Benzoyl chloride, C6H5COCl, can be made from ethyl benzene in a two-step process. A reaction scheme is shown. [Figure showing ethyl benzene --step 1--> compound M --step 2--> benzoyl chloride]

1. (a)(i)Draw the intermediate organic compound M in the box. [Figure with empty box for compound M][1]
2. (a)(ii)Suggest suitable reagents and conditions for step 1 and step 2. step 1 step 2[2]
3. (a)(iii)Identify the type of reaction in step 1 and step 2. step 1 step 2[2]
4. (b)C6H5COCl reacts with phenol, C6H5OH, to give the ester phenyl benzoate, C6H5COOC6H5. An incomplete description of the mechanism of this reaction is shown in Fig. 9.1. [Figure 9.1 showing box one (reactants), box two (intermediate), box three (products)]
5. (b)(i)Complete the mechanism in Fig. 9.1 and include: • all relevant dipoles (δ+ and δ–) and full electric charges (+ and –) on the species in box one and in box two • all relevant lone pairs on the species in box one and in box two • all relevant curly arrows to show the movement of electron pairs in box one and in box two • the formula of the second product in box three.[4]
6. (b)(ii)Name this mechanism.[1]
7. (c)Benzoyl chloride, chlorobenzene and chloroethane differ in their rates of hydrolysis when each compound is added separately to water at 25°C. Suggest the relative ease of hydrolysis of these three compounds. Explain your answer. hardest to hydrolyse explanation easiest to hydrolyse[3]

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