Nucleophilic substitution: AQA A‑Level Chemistry questions

AQA A-Level Chemistry past-paper questions on 3.3.3.1 Nucleophilic substitution, 2008–2025, with mark schemes and examiner’s reports where available.

All 92 questions on Nucleophilic substitution, as a list

June 2025, Paper 2, Q09.5 (1 mark): The rate equation for the reaction between a different bromoalkane (R2CHBr) and an aqueous solution of KOH is rate = k [R2CHBr] Which of these is a correct mech
June 2025, Paper 2, Q09.6 (2 marks): Explain, in terms of bond polarity, why R2CHBr and KOH react together. [2 marks]
June 2025, Paper 3, Q08 (1 mark): Each of the conversions shown uses KOH as a reactant. In which conversion does KOH not act as a base? [1 mark] A (CH3)2NH2+Br – to (CH3)2NH B CH3COOH to CH3COO–
June 2025, AS Paper 2, Q01.1 (2 marks): Halogenoalkanes undergo substitution reactions with nucleophiles such as CN–, NH3 and OH– Explain why halogenoalkanes react with nucleophiles. [2 marks]
June 2025, AS Paper 2, Q01.2 (3 marks): 2-Bromobutane reacts with ammonia to form CH3CH(NH2)CH2CH3 Complete the mechanism for this reaction. [3 marks] 2-Bromobutane reacts with KOH to give a mixture o
June 2025, AS Paper 2, Q01.3 (1 mark): Identify the solvent that should be used to ensure that butan-2-ol is the main organic product when 2-brombutane reacts with KOH [1 mark]
June 2024, Paper 2, Q05.1 (2 marks): Silver nitrate solution can be used to distinguish between propanoyl chloride and 1-chloropropane. Give the observations you would expect when a few drops of si
June 2024, Paper 2, Q08.2 (2 marks): Identify compound J. State the reagent(s) and conditions needed for Step 2. [2 marks] Compound J Reagent(s) and conditions
June 2024, AS Paper 2, Q06.1 (1 mark): Identify the yellow precipitate formed in the reaction. [1 mark]
June 2024, AS Paper 2, Q06.3 (3 marks): The student repeats the investigation using 1-bromobutane instead of 1-iodobutane. State and explain how the rate of reaction for 1-bromobutane compares with th
June 2024, AS Paper 2, Q07.4 (3 marks): Name and outline the mechanism for Step 1. [3 marks] Name of mechanism Outline of mechanism
June 2024, AS Paper 2, Q07.5 (1 mark): Suggest one reason why water is not a suitable solvent for Step 1. [1 mark]
June 2024, AS Paper 2, Q11 (1 mark): Which labelled curly arrow shows an incorrect movement of an electron pair? [1 mark] A B C D
June 2023, Paper 2, Q04.3 (2 marks): Identify the reagent that is warmed with isomer W in reaction 2. State the other reaction condition needed. [2 marks] Reagent Condition
June 2023, Paper 3, Q29 (1 mark): Which is not a possible product of a reaction between KOH and ? [1 mark] A B C D
June 2023, AS Paper 2, Q03.1 (2 marks): Outline the mechanism for the nucleophilic substitution reaction of 1-bromobutane with sodium hydroxide. [2 marks]
June 2023, AS Paper 2, Q03.2 (2 marks): State how Figure 1 shows that the rate of reaction of 1-iodobutane is faster than the rate of reaction of 1-bromobutane. State why the rates are different. [2 m
June 2023, AS Paper 2, Q13 (1 mark): Which is not a possible product of the reaction of this compound with potassium hydroxide? [1 mark] A B C D
June 2022, Paper 3, Q03.7 (2 marks): A student compares the rates of hydrolysis of 1-chlorobutane, 1-bromobutane and 1-iodobutane. The suggested method is: • add equal volumes of the three halogeno
June 2022, Paper 3, Q23 (1 mark): Which compound is formed from bromoethane in a nucleophilic substitution reaction? [1 mark] A CH3CN B CH3CH2NH2 C CH2=CH2 D CH3CH2OSO2OH
