Draw the mechanism of the reaction of chlorine with benzene in the presence of an aluminium chloride catalyst, with ${\mathrm{Cl}}^{+}$ as the attacking species and using curly arrows to show the movement of electron pairs.

Copy and complete the equation below, which can be used to show the nitration of methylbenzene:

${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CH}}_3+{\mathrm{NO}}_2^{+}\to \mathrm{\_\_\_\_\_}+\mathrm{\_\_\_\_\_}.$

Copy and complete the equation below, which can be used to show the nitration of methylbenzene:

${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CH}}_3+{\mathrm{HNO}}_3\stackrel{{\mathrm{H}}_2{\mathrm{SO}}_4}{\to }\mathrm{\_\_\_\_\_}+\mathrm{\_\_\_\_\_}.$

Copy and complete the two equations below, which can both be used to show the nitration of methylbenzene:

i. ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CH}}_3+{\mathrm{NO}}_2^{+}\to \mathrm{\_\_\_\_\_}+\mathrm{\_\_\_\_\_}.$

ii. ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CH}}_3+{\mathrm{HNO}}_3\stackrel{{\mathrm{H}}_2{\mathrm{SO}}_4}{\to }\mathrm{\_\_\_\_\_}+\mathrm{\_\_\_\_\_}.$

Name the possible mono-substituted products in parts i and ii.