The structural and displayed formulae of three aromatic compounds, A, B and C, are shown in Fig. 7.1. [Figure 7.1] Compare the relative acidities of A, B and C. > most acidic least acidic Explain your answer. [3]

1. (a)The structural and displayed formulae of three aromatic compounds, A, B and C, are shown in Fig. 7.1. C₆H₅CH₂CH₂COOH HO O CH₃C₆H₄OH OH CHCH₂CHCICO₂H HO Cl A B C Fig. 7.1 Compare the relative acidities of A, B and C. > most acidic least acidic Explain your answer. [3][3]
2. (b)Methylbenzene, C₆H₅CH₃, can be made from benzene by an electrophilic substitution reaction.
3. (b)(i)Identify a compound that reacts with benzene to form methylbenzene. Identify the catalyst used. compound ............................................................................................................................... catalyst .................................................................................................................................... [1][1]
4. (b)(ii)The first step in the reaction is the generation of the CH₃⁺ electrophile. Write an equation for the reaction that generates this electrophile. [1][1]
5. (b)(iii)Describe the mechanism for the reaction between benzene and the CH₃⁺ electrophile. Include all relevant curly arrows and charges. [Figure 7.2: Benzene reacting with CH3+] [3][3]
6. (b)(iv)Identify a suitable reagent to oxidise methylbenzene to benzoic acid, C₆H₅COOH. Write an equation for this reaction using [O] to represent one atom of oxygen from the oxidising agent. reagent .................................................................................................................................... equation .................................................................................................................................... [2][2]
7. (b)(v)Methylbenzene and benzoic acid are both nitrated with a mixture of concentrated nitric acid and sulfuric acid to give mononitrated products. The structural formulae of these products are CH₃C₆H₄NO₂ and HOOCC₆H₄NO₂ respectively. Draw the structures of these two products. [1][1]
8. (c)A reaction scheme is shown in Fig. 7.2. [Figure 7.2] reaction 1 CH₃C₆H₄NO₂ CH₃C₆H₄NH₂ reaction 2 reaction 3 CH₃C₆H₄OH CH₃C₆H₄N₂⁺Cl⁻ reaction 4 dye molecule Y Fig. 7.2
9. (c)(i)Describe the reagents and conditions to produce CH₃C₆H₄N₂⁺Cl⁻ from CH₃C₆H₄NH₂ in reaction 2. reagents .................................................................................................................................... conditions .................................................................................................................................... [1][1]
10. (c)(ii)Describe how CH₃C₆H₄OH can be produced from CH₃C₆H₄N₂⁺Cl⁻ in reaction 3. [1][1]
11. (c)(iii)Draw the structure of the dye molecule Y formed when CH₃C₆H₄N₂⁺Cl⁻ and CH₃C₆H₄OH react together in reaction 4. Describe the conditions for this reaction. structure conditions .................................................................................................................................... [2][2]

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