June 2022, AS Paper 2, Q05.1 (5 marks): Name and outline the mechanism for this reaction. [5 marks] Name of mechanism Outline of mechanism
June 2022, AS Paper 2, Q16 (1 mark): Which reaction does not result in a change in the shape around a carbon atom? [1 mark] A chloromethane with aqueous sodium hydroxide B ethene with bromine C pro
June 2022, AS Paper 2, Q21 (1 mark): Which of these compounds is not produced? [1 mark] A butan-1-ol B butan-2-ol C but-1-ene D E-but-2-ene
November 2021, Paper 2, Q08.2 (4 marks): State the reagents needed and give equations for step 2 and step 3. Show the structure of Compound G in your equations. [4 marks] Step 2 reagent Step 2 equation
November 2021, AS Paper 2, Q07.1 (1 mark): Prop-2-en-1-ol can be prepared by reacting 3-chloroprop-1-ene with dilute aqueous sodium hydroxide. Name the mechanism for this reaction. [1 mark]
November 2021, AS Paper 2, Q14 (1 mark): What is the organic product of this reaction? [1 mark] A propylamine B butylamine C propanenitrile D butanenitrile
November 2021, AS Paper 2, Q15 (1 mark): Which is the correct mechanism for the reaction? [1 mark] A B C D
November 2021, AS Paper 2, Q16 (1 mark): The reactions of 1-bromopropane and 1-chloropropane with potassium cyanide in aqueous ethanol occur at different rates under the same conditions. Which row corr
November 2020, Paper 2, Q05.2 (4 marks): Outline the mechanism for the reaction of 2-bromopropane with an excess of ammonia. [4 marks]
November 2020, AS Paper 2, Q01.5 (5 marks): Ammonia reacts with 1-chloropropane to form propylamine. Name and outline the mechanism for this reaction. [5 marks] Name of mechanism Outline of mechanism
June 2019, Paper 2, Q01.3 (3 marks): 1,6-Diaminohexane can also be formed in a two-stage synthesis starting from 1,4-dibromobutane. Suggest the reagent and a condition for each stage in this altern
June 2019, AS Paper 2, Q02.1 (2 marks): Outline the mechanism for this reaction. [2 marks]
June 2019, AS Paper 2, Q16 (1 mark): Which compound can react with ammonia to produce propylamine? [1 mark] A CH3CH═CH2 B CH3CH2CH2OH C CH3CH2CH2Br D CH3CH2CH3
June 2019, AS Paper 2, Q19 (1 mark): Which species can act as a nucleophile? [1 mark] A NH4 + B CH3OH C CH4 D H+
June 2019, AS Paper 2, Q22 (1 mark): Which compound could not be produced by reacting 2-bromo-3-methylbutane with sodium hydroxide? [1 mark] A 2-methylbut-1-ene B 3-methylbut-1-ene C 2-methylbut-2-
June 2018, Paper 2, Q02.2 (3 marks): Reaction 1 occurs via a nucleophilic substitution mechanism. Explain why the halogenoalkane is attacked by the nucleophile in this reaction. [3 marks]
June 2018, Paper 3, Q10 (1 mark): Which statement is correct about the molecule shown? [1 mark] A It reacts with HBr in an electrophilic substitution reaction. B It reacts with NaBH4 in a nucleo
June 2018, AS Paper 2, Q06.3 (4 marks): Reaction of A with warm, dilute aqueous sodium hydroxide forms alcohol B. Name the mechanism for this reaction. Outline the mechanism using the structure of A s
June 2018, AS Paper 2, Q06.6 (1 mark): Compound D reacts with dilute aqueous sodium hydroxide in a similar way to A to form alcohol B. Compound A Compound D Explain why D reacts more quickly than A w
June 2018, AS Paper 2, Q18 (1 mark): Which species could act as a nucleophile? [1 mark] A BH3 B NH4 + C PH3 D SiH4
June 2017, Paper 2, Q01.1 (1 mark): Draw the displayed formula of compound J. [1 mark
June 2017, Paper 2, Q01.2 (2 marks): Name the mechanism for Reaction 2 and give an essential condition used to ensure that CH3CH2CH2NH2 is the major product. [2 marks Name of mechanism Condition
