Complete Table 5.1 to show how many $sp^2$ and $sp^3$ hybridised carbon atoms are present in one molecule of cumene.
Name the mechanism involved in the Friedel-Crafts alkylation shown in Fig. 5.2.
The initial step of the reaction produces the $(\text{CH}_3)_2\text{CH}^+$ cation. Identify an appropriate reagent for forming this cation from 2-bromopropane, $(\text{CH}_3)_2\text{CHBr$.
Complete Fig. 5.3 to show the mechanism for the reaction of benzene with the $(\text{CH}_3)_2\text{CH}^+$ cation. Include every relevant curly arrow and charge.
The Friedel-Crafts alkylation of benzene using 1-bromopropane, $\text{CH}_3\text{CH}_2\text{CH}_2\text{Br}$, also gives cumene as the main product. In the first step, the $\text{CH}_3\text{CH}_2\text{CH}_2^+$ cation rapidly rearranges to the $(\text{CH}_3)_2\text{CH}^+$ cation. Suggest why this happens. Explain your answer.
Cumene is oxidised by air to give phenol, $\text{C}_6\text{H}_5\text{OH}$, and propanone, $\text{CH}_3\text{COCH}_3$. Reaction 1: $\text{C}_6\text{H}_5\text{CH}((\text{CH}_3)_2) + \text{O}_2 \rightarrow \text{C}_6\text{H}_5\text{OH} + \text{CH}_3\text{COCH}_3$ , $\Delta H^\circ = -371\ \text{kJ mol}^{-1}$. Calculate the standard entropy change, $\Delta S^\circ$, of reaction 1.
Show that reaction 1 is feasible at $25^\circ\text{C}$.
Fig. 5.4 shows two reactions of phenol. State the conditions for the bromination of phenol in reaction 2. Explain why these conditions are different from those for the bromination of benzene.
Draw the structure of organic compound Q in Fig. 5.4.
Identify organic reagent R.
Name the functional group that is formed in reaction 3.
The reaction of phenol with $\text{HNO}_3$ gives a mixture of isomers with molecular formula $\text{C}_6\text{H}_5\text{NO}_3$. Identify the two isomers produced in the greatest amounts. Explain your answer.