(a) Chlorobenzene and phenol both show a lack of reactivity towards reactants that cause the breaking of the C–X bond (X = Cl or OH). Explain why.

1. (a)Explain why. [3][3]
2. (b)When phenol is reacted with bromine dissolved in an inert solvent, two isomeric bromophenols, C6H4BrOH, are formed. Suggest structures for these products. Name each compound. [Figure: Box for structure 1] name: ..................................................... [Figure: Box for structure 2] name: ..................................................... [2][2]
3. (c)A student suggested that phenol can be prepared from benzene by the method shown. [Figure: Reaction scheme. Benzene (step 1) → nitrobenzene (NO₂ on ring) (step 2) → phenylamine (NH₂ on ring) (step 3) → diazonium salt (N₂⁺Cl⁻ on ring) at 5°C with NaNO₂(aq)/HCl(aq) (step 4) → phenol (OH on ring) and product K.]
4. (c)(i)Suggest reagents and conditions for each of the following steps. step 1 .......................................................................................................................................... step 2 .......................................................................................................................................... step 4 .......................................................................................................................................... [3][3]
5. (c)(ii)Deduce the structure for K and draw its structural formula in the box. [Figure: Box for structure K] [1][1]
6. (c)(iii)Name the mechanism for step 1. [1][1]
7. (c)(iv)Write an equation for step 2. Use [H] for the reducing agent in this equation. [1][1]