Compare the relative acid strengths of benzoic acid ($\text{C}_6\text{H}_5\text{COOH}$), phenylmethanol ($\text{C}_6\text{H}_5\text{CH}_2\text{OH}$), and phenol ($\text{C}_6\text{H}_5\text{OH}$). Give reasons for your answer.
Complete the table by putting a tick (✓) in the appropriate box when a reaction occurs. Put a cross (\times) in the box when no reaction occurs.
Complete the equations for the reactions:\nreaction 1: $\text{C}_6\text{H}_5\text{COOH} + \text{PCl}_5 \rightarrow \text{C}_6\text{H}_5\text{COCl} + \ldots + \ldots$\nreaction 2: $\text{C}_6\text{H}_5\text{COOH} + \text{SOCl}_2 \rightarrow \text{C}_6\text{H}_5\text{COCl} + \ldots + \ldots$
Use your answer to part (c)(i) to suggest why it is simpler to isolate the $\text{C}_6\text{H}_5\text{COCl}$ from reaction 2 in a pure form than from reaction 1.
Benzoyl chloride is hydrolysed by water at room temperature to form benzoic acid. Complete the diagram to show the mechanism for the reaction between $\text{C}_6\text{H}_5\text{COCl}$ and $\text{H}_2\text{O}$. Include charges, dipoles, lone pairs of electrons and curly arrows where needed.
Name the mechanism type shown in (d)(i).
Acyl chlorides react with sodium carboxylates to make acid anhydrides as shown in Fig. 5.1. The condensation polymers, polyanhydride and polyester, are made by similar routes. The repeat unit for a polyanhydride is shown in Fig. 5.2. Use Fig. 5.1 and Fig. 5.2 to suggest the structures of the two monomers used to prepare this polyanhydride.
Polyanhydrides are biodegradable polymers. Suggest how this polyanhydride can be degraded.