Benzene, C₆H₆, is an aromatic molecule.

1. (a)State the C–C–C bond angle and the hybridisation shown by the carbon atoms in benzene. bond angle hybridisation[1]
2. (b)(i)Benzene reacts with chloroethane in the presence of a catalyst. The reaction mechanism is called electrophilic substitution. The first step in the reaction is the generation of the ⁺CH₂CH₃ electrophile. Write an equation for the reaction that generates this electrophile.[1]
3. (b)(ii)Describe the mechanism for the reaction between benzene and the ⁺CH₂CH₃ electrophile. Include all relevant curly arrows and charges. [Figure with benzene and electrophile to complete intermediate and products][3]
4. (c)(i)Chlorobenzene and chloroethane have different reactivities in nucleophilic substitution reactions. Identify a suitable reagent to illustrate this difference in reactivity. The reagent chosen should give visibly different results with chlorobenzene and chloroethane.[1]
5. (c)(ii)Write equations to describe any reactions that occur.[1]
6. (c)(iii)Explain the difference in the reactivities of chlorobenzene and chloroethane in nucleophilic substitution reactions.[1]

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