Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

The following reactions of ethanol are shown. $\text{CH}_3\text{CH}_2\text{Cl} \xrightleftharpoons[\text{reaction 2}]{\text{reaction 1}} \text{CH}_3\text{CH}_2\text{OH}$. $\text{CH}_3\text{CH}_2\text{Cl}$ is warmed with $\text{NaOH}$ in ethanol to give $X$. $\text{CH}_3\text{CH}_2\text{OH}$ is distilled with $\text{Cr}_2\text{O}_7^{2-} + \text{H}^+$ to give $Y$.
(a(i))[2]

Give an equation for reaction 2, and include the reagent needed for the 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 the reaction of $\text{CH}_3\text{CH}_2\text{Cl}$ with $\text{NaOH}$ in ethanol. Silver nitrate solution is then added to this mixture. State what you would observe.

(b(iii))[1]

Write an ionic equation, with state symbols included, for the reaction that causes the observation in (ii).

(c(i))[1]

Identify the organic product $Y$ that distils from the reaction mixture.

(c(ii))[3]

Explain, in terms of the properties of and intermolecular forces in $\text{CH}_3\text{CH}_2\text{OH}$ and $Y$, why these conditions ensure that $Y$ is the product.

Worked solution & mark scheme

This 11-mark question has a full step-by-step worked solution and mark scheme. One marking point: Correct substitution equations producing $CH_3CH_2Cl$ with $HCl$, $PCl_5$ or $SOCl_2$

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