Chlorobenzene and phenol both show a lack of reactivity towards reactants that cause the breaking of the C–X bond (X = Cl or OH). A student suggested that phenol can be prepared from benzene by the method shown. [Figure showing reaction scheme: benzene → step 1 → nitrobenzene → step 2 → phenylamine → step 3 (NaNO₂(aq)/HCl(aq), 5°C) → K → step 4 → phenol]

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. [Two boxes for structure and two lines for name] [2][2]
3. (c)(i)Suggest reagents and conditions for each of the following steps. step 1 ...................................................................................................................................................................................................................... step 2 ...................................................................................................................................................................................................................... step 4 ...................................................................................................................................................................................................................... [3][3]
4. (c)(ii)Deduce the structure for K and draw its structural formula in the box. [1][1]
5. (c)(iii)Name the mechanism for step 1. [1][1]
6. (c)(iv)Write an equation for step 2. Use [H] for the reducing agent in this equation. [1][1]

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