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HL Paper 2

A student performs a titration to determine the concentration of ethanoic acid, CH3COOH, in vinegar using potassium hydroxide.

The pH curve for the reaction is given.

Write a balanced equation for the reaction.

[1]
a.

Identify the major species, other than water and potassium ions, at these points.

[2]
b(i).

State a suitable indicator for this titration. Use section 22 of the data booklet

[1]
b(ii).

Suggest, giving a reason, which point on the curve is considered a buffer region.

[1]
b(iii).

State the Ka expression for ethanoic acid.

[1]
c.

Calculate the Kb of the conjugate base of ethanoic acid using sections 2 and 21 of the data booklet.

[1]
d.

In a titration, 25.00cm3 of vinegar required 20.75cm3 of 1.00moldm-3 potassium hydroxide to reach the end-point.

Calculate the concentration of ethanoic acid in the vinegar.

[2]
e.

Potassium hydroxide solutions can react with carbon dioxide from the air. The solution was made one day prior to using it in the titration.

State the type of error that would result from the student’s approach.

[1]
f(i).

Potassium hydroxide solutions can react with carbon dioxide from the air. The solution was made one day prior to using it in the titration.

Predict, giving a reason, the effect of this error on the calculated concentration of ethanoic acid in 5(e).

 

[2]
f(ii).



Compound A is in equilibrium with compound B.

Predict the electron domain and molecular geometries around the oxygen atom of molecule A using VSEPR

 

[2]
a.

State the type of hybridization shown by the central carbon atom in molecule B.

[1]
b.

State the number of sigma (σ) and pi (π) bonds around the central carbon atom in molecule B.

[1]
c.

The IR spectrum of one of the compounds is shown:

COBLENTZ SOCIETY. Collection © 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.

Deduce, giving a reason, the compound producing this spectrum.

[1]
d.

Compound A and B are isomers. Draw two other structural isomers with the formula C3H6O.

[2]
e.

The equilibrium constant, Kc, for the conversion of A to B is 1.0×108 in water at 298K.

Deduce, giving a reason, which compound, A or B, is present in greater concentration when equilibrium is reached.

[1]
f(i).

Calculate the standard Gibbs free energy change, G, in kJmol1, for the reaction (A to B) at 298K. Use sections 1 and 2 of the data booklet.

[1]
f(ii).

Propanone can be synthesized in two steps from propene. Suggest the synthetic route including all the necessary reactants and steps.

[3]
g(i).

Propanone can be synthesized in two steps from propene.

Suggest why propanal is a minor product obtained from the synthetic route in (g)(i).

[2]
g(ii).



This question is about carbon and chlorine compounds.

Ethane, C 2 H 6 , reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.

M17/4/CHEMI/HP2/ENG/TZ1/06.a

[1]
a.

Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.

M17/4/CHEMI/HP2/ENG/TZ1/06.bi

[3]
b.i.

Deduce the splitting patterns in the 1H NMR spectrum of C2H5Cl.

[1]
b.ii.

Explain why tetramethylsilane (TMS) is often used as a reference standard in 1H NMR.

[2]
b.iii.

One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.

[2]
c.i.

The mass and 1H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.

[3]
c.ii.

When the product X is reacted with NaOH in a hot alcoholic solution, C2H3Cl is formed. State the role of the reactant NaOH other than as a nucleophile.

[1]
c.iii.

Chloroethene, C 2 H 3 Cl , can undergo polymerization. Draw a section of the polymer with three repeating units.

[1]
d.



Chlorine undergoes many reactions.

2.67g of manganese(IV) oxide was added to 200.0cm3 of 2.00moldm-3 HCl.

MnO2(s)+4HCl(aq)Cl2(g)+2H2O(l)+MnCl2(aq)

Chlorine gas reacts with water to produce hypochlorous acid and hydrochloric acid.

Cl2(g)+H2O(l)HClO(aq)+HCl(aq)

CCl2F2 is a common chlorofluorocarbon, CFC.

State the full electron configuration of the chlorine atom.

[1]
a(i).

