A2 Chem Help Please!!! 6CH04/01 URGENT HELP REQUIRED

I am stuck on the last question of the January 2010 Unit 4 Chemistry Paper (EDEXCEL) It is question 26 showing two NMR Spectra and I am being asked to identify the structures of X and Y. I would really appreciate any help! I attempted the question and understood the first bit but the splitting patterns that I got don't match with the MS :/ Does it matter what order it is in?

I am stuck on the last question of the January 2010 Unit 4 Chemistry Paper (EDEXCEL) It is question 26 showing two NMR Spectra and I am being asked to identify the structures of X and Y. I would really appreciate any help! I attempted the question and understood the first bit but the splitting patterns that I got don't match with the MS :/ Does it matter what order it is in?

It would help if you posted your working and the question, if possible. Do you know how to link to an image or attach one?

http://qualifications.pearson.com/content/dam/pdf/A%20Level/Chemistry/2013/Exam%20materials/6CH04_01_que_20100127.pdf

This is the link, it's the very last question (Q26). Hope this helps

This question is about compounds X, C4H10O, and Y, C4H8O.
(a) Compound X, C4H10O, can be oxidized to compound Y, C4H8O.

The IR of X suggests hydrogen bonded OH group, i.e. we are dealing with an alcohol.

NMR X:

multiplet 3.7
singlet 2.4
multiplet 1.5
doublet 1.2
triplet 0.9

five different environments
primary alcohol
CH₃CH₂CH₂CH₂OH = five environments

secondary alcohol
CH₃CHOHCH₂CH₃ = five environments

tertiary alcohol can't be oxidised

So we look at the splitting patterns:
primary alcohol
CH₃CH₂CH₂CH₂OH

In order (left to right)
CH₃ gives a triplet (adjacent to CH2)
CH₂ gives a triplet of quartets (nasty multiplet)
CH₂ gives a triplet of triplets (nasty multiplet)
CH₂ gives a triplet (not split by OH)
OH gives a singlet (not split by CH2)

secondary alcohol
CH₃CHOHCH₂CH₃

CH₃ gives a doublet (adjacent to CH)
CH gives a triplet of quartets (nasty multiplet)
CH₂ gives a doublet of quartets (nasty multiplet)
CH₃ gives a triplet
OH gives a singlet (not split by CH)

Hence spectrum given is the secondary alcohol.

On oxidation the secondary alcohol would produce a ketone, butan-2-one

CH₃COCH₂CH₃

NMR of this would expect:
CH₃ gives a singlet
CH₂ gives quartet (adjacent to CH3)
CH₃ gives a triplet

Which matches perfectly the spectrum given.

The last stage is to show that the chemical shift of each signal corresponds to its data book value.