Task 1: 3

I think that based on the data I have analyzed the correct structure is structure d. I think this because
the molecular Mass of structure d is 74 g mol-1 and the M+ ion is 74 m/z. There are fragments on the
mass spectrum graph, there is one at 59 m/z which is CHOHCH3, there is another peak at 29 m/z
which is CH3CH2 and both of these fragments add together to make 74 m/z and to make the formula
CH3CH2 + CHOHCH3 = CH3CH2CHOHCH3 which is why I can say it is structure d. There is a peak at
M+=18 m/z which is due to the loss of a water molecule as the structure is an alcohol.

Structure d has 4 carbon environments which is required by the 13C NMR. Structure d also has 13C
peaks at 22 and 36ppm which is saturated alkanes such as CH fragments and a CH3- fragment which
is a component in this structure, there is also another peak at 70ppm which is C-OH, and a peak at
10 which is CH3CH2-. All of these fragments are necessary for the structure and combine to from
structure d (CH3CH2 + C-OH + CH + CH3 = CH3CH2CHOHCH3).

Structure D has a sharp medium strong O-H peak as required by the Infrared spectrum which is
located at about 3400 cm-1, this is a necessary component for an alcohol. The IR Spectrum also tells
us that there is a Sharp medium peak at 1380 cm-1 which is a C-O fragment.

The combined spectrum tells us that the sample is an alcohol and this structure is a secondary
alcohol.

The sample can’t be structure A because the mass of structure a is only 73 g mol-1 and it has nitrogen
present which the mass spectrum tells as cant be possible. The IR spectrum tells us that there must
be an O-H fragment in the sample which molecule a and b don’t have so it cant be them. The 13C
NMR tells us that there is 4 carbon environments and Molecule B has 2, C has 3 and e has 3 meaning
that they can’t be the structure. The MS also tells us that the Molecular mass is 74 m/z and A is 73, b
is 58, C is 46 which means they can’t be the structure. The IR spectrum and the 13C NMR don’t show
any double bonds meaning it can b E. 13C also doesn’t show any N-H peaks meaning it cant be A. MS
doesn’t show C=O peaks meaning it cant be E. IR shows C-H sharp peak which would mean molecule
C is to small
Task 3: 3

I think based on the data I have analyzed the correct structure is structure C. I think this because the
molecular mass of structure C is 46 g mol-1 and the Mass spectrum tells us the M+ ion is 46 m/z.
There are fragments on the Mass Spectrum graph, one is at 15 m/z which is CH3 and another at 31
m/z which is CH2OH which add together to make 46 m/z and the structure CH3CH2OH which is
structure C.

Structure C has 2 Carbon environments which is required by the 13C NMR. Structure C also has peaks
at 59 ppm which is C-OH bond, -CH2- at 19 ppm. All of these fragments are necessary for the
structure C and add to form structure C.

Structure C has a sharp medium strong O-H peak at 3300 cm-1. There is also a C-O Peak at 1060 cm-1
which is in the structure C.

The combined spectrum tells us that the sample is a primary alcohol.

The sample can’t be structure A because there are Nitrogen’s present which the Mass Spectrum tells
us there cant be. The IR spectrum tells us there are no double bonds so it can’t be E. The Mass
Spectrum tells us the Molecular mass is 46 m/z and none of the other structures have this mass. The
IR spectrum tells us there is a O-H bond which A and b don’t have. The 13C NMR tells us there are 2
Carbon environments and A has 3, d has 4, e has 3 and f has 3. There is no CH3CH2 as needed by the
spectrum in f.