M1Module 1 — Development of practical skills in chemistry
Note: most practical-skill testing is embedded within questions across the other topics, not listed here separately. Wherever you see a PS badge next to a question, that question also tests a practical skill (e.g. calculating a mean titre, evaluating an uncertainty, justifying a method) alongside its main content. This section only lists questions that test a practical skill on its own, without needing topic-specific content knowledge to answer. Because practical skills draw on knowledge from across the course, you may find it useful to revisit this section towards the end of your revision.
19(c)(i) — Draw a labelled diagram to show how the student would carry out the hydrolysis of haloalkane E PS
23(a) — Explain why the student uses reflux in Step 1 PS
4 — Identify the correct apparatus set-up for converting ethanol to ethanoic acid PS
2 — Identify the reason for heating under reflux PS
20(a)* — Draw a labelled distillation set-up and describe how to obtain pure cyclohexanone from the distillate (6-mark) PS
18(c)(ii) — Draw a labelled diagram of the apparatus for distillation PS
M2Module 2 — Foundations in chemistry
Atoms, ions, and compounds
18(b)(ii) — Estimate the number of repeat units in a sample of Nylon 6,6 of Mr 21500
18(d) — Calculate the Mr of a polyester formed from 200 molecules of 4-hydroxybenzoic acid
19(d)(ii) — Calculate the Mr of the polymer formed from 400 molecules of 2-aminopropanoic acid
22(a) — Determine the molar mass of a polymer formed from 500 molecules of the α-amino acid
22(c)(ii) — Construct a balanced equation for the synthesis of solketal from propane-1,2,3-triol and a carbonyl compound
17(b) — Suggest an equation, using molecular formulae, for the trimerisation of propanone to form compound C
17(b)(ii) — Write an equation for the formation of nitrogen monoxide in an aircraft engine
Amount of substance
3 — Identify the sample containing the greatest number of carbon atoms
18(c)(ii) — Calculate the number of ibuprofen molecules in one 400 mg tablet, to 3 significant figures
20(b)(ii) — Calculate the number of PAS molecules in the maximum daily dosage for a 20.0 kg child
3 — Identify the molecular formula of a compound from the volumes of CO2 and water vapour formed on complete combustion
20(a) — Determine the molecular formula of the aromatic compound from its percentage composition and mass spectrum
22(c)(i) — Calculate the molecular formula of compound N from combustion data and suggest a possible structure
11 — Determine the empirical formula of a hydrocarbon from the mass of CO2 formed on combustion
7 — Determine the molecular formula of an alkane from the mass of water formed on combustion
5 — Identify the formula of hydrocarbon X from combustion gas volumes
16(e)(i) — Calculate the volume of hydrogen at RTP needed to saturate 204 mg of myrcene
21(b)(iii) — Calculate how many cans of diet drink a typical adult can safely drink in one day
8 — Calculate the mass of paracetamol in a tablet from the amount in mol
9 — Calculate the volume of hydrogen at RTP that reacts with 0.0500 mol of the given compound
17 — Determine the molar mass and molecular formula of Compound X and draw a possible structure
8 — Identify the alkane from the volume of oxygen needed for complete combustion of 0.100 mol
16(b)(iii) — Determine a possible molecular formula of compound B from its mass and vapour volume
6 — Calculate the volume of oxygen at RTP needed to burn 4.30 g of C5H9OH
10 — Calculate the concentration of ethylammonium chloride formed from ethylamine and hydrochloric acid
2 — Calculate the mass of Br2 needed to saturate 0.0200 mol of the given compound
16(b) — Use the mass, volume, pressure and temperature data to suggest the identity of the toxic gas
2 — Calculate the amount, in moles, of ibuprofen in a 200 mg tablet
17(b)(i) — Calculate the volume of CO2 released during a typical flight, in standard form to 3 significant figures
8 — Calculate the volume of HCl that reacts with 0.25 mol of the given compound
16(d)(iii) — Calculate the number of O3 molecules removed by one Cl• radical, in standard form to 3 significant figures
17(b)(ii) — Determine the molar mass of α-amino acid G and suggest its structure
5 — Identify the type of reaction with the greatest atom economy
7 — Identify the reaction for preparing ethanol with the lowest atom economy
11 — Calculate the percentage yield of C6H5NHCOCH3 from the given masses
6 — Identify the process with the highest atom economy for preparing ethene
18(b) — Determine the percentage yield of 1,3-dinitrobenzene to 3 significant figures
23(c) — Calculate the percentage yield of compound H to three significant figures
6 — Identify the reaction for preparing propene with the lowest atom economy
18(a)(iii) — Calculate the mass of phenol used, to 3 significant figures
Acids and redox
17(a)(ii) — Determine which amino acid the student used from the titration results
19(c) — Use the titration results to identify compound K
Electrons and bonding
18(d)(ii) — Suggest why tablets based on a salt of ibuprofen act faster than ibuprofen
1 — Identify what the electrostatic attraction in a covalent bond is between
19(b)(ii) — Draw a dot-and-cross diagram of NaBH4 and give the electron configuration of Na+
Shapes of molecules and intermolecular forces
6 — Identify the labelled atom with a trigonal planar arrangement of bonds
5 — Identify the molecule that is not planar
8 — Identify the compound containing a bond angle of approximately 120°
15 — Identify which ions contain bond angles of approximately 120°
17(b)(i) — Use electron pair repulsion to predict the shapes and bond angles around atoms A and B in serine
19(a)(iii) — Suggest a value for each bond angle a–c in lactic acid
