(a) Benzene reacts with D in the presence of a suitable catalyst to give cumene and non-organic product E. This is an electrophilic substitution reaction. [Figure for reaction scheme]

1. (a)(i)Name the reactant D and the non-organic product E. D E[2]
2. (a)(ii)Give the name of the type of aromatic electrophilic substitution reaction taking place.[1]
3. (b)(i)Cumene undergoes substitution reactions with chlorine to give several different isomeric products with the formula C9H₁₁Cl. The substitution can occur in the aromatic ring or in the side-chain of cumene. Describe the conditions that are used to ensure substitution takes place only in the aromatic ring.[1]
4. (b)(ii)Draw the structures of the two major isomeric products of the reaction, formula C9H₁₁Cl, when substitution takes place in the aromatic ring.[1]
5. (b)(iii)Describe the conditions that are used to ensure substitution takes place only in the side-chain.[1]
6. (b)(iv)Draw the structures of two isomeric products of the reaction, formula C9H₁₁Cl, when substitution takes place in the side-chain.[1]
7. (c)Complete the following table to show the structures of the organic products formed when cumene reacts with each reagent. reagent | structure of organic product --- | --- hot KMnO4(aq) | H₂ + Ni, high pressure | [2]
8. (d)Cumene can be nitrated using a mixture of concentrated nitric and sulfuric acids. The mechanism for this reaction is similar to the mechanism for the nitration of benzene. Complete the mechanism for this reaction. Include all relevant charges and curly arrows showing the movement of electron pairs. Draw the structure of the intermediate. You do not need to draw the products. [Figure for mechanism][4]

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