Phenol is an important industrial chemical used in the manufacture of dyestuff and other substances.

1. (a)Suggest two different substances that react with phenol to produce potassium phenoxide, C6H5O⁻K⁺. Identify the second product formed in each case.[3]
2. (b)(i)On the diagram of Sudan I above circle the bond or bonds that make this substance a dyestuff.[1]
3. (b)(ii)Describe how Sudan I can be made using phenylamine and 2-naphthol as the organic starting materials.[3]
4. (c)(i)Describe the conditions used for the nitration of phenol. Explain how these conditions show phenol to be more reactive than benzene.[2]
5. (c)(ii)Suggest why phenol is more reactive than benzene.[1]
6. (c)(iii)Complete the mechanism for the nitration of phenol to form 2-nitrophenol. You should assume that the mechanism is the same as that for the nitration of benzene. • Include all relevant charges and curly arrows to show the movement of electron pairs. • Draw the structure of the intermediate. You do not need to draw the products.[3]
7. (c)(iv)Name the isomer of 2-nitrophenol which is also a major product of this reaction.[1]

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.