Halogen compounds — Paper 1 · A Level Chemistry 9701

38 For the reaction (CH3)3SiCl + C2H5O– → (CH3)3SiOC2H5 + Cl – which statements are likely to be true? 1 It involves nucleophilic attack by C2H5O–. 2 Cl – is displaced by C2H5O–. 3 The oxygen-carbon bond is not broken.

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2005

38 Which are properties of fluoroalkanes? 1 They are less reactive than the corresponding chloroalkanes. 2 They are non-flammable. 3 The C-F bond is stronger than a C-Cl bond.

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2006

38 Which of the following would be suitable for use in a fire extinguisher? 1 CBrF3 2 CH3(CH2)5CH2Br 3 HCl

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2008

21 Many different compounds have been used in aerosol sprays, refrigerators and in making foamed plastics. Which compound will cause the most ozone depletion? A CCl 3F B CH2FCHCl F C CH3CH2CH2CH3 D N2O

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2011

40 X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this precipitate remains undissolved when an excess of dilute aqueous ammonia is added. What could be the identity of X? 1 2-chlorobutane 2 2-bromobutane 3 iodomethane

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2011

38 Y is an organic compound. Y gives a precipitate with aqueous silver nitrate. All of this precipitate dissolves when concentrated aqueous ammonia is added. What is a possible identity for Y? 1 1-bromopropane 2 chloroethane 3 2-iodo-2-methylpropane

1 marks

This question in 9701/12 Oct/Nov 2011

37 X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this precipitate remains undissolved when an excess of dilute aqueous ammonia is added. What could be the identity of X? 1 2-chlorobutane 2 2-bromobutane 3 iodomethane

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2011

29 Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A CH3OH + PCl 5 → CH3Cl + POCl 3 + HCl B CH3CH2Br + KCN → CH3CH2CN + KBr C CH3CH2OH → C2H4 + H2O D CH3CH2CN + 2H2O → CH3CH2CO2H + NH3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2012

37 Chloroethane can be formed from bromoethane in two steps. step X step Y C2H5Br C2H5OH C2H5Cl Which statements about these steps are correct? 1 Hot aqueous sodium hydroxide is the reagent in step X. 2 SOCl 2 is the reagent in step Y. 3 Step X is a substitution reaction.

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2012

30 CCl 2FCCl F2 can be converted into CH2FCF3 by the following route. step 1 step 2 step 3 CCl 2FCCl F2 CCl 3CF3 CCl 2FCF3 CH2FCF3 What type of reaction is step 1? A addition B elimination C isomerisation D oxidation

1 marks

Answer: C

This question in 9701/13 May/June 2013

37 The organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous ammonia is added. What is a possible identity for X? 1 1-bromopropane 2 2-chlorobutane 3 2-iodo,2-methylpropane

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2013

27 Dichlorodifluoromethane, CCl 2F2, has been used in aerosol propellants and as a refrigerant. Which statement helps to explain why dichlorodifluoromethane is chemically inert? A All fluorine compounds are non-flammable. B Fluorine is highly electronegative. C The carbon-fluorine bond energy is large. D The carbon-fluorine bond has a low polarity.

1 marks

Answer: C

This question in 9701/12 May/June 2014

38 X is an organic compound that gives a precipitate with aqueous silver nitrate. This precipitate remains undissolved when concentrated aqueous ammonia is added. What is a possible identity for X? 1 iodomethane 2 2-bromobutane 3 2-chlorobutane

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

38 X is an organic compound that gives a precipitate with aqueous silver nitrate. This precipitate remains undissolved when concentrated aqueous ammonia is added. What is a possible identity for X? 1 iodomethane 2 2-bromobutane 3 2-chlorobutane

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2014

24 Coniine is the major constituent of the poison ‘oil of hemlock’. N CH2CH2CH3 H coniine Coniine can be synthesised by reacting ammonia with a dibromo compound, X. NH3 + C8H16Br2 → coniine + 2HBr X What is the name of compound X? A 1,1-dibromo-2-propylcyclopentane B 1,2-dibromo-2-propylcyclopentane C 1,4-dibromooctane D 1,5-dibromooctane

1 marks

Answer: D

This question in 9701/11 May/June 2015

26 The presence of a halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would be the quickest to produce a precipitate? A B C D Cl F F Cl Cl Cl F Br Cl F I F

1 marks

Answer: C

This question in 9701/11 May/June 2015

25 Compound X has been investigated for use as an artificial sweetener. OH Cl O O OH OH O Cl OH OH X The two C–Cl bonds can be hydrolysed by hot NaOH(aq). The C-O-C bonds cannot be hydrolysed by hot NaOH(aq). What are the numbers of specified types of –OH groups before and after hydrolysing the two C–Cl bonds? before after hydrolysis hydrolysis secondary primary secondary tertiary A 0 1 2 4 B 0 2 1 4 C 4 1 5 1 D 4 2 4 1

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This question in 9701/12 Oct/Nov 2015

38 X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this precipitate remains undissolved when excess dilute aqueous ammonia is added. What could be the identity of X? 1 2-chlorobutane 2 2-bromobutane 3 iodomethane

1 marks

This question in 9701/12 Oct/Nov 2015

38 Which compounds, on heating with ethanolic NaOH, produce more than one product with molecular formula C4H8? 1 2-bromobutane 2 2-bromo-2-methylpropane 3 1-bromo-2-methylpropane

1 marks

Answer: D

This question in 9701/13 May/June 2017

38 Organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous ammonia is added. What could X be? 1 1-bromopropane 2 2-chlorobutane 3 2-iodo-2-methylpropane

1 marks

Answer: B

This question in 9701/12 Feb/March 2018

39 Chlorofluoroalkanes have been used as the refrigerant in refrigerators but care has to be taken in disposing of old refrigerators. Which statements about chlorofluoroalkanes are correct? 1 C–Cl bonds more readily undergo homolytic fission than C–F bonds. 2 Care is taken in the disposal of old refrigerators because of possible ozone depletion. 3 C2H4Cl F is more volatile than C2H6.