June 2017, Paper 3, Q14 (1 mark): The reaction sequence shows how CH3CH3 can be converted into BrCH2CH2Br Which step occurs by nucleophilic substitution? [1 mark] A Step A B Step B C Step C D St
June 2017, AS Paper 2, Q06.1 (3 marks): Name and outline the mechanism for this reaction. [3 marks] Name of mechanism Mechanism
June 2017, AS Paper 2, Q16 (1 mark): Which compound has the fastest rate of reaction with potassium cyanide to form pentanenitrile? [1 mark] A 1-bromobutane B 1-chlorobutane C 1-fluorobutane D 1-io
June 2016, AS Paper 2, Q10 (1 mark): Pentanenitrile can be made by reaction of 1-bromobutane with potassium cyanide. Which of these is the correct name for the mechanism of this reaction? [1 mark]
Specimen, Paper 3, Q28 (1 mark): Why are fluoroalkanes unreactive? [1 mark] A Fluorine is highly electronegative. B The F– ion is very stable. C They are polar molecules. D The C F bond is very
June 2016, CHEM4 (old spec), Q3(b) (1 mark): Name the mechanism for Step 2. [1 mark]
June 2016, CHEM4 (old spec), Q8(a) (3 marks): Give the reagent and conditions for Step 1. State how you could obtain a sample of the alcohol from the reaction mixture formed in Step 1. [3 marks]
June 2016, CHEM4 (old spec), Q8(b) (5 marks): Draw the structure of compound S. For each of Steps 3 and 4, give a reagent and one condition, other than heat. [5 marks]
June 2016, CHEM2 (old spec), Q8(a) (8 marks): The same reagent is used in both reactions. The product is determined by the choice of conditions. State the reagent and the conditions for each of reaction 1 a
June 2016, CHEM2 (old spec), Q8(c) (4 marks): The rates of hydrolysis of two chloroalkanes can be investigated by adding aqueous silver nitrate to the chloroalkanes. During the hydrolysis reactions, chlorid
June 2015, CHEM2 (old spec), Q8(c) (5 marks): The conversion of Q into R in Reaction 2 uses NH3 Name and outline a mechanism for this reaction. [5 marks]
June 2014, CHEM2 (old spec), Q8(a)(i) (2 marks): Use your knowledge of organic reaction mechanisms to complete the mechanism for this step by drawing two curly arrows on the following equation. [2 marks] Br- H
June 2014, CHEM2 (old spec), Q8(a)(ii) (2 marks): Deduce the name of the mechanism in Question 8 (a) (i). Give the IUPAC name of (CH3)2CHCH2Br [2 marks]
June 2013, CHEM2 (old spec), Q5(b)(i) (1 mark): Draw the displayed formula for X. (1 mark)
June 2013, CHEM2 (old spec), Q5(b)(ii) (1 mark): Suggest one change to the reaction conditions that would increase the yield of X. (1 mark)
June 2013, CHEM2 (old spec), Q5(b)(iii) (1 mark): State the type of mechanism for the conversion of 2-bromo-3-methylbutane into X. (1 mark)
June 2013, CHEM2 (old spec), Q8(d) (1 mark): Draw the structure of the organic product with Mr = 73, made from the reaction between 2-bromobutane and ammonia. (1 mark)
January 2013, CHEM4 (old spec), Q1(c)(ii) (1 mark): Outline a mechanism for this step using a curly arrow. (1 mark)
January 2013, CHEM2 (old spec), Q8(b) (5 marks): Name and outline a mechanism for Reaction 2. Name of mechanism Mechanism (5 marks)
June 2012, CHEM4 (old spec), Q5(c) (3 marks): For Step 3, give the reagent, give a necessary condition and name the mechanism. Reagent Condition Name of mechanism (3 marks)
June 2012, CHEM2 (old spec), Q8(b)(i) (3 marks): Name and outline a mechanism for the following reaction that occurs in Process 1. BrCH2CH2CH2CH2Br + NaOH BrCH2CH2CH2CH2OH + NaBr (3 marks)
January 2012, CHEM4 (old spec), Q10(b) (6 marks): For the reaction of CH3CH2CH2Cl with an excess of ammonia, name and outline the mechanism and name the organic product.
