This question is about compound T, CₓH_yO₂. (a) Part of the mass spectrum of T is shown. The peak heights of the M and M+1 peaks are 33.9 and 3.4 respectively. [Figure: Mass spectrum of T]

1. (a)(i)Calculate x, the number of carbon atoms present in T.[2]
2. (a)(ii)Deduce the molecular formula of T.[1]
3. (a)(iii)The mass spectrum has a peak at m/e = 119. Identify the fragment lost from T to produce this peak.[1]
4. (b)The infra-red spectrum of T is shown. [Figure: IR spectrum of T with peaks V and W marked] Identify the type of bond responsible for each of the peaks V and W. Use the Data Booklet to help you. V W[1]
5. (c)(i)Complete the table for the proton NMR spectrum of T. Use the Data Booklet to help you. δ/ppm type of proton 3.9 7.2–7.9[1]
6. (c)(ii)The peak at δ = 2.4 ppm is due to a proton attached to a saturated carbon atom. State the two possible types of proton.[1]
7. (c)(iii)Adding D₂O to T does not change its proton NMR spectrum. What does this tell you about the functional groups present in T?[1]
8. (d)Use the information to draw two possible structures of T which are functional group isomers of each other.[2]

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