1 marks

Answer: B

This question in 9701/11 May/June 2018

38 The halogenoalkanes listed below all react with NaOH(aq). Which reactions proceed mainly by an SN1 mechanism? 1 1-iodopropane 2 2-iodo-2-methylpropane 3 2-bromo-2-methylbutane

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2018

38 Halogenoalkanes can undergo reaction with hydroxide ions. RBr + OH– → ROH + Br – The reaction of some halogenoalkanes proceeds by the SN1 mechanism. Which statements about the SN1 mechanism are correct? 1 A carbocation is formed which is stabilised by the inductive effect of the alkyl groups present. 2 Only tertiary halogenoalkanes are hydrolysed in this way. 3 The intermediate formed includes a carbon atom with five bonds attached to it.

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2018

39 Chlorofluoroalkanes that diffuse into the stratosphere are broken down by ultraviolet radiation. Radicals are generated that cause depletion of ozone. What are these radicals? 1 chlorine radicals 2 fluorine radicals 3 alkyl radicals

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Answer: D

This question in 9701/11 May/June 2020

12 Which observations are made when a sample of silicon chloride, SiCl 4, is added to a beaker of water? A No visible change is observed. B Steamy fumes and a precipitate are both observed. C The appearance of a precipitate is the only observation. D The appearance of steamy fumes is the only observation.

1 marks

Answer: B

This question in 9701/12 Feb/March 2021

37 Which statements are correct? 1 1,1-difluoroethane is less reactive than 1,1-dichloroethane. 2 1,1-difluoroethane is polar. 3 The C–F bond is stronger than the C–Cl bond.

1 marks

Answer: A

This question in 9701/11 May/June 2021

39 Which statements about chlorofluoroalkanes are correct? 1 Both the C–Cl and C–F bonds are readily dissociated by ultra-violet light. 2 They have caused ozone depletion. 3 They are relatively chemically inert.

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2021

32 The presence of a halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would be the quickest to produce a precipitate? A B C D Cl F F Cl Cl Cl F Br Cl F I F

1 marks

Answer: C

This question in 9701/11 May/June 2022

30 Limonene is found in lemon and orange oils. limonene What is the major product when limonene reacts with an excess of dry hydrogen chloride? A B C D Cl Cl Cl Cl Cl Cl

1 marks

Answer: C

This question in 9701/13 May/June 2022

32 Compound J, C15H23Br2Cl , is reacted with an excess of a hot concentrated solution of sodium hydroxide in ethanol. One of the products is X. compound J excess NaOH Cl Br in ethanol X Br What could be the skeletal formula of X? A B C D

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Answer: A

This question in 9701/13 May/June 2022

39 Compound V polymerises to form polymer W. A section of polymer W is shown. polymer W Cl Cl Cl Cl Cl Cl polymerisation V Cl Cl Cl What is the correct name of compound V? A 1,1,2-trichlorobutene B 1,1,2-trichloroethene C 1,1,2-trichloropropene D 1,1,2-trichloro-2-methylethene

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2022

31 Which compound reacts most rapidly with aqueous silver nitrate by an SN1 mechanism? A 1-chloromethylpropane B 2-chloromethylpropane C 1-iodomethylpropane D 2-iodomethylpropane

1 marks

Answer: D

This question in 9701/12 Feb/March 2023

31 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A addition B elimination C oxidation D substitution

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

35 1-chloro-2-methylpropane and 2-bromo-2-methylbutane react separately with aqueous silver nitrate in ethanol. Both reactions proceed via nucleophilic substitution and a precipitate is formed. The time taken for 1-chloro-2-methylpropane to form a precipitate is T1. The time taken for 2-bromo-2-methylbutane to form a precipitate is T2. Which row is correct? main reaction time taken for compound mechanism precipitate to appear A 1-chloro-2-methylpropane SN1 T2 > T1 B 1-chloro-2-methylpropane SN2 T1 > T2 C 2-bromo-2-methylbutane SN1 T2 > T1 D 2-bromo-2-methylbutane SN2 T1 > T2

1 marks

Answer: B

This question in 9701/12 Feb/March 2025

33 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane are put separately into three test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60 °C. In each case, a hydrolysis reaction occurs. H2O(l) + R–X(l) + Ag+(aq)  R–OH(aq) + AgX(s) + H+(aq) R represents C4H9 and X represents the halogen atom. The rate of formation of cloudiness in the test-tubes is in the order RCl < RBr < RI. Why is this? A The bond energy of R–X decreases from RCl to RI. B The first ionisation energy of the halogen decreases from Cl to I. C The solubility of AgX(s) decreases from AgCl to AgI. D The R–X bond polarity decreases from RCl to RI.

1 marks

Answer: A

This question in 9701/12 May/June 2025

30 Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. CH2Cl Cl I compound X What is the colour of this precipitate and what is the structural formula of the first organic product? colour of the precipitate structural formula of the first organic product A cream CH2Cl HO OH B cream CH2OH HO OH C white CH2OH HO I D yellow CH2Cl Cl OH

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2025

30 Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. CH2Cl Cl I compound X What is the colour of this precipitate and what is the structural formula of the first organic product? colour of the precipitate structural formula of the first organic product A cream CH2Cl HO OH B cream CH2OH HO OH C white CH2OH HO I D yellow CH2Cl Cl OH

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2025