(a)[3]
Chlorobenzene and phenol are both unreactive towards reagents that bring about cleavage of the C-X bond (X = Cl or OH). Explain why.
(b)[2]
Phenol is reacted with bromine in an inert solvent, giving two isomeric bromophenols, $\text{C}_6\text{H}_4\text{BrOH}$. Suggest structures for these products and name each compound.
(c(i))[3]
Suggest reagents and conditions for step 1, step 2 and step 4.
(c(ii))[1]
Deduce the structure of K and draw its structural formula in the box.
(c(iii))[1]
Name the mechanism for step 1.
(c(iv))[1]
Write an equation for step 2. In this equation, use [H] for the reducing agent.