14 — Identify the bond angles present in a molecule of but-2-en-1-ol
16(a) — Explain why branched compound A has a lower melting point than its isomer, compound B
17(b)(ii) — Explain why more repeat units increase the boiling point of the lubricating oil
6 — Identify why butan-1-ol has a higher boiling point than 2-methylpropan-2-ol
16(e)* — Identify compounds B–F from their boiling points and explain your reasoning (6-mark)
M4Module 4 — Core organic chemistry
Basic concepts of organic chemistry
2 — Identify how the given cyclic alcohol can be described
4 — Identify the structure that represents an alicyclic compound
19(a)(i) — Explain the term homologous series
13 — Identify which compounds are aliphatic
16(a) — Identify which hydrocarbons are unsaturated
16(b) — Identify which hydrocarbons are alicyclic
1 — Identify the compound that is alicyclic and unsaturated
21(a) — State what a functional group is
15 — Identify the terms that best describe the given molecule
16(a)(i) — Define the term homologous series
16(b)(i) — Name compound C, CH3CH2CH=CHCH2CH2OH
19(c)(ii) — Name compound K
16(a)(i) — Give the systematic name of alcohol A
3 — Identify the name of the given alkene
18(a)(i) — Give the systematic name of ester A
16(a) — Give the systematic name for (CH3)3CCHBrCH3
19(a)(i) — Give the systematic name for prenal
16(a)(i) — Give the systematic name of hydrocarbon A
7 — Identify the systematic name for the given compound
21(b)(i) — Give the systematic name of valine
20(b)(i) — Give the systematic name for ester F
16(a) — Give the systematic name of compound A
1 — Identify the systematic name of the given ester
19(a)(ii) — Give the full systematic name for compound G
17(a) — Name hydrocarbon D
9 — Identify the systematic name of the given compound
9 — Identify the molecular formula of the compound shown as a skeletal formula
16(a)(ii) — Give the structural formula of alcohol A
16(b)(ii) — Give the molecular formula of geraniol
9 — Identify the structural formula of ethyl 3-methylbutanoate
12 — Identify the molecular formula of the given steroid molecule
19(a)(ii) — Predict the molecular formula of the member of the homologous series with 24 carbon atoms
18(c)(i) — Give the molecular formula of ibuprofen
3 — Identify the general formula of the alkynes
5 — Determine the number of H atoms in a molecule of oxymetazoline
16(c) — Identify which hydrocarbons have the general formula CnH2n
3 — Determine the number of hydrogen atoms in the molecular formula of the given drug
16(a)(i) — Give the molecular formula of MAC
16(a)(ii) — Draw the skeletal formula of MAC
16(a)(ii) — Give the general formula of the alcohols homologous series
15 — Identify which compounds are structural isomers of C6H12O2
16(b)(iii) — Explain why geraniol and citronellal are structural isomers
10 — Determine the number of alicyclic structural isomers of C5H10
1 — Determine the number of structural isomers of C5H11Cl that could form from the radical substitution of 2-methylbutane
16(b)(i) — State what is meant by the term structural isomers
16(a)(iii) — State what is meant by structural isomers
20(a)(i) — State what a curly arrow shows in a reaction mechanism
20(a)(ii) — Draw the products of the given reaction mechanism
20(a)(iii) — Use the mechanism in (a)(ii) to explain heterolytic fission
20(b)(i) — Complete the given mechanism by adding curly arrows and missing species
19(c)(ii) — Explain why the mechanism in (c)(i) involves heterolytic fission
16(d)(i) — Add curly arrows to complete the mechanism for the Diels-Alder reaction
16(c)(ii) — Draw the product(s) of the first step of ozonolysis from the curly arrows shown
19(b)(ii) — Add dipoles and curly arrows to complete the mechanism for the hydrolysis of methyl lactate
Alkanes
1 — Identify the alkane with the highest boiling point
16(a) — State and explain the trend in boiling points of three C6 alkanes
14 — Identify the radicals present in the radical substitution of ethane with chlorine
22(a) — Write an equation for the incomplete combustion of heptane
2 — Identify the propagation step in the reaction of butane with chlorine in UV light
16(c) — Complete the table to show the mechanism for the reaction of hydrocarbon A with Br2
16(d) — State two limitations of radical substitution in organic synthesis
13 — Identify the equations that could be propagation steps in the radical substitution of C5H12
16(b)(i) — Complete the table to show the mechanism for forming 3-bromo-2-methylpentane, including three termination equations
16(b)(ii) — Write the equation, using molecular formulae, for forming compound A from 2-methylpentane
18(a)(i) — Write the equation for forming 2-bromo-2-methylpropane from an alkane, and name the mechanism and bond fission
18(a)(ii) — Describe two limitations of synthesising 2-bromo-2-methylpropane from an alkane and bromine
16(d) — Construct an equation for the incomplete combustion of 1.0 mol of hexane with 6.0 mol of oxygen
17(c)* — Describe the radical substitution of propane with chlorine, including equation, conditions, mechanism and limitations (6-mark)
1 — Identify the mechanism of the reaction of propane with chlorine
Alkenes
16(c) — Complete the diagram to show how p-orbitals are involved in forming a π-bond
5 — Identify the types of bond broken and formed in the reaction of ethene with bromine
2 — Identify the correct statement about σ- and π-bonds
16(a)(i) — Explain what is meant by the terms σ-bond and π-bond
16(a)(ii) — Determine the number of σ- and π-bonds in one molecule of buta-1,3-diene
4 — Identify the shapes around the labelled carbon atoms in but-1-ene
16(b) — Complete the table of molecular formula and numbers of σ and π bonds for two hydrocarbons
16(b)(ii) — Define the term stereoisomers
16(b)(iii) — Draw the structures of the cis and trans stereoisomers of compound C
