(a)

Describe the difference in reactivity between chloroethane and chlorobenzene with $\mathrm{OH}^{-}(\mathrm{aq})$ .
Explain your answer.

[ 2 ]

(a)

Organochlorine compounds can undergo hydrolysis.

\mathrm{R}-\mathrm{Cl}+\mathrm{H}_{2} \mathrm{O} \rightarrow \mathrm{R}-\mathrm{OH}+\mathrm{HCl}

State and explain the relative rates of hydrolysis of the following compounds.

\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl} \quad \mathrm{CH}_{3} \mathrm{COCl} \quad \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}

[ 3 ]

[Maximum number: 3]

Benzene, $\mathrm{C}_{6} \mathrm{H}_{6}$ , is an aromatic molecule.

(a)

Chlorobenzene and chloroethane have different reactivities in nucleophilic substitution reactions.

[ 3 ]

(i)

Identify a suitable reagent to illustrate this difference in reactivity.

The reagent chosen should give visibly different results with chlorobenzene and chloroethane.

[ 1 ]

(ii)

Write equations to describe any reactions that occur.

[ 1 ]

(iii)

Explain the difference in the reactivities of chlorobenzene and chloroethane in nucleophilic substitution reactions.

[ 1 ]