NMR part 3

NMR Exam advice

Break it down: into the 4 points discussed in the previous pages, you can go through them one at a time
and get marks for each point you talk about.

Show them you can do NMR: the marks come from being able to pick out information, if you dont get
the final structure it doesnt really matter. Its a bit like calculation questions, you need to put down the
working and not just the final answer.

Do not be afraid to get things wrong: you might not get it right first time. Ive been doing these for years
and I still need to do it step by step. To get the final structure you need to put all the pieces of the jigsaw
together.

Write something down and work with it: once you have an answer you can see if it fits the spectrum,
which is a better starting point than a blank page.

Interpreting NMR Spectra

The structure that gave the above spectrum is:

In questions, you may or may not be given the structure, but you will probably be given additional
information such as mass spectroscopy, IR or the molecular formula.

So what can you tell from this spectrum?

Following our 4 main points:

Number of environments: from the spectrum there are clearly 3.

Look at the chemical shifts: around 1ppm is likely to be a CH3. One of the CH3s is next to a carbonyl,
which causes it to be shifted up the left a bit higher than normal. Its just a rough idea at this stage.

The peak ratios: no use here as we do not have an integral.

The splitting pattern: the CH3 next to the carbonyl is too far away from the other hydrogens to be split
i.e. the adjacent carbon has no hydrogens, therefore it is a single peak.

The CH2 is next to a CH3 so we use the n+1 rule to get 4 peaks, which is the peak at 2.5 ppm (quartet).

As there is a carbonyl next to a CH3 and the CH2 both there peaks are shifted to (2.1 and 2.5ppm).

The other CH3 is next to a CH2 therefore it must be split into 3 and comes around 1 ppm as it is a
normal CH3 with no shifting to the left.

Another example (difficult)

This time I wont tell you the structure but the molecule has the formula C4H10O. Also, the IR spectrum
shows an OH group at 3400 cm-1.

Lets apply the rules again:

There are 5 different regions.

CH3: around 1 ppm there are two regions that are likely to be 2 x CH3? There is a peak above 3.5 ppm,
split into more than 4 peaks, which is likely to be a CH, just from the ppm value.

OH: ALWAYS single peaks so that has to be the peak at 2.4ppm as its the only single peak.

3.6 ppm: has 6 peaks so the group must be next to 5 hydrogens.the only possible combination is
between a CH3 and a CH2.

CH3-?-CH2 (Ive put ? as we dont know what it is yet, only what it is split by)

But it must be a CH or a CH2. There is no other possibility!

1.5 ppm: has 5 peaks so it must be next to 4 hydrogens, which could be either 2 x CH 2 or one CH3 and one
CH.
1 ppm: a triplet so it has to be next to a CH2. The chemical shift is very low so must be a CH3. This gives us:

CH3-CH2

1.2 ppm: doublet therefore must be due to splitting from a CH, so this tells us there MUST be a CH in the
structure.

?-CH-? (I put ? as we dont know what is either side of it yet)

1.5ppm: split into 5 peaks, which could come from a CH and CH3 possibly. As we know there is a CH in the
molecule, this would be a logical guess.

CH3-?-CH (possibly)

The final structure

Start to draw what you know, this is where you get the marks. Remember to use the molecular formula
C4H10O as well.

From above we know that we have:

CH3-?-CH2

CH3-CH2

?-CH-?

CH3-?-CH (possibly)

People that are good at problem solving will find these easier, it really is trial and error, so have patience
and dont be afraid to draw several possibilities. You dont have to get it on your first attempt!

be careful with the fragments as sometimes you may draw the same part twice.

We can now draw:

CH3-?-CH2-CH3

We still need to fit in the CH somewhere, so it could replace the ?: CH3-CH-CH2-CH3

Try matching the structure to the spectrum. Does it match the splitting pattern? Yes it does. If it didnt
match, I could go back and amend the structure where necessary.

So we have used C4H9.we are only missing the OH. It has to go on to the CH as CH only has 3 bonds and
it needs 4:
 this is probably too difficult for most people to work out. I was just trying to show the thought
processes and problem solving mentality required. There are many far easier questions than this!