16(b)(iv) — Explain the term stereoisomerism
16(c)(i) — Explain the term stereoisomerism
16(c)(ii) — Explain whether the student is correct that buta-1,3-diene shows stereoisomerism
16(b)(ii) — State what is meant by the term stereoisomers
16(b)(iii) — Draw the cis and trans isomers of branched hydrocarbon B
16(c)(i) — Draw the structures of the E and Z stereoisomers of compound B
16(c)(ii) — Explain why compound B can form E and Z stereoisomers
16(a)(ii) — Explain the term stereoisomers and draw the skeletal formulae of the two stereoisomers of alkene B
4 — Identify which of four structures is a Z-isomer
20(a) — Explain why methylcinnamaldehyde is an E stereoisomer using the CIP rules
4 — Identify the term that correctly describes the given stereoisomer
1 — Identify the name of the given bromoalkene
16(e) — Explain why hydrocarbon D is a Z-stereoisomer
16(d)(ii) — Draw the structures of the two organic compounds E and F formed from compound D and HBr
16(e)(ii) — Construct a balanced equation, using molecular formulae, for the reaction of β-carotene with hydrogen
16(b)(iii) — Determine how many saturated organic products could form from buta-1,3-diene and excess hydrogen bromide
2 — Identify why hydrogen reacts much more readily with alkenes than with alkanes
16(e) — Complete the flowchart of reactions of compound C, including the reagent, catalyst and products
16(c)(i) — Complete the flowchart with the product of Reaction 1 and the minor product of Reaction 2
16(d)(i) — Suggest how an HBr molecule can act as an electrophile
16(d)(iii) — Outline the mechanism of the reaction between compound D and hydrogen bromide
16(d)(iv) — Identify the major organic product, E or F, and explain your choice
20(d)* — Outline the mechanism for the electrophilic addition of ICl to methylcinnamaldehyde and explain which product is more likely (6-mark)
16(a)(i) — Outline the mechanism for the reaction of 3-methylbut-2-enal with hydrogen bromide
16(a)(ii) — Explain why one organic product forms in a much greater quantity than the other
16(b)(i) — Outline the mechanism for the formation of the major product of but-1-ene with hydrogen bromide
16(b)(ii) — Explain why one organic product forms in a much greater quantity than the other
16(a)(ii) — Outline the mechanism for the reaction of hydrocarbon A with bromine
21(a)(i) — State what is meant by the term electrophile
8 — Identify the correct statement about the reaction of ethene with hydrogen bromide
7 — Identify the major intermediate in the reaction of hydrogen bromide with 3-methylbut-1-ene
16(c)(ii) — Draw the mechanism for the formation of compound A
16(c)(iii) — Explain why compound B is the minor product of Reaction 2
21(b) — Outline and name the mechanism for Reaction 1
2 — Identify the name of the major product of the given alkene with HBr
5 — Identify the structure that shows a section of poly(propene)
17(b)(i) — Draw the repeat unit of the oligomer made from 2-chloro-1,1,2-trifluoroethene
19(c)(i) — Draw pent-3-enoic acid and two repeat units of its addition polymer
19(a)(iii) — Suggest a structure for compound H and draw the repeat unit of its addition polymer
16(b)(i) — Write a balanced equation for the addition polymerisation of phenylethene
21(c)(i) — Draw the repeat unit of the addition polymer formed from compound M
2 — Identify the correct statement about absorption of radiation
18(b)(i) — Suggest why a polymer containing chlorine is difficult to dispose of by incineration
19(a)(iv) — State two methods, apart from recycling, for usefully processing waste polymers
16(b)(ii) — State one way of processing waste polymers usefully, other than landfill and recycling
19(b) — Suggest one way of processing waste polymer I other than landfill and recycling
Alcohols
19(b)(i) — Explain, with a diagram, why ethanol is soluble in water
19(b)(ii) — Explain the difference in solubility of hexan-1-ol and hexane-1,6-diol in water
22(b) — Explain the difference in the boiling points of the fuels in Table 22.1
17(a)(ii) — Explain, with a diagram, why compound D is very soluble in water
8 — Identify the molecule that is most soluble in water
19(a) — Construct an equation for the complete combustion of an unsaturated alcohol with 5 carbon atoms
19(d) — Describe both oxidation reactions of butan-1-ol, including equations, products and conditions
16(a)(iii) — Draw the structures of the two alkenes formed when alcohol A is heated with an acid catalyst
16(a)(iv) — Construct a balanced equation for the reaction of alcohol A with sodium chloride and sulfuric acid
16(b) — Complete the equation for the oxidation of compound B by excess acidified dichromate under reflux
4 — Identify the compound that forms a product C5H8O2 when refluxed with acidified dichromate
6 — Identify the alcohol that forms a mixture of stereoisomers with an acid catalyst
18(a)(i) — State the reagents and conditions and write an equation for the oxidation of HO(CH2)4OH
4 — Identify the correct equation for the incomplete combustion of butan-1-ol
7 — Identify a structure that could form when menthol is heated with an acid catalyst
20(c) — Write an equation for the oxidation of compound J with acidified dichromate under reflux
17(a) — Construct an equation for the complete combustion of an unsaturated alcohol with 6 carbon atoms
17(b) — Complete the equation for the oxidation of compound C by excess acidified dichromate under reflux
17(c)(i) — Draw the three isomers of C7H10 formed when compound D is refluxed with H2SO4
17(c)(ii) — Suggest reagents to convert compound D into a diiodoalkane
17(a) — Choose reagent(s) and show the organic product for the elimination reaction of butan-1-ol
17(b) — Choose reagent(s) and show the organic product for the oxidation of CH3CH2CHOHCH3
