The proton NMR spectrum of compound E in the solvent CDCl3 is shown. The molecular formula of compound E is C9H10O2. [Figure of proton NMR spectrum, with relative integral values of 3, 2, 2, and 5 for peaks from right to left (low to high δ) respectively. Small peak at δ=0 is TMS.]

1. (a)Explain why CDCl3 is used as a solvent instead of CHCl3.[1]
2. (b)Explain why TMS is added to give the small peak at chemical shift δ = 0.[1]
3. (c)Compound E is hydrolysed by hot NaOH(aq), giving two organic products only. One of these products is ethanol. Name the functional group in compound E that is hydrolysed by hot NaOH(aq).[1]
4. (d)(i)Describe and explain the splitting patterns of the peaks at δ = 1.4 and δ = 4.3.[2]
5. (d)(ii)Each molecule of compound E contains five protons which give rise to the peaks between δ = 7.0 and δ = 8.5. Identify the functional group in compound E which contains these protons.[1]
6. (d)(iii)Give the structural formula of compound E.[1]
7. (e)The mass spectrum of compound E includes fragment ions with m/e values of 29 and 77. Give the formulae of these fragment ions.[2]

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