Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

(a)[3]

Organohalogen compounds may be hydrolysed. $\text{R--Cl} + \text{H}_2\text{O} \rightarrow \text{R--OH} + \text{HCl}$. State the relative rates of hydrolysis for the following compounds: $\text{CH}_3\text{CH}_2\text{CH}_2\text{Cl}$, $\text{CH}_3\text{CH}_2\text{COCl}$, and $\text{C}_6\text{H}_5\text{Cl}$. Explain your answer.

(b)[2]

Aminoelaevulinic acid takes part in the synthesis of haemoglobin and chlorophyll. Name the three functional groups present in aminoelaevulinic acid.

(c(i))[3]

Aminoelaevulinic acid reacts readily with bromoethane. On the diagram, show the mechanism for the first step of this reaction. Include every relevant curly arrow, lone pair and dipole.

(c(ii))[1]

State the mechanism name in (c)(i).

(c(iii))[1]

Identify the inorganic product formed in this reaction.

(d)[3]

Aminoelaevulinic acid undergoes three reactions as shown. Draw the structures of W, X and Y in the boxes provided.

(e)[2]

Aminoelaevulinic acid may undergo polymerisation. Draw the polymer structure showing two repeat units, and display the links between monomer units in full.

Worked solution & mark scheme

This 15-mark question has a full step-by-step worked solution and mark scheme. One marking point: Correct order of reactivity $\mathrm{CH_3CH_2COCl > CH_3CH_2CH_2Cl > C_6H_5Cl}$ with acceptable explanations

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