Phenol, C₆H₅OH, is a weak acid.

1. (a)Phenol can be made from phenylamine, C₆H₅NH₂. Give the reagents and conditions for this reaction.[2]
2. (b)Phenol reacts with dilute aqueous nitric acid under room conditions to give a mixture of two isomeric products with molecular formula C₆H₅NO₃. Use the Data Booklet to draw the structural formulae of these two products in the boxes and name each product. name name[2]
3. (c)(i)Phenol reacts with an excess of aqueous bromine. Draw and name the organic product of this reaction in the box. name[2]
4. (c)(ii)Describe two visual observations that can be made when phenol reacts with an excess of aqueous bromine. observation 1 observation 2[1]
5. (d)Write an equation for a neutralisation reaction in which phenol behaves as an acid.[1]
6. (e)Water, phenol and ethanol can all behave as acids. Place these three compounds in order of acidity, starting with the most acidic. Explain your answer. most acidic > > least acidic[3]

This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.