17(c) — Choose reagent(s) and show the organic product for a substitution reaction of (CH3)2CHCH2OH
13 — Identify which molecules would form a ketone group when oxidised
19(b)(i) — Suggest suitable reagents to convert propan-1-ol into 1-bromopropane
20(b) — Suggest how you could tell when the excess dichromate has completely reacted
1 — Identify the conditions for preparing bromoethane from ethanol and NaBr
5 — Identify the organic product of butan-1-ol with acidified dichromate in the apparatus shown
16(a)(i) — State the type of reaction in Equation 16.1
16(a)(iii) — Suggest the structure of alkene C
3 — Identify the Mr of the organic product of the given compound with NaBr and H2SO4
Haloalkanes
1 — Identify the reagent used to compare the rates of hydrolysis of 1-chloropropane and 1-bromopropane PS
3 — Identify the compound that does not react with nucleophiles
19(a) — State and explain how the halogen in a haloalkane affects the rate of hydrolysis
19(b) — Outline the mechanism for the hydrolysis of chlorocyclohexane with aqueous sodium hydroxide
19(c)(ii) — Analyse the information to identify haloalkane E, organic product F and precipitate G
6 — Identify the organic product of the given compound with KOH(aq)
20(b)(ii) — State the role of OH− in the mechanism
1 — Identify the correct statement about the rates of hydrolysis of RCl and RBr
14 — Identify which species could react as a nucleophile
3 — Identify the colour of precipitate when iodoalkanes are hydrolysed with silver nitrate in ethanol
16(c)(iv) — Draw the product of MAC with water, AgNO3(aq) and ethanol, and state the observation
9 — Identify the organic compound that gives a cream solid with aqueous silver nitrate and ethanol
15 — Identify the true statements about the rate of hydrolysis of haloalkanes
19(b)(i) — Suggest how the hydroxide ion can act as a nucleophile
16(c)(i) — Outline the mechanism of the reaction of 1-bromobutane with aqueous sodium hydroxide
16(c)(ii) — Name the type of mechanism in (c)(i)
16(c)(iii) — Identify a haloalkane that forms the product faster and explain
8 — Identify the propagation step in the breakdown of ozone catalysed by NO radicals
17(a) — Explain, with equations, how Freon-13 can lead to ozone depletion
8 — Identify the UV initiation step for CCl2F2 that could catalyse ozone breakdown
16(d)(i) — Construct an equation for the formation of Cl• radicals from chlorotrifluoromethane
16(d)(ii) — Write the equations for the two steps and the overall breakdown of ozone by Cl• radicals
Organic synthesis
20(a)* — Calculate the mass of cyclopentanol needed and explain how pure cyclopentene could be obtained from the distillate (6-mark) PS
23(d) — Describe how to purify the impure compound H from the two layers in Step 2 PS
19(b)(ii) — Describe how to obtain pure 1-bromopropane from the two-layer mixture PS
6 — Identify how to remove an acid impurity from an organic liquid PS
16(a)(iv)* — Describe how to obtain pure, dry alkene B and calculate the mass produced (6-mark) PS
20(e) — Suggest reagents, conditions and equations for the two-stage synthesis of 1-phenylethanol from 2-phenylethanol
17* — Plan a two-stage synthesis of compound F from compound D, including the mass needed for a 31.5% yield (6-mark)
10 — Identify the intermediate in the two-step synthesis
Spectroscopy
9 — Identify the compound that could have produced the given IR spectrum
20(b) — Explain how the IR spectrum shows that cyclopentene formed and that the reaction is incomplete
11 — Identify the compound that could have produced the given IR spectrum
11 — Identify the compound that could have produced the given IR spectrum
11 — Identify the compound that could have produced the given IR spectrum
7 — Identify a valid scientific reason for global warming
11 — Identify the compound that could have produced the given IR spectrum
12 — Identify the process that does not involve infrared radiation
12 — Identify the ion responsible for the base peak in the mass spectrum of (CH3)2CHCH2OH
21(c)(ii) — Deduce possible structures for esters J, L and M from the mass spectrometry results
18(e)(ii) — Suggest structures for the species responsible for peaks Y and Z in the mass spectrum of ester C
12 — Identify the peak in the mass spectrum of propanal but not of propanone
18(b) — Identify carbonyl compounds F and G from their percentage composition and mass spectra
10 — Identify the ester most likely to give a fragment ion at m/z = 43
11 — Identify the molecule that does not give a mass spectrum peak at m/z = 29
16(d) — Deduce the structure of compound C from its percentage composition and IR spectrum
12 — Identify the statement most likely to be true about the mass spectrum of the given ester
16(b) — Determine the structure of alcohol A and fragment ion X from the mass spectrum
M6Module 6 — Organic chemistry and analysis
Aromatic chemistry
13 — Identify the statements that support the delocalised model of benzene
19(a)(i) — Describe the similarities and differences in orbital overlap between the Kekulé and delocalised models of benzene
19(a)(ii) — Describe two pieces of evidence for the delocalised model of benzene
14 — Identify the statements that provide evidence for the delocalised model of benzene
3 — Determine the number of sigma bonds in a molecule of methylbenzene
6 — Identify the statement that supports the delocalised model of benzene and not the Kekulé model
16(d) — Give the systematic name of hydrocarbon C
20(a) — Suggest two other pieces of evidence for the delocalised model of benzene
14 — Identify the statements that support the delocalised model of benzene
18(a) — Explain the evidence for the updated model of benzene and describe its bonding
4 — Determine the number of sigma bonds in a benzene molecule