State, giving a reason, whether the chlorine atom or the chloride ion has a larger radius.

[1]
a(ii).

Outline why the chlorine atom has a smaller atomic radius than the sulfur atom.

[2]
a(iii).

The mass spectrum of chlorine is shown.

NIST Mass Spectrometry Data Center Collection © 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.


Outline the reason for the two peaks at m/z=35 and 37.

[1]
a(iv).

Explain the presence and relative abundance of the peak at m/z=74.

[2]
a(v).

Calculate the amount, in mol, of manganese(IV) oxide added.

[1]
b(i).

Determine the limiting reactant, showing your calculations.

[2]
b(ii).

Determine the excess amount, in mol, of the other reactant.

[1]
b(iii).

Calculate the volume of chlorine, in dm3, produced if the reaction is conducted at standard temperature and pressure (STP). Use section 2 of the data booklet.

[1]
b(iv).

State the oxidation state of manganese in MnO2 and MnCl2.

[2]
b(v).

Deduce, referring to oxidation states, whether MnO2 is an oxidizing or reducing agent.

[1]
b(vi).

Hypochlorous acid is considered a weak acid. Outline what is meant by the term weak acid.

 

[1]
c(i).

State the formula of the conjugate base of hypochlorous acid.

[1]
c(ii).

Calculate the concentration of H+(aq) in a HClOaq solution with a pH=3.61.

[1]
c(iii).

State the type of reaction occurring when ethane reacts with chlorine to produce chloroethane.

[1]
d(i).

Predict, giving a reason, whether ethane or chloroethane is more reactive.

[1]
d(ii).

Explain the mechanism of the reaction between chloroethane and aqueous sodium hydroxide, NaOH(aq), using curly arrows to represent the movement of electron pairs.

[3]
d(iii).

Ethoxyethane (diethyl ether) can be used as a solvent for this conversion.
Draw the structural formula of ethoxyethane

[1]
d(iv).

Deduce the number of signals and chemical shifts with splitting patterns in the 1H NMR spectrum of ethoxyethane. Use section 27 of the data booklet.

[3]
d(v).

Calculate the percentage by mass of chlorine in CCl2F2.

[2]
e(i).

Comment on how international cooperation has contributed to the lowering of CFC emissions responsible for ozone depletion.

[1]
e(ii).

CFCs produce chlorine radicals. Write two successive propagation steps to show how chlorine radicals catalyse the depletion of ozone.

[2]
e(iii).



A student titrated two acids, hydrochloric acid, HCl (aq) and ethanoic acid, CH3COOH (aq), against 50.0 cm3 of 0.995 mol dm–3 sodium hydroxide, NaOH (aq), to determine their concentration. The temperature of the reaction mixture was measured after each acid addition and plotted against the volume of each acid.

Using the graph, estimate the initial temperature of the solutions.

[1]
a.

Determine the maximum temperature reached in each experiment by analysing the graph.

[2]
b.

Suggest why the enthalpy change of neutralization of CH3COOH is less negative than that of HCl.

[2]
e.



A compound with a molecular formula C7H14O produced the following high resolution 1H NMR spectrum.

Deduce what information can be obtained from the 1H NMR spectrum.

[3]
a.i.

Identify the functional group that shows stretching at 1710 cm–1 in the infrared spectrum of this compound using section 26 of the data booklet and the 1H NMR.

[1]
a.ii.

Suggest the structural formula of this compound.

[2]
a.iii.

Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.

[1]
b.i.

Deduce the structural formula of the main organic product when hex-1-ene reacts with hydrogen bromide.

[1]
b.ii.

State the reagents and the name of the mechanism for the nitration of benzene.

[2]
c.i.

Outline, in terms of the bonding present, why the reaction conditions of halogenation are different for alkanes and benzene.

[1]
c.ii.

Below are two isomers, A and B, with the molecular formula C4H9Br.

Explain the mechanism of the nucleophilic substitution reaction with NaOH(aq) for the isomer that reacts almost exclusively by an SN2 mechanism using curly arrows to represent the movement of electron pairs.

[3]
d.



