Compare the 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 your explanation.
Nine separate experiments are shown in Table 5.1. Finish the table by entering a tick ($\checkmark$) in the appropriate box when a reaction takes place. Put a cross ($\times$) in the box when no reaction takes place.
Benzoyl chloride, $\text{C}_6\text{H}_5\text{COCl}$, may be made by reacting benzoic acid with either $\text{PCl}_5$ or $\text{SOCl}_2$. Complete the equations for these reactions. Reaction 1: $\text{C}_6\text{H}_5\text{COOH} + \text{PCl}_5 \rightarrow \text{C}_6\text{H}_5\text{COCl} + \ldots + \ldots$ Reaction 2: $\text{C}_6\text{H}_5\text{COOH} + \text{SOCl}_2 \rightarrow \text{C}_6\text{H}_5\text{COCl} + \ldots + \ldots$
Using your answer to part (c)(i), suggest why it is simpler to isolate $\text{C}_6\text{H}_5\text{COCl}$ in pure form from reaction 2 than from reaction 1.
Benzoyl chloride is hydrolysed by water at room temperature to make benzoic acid. Complete the diagram so that it shows 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 you showed 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 prepared 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.