Samples of phenol, C₆H₅OH, are reacted separately with sodium and with dilute nitric acid. [Figure 9.1]

1. (a)(i)Write the equation for the reaction of C₆H₅OH with Na.[1]
2. (a)(ii)Draw the structures of the two major isomeric organic products formed in the reaction of phenol with dilute HNO₃.[1]
3. (b)Salicylic acid can be synthesised from phenol. [Figure 9.2] One of the steps in this synthesis is the electrophilic substitution reaction of carbon dioxide with the phenoxide ion, C₆H₅O⁻. Complete the mechanism in Fig. 9.3 for the reaction of C₆H₅O⁻ with CO₂. Include all relevant curly arrows, dipoles and charges. Draw the structure of the organic intermediate. [Figure 9.3][3]
4. (c)(i)Some syntheses use Diels–Alder reactions, which normally involve a diene and an alkene reacting together to form a cyclohexene. Draw three curly arrows in Fig. 9.4 to complete the mechanism for the Diels–Alder reaction between buta-1,3-diene and ethene. [Figure 9.4][1]
5. (c)(ii)Another Diels–Alder reaction of buta-1,3-diene is shown in Fig. 9.5. Predict the product formed in this reaction. [Figure 9.5][1]

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