Ethanol is obtained by the hydration of ethene, C2H4.

Alternative synthetic routes exist to produce alcohols.

Ethanol is obtained by the hydration of ethene, C2H4.

State the class of compound to which ethene belongs.

[1]
a(i).

State the molecular formula of the next member of the homologous series to which ethene belongs.

[1]
a(ii).

Justify why ethene has only a single signal in its 1H NMR spectrum.

[1]
b(i).

Deduce the chemical shift of this signal. Use section 27 of the data booklet.

[1]
b(ii).

Suggest two possible products of the incomplete combustion of ethene that would not be formed by complete combustion.

[1]
c.

A white solid was formed when ethene was subjected to high pressure.

Deduce the type of reaction that occurred.

[1]
d.

Sketch the mechanism for the reaction of propene with hydrogen bromide using curly arrows.

[3]
e(i).

Explain why the major organic product is 2-bromopropane and not 1-bromopropane.

[2]
e(ii).

Explain why the major organic product is 2-bromopropane and not 1-bromopropane.

[2]
e(ii).

2-bromopropane can be converted directly to propan-2-ol. Identify the reagent required.

[1]
e(iii).

Propan-2-ol can also be formed in one step from a compound containing a carbonyl group.

State the name of this compound and the type of reaction that occurs.

[2]
e(iv).



Urea, (H2N)2CO, is excreted by mammals and can be used as a fertilizer.

Urea can also be made by the direct combination of ammonia and carbon dioxide gases.

2NH3(g) + CO2(g) (H2N)2CO(g) + H2O(g)     ΔH < 0

Calculate the percentage by mass of nitrogen in urea to two decimal places using section 6 of the data booklet.

[2]
a.i.

Suggest how the percentage of nitrogen affects the cost of transport of fertilizers giving a reason.

[1]
a.ii.

The structural formula of urea is shown.

M18/4/CHEMI/HP2/ENG/TZ1/01.b_01

Predict the electron domain and molecular geometries at the nitrogen and carbon atoms, applying the VSEPR theory.

M18/4/CHEMI/HP2/ENG/TZ1/01.b_02

 

[3]
b.

Urea can be made by reacting potassium cyanate, KNCO, with ammonium chloride, NH4Cl.

KNCO(aq) + NH4Cl(aq) → (H2N)2CO(aq) + KCl(aq)

Determine the maximum mass of urea that could be formed from 50.0 cm3 of 0.100 mol dm−3 potassium cyanate solution.

[2]
c.

State the equilibrium constant expression, Kc.

[1]
d.i.

Predict, with a reason, the effect on the equilibrium constant, Kc, when the temperature is increased.

[1]
d.ii.

Determine an approximate order of magnitude for Kc, using sections 1 and 2 of the data booklet. Assume ΔGΘ for the forward reaction is approximately +50 kJ at 298 K.

[2]
d.iii.

Suggest one reason why urea is a solid and ammonia a gas at room temperature.

[1]
e.i.

Sketch two different hydrogen bonding interactions between ammonia and water.

[2]
e.ii.

The combustion of urea produces water, carbon dioxide and nitrogen.

Formulate a balanced equation for the reaction.

[2]
f.

Calculate the maximum volume of CO2, in cm3, produced at STP by the combustion of 0.600 g of urea, using sections 2 and 6 of the data booklet.

[1]
g.

Describe the bond formation when urea acts as a ligand in a transition metal complex ion.

[2]
h.

The C–N bonds in urea are shorter than might be expected for a single C–N bond. Suggest, in terms of electrons, how this could occur.

[1]
i.

The mass spectrum of urea is shown below.

M18/4/CHEMI/HP2/ENG/TZ1/01.j_01

Identify the species responsible for the peaks at m/z = 60 and 44.

[2]
j.

The IR spectrum of urea is shown below.

M18/4/CHEMI/HP2/ENG/TZ1/01.k_01

Identify the bonds causing the absorptions at 3450 cm−1 and 1700 cm−1 using section 26 of the data booklet.

[2]
k.

