Compound X is made from benzene by the route shown in Fig. 9.1. [Figure 9.1]

1. (a)Describe the bonding in benzene, C6H6. Your answer should include: • the hybridisation of the six carbon atoms • the types of bond between the carbon atoms • the orbitals that overlap to produce the bonds between the carbon atoms • the type of bond between the carbon atoms and the hydrogen atoms • the orbitals that overlap to produce the bonds between the carbon atoms and the hydrogen atoms.[3]
2. (b)Describe the reagents and conditions required for step 1 in Fig. 9.1.[1]
3. (c)In step 1 of Fig. 9.1 benzene reacts with +CH3. Complete Fig. 9.2 to show the mechanism for this reaction, including: • the movement of electron pairs using curly arrows • the structure of the intermediate involved. [Figure 9.2][3]
4. (d)Describe the reagents and conditions required for step 2 of Fig. 9.1.[2]
5. (e)Identify the reagents required for step 3 of Fig. 9.1. Compound W is the product of this step.[1]
6. (f)Name compound W.[1]
7. (g)The reagents commonly used for step 4 will not reduce the –COOH group. Identify the reagents and conditions required for step 4 of Fig. 9.1.[1]
8. (h)Benzene can also be used as a starting material to make compound Y. [compound Y structure] Describe how the route described in Fig. 9.1 (repeated below) can be changed to give compound Y instead of compound X. Explain your answer. [Figure 9.1 repeated][2]

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