to take a look at this NMR problem?

[Anonymous No.8326125]

If you click this link:

http://www3.nd.edu/~smithgrp/structure/workbook.html

then click do the problems and then click problem 12 you will see the spectra. This is the structure I came up with. What do you think?

[chemfag No.8326141]

>>8326125
two doubles at 7.12 with total intensity of 1H must be due to cis,trans-isomers

[Anonymous No.8326149]

>>8326141
Why must they. A doublet of doublets could arise in plenty of other conditions too no? Wouldn't the H atom in OP strucutre that is para to the aldehyde give a doublet of doublets?

Also, do vinylic protons generally appear so far downfield?

[chemfag No.8326158]

>>8326149
my bad

[Anonymous No.8326164]

The signals at 11.4 and 10.2 I am fairly certain can be attributed to an acid (the fact that this proton exchanges is further evidence) and an aldehyde respectively. The other 3 protons all fall with in the aromatic shift range. It's the nitrogen atom and the final oxygen atom that are tripping me up.

[Anonymous No.8326165]

>>8326158
no prob friendo thanks for the reply

[chemfag No.8326179]

3 aromatic protons with neighbours
5 aromatic carbons
one aldehyde, one acid
seems about right
I dunno

[Anonymous No.8326876]

this problem is too hard for forchong