Predict the number of signals in the 1H NMR spectrum of urea.

[1]
l.i.

Predict the splitting pattern of the 1H NMR spectrum of urea.

[1]
l.ii.

Outline why TMS (tetramethylsilane) may be added to the sample to carry out 1H NMR spectroscopy and why it is particularly suited to this role.

[2]
l.iii.



Calcium carbonate reacts with hydrochloric acid.

CaCO3(s) + 2HCl(aq) → CaCl2(aq) + H2O(l) + CO2(g)

The results of a series of experiments in which the concentration of HCl was varied are shown below.

M18/4/CHEMI/HP2/ENG/TZ1/X04.b

Outline two ways in which the progress of the reaction can be monitored. No practical details are required.

[2]
a.

Suggest why point D is so far out of line assuming human error is not the cause.

[1]
b.i.

Draw the best fit line for the reaction excluding point D.

[1]
b.ii.

Suggest the relationship that points A, B and C show between the concentration of the acid and the rate of reaction.

[1]
b.iii.

Deduce the rate expression for the reaction.

[1]
b.iv.

Calculate the rate constant of the reaction, stating its units.

[2]
b.v.

Predict from your line of best fit the rate of reaction when the concentration of HCl is 1.00 mol dm−3.

[1]
c.

Describe how the activation energy of this reaction could be determined.

[3]
d.



Organic chemistry can be used to synthesize a variety of products.

Combustion analysis of an unknown organic compound indicated that it contained only carbon, hydrogen and oxygen.

Several compounds can be synthesized from but-2-ene. Draw the structure of the final product for each of the following chemical reactions.

[2]
a.

Determine the change in enthalpy, ΔH, for the combustion of but-2-ene, using section 11 of the data booklet. 

CH3CH=CHCH3 (g) + 6O2 (g) → 4CO2 (g) + 4H2O (g)

[3]
b.

State the hybridization of the carbon I and II atoms in but-2-ene.

[1]
c.

Draw diagrams to show how sigma (σ) and pi (π) bonds are formed between atoms.

[2]
d.

Sketch the mechanism for the reaction of 2-methylbut-2-ene with hydrogen bromide using curly arrows.

[3]
e.

Explain why the major organic product is 2-bromo-2-methylbutane and not 2-bromo-3-methylbutane.

[2]
f.

Deduce two features of this molecule that can be obtained from the mass spectrum. Use section 28 of the data booklet.

NIST Mass Spectrometry Data Center Collection © 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.

[2]
g(i).

Identify the bond responsible for the absorption at A in the infrared spectrum. Use section 26 of the data booklet.

NIST Mass Spectrometry Data Center Collection © 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.

 

[1]
g(ii).

Deduce the identity of the unknown compound using the previous information, the 1H NMR spectrum and section 27 of the data booklet.

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

[2]
g(iii).

Draw the stereoisomers of butan-2-ol using wedge-dash type representations.

[1]
h(i).

Outline how two enantiomers can be distinguished using a polarimeter.

[2]
h(ii).



3.26 g of iron powder are added to 80.0 cm3 of 0.200 mol dm−3 copper(II) sulfate solution. The following reaction occurs:

Fe (s) + CuSO4 (aq) → FeSO4 (aq) + Cu (s)

Determine the limiting reactant showing your working.

[2]
a.i.

The mass of copper obtained experimentally was 0.872 g. Calculate the percentage yield of copper.

[2]
a.ii.

The reaction was carried out in a calorimeter. The maximum temperature rise of the solution was 7.5 °C.

Calculate the enthalpy change, ΔH, of the reaction, in kJ, assuming that all the heat released was absorbed by the solution. Use sections 1 and 2 of the data booklet.

[2]
b.i.

State another assumption you made in (b)(i).

[1]
b.ii.

The only significant uncertainty is in the temperature measurement.

Determine the absolute uncertainty in the calculated value of ΔH if the uncertainty in the temperature rise was ±0.2 °C.

[2]
b.iii.

Sketch a graph of the concentration of iron(II) sulfate, FeSO4, against time as the reaction proceeds.

