A set of reactions involving ethanol is shown. $\text{CH}_3\text{CH}_2\text{Cl} \xrightleftharpoons[\text{reaction 2}]{\text{reaction 1}} \text{CH}_3\text{CH}_2\text{OH}$. $\text{CH}_3\text{CH}_2\text{OH}$ is distilled with $\text{Cr}_2\text{O}_7^{2-} + \text{H}^+$ to give $Y$. $\text{CH}_3\text{CH}_2\text{Cl}$ is heated with NaOH in ethanol to give $X$.
(a(i))[2]
Write an equation for reaction 2 and include the reagent needed for this conversion.
(a(ii))[2]
State the reagent and conditions needed for reaction 1.
(b(i))[1]
Identify the organic product $X$.
(b(ii))[1]
Nitric acid is added to the products from reaction of $\text{CH}_3\text{CH}_2\text{Cl}$ with NaOH in ethanol. Silver nitrate solution is then added to this mixture. State what you would observe.
(b(iii))[1]
Write an ionic equation, including state symbols, for the reaction that causes the observation in (ii).
(c(i))[1]
Identify the organic product $Y$ distilled from the reaction mixture.
(c(ii))[3]
Explain, using the properties of and intermolecular forces in $\text{CH}_3\text{CH}_2\text{OH}$ and $Y$, why the reaction conditions chosen make $Y$ the product.
Worked solution & mark scheme
This 11-mark question has a full step-by-step worked solution and mark scheme. One marking point: “A correct substitution equation, e.g. $\mathrm{CH_3CH_2OH+HCl\rightarrow CH_3CH_2Cl+H_2O}$ OR with $\mathrm{PCl_5}$ or $\mathrm{SOCl_2}$” …