Halogen compounds: past paper questions

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• Question 31May/June 2026, paper 11Multiple choice1 mark

  Structural isomerism and stereoisomerism should be taken into account when answering this question.

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• Question 30Oct/Nov 2025, paper 11Multiple choice1 markHas a diagram

  Compound X, ${\text{C}}_7{\text{H}}_{11}{\text{ICl}}_2$, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately.

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• Question 32Oct/Nov 2024, paper 11Multiple choice1 markHas a diagram

  When X is added to $\text{NaOH}(\text{aq})$ and heated under reflux, pentan-2-ol is made. Which organic product is made when X is heated with a solution of KCN dissolved in ethanol?

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• Question 31Oct/Nov 2023, paper 11Multiple choice1 mark

  1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal.

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• Question 32May/June 2026, paper 11Multiple choice1 mark

  Which organic reaction has a nucleophilic substitution mechanism?

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• Question 31Oct/Nov 2025, paper 11Multiple choice1 mark

  1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further reaction takes place. What is the relative formula mass of the major organic product?

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• Question 33Oct/Nov 2024, paper 11Multiple choice1 markHas a diagram

  1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a nucleophilic substitution mechanism. Which reaction has the greatest rate under the same conditions and which mechanism is followed by this reaction?

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• Question 32Oct/Nov 2023, paper 11Multiple choice1 markHas a diagram

  Propanoic acid can be made from bromoethane using a two-stage synthesis. Which pair of reagents is most suitable?

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• Question 29May/June 2026, paper 12Multiple choice1 mark

  Tertiary halogenoalkanes undergo a hydrolysis reaction with water. In the equation, X represents either an iodine atom or a chlorine atom.

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• Question 30Oct/Nov 2025, paper 12Multiple choice1 mark

  Which reaction mixture produces a nitrile?

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• Question 29Oct/Nov 2024, paper 12Multiple choice1 mark

  The diagram shows a synthetic route to produce 1-methylcyclohexanol. What is reagent Y?

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• Question 28Oct/Nov 2023, paper 12Multiple choice1 markHas a diagram

  Which row shows the correct name and classification of the halogenoalkane shown?

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• Question 30May/June 2026, paper 12Multiple choice1 markHas a diagram

  A sample of 1-bromopropane, ${\text{C}}_3{\text{H}}_7\text{Br}$, of mass $36.9\text{ g}$ is heated with an excess of $\text{KCN}$ in ethanol. The reaction gives a $78.0\mathrm{\%}$ yield of the desired organic product. Which row is correct?

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• Question 31Oct/Nov 2025, paper 12Multiple choice1 mark

  Which reaction is classified as ${\text{S}}_{\text{N}}1$?

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• Question 30Oct/Nov 2024, paper 12Multiple choice1 markHas a diagram

  X and Y are the reagents required to convert 1-bromopropane into butanoic acid.

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• Question 14May/June 2026, paper 13Multiple choice1 markHas a diagram

  The reaction pathway diagram shows the reaction which occurs when $({\text{CH}}_3{)}_3\text{CCl}$ reacts with ${\text{OH}}^{-}$. Which statements are correct?

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• Question 31Oct/Nov 2024, paper 12Multiple choice1 markHas a diagram

  The table shows three sets of reagents and reaction conditions.

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• Question 29May/June 2026, paper 13Multiple choice1 markHas a diagram

  Structural isomerism and stereoisomerism should be taken into account when answering this question. Two compounds, X and Y, both have the molecular formula ${\text{C}}_5{\text{H}}_{11}\text{Br}$.

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• Question 29May/June 2023, paper 11Multiple choice1 markHas a diagram

  Which row describes the solvent used and type of reaction occurring when bromoethane reacts with $\mathrm{N}\mathrm{a}\mathrm{O}\mathrm{H}$ to form ethene?

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• Question 30May/June 2026, paper 13Multiple choice1 mark

  Which halogenoalkane tends to react with water by an ${\text{S}}_{\text{N}}1$ mechanism and produces a yellow precipitate when ${\text{AgNO}}_3\text{(aq)}$ is added to it?

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• Question 30May/June 2025, paper 11Multiple choice1 mark

  Structural isomerism and stereoisomerism should be considered when answering this question. 2,5-dibromohexane is heated under reflux with ethanolic KOH. How many isomeric compounds are formed with molecular formula ${\text{C}}_6{\text{H}}_{10}$?

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• Question 31May/June 2023, paper 11Multiple choice1 mark

  Which statement describes what happens when 2-chloro-2-methylpropane is warmed with $\mathrm{N}\mathrm{a}\mathrm{O}\mathrm{H}(\mathrm{a}\mathrm{q})$?

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• Question 33May/June 2026, paper 13Multiple choice1 mark

  Two reactions are described. 1 1-bromopropane with ammonia 2 propanal with hydrogen cyanide Which of these reactions has a nucleophilic mechanism?

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• Question 33May/June 2025, paper 11Multiple choice1 markHas a diagram

  A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown.

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• Question 4Oct/Nov 2024, paper 22Structured17 marksHas a diagram

  Bromoalkanes are used widely in industry, although there is increasing concern about their environmental impact. Fig. 4.1 shows a reaction scheme involving 1,2-dibromoethane. Complete Fig. 4.2 to show the mechanism for the formation of 1,2-dibromoethane in reaction 1.

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• Question 29May/June 2023, paper 12Multiple choice1 mark

  When bromoethane reacts with hot ethanolic sodium hydroxide a colourless gas is formed. This gas decolourises aqueous bromine. What is the colourless gas?

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• Question 37May/June 2026, paper 13Multiple choice1 markHas a diagram

  2-methyl-1-bromopropane is reacted with a reagent under certain conditions to form primary amine Z. The reaction produces $4.50\text{ g}$ of Z with a $56.0\mathrm{\%}$ yield. [$A_{\text{r}}$: C, 12.0; H, 1.0; Br, 79.9; N, 14.0] Which row is correct?

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• Question 35May/June 2025, paper 11Multiple choice1 markHas a diagram

  Two reactions are described. 1 2-bromo-2-methylbutane heated with $\text{NaOH}(\text{aq})$ 2 2-chloro-2-methylbutane heated with $\text{NaOH}(\text{aq})$ In both reactions, the conditions are the same and $\text{NaOH}(\text{aq})$ is in excess.

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• Question 30May/June 2024, paper 11Multiple choice1 markHas a diagram

  Q is either a primary or a tertiary halogenoalkane. Q undergoes hydrolysis with aqueous sodium hydroxide. The first step in the mechanism of this reaction involves two species reacting together.

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• Question 25May/June 2025, paper 12Multiple choice1 mark

  Which statement about the mechanism of an ${\mathrm{S}}_{\mathrm{N}}1$ reaction of a halogenoalkane is correct?

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