Chemistry 9701 · AS & A Level · Hydrocarbons

Hydrocarbons — practice question

Ethyne gas, $\mathrm{C_2H_2}$, better known as acetylene, is produced for making organic compounds by synthesis. It is also burned with oxygen in oxy-acetylene torches for cutting and welding metals. On an industrial scale, ethyne is prepared from calcium carbide, $\mathrm{CaC_2}$, or by cracking liquid hydrocarbons.
(a)[1]

When calcium carbide reacts with water, ethyne and calcium hydroxide are produced. Write a balanced equation for this reaction.

(b(i))[2]

Ethyne may also be prepared from ethene through the following reaction sequence: $\mathrm{CH_2CH_2} \xrightarrow{\text{step 1}} \mathrm{ClCH_2CH_2Cl} \xrightarrow{\text{step 2}} \mathrm{HC{\equiv}CH}$. What reaction types occur in step 1 and step 2?

(b(ii))[3]

Suggest which reagent and conditions would be used in a laboratory for step 2.

(c(i))[2]

When ethyne is passed into water at $60^{\circ}\mathrm{C}$, in the presence of a little $\mathrm{H_2SO_4}$ and $\mathrm{Hg^{2+}}$ ions, a pungent, colourless organic liquid $Q$, with $M_r$ of 44 is obtained (step 3). When $Q$ is warmed with Tollens’ reagent in a test-tube, a silver mirror is formed. On acidification, the solution remaining in the test-tube is found to contain the organic compound $R$ which has $M_r$ of 60 (step 4). Give the structural formulae of $Q$ and $R$.

(c(ii))[2]

What type of reaction occurs in step 3 and step 4?

(d(i))

The standard enthalpy change of combustion of $\text{C}_2\text{H}_2$, $\Delta H_c^{\circ}$, is $-1300\,\text{kJ mol}^{-1}$ at $298\,\text{K}$. Values of relevant standard enthalpy changes of formation, $\Delta H_f^{\circ}$, measured at $298\,\text{K}$ are given: $\text{CO}_2(g)$, $-394\,\text{kJ mol}^{-1}$; $\text{H}_2\text{O}(l)$, $-286\,\text{kJ mol}^{-1}$. Write balanced equations, with state symbols, that represent the standard enthalpy change of combustion, $\Delta H_c^{\circ}$, of $\text{C}_2\text{H}_2$ and the standard enthalpy change of formation, $\Delta H_f^{\circ}$, of $\text{C}_2\text{H}_2$.

(d(ii))[6]

Using the data above and your answer to part (i), calculate the standard enthalpy change of formation, $\Delta H_f^{\circ}$, of $\text{C}_2\text{H}_2$. Show clearly whether the standard enthalpy change of formation of $\text{C}_2\text{H}_2$ is positive or negative.

Worked solution & mark scheme

This 16-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\text{CaC}_2 + 2\text{H}_2\text{O} \rightarrow \text{Ca(OH)}_2 + \text{C}_2\text{H}_2$

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