17(a)(i) — Outline the mechanism for the nitration of benzoic acid, showing how H2SO4 acts as a catalyst
18(b) — Complete the mechanism for the reaction of methylbenzene with SO3
19(b)(iii) — Complete the mechanism for the reaction of benzene with ethanoyl chloride and AlCl3
17(a)(i) — Draw the organic products of compounds B and C with chlorine
17(a)(ii) — Explain the relative resistance to chlorination of compound C compared with compound B
17(a)(iii) — Outline the mechanism for the reaction of compound C with chlorine, showing the role of the halogen carrier
20(a)(i) — Complete the mechanism for Stages 1 and 2 in the preparation of salicylic acid from phenol
20(a)(ii) — State the roles of –OH and CO2 in the mechanism
20(a)(iii) — Outline the mechanism for the 4-substitution of compound J by chlorine, showing the role of the catalyst
18(a) — Outline the mechanism for the nitration of nitrobenzene, including the role of H2SO4 as a catalyst
21(a)(ii) — Outline the mechanism for the reaction of benzene with chloroethane and AlCl3, including the role of AlCl3
20(c)(ii) — Outline the mechanism for Stage 2, showing the role of H2SO4 as a catalyst
4 — Identify the mechanism for the nitration of benzene
18(b) — Outline the mechanism for forming 4-chloromethylbenzene, showing how AlCl3 acts as a catalyst
18(a)(i) — Complete the mechanism for Stage 2 with dipoles, curly arrows and the intermediate
17(b)(i) — State the trend in the relative ease of nitration of phenol, benzene and benzoic acid
17(b)(ii) — Explain the trend in ease of nitration using the bonding in arenes
18(a)(ii) — Explain why phenol is nitrated more readily than benzene
8 — Identify the least likely organic product of phenol reacting with bromine
14 — Identify which chemicals can react with phenol
7 — Identify the reagent that reacts with both ethanoic acid and phenol
20(b) — Explain why compounds K and L react with chlorine more readily than compound J
21(b)(ii) — Write an equation for the tri-substitution of C6H5NH2 with chlorine
21(b)(iii) — Explain why chlorine reacts much more readily with C6H5NH2 than with benzene
20(b)(i) — Explain the difference in reactivity of benzene and phenol with bromine
20(b)(ii) — Construct an equation for the reaction of phenol with excess bromine
18(a)(ii) — Explain why the FeCl3 catalyst is not needed with quinol
7 — Identify what the student would see when bromine water is added to phenol
18(c)(ii) — Draw the product of the tri-substitution of C6H5N(CH3)2 with chlorine
18(c)(iii) — Explain why chlorine reacts much more readily with C6H5N(CH3)2 than with benzene
11 — Identify the reagent that could distinguish between CH3CH2OH and C6H5OH
18(a)(ii) — State and explain the type of reaction in Stages 1 and 3
17(c)(ii) — Explain why reducing before brominating gives two isomers, and suggest their structures
21(b)(i) — Draw all monosubstituted products of the given reactions using the directing effects table
20(c)(iii) — Suggest why Synthesis 2 fails and the structure of the compound it forms
9 — Identify the organic products of bromine with nitrobenzene and with phenylamine
18(a)(i) — Suggest the identity and structure of the product C14H22O2
18(c)(i) — Draw all monosubstituted products of the given reactions using the directing effects table
Carbonyls and carboxylic acids
19(c)(i) — Complete the flowchart of reactions that form and use an alcohol
13 — Identify which alcohols could be formed by reacting a carbonyl compound with NaBH4
19(c)(i) — Outline the mechanism for the reaction of F with NaCN(aq)/H+(aq) and name the mechanism
5 — Identify the correct statement about the reaction of 2-methylcyclopentanone with NaCN(aq)/H+(aq)
22(a)(i) — Outline the mechanism for the reaction of acrolein with NaCN(aq)/H+(aq)
22(a)(ii) — Name the type of mechanism in (a)(i)
19* — Describe one addition reaction of an alkene and one of a carbonyl compound, including reagents and mechanisms (6-mark)
21(d) — Outline the mechanism for the reaction of pyruvic acid with NaBH4
13 — Identify what happens to the smell of menthone in a two-step reaction
19(b)(i) — State an oxidising agent and equation for Step 1, and outline the mechanism for Step 2
3 — Identify the functional group formed when the given molecule reacts with NaBH4
10 — Identify the organic product of benzaldehyde with NaCN(aq)/H+(aq)
19(a)(i) — Draw the structure of compound E
20(b)(ii) — Describe a chemical test, with reagent and observations, to confirm both compounds contain an aldehyde group PS
20(b)(iii) — Describe a test for a carbonyl group and how its products could distinguish the two compounds PS
16(b)(i) — Describe how a chemical test would distinguish between geraniol and citronellal PS
18(a)(i) — Describe a chemical test for a carbonyl group and how its product could identify the compound PS
18(a)(ii) — Describe a chemical test, with reagent and observations, to identify whether a carbonyl compound is an aldehyde PS
2 — Identify the compound that reacts with 2,4-DNP but not with Tollens' reagent
21(b) — Suggest the reagent and observation of a test that is positive for all three carbonyl compounds PS
20(d) — Plan a chemical test to confirm the identity of the pure organic product PS
20(b) — Explain, with a chemical test, how compound J could be identified PS
20(a)(ii) — Suggest a test, with observation and equation, to identify the aldehyde PS
20(b) — Suggest a chemical test to distinguish the ketone from the two esters PS
12 — Determine the number of water molecules formed when a dicarboxylic acid reacts with aqueous NaOH
18(a)(ii) — Explain, using a labelled diagram, why HOOC(CH2)2COOH is soluble in water
19(a) — Write equations for reactions of carboxylic acids with an alkali, a metal and a carbonate
20(a) — Explain, with a labelled diagram, how methanoic acid interacts with water when it dissolves