[2]
c.i.

Outline how the initial rate of reaction can be determined from the graph in part (c)(i).

[2]
c.ii.

Explain, using the collision theory, why replacing the iron powder with a piece of iron of the same mass slows down the rate of the reaction.

[2]
c.iii.

A student electrolyzed aqueous iron(II) sulfate, FeSO4 (aq), using platinum electrodes. State half-equations for the reactions at the electrodes, using section 24 of the data booklet.

[2]
d.



When heated in air, magnesium ribbon reacts with oxygen to form magnesium oxide.

The reaction in (a)(i) was carried out in a crucible with a lid and the following data was recorded:

Mass of crucible and lid = 47.372 ±0.001 g

Mass of crucible, lid and magnesium ribbon before heating = 53.726 ±0.001 g

Mass of crucible, lid and product after heating = 56.941 ±0.001 g

 

When magnesium is burnt in air, some of it reacts with nitrogen to form magnesium nitride according to the equation:

3 Mg (s) + N2 (g) → Mg3N2 (s)

The presence of magnesium nitride can be demonstrated by adding water to the product. It is hydrolysed to form magnesium hydroxide and ammonia.

Most nitride ions are 14N3–.

Write a balanced equation for the reaction that occurs.

[1]
a(i).

Identify a metal, in the same period as magnesium, that does not form a basic oxide.

[1]
a(ii).

Calculate the amount of magnesium, in mol, that was used.

[1]
b(i).

Determine the percentage uncertainty of the mass of product after heating.

[2]
b(ii).

Assume the reaction in (a)(i) is the only one occurring and it goes to completion, but some product has been lost from the crucible. Deduce the percentage yield of magnesium oxide in the crucible.

 

[2]
b(iii).

Evaluate whether this, rather than the loss of product, could explain the yield found in (b)(iii).

[1]
c(i).

Suggest an explanation, other than product being lost from the crucible or reacting with nitrogen, that could explain the yield found in (b)(iii).

[1]
c(ii).

Calculate coefficients that balance the equation for the following reaction.

[1]
d(i).

Ammonia is added to water that contains a few drops of an indicator. Identify an indicator that would change colour. Use sections 21 and 22 of the data booklet.

[1]
d(ii).

Determine the oxidation state of nitrogen in Mg3N2 and in NH3.

[1]
d(iii).

Deduce, giving reasons, whether the reaction of magnesium nitride with water is an acid–base reaction, a redox reaction, neither or both.

[2]
d(iv).

State the number of subatomic particles in this ion.

[1]
e(i).

Some nitride ions are 15N3–. State the term that describes the relationship between 14N3– and 15N3–.

[1]
e(ii).

The nitride ion and the magnesium ion are isoelectronic (they have the same electron configuration). Determine, giving a reason, which has the greater ionic radius.

[1]
e(iii).

Suggest, giving a reason, whether magnesium or nitrogen would have the greater sixth ionization energy.

[1]
e(iv).

Suggest two reasons why atoms are no longer regarded as the indivisible units of matter.

[2]
f.

State the types of bonding in magnesium, oxygen and magnesium oxide, and how the valence electrons produce these types of bonding.

[4]
g.



A 4.406 g sample of a compound containing only C, H and O was burnt in excess oxygen. 8.802 g of CO2 and 3.604 g of H2O were produced.

The following spectrums show the Infrared spectra of propan-1-ol, propanal and propanoic acid.

NIST Mass Spectrometry Data Center Collection © 2021 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. Available at: https://webbook.nist.gov/cgi/cbook.cgi?ID=C71238&Units=SI&Type=IRSPEC&Index=3#IR-SPEC [Accessed 6 May 2020]. Source adapted.

NIST Mass Spectrometry Data Center Collection © 2021 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. Available at: https://webbook.nist.gov/cgi/cbook.cgi?ID=C79094&Units=SI&Mask=80#IR-Spec [Accessed 6 May 2020]. Source adapted.

