The structure of phenylethanoic acid is shown. [Figure X.X showing the structure of phenylethanoic acid]

1. (a)Give the number of different peaks in the carbon-13 (¹³C) NMR spectrum of phenylethanoic acid.[1]
2. (b)Phenylethanoic acid, ethanol and phenol can all behave as acids. Compare and explain the relative acidities of these three compounds.[4]
3. (c)(i)Phenylethanoic acid can be synthesised using benzene as the starting material. In the first stage of this synthesis, benzene reacts with chloromethane in the presence of an AlCl₃ catalyst to form methylbenzene. Chloromethane reacts with AlCl₃ to form two ions. One of these is the carbocation ⁺CH₃. Write an equation for the reaction between chloromethane and AlCl₃.[1]
4. (c)(ii)Draw the mechanism of the reaction between benzene and ⁺CH₃. Include all relevant curly arrows, charges and the structure of the intermediate.[3]
5. (d)(i)A three-step synthesis of phenylethanoic acid from methylbenzene is shown. [Flowchart showing synthesis of phenylethanoic acid from methylbenzene] State reagents and conditions for step 1.[1]
6. (d)(ii)Suggest the structure of compound Q.[1]
7. (d)(iii)State reagents and conditions for steps 2 and 3.[2]
8. (d)(iv)Draw the structure of an organic by-product that forms in step 1.[1]

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