Chemistry 9701 · AS & A Level · Hydroxy compounds

Hydroxy compounds — practice question

(a)[3]

Chlorobenzene and phenol are both less reactive towards reagents that bring about breaking of the C-X bond (X = Cl or OH). Explain why.

(b)[2]

If phenol is treated with bromine in an inert solvent, two isomeric bromophenols, $\text{C}_6\text{H}_4\text{BrOH}$, are produced. Suggest structures for these compounds. Name each one.

(c(i))[3]

Suggest reagents and conditions for each of the following stages. step 1 step 2 step 4

(c(ii))[1]

Deduce the structure for $K$ 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. Use $[\text{H}]$ for the reducing agent in this equation.

Worked solution & mark scheme

This 11-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\text{C-X}$ bond is stronger in chlorobenzene/phenol

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