NIST Mass Spectrometry Data Center Collection © 2021 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. Available at: https://webbook.nist.gov/cgi/cbook.cgi?Name=propanal&Units=SI&cIR=on&cTZ=on#IRSpec [Accessed 6 May 2020]. Source adapted.

Determine the empirical formula of the compound using section 6 of the data booklet.

[3]
a.

Determine the molecular formula of this compound if its molar mass is 88.12 g mol−1. If you did not obtain an answer in (a) use CS, but this is not the correct answer.

[1]
b.

Identify each compound from the spectra given, use absorptions from the range of 1700 cm−1 to 3500 cm−1. Explain the reason for your choice, referring to section 26 of the data booklet.

[3]
c.

Predict the number of 1H NMR signals, and splitting pattern of the –CH3 seen for propanone (CH3COCH3) and propanal (CH3CH2CHO).

[2]
d.

Predict the fragment that is responsible for a m/z of 31 in the mass spectrum of propan‑1‑ol. Use section 28 of the data booklet.

[1]
e.



Butanoic acid, CH3CH2CH2COOH, is a weak acid and ethylamine, CH3CH2NH2, is a weak base.

State the equation for the reaction of each substance with water.

[2]
a.i.

Draw a diagram showing the delocalization of electrons in the conjugate base of butanoic acid.

[1]
a.ii.

Deduce the average oxidation state of carbon in butanoic acid.

[1]
a.iii.

A 0.250 mol dm−3 aqueous solution of butanoic acid has a concentration of hydrogen ions, [H+], of 0.00192 mol dm−3. Calculate the concentration of hydroxide ions, [OH], in the solution at 298 K.

[1]
b.i.

Determine the pH of a 0.250 mol dm−3 aqueous solution of ethylamine at 298 K, using section 21 of the data booklet.

[3]
b.ii.

Sketch the pH curve for the titration of 25.0 cm3 of ethylamine aqueous solution with 50.0 cm3 of butanoic acid aqueous solution of equal concentration. No calculations are required.

[3]
c.

Explain why butanoic acid is a liquid at room temperature while ethylamine is a gas at room temperature.

[2]
d.

State a suitable reagent for the reduction of butanoic acid.

[1]
e.i.

Deduce the product of the complete reduction reaction in (e)(i).

[1]
e.ii.



Magnesium is a reactive metal often found in alloys.

Magnesium is sometimes used as a sacrificial anode to protect steel from corrosion.

A graph of the volume of gas produced by reacting magnesium with a large excess of 1 mol dm–3 hydrochloric acid is shown.

Suggest an experiment that shows that magnesium is more reactive than zinc, giving the observation that would confirm this.

[2]
a.

Calculate the standard potential, in V, of a cell formed by magnesium and steel half-cells. Use section 24 of the data booklet and assume steel has the standard electrode potential of iron.

[1]
b(i).

Calculate the free energy change, ΔG, in kJ, of the cell reaction. Use sections 1 and 2 of the data booklet.

[2]
b(ii).

This cell causes the electrolytic reduction of water on the steel. State the half-equation for this reduction.

[1]
b(iii).

Use the graph to deduce the dependence of the reaction rate on the amount of Mg.

[1]
c(i).

The reaction is first order with respect to HCl. Calculate the time taken, in seconds (s), for half of the Mg to dissolve when [HCl] = 0.5 mol dm–3.

[1]
c(ii).

Carbonates also react with HCl and the rate can be determined by graphing the mass loss. Suggest why this method is less suitable for the reaction of Mg with HCl.

[1]
c(iii).



The thermal decomposition of dinitrogen monoxide occurs according to the equation:

2N2O (g) → 2N2 (g) + O2 (g)

The reaction can be followed by measuring the change in total pressure, at constant temperature, with time.

The x-axis and y-axis are shown with arbitrary units.

This decomposition obeys the rate expression:

d [ N 2 O] d t = k[N2O]

Explain why, as the reaction proceeds, the pressure increases by the amount shown.

[2]
a.

Outline, in terms of collision theory, how a decrease in pressure would affect the rate of reaction.

[2]
b.

Deduce how the rate of reaction at t = 2 would compare to the initial rate.