January 2012, CHEM2 (old spec), Q9(b) (6 marks): Give a reagent and conditions for Reaction 2. Reaction 2 CH3CH2Br CH3CH2OH Name and outline a mechanism for Reaction 2. Suggest one reason, other than safety, w
June 2011, CHEM4 (old spec), Q8(c) (6 marks): Cyclohexene can be converted into amine W by the two-step synthesis shown below. Suggest an identity for compound V. For Reaction 3, give the reagent used and n
June 2011, CHEM2 (old spec), Q3(f)(iv) (1 mark): The bromoalkane that reacts with sodium cyanide to produce propanenitrile. (1 mark)
June 2011, CHEM2 (old spec), Q9(c) (5 marks): Name and outline a mechanism for the following conversion. NH3 CH3CH2CH2Br CH3CH2CH2NH2 (5 marks)
January 2011, CHEM2 (old spec), Q8(a)(i) (1 mark): nucleophile (1 mark)
January 2011, CHEM2 (old spec), Q8(a)(ii) (1 mark): substitution, as applied to nucleophilic substitution in a haloalkane (1 mark)
January 2011, CHEM2 (old spec), Q8(a)(iii) (1 mark): hydrolysis (1 mark)
January 2011, CHEM2 (old spec), Q8(b) (2 marks): Outline a mechanism for the nucleophilic substitution reaction in which 2-bromopropane (CH3CHBrCH3) reacts with potassium hydroxide to form propan-2-ol. (2 mark
June 2010, CHEM4 (old spec), Q3(d)(i) (4 marks): Outline a mechanism for Reaction 3. (4 marks)
June 2010, CHEM2 (old spec), Q2(a)(i) (1 mark): State the meaning of the term hydrolysis. (1 mark)
June 2010, CHEM2 (old spec), Q2(b) (1 mark): The student used the following enthalpy data to try to account for the different initial rates of hydrolysis of the haloalkanes used in part (a). The student de
June 2010, CHEM2 (old spec), Q2(c)(i) (1 mark): State the meaning of the term nucleophile. (1 mark)
June 2010, CHEM2 (old spec), Q2(c)(ii) (2 marks): When a hydroxide ion collides with a molecule of 1-bromobutane, the following reaction occurs. CH3CH2CH2CH2Br + OH– CH3CH2CH2CH2OH + Br– Outline the nucleophili
June 2010, CHEM2 (old spec), Q2(d)(i) (1 mark): Complete the following equation by drawing the structure of the carbocation formed when the C–Br bond in 2-bromo-2-methylpropane is broken. (1 mark) CH3 CH3 C B
June 2010, CHEM2 (old spec), Q2(d)(ii) (1 mark): Suggest one reason why this reaction occurs by a mechanism involving a carbocation, but the reaction in part (c) (ii) does not. (1 mark)
January 2010, CHEM2 (old spec), Q7(a)(i) (3 marks): Name and outline a mechanism for this reaction. Name of mechanism Mechanism (3 marks)
January 2010, CHEM2 (old spec), Q7(a)(iii) (1 mark): Identify the characteristic of the haloalkane molecule that enables it to undergo this type of reaction. (1 mark)
June 2009, CHEM2 (old spec), Q8(a) (1 mark): 8 (a) State what is meant by the term nucleophile. (1 mark)
June 2009, CHEM2 (old spec), Q8(b) (2 marks): 8 (b) Outline a mechanism for the reaction of potassium cyanide with bromoethane (Reaction 1). (2 marks)
June 2008, CHM3W (2008 spec), Q4(a)(i) (1 mark): 4 (a) (i) What feature of the bromoethane molecule makes it susceptible to attack by an ammonia molecule? (1 mark)
June 2008, CHM3W (2008 spec), Q4(a)(ii) (4 marks): 4 (a) (ii) Outline a mechanism for this reaction. (4 marks)
June 2008, CHM3W (2008 spec), Q4(b) (2 marks): 4 (b) Bromoethane is converted into compound B by reaction with reagent A. Identify reagent A and give the name of compound B. Identity of reagent A Name of com
June 2008, CHM3W (2008 spec), Q4(c)(i) (1 mark): 4 (c) (i) State what is meant by the term nucleophile. (1 mark)
June 2008, CHM3W (2008 spec), Q4(c)(ii) (1 mark): 4 (c) (ii) Identify the nucleophile in the reaction of potassium hydroxide with bromoethane. (1 mark)
June 2008, CHM5 (2008 spec), Q1(c) (1 mark): 1 (c) Define the term nucleophile. (1 mark)
June 2008, CHM6W (2008 spec), Q21 (1 mark): 21 A substitution reaction occurs when ammonia reacts with 1 [Cu(H2O)6]2+ 2 BF3 3 CH3Br 4 HBr
January 2008, CHM3W (2008 spec), Q5(c) (2 marks): (c) Complete and balance the following equation for the reaction of ammonia with bromomethane. Give the name of the organic product of this reaction. CH3Br + ……
January 2008, CHM3W (2008 spec), Q6(d) (3 marks): (d) Name and outline a mechanism for the conversion of A into D (Reaction 3). (3 marks)

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