23(b)(i) — Write equations for removing the sulfuric acid and unreacted compound G with Na2CO3(aq)
5 — Determine the number of water molecules formed when HOOCCH2CH2COOH reacts with NaOH
10 — Identify which compound gives the most acidic solution when added to water
13 — Identify the reagents that could be used to prepare CH3CH2CONHCH3
18(a)(ii) — Draw the organic products of the acid and alkaline hydrolysis of ester A
18(a)(iii) — Name the type of reaction of ester A in (a)(ii)
14 — Identify which reactions produce propan-1-ol
18(b)(iii) — Complete the equation for the formation of a diacyl dichloride from HOOC(CH2)2COOH
6 — Identify the two organic products of heating CH3CH2COOCH3 with aqueous sodium hydroxide
20(a)(iii) — Write the equation for two molecules of salicylic acid reacting to form compound B
10 — Identify a product of the hydrolysis of butyl propanoate by aqueous sodium hydroxide
20(f) — Suggest an equation for the reaction of benzoic anhydride with butan-2-ol
12 — Identify the compound that reacts with ethanoyl chloride
14 — Identify which compounds are hydrolysed by HCl(aq) to produce butanoic acid
17(d) — Choose reagent(s) and show the organic product for an esterification reaction of (CH3)3COH
20(b)(ii) — Write equations for converting a carboxylic acid into ester F via an acyl chloride
23(b)(ii) — Comment on whether using NaOH(aq) instead of Na2CO3(aq) would improve the preparation PS
9 — Identify the reagents a student could use to prepare the given ester
18(c) — Complete the equation for the reaction of 3-hydroxybutanoic acid with ethanoic anhydride
10 — Identify the alcohol that could be used to prepare HCOOCH(CH3)2
18(b)(i) — State suitable reactant(s) and conditions for step 1
19(b)(iii) — Complete the equation for the reaction of methyl lactate with ethanoyl chloride
6 — Identify the compound that cannot be hydrolysed
18(b) — Draw skeletal formulae for the products of salicylic acid with ethanoic anhydride
18(c)(i) — Suggest the structure of oil of wintergreen and the conditions to prepare it
20(c)(i) — Write an equation for the hydrolysis of one ester with aqueous sodium hydroxide
Amines, amino acids, and polymers
7 — Identify which of four molecules is a secondary amine
18(a)(iii) — Explain why compound H reacts with dilute hydrochloric acid and suggest a structure for the salt
9 — Identify the reaction that is not a reduction
20(d)(i) — Add the reagents for each stage of the two-stage synthesis of an amine from compound J
20(d)(ii) — Fill in the equation for the reduction stage of the synthesis
20(c)(iv) — Suggest reagents and complete the equation for reducing compound G to amine H
18(b)(ii) — Write an equation for the reduction of compound F by tin and concentrated hydrochloric acid
7 — Identify the reagents needed to prepare the given compound from phenol
13 — Identify the main organic product of CH3CH2Cl with excess ethanolic NH3
8 — Determine the number of chiral centres in the given molecule
2 — Identify which of four structures is a secondary amide
11 — Determine how many straight-chain structural isomers of C7H15Cl contain a chiral carbon atom
17(a) — Draw 3-D diagrams to show the optical isomers of cysteine
17(b) — Draw the structure of the salt formed when lysine reacts with excess dilute hydrochloric acid
7 — Determine the number of chiral carbon atoms in the steroid molecule
16(b)(v) — Explain the types of stereoisomerism shown by geraniol and citronellal, with diagrams
17(a)(i) — Draw the organic products of the reactions of serine shown in the boxes
16(b)(i) — Explain the term stereoisomers and name the type of stereoisomerism shown
16(b)(ii) — Draw 3D diagrams for the stereoisomers of (CH3)3CCHBrCH3
2 — Identify the type(s) of stereoisomerism shown by 2,4-dimethylhex-2-ene
18(a)(i) — Explain the term optical isomerism
18(a)(ii) — Draw 3-D diagrams to show the optical isomers of alanine
18(a)(iii) — Determine how many optical isomers threonine has
18(d)(i) — Suggest the structure of each ion in the lysine salt of ibuprofen
5 — Determine the number of chiral carbon atoms in the given drug molecule
16(b)(iv) — Draw 3D structures for the optical isomers of compound C
21(a) — Explain the term optical isomerism
21(b)(ii) — Draw 3D structures of the optical isomers of valine
21(c)(i) — Determine how many optical isomers are possible for compound E
9 — Identify which compound is a secondary amide
10 — Determine the number of stereoisomers of CH3CH(Br)CH=CHCH(Cl)CH3
22(a)(ii) — Draw both possible structures of compound S
22(b)(ii) — Suggest the difference between an α-keto acid and a β-keto acid
3 — Determine the number of stereoisomers of CH3CH=CHCH(OH)CH2CH=CH2
17(b)(ii) — Draw the ionic product of serine with excess NaOH(aq) and outline how to purify it PS
17(c)(i) — Mark each chiral centre in tabtoxin with an asterisk
5 — Determine the number of chiral centres in the given molecule
17(a)(i) — Explain the term optical isomers and draw the two optical isomers of serine
17(a)(ii) — Draw the three products of serine reacting with glycine
17(b)(i) — Draw aspartic acid and the missing organic products in the flowchart
18(a)(iv) — Draw two repeat units of polymer J and suggest why it is biodegradable
18(b)(i) — Draw the structures of two monomers that can form Nylon 6,6
17(c) — Draw the organic products formed when a section of protein is hydrolysed with hot NaOH(aq)
21(b) — Complete the flowchart for making polymer I from compound H via an acyl chloride
9 — Identify the monomers that could form the polymer with the given repeat unit
19(b)(i) — Draw two repeat units of the polymers formed from compounds D and E
19(b)(ii) — State the type of polymer formed from compounds D and E
18(b)(i) — Draw one repeat unit of polymer E with the functional groups displayed
