State the number of separate peaks in the carbon-13 ($^{13}\text{C}$) NMR spectrum of phenylethanoic acid.
Phenylethanoic acid, ethanol and phenol can each act as acids. Compare their acid strengths and explain the relative order.
Phenylethanoic acid can be made from benzene as the starting material. In the first stage of this synthesis, benzene reacts with chloromethane in the presence of an $\text{AlCl}_3$ catalyst to produce methylbenzene. Chloromethane reacts with $\text{AlCl}_3$ to make two ions. One of these is the carbocation $^+\text{CH}_3$.
Write an equation for the reaction between chloromethane and $\text{AlCl}_3$.
Draw the mechanism of the reaction between benzene and $^+\text{CH}_3$. Include all relevant curly arrows, charges and the structure of the intermediate.
A three-step synthesis of phenylethanoic acid from methylbenzene is shown.
State reagents and conditions for step 1.
Suggest the structure of compound Q.
State reagents and conditions for steps 2 and 3.
Draw the structure of an organic by-product that forms in step 1.