The Student Room Group

NMR question

The infrared spectrum (Figure 1) and the 1H NMR spectrum (Figure 2) of compound R with molecular formula C6H14O are shown.
Figure 1

Figure 2

The relative integration values for the NMR peaks are shown on Figure 2.
Deduce the structure of compound R by analysing Figure 1 and Figure 2.
Explain each stage in your deductions.

I've read the mark scheme and still don't quite understand the parts about CH2 and CH3. Can somebody explain this for me please?
(edited 1 year ago)
Original post by bangdula
The infrared spectrum (Figure 1) and the 1H NMR spectrum (Figure 2) of compound R with molecular formula C6H14O are shown.
Figure 1

Figure 2

The relative integration values for the NMR peaks are shown on Figure 2.
Deduce the structure of compound R by analysing Figure 1 and Figure 2.
Explain each stage in your deductions.

I've read the mark scheme and still don't quite understand the parts about CH2 and CH3. Can somebody explain this for me please?

Sure, I’ll attempt to explain… once I can actually see the spectra and the mark scheme
Original post by TypicalNerd
Sure, I’ll attempt to explain… once I can actually see the spectra and the mark scheme

Not my post but I'm stuck on this question too and i'd really appreciate some help :smile:
https://learnah.org/question/aqa-specimen-paper-2-q10/
Original post by anon25x
Not my post but I'm stuck on this question too and i'd really appreciate some help :smile:
https://learnah.org/question/aqa-specimen-paper-2-q10/


First and foremost, they have given you the IR spectrum of the compound.

Use the wavenumber ranges where the transmittance is low and the data book values that match these ranges to identify the types of bond contained within the compound. You will likely get a few marks for starting there.

After that, I’ll talk you through how to analyse the nmr spectrum.
Original post by TypicalNerd
First and foremost, they have given you the IR spectrum of the compound.

Use the wavenumber ranges where the transmittance is low and the data book values that match these ranges to identify the types of bond contained within the compound. You will likely get a few marks for starting there.

After that, I’ll talk you through how to analyse the nmr spectrum.


I managed to do the empirical formula bit and got 4:1:3:6
And identified theres 4 peaks so 4 different hydrogen environments and that a triplet and a quartet means there's CH2CH3
But I don't understand that if I put a value slightly different to 3360 cm-1 for the alcohol would I still get the mark e.g 3400cm-1 as that's where it looks like the peak is ?
Original post by anon25x
I managed to do the empirical formula bit and got 4:1:3:6
And identified theres 4 peaks so 4 different hydrogen environments and that a triplet and a quartet means there's CH2CH3
But I don't understand that if I put a value slightly different to 3360 cm-1 for the alcohol would I still get the mark e.g 3400cm-1 as that's where it looks like the peak is ?

Considering it’s a specimen paper, the MS is going to be much less in depth than one produced for an actual exam sitting.

The chances are they would be more lenient than specified and you’d still get your mark for the wavenumber value you have stated, especially since it is within the wavenumber range stated for the O-H bond in the data book.

If you are familiar with the n+1 rule:

A triplet implies a peak is adjacent to 2 non-equivalent hydrogens, since it is split 3 times and so n+1 = 3, so n = 2.

A quartet implies a peak is adjacent to 3 non-equivalent hydrogens, since it is split 4 times and so n+1 = 4, so n = 3.

Next, look at the shift values of the peaks and see what they correspond to.

The quartet is around 1.5 ppm and the triplet is around 0.9 ppm. What does that imply the possible environments may be and what does the ratio you established suggest about the numbers of these environments?
(edited 1 year ago)

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