18(b)(ii) — Suggest why polymer E is able to biodegrade
21(b)(ii) — Draw the three organic products of the complete acid hydrolysis of aspartame
17(c) — Draw the two monomers and one repeat unit of the polymer they form
19(c)(ii) — Draw one repeat unit of the condensation polymer from butanedicarboxylic acid and 1,4-dihydroxy-2-methylbenzene
19(c)(iii) — Draw the monomer required to form the given condensation polymer
19(d)(i) — Draw one repeat unit of the polymer formed from 2-aminopropanoic acid
20(b)(i) — Draw a section of a PAS polymer containing one amide and one ester linkage
21(c)(ii) — Draw the organic products of hydrolysing compound E with dilute hydrochloric acid
12 — Identify the other product formed when 1,6-diaminohexane reacts with hexanedioyl dichloride
20(c) — Draw the monomers required to form the given polyester
20(d) — Draw the organic products of the complete alkaline hydrolysis of a compound containing an ester and an amide group
22(b) — Draw 2 repeat units of the addition and condensation polymers of the given amino acid
7 — Identify the organic products of the acid hydrolysis of CH3CH2CONHCH3
18(a) — Draw two repeat units of each polymer and state the type of polymerisation
18(b)(ii) — Suggest the structural feature that allows the polymer of 3-hydroxybutanoic acid to be hydrolysed
17(a)(iii) — Draw a possible repeat unit of the condensation polymer of compound D and propanedioic acid
17(c)(ii) — Draw all the organic products of the alkaline hydrolysis of tabtoxin
13 — Identify which monomers could be used to make the given polymer
21(c)(ii) — Draw two repeat units of the condensation polymer formed from compound M
21(d) — Draw all the organic compounds formed by the acid hydrolysis of neotame
Organic synthesis
18(a)(i) — Outline the mechanism for the reaction of 1-chloropropane with ethanolic sodium cyanide
18(a)(ii) — Complete the flowchart showing compound G and the reagents for Reactions 2 and 3
10 — Identify the organic reagent that forms phenylethanone from benzene with a halogen carrier
15 — Identify which reagents could react with the given compound to form a carbon–carbon bond
15 — Identify which compounds could be made from benzene and an acyl chloride with a halogen carrier
21* — Describe the formation of C–C bonds in aliphatic compounds by two different mechanisms (6-mark)
19(a)(i) — Outline the mechanism for the reaction of 2-bromopropane with cyanide ions
19(a)(ii) — Name the type of mechanism in (a)(i)
20(c)(i) — Suggest a reagent and halogen carrier for Stage 1 of Synthesis 1
11 — Identify the mechanisms for the reactions of CN− with haloalkanes and with carbonyl compounds
19(a)(ii) — Suggest a reagent for Step 2
17(a)(ii)* — Describe how to purify impure 3-nitrobenzoic acid, determine the percentage yield and check its purity (6-mark) PS
14 — Identify the true statements about recrystallisation PS
20(b)(i) — Describe how the student could recrystallise the impure crystals to obtain pure C PS
18(c) — Describe how to purify the impure crystals in Step 3 PS
17(c)(i) — Complete the flowchart for the synthesis of 3-bromophenylamine from nitrobenzene
16(c) — Draw the organic products of the reactions of compound C in the flowchart
20(c) — Complete the flowchart of reactions starting with cinnamaldehyde, including the missing reagent(s)
21(a) — Draw the organic products of the reactions of compound H in the flowchart
15 — Identify the functional groups in the given influenza drug molecule
18(e)(i)* — Plan a two-stage synthesis of ester C from 2-methylpropanal, including the mass needed for a 40% yield (6-mark)
19(b)(iv) — Complete the flowchart for the synthesis of compounds D and E from phenylethanone
3 — Identify the reagent that will not react with HOCH2CH2CH2COOH
17(c)(ii) — Complete the flowchart for the three-stage synthesis of compound D from compound C
21(a) — Complete the flowchart for the synthesis of salt H from propanone
21(b)(i) — Name the functional groups in aspartame, apart from the benzene ring
15 — Identify which compounds react when heated with NaOH(aq)
16(d)(ii) — Draw the organic products of two more Diels-Alder reactions of buta-1,3-diene
18(b) — Complete the flowchart for two synthetic routes to the amino acid valine
19(a)(ii) — Complete the flowchart for the synthesis of two compounds from prenal
19(b)* — Plan a two-stage synthesis of compound A from (chloromethyl)benzene, including the mass needed for a 25% yield (6-mark)
4 — Identify the functional groups in the given skeletal formula
16(c)(i) — Draw the products expected from the ozonolysis of the two given compounds
19(b) — Fill in the flowchart for reactions involving 2-hydroxybutanoic acid
19(e)* — Plan a synthesis of compound I from 2-chloropropanoic acid, including the starting mass for a 64% yield (6-mark)
4 — Identify the functional groups present in paracetamol
19* — Plan a three-stage synthesis of compound Z, showing reagents, intermediates and equations (6-mark)
20(a) — Complete the flowchart by adding the organic products of reactions of salicylic acid
22(b) — Complete the flowchart of reactions starting from acrolein
18(b) — Complete the flowchart of reactions starting from bromoethane
14 — Identify which reagents will react with vitamin C
21(e) — Complete the flowchart for the reactions of pyruvic acid
22(b)(i) — Draw the organic products expected from the decomposition of two other β-keto acids
12 — Identify the statement that is not true about the given pain reliever molecule
17(a)(i) — Devise a two-step synthesis of compound D from ethanal, with reagents, conditions and equations
19(a)(i) — Fill in the boxes to show the organic products of Reactions 1 and 2
14 — Identify the correct statements about the functional groups in the given molecule
