In the MS, the molecular ion occurs at m/z = 60 indicating the MW = 60
g / mol.
The IR shows an -OH (3350 cm-1) and C-O (1075 cm-1)
but no C=O (around 1700 cm-1), or C=C (around 1600 cm-1)
13 C-nmr shows 3 types of C, including a deshielded C (69 ppm), and 2 other
hydrocarbon C (27 and 10 ppm)
H-nmr
d/ppm
multiplicity
integration
assignment
3.6
triplet
2
CH2 coupled to 2H, deshielded
2.3
singlet
1
isolated H (-OH ?)
1.6
multiplet
2
CH2 coupled to many H
0.9
triplet
3
CH3 coupled to 2H
From the data, we can get a molecular formula of C3H8O
which matches the MW = 60 g / mol
This has an IHD = O, so no p bonds or rings.
The following pieces can be deduced from the spectra -OH, -CH3,
and 2 different -CH2-.
Given these pieces, we can start to fit them together based on the coupling
patterns and chemical shifts as: -CH2-OH and CH3-CH2-.
There is only one way they can all fit together:
Checking the H-nmr, the middle -CH2- is actually six lines since
it has a total of 5 similar neighbours. The -OH deshields the other
-CH2- but does not couple to it.
