Note from JN: This third report (1c) is based on the same data as 1a and 1b.

It has the spectra attached but no

summary of the tests and spectra. It goes through the motions of analysing the data but does not really use it to
deduce the structure. In fact, the whole id rests on the smell of the compound and the fact that the melting point
of #88 is close to that of the proposed structure. The writer doesn’t even bother to go back and show that the
spec and chemical evidence is consistent with the proposed structure. Early in the report, she is suggesting that
#88 is probably a ketone while her final structure has an aldehyde group. Without the characteristic odour of
#88, she’d be lost. The start of the report was OK (although a bit terse – eg WHAT solubility tests showed that
#88 was a phenol?) but then it degenerated badly. I’d give it 8 or 9 out of 20. And that’s being generous.

Identification of Compound #88 (Individual unknown)

8.5/20
Mass of #88 is 152 (mass spectrum).
Solubility tests showed that #88 was a phenol.
The IR spectrum showed a C=O band at 1680.

C9H12O2 has ((9*2)+2-12)=4 degrees of unsaturation.

Unfortunately the presence of a benzene ring (4° unsat) and C=O (1°) requires 5° of unsat.
So this formula cannot be correct.
So assume C8H10O3

Chemical tests indicated that #88 is an aldehyde or a ketone (probably a ketone)

The 13C NMR spectrum contained 8 peaks corresponding to the 8 C in the molecular formula.
Only one peak (56ppm) has a chemical shift < 77ppm. So most C are sp2 (consistent with having
benzene ring (6C) and C=O) and only the one at 56ppm is sp3. The chemical shift of the sp3 C
suggests it’s next to something electronegative (probably O).
1
H NMR spectrum was analysed. The results of this analysis are outlined in the table below.

Chemical # of
multiplicity integration #H Conclusion/s
Shift neigbours

9.8 ppm singlet none 376 1H HC=O

7.4 ppm ???? mess ??? 700 2H 2 benzene H

7.0 ppm d 1 365 1H 1 benzene H

6.4 ppm s none 331 1H OH

4.0 ppm s none 1000 3H OCH3

8H

OH
Unknown #88 smelled like vanilla. 7.0 ppm
H3CO H
The active component of vanilla is vanillin, 4-hydroxy-3-
methoxybenzaldehyde. H H
The melting point of #88 was 80-81°C. 7.4 ppm
C
7.4 ppm
H O
The literature melting point of vanillin is 82-83°C.
possibility B1

So the structure of #88 is