20(a) — Draw the structures of compounds F, G, H, I, J and K
21(a) — Complete the flowchart of reactions of compound L by drawing the missing structures
17(d) — Draw compound H and add the reagents for the two-stage synthesis of alanine from lactic acid
19(a) — Complete the flowchart for the synthesis of polymer I from benzene
Chromatography and spectroscopy
21(c)(i) — Calculate the concentration of ester M from the gas chromatography results, to two significant figures
17(b)(i) — Calculate the Rf value of serine in solvent W
17(b)(ii) — Analyse the two TLC chromatograms to identify the unknown amino acid
13 — Identify the correct statements about gas chromatography
10 — Determine the Rf value of the compound most strongly adsorbed onto the stationary phase
13 — Identify the true statements about the gas chromatogram of X, Y and Z
22(a)(i) — Determine the Rf values of the two α-amino acids in the chromatogram
20(c) — Outline how TLC could be used to monitor the course of the reaction PS
17(c)(i) — Analyse the chromatogram to identify the amino acids
17(c)(ii) — Predict and explain the effect of a more polar solvent on the Rf values
20(b) — Determine the functional groups in the compound from the qualitative test results
20(b)(i) — Suggest a chemical test, with reagent and observations, to show both compounds are unsaturated PS
19(b) — Describe chemical tests, with observations, to confirm the functional groups in F and G PS
20(a)(i) — State chemical test(s) to confirm the phenol group in compounds K and L PS
5 — Identify the pair of reagents that identifies both functional groups in geraniol
21(c) — Complete the table of expected observations for three chemical tests on the three compounds
4 — Identify compound W from the results of two chemical tests
8 — Determine the minimum number of C atoms in aromatic compound Y from two test results
20(a)(i) — Suggest a test, with observation and equation, to identify the carboxylic acid PS
20(c)(ii) — Suggest a test on the hydrolysis products that would identify the two esters, with an equation PS
1 — Identify the compound used as a standard for NMR chemical shift measurements
22(a) — Explain the use of two deuterated compounds in NMR spectroscopy
1 — Identify the compound used for proton exchange in NMR spectroscopy
18(a)(i) — Explain whether 13C NMR spectroscopy could distinguish between three nitrophenols
10 — Identify the compound that shows 4 peaks in its carbon-13 NMR spectrum
12 — Identify the compound that could have produced the given 13C NMR spectrum
18(c) — Draw a possible structure for compound B, a structural isomer of ester A
8 — Identify the isomer of C6H12O2 with the fewest peaks in its 13C NMR spectrum
17(c)(i) — Predict the number of peaks in the 13C NMR spectra of compounds C and D
13 — Identify which compounds have four peaks in a 13C NMR spectrum
15 — Identify which isomers of C5H12O have 4 peaks in their 13C NMR spectrum
20(a)(ii) — Explain whether 13C NMR spectroscopy could distinguish between compounds J, K and L
17(d) — Explain whether carbon-13 NMR could distinguish the four alcohol isomers of C4H10O
14 — Identify which compounds would give a carbon-13 NMR spectrum with 2 peaks
15 — Identify which compounds have three peaks in their 13C NMR spectrum
12 — Determine the number of peaks in the 13C NMR spectrum of 1,3-dimethylbenzene
20(c)(iii) — Explain whether 13C and 1H NMR could identify the two esters
11 — Determine the number of peaks in the 1H NMR spectrum of the given compound
6 — Determine the number of peaks in the 1H NMR spectrum of HOOCCH2CHOHCH2COOH
18(b) — Complete the table to predict the proton NMR spectrum of ester A
12 — Identify the compound that produces two triplets in its 1H NMR spectrum
9 — Identify the compound with the greatest number of peaks in its proton NMR spectrum
15 — Identify the true statements about the NMR spectra of molecule Z
11 — Determine the number of peaks in the 1H NMR spectrum of the given hydrocarbon
20(c) — Determine the structure of the compound using the 13C NMR spectrum and earlier results
21* — Suggest a structure for compound L from its 1H NMR spectrum and the IR spectra of its hydrolysis products (6-mark)
22(d)* — Suggest a structure for the fuel additive from elemental analysis, mass spectrum and 1H NMR in D2O (6-mark)
21* — Suggest a structure for the unknown compound from elemental analysis, mass spectrum, IR and 1H NMR in D2O (6-mark)
22(b)* — Determine the structure of compound I from elemental analysis, mass spectrum, IR and proton NMR (6-mark)
20(b)(ii) — Analyse the composition, mass spectrum, 13C NMR and directing effects to suggest the structure of C
21* — Analyse the test-tube observations and NMR results to identify isomers D, E and F (6-mark)
16(b)(v) — Draw the structures of D and E and explain how the NMR and IR data support them
18(c) — Analyse the 1H NMR spectrum to suggest a structure for compound H
23* — Identify the unknown compound from the 2,4-DNP test, elemental analysis, mass spectrum, IR and proton NMR (6-mark)
24* — Determine the structure of compound J from elemental analysis, mass spectrum, IR and proton NMR (6-mark)
23(a) — Suggest the functional group in compound K and possible structures for K, L and M
23(b)* — Determine the structure of compound N from elemental analysis, mass spectrum and proton NMR (6-mark)
21* — Suggest a structure for compound L from its mass spectrum and 1H (with and without D2O) and 13C NMR spectra (6-mark)
22 — Identify the compound in the ink from elemental analysis, mass spectrum, IR and 1H NMR
20(d) — Suggest all possible structures for the ketone and identify the aldehyde from the NMR data
21* — Suggest a structure for compound J from elemental analysis, mass spectrum, IR and 1H NMR (6-mark)
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