[1]
c(i).

It has been suggested that the reaction occurs as a two-step process:

Step 1: N2O (g) → N2 (g) + O (g)

Step 2: N2O (g) + O (g) → N2 (g) + O2 (g)

Explain how this could support the observed rate expression.

[2]
c(ii).

The experiment is repeated using the same amount of dinitrogen monoxide in the same apparatus, but at a lower temperature.

Sketch, on the axes in question 2, the graph that you would expect.

[2]
d.

The experiment gave an error in the rate because the pressure gauge was inaccurate.

Outline whether repeating the experiment, using the same apparatus, and averaging the results would reduce the error.

[1]
e.

The graph below shows the Maxwell–Boltzmann distribution of molecular energies at a particular temperature.

The rate at which dinitrogen monoxide decomposes is significantly increased by a metal oxide catalyst.

Annotate and use the graph to outline why a catalyst has this effect.

[2]
f.

Determine the standard entropy change, in J K−1, for the decomposition of dinitrogen monoxide.

2N2O (g) → 2N2 (g) + O2 (g)

[2]
g(i).

Dinitrogen monoxide has a positive standard enthalpy of formation, ΔHfθ.

Deduce, giving reasons, whether altering the temperature would change the spontaneity of the decomposition reaction.

[3]
g(ii).



This question is about the decomposition of hydrogen peroxide.

Hydrogen peroxide decomposes to water and oxygen when a catalyst such as potassium iodide, KI, is added.


2H2O2 (aq)  KI (aq) O2 (g) + 2H2O (l)

Suggest why many chemicals, including hydrogen peroxide, are kept in brown bottles instead of clear colourless bottles.

[1]
a.

In a laboratory experiment solutions of potassium iodide and hydrogen peroxide were mixed and the volume of oxygen generated was recorded. The volume was adjusted to 0 at t = 0.

The data for the first trial is given below.

Plot a graph on the axes below and from it determine the average rate of
formation of oxygen gas in cm3 O2 (g) s−1.

Average rate of reaction:

[3]
b(i).

Two more trials (2 and 3) were carried out. The results are given below.

Determine the rate equation for the reaction and its overall order, using your answer from (b)(i).

Rate equation: 

Overall order: 

[2]
b(ii).

Additional experiments were carried out at an elevated temperature. On the axes below, sketch Maxwell–Boltzmann energy distribution curves at two temperatures T1 and T2, where T2 > T1.

[2]
b(iii).

Apart from a greater frequency of collisions, explain, by annotating your graphs in (b)(iii), why an increased temperature causes the rate of reaction to increase.

[2]
b(iv).

MnO2 is another possible catalyst for the reaction. State the IUPAC name for MnO2.

[1]
b(v).

Comment on why peracetic acid, CH3COOOH, is always sold in solution with ethanoic acid and hydrogen peroxide.

H2O2 (aq) + CH3COOH (aq) ⇌ CH3COOOH (aq) + H2O (l)

[1]
c.

Sodium percarbonate, 2Na2CO3•3H2O2, is an adduct of sodium carbonate and hydrogen peroxide and is used as a cleaning agent.

Mr (2Na2CO3•3H2O2) = 314.04

Calculate the percentage by mass of hydrogen peroxide in sodium percarbonate, giving your answer to two decimal places.

[2]
d.



Propene is an important starting material for many products. The following shows some compounds which can be made from propene, C3H6.


Propene (C3H6) → C3H7Cl → C3H8O → C3H6O

Consider the conversion of propene to C3H7Cl.

An experiment was carried out to determine the order of reaction between one of the isomers of C3H7Cl and aqueous sodium hydroxide. The following results were obtained.

State the type of reaction.

[1]
a(i).

State the IUPAC name of the major product.

[1]
a(ii).

Outline why it is the major product.

[1]
a(iii).

Write an equation for the reaction of the major product with aqueous sodium hydroxide to produce a C3H8O compound, showing structural formulas.

[1]
a(iv).

Determine the rate expression from the results, explaining your method.

[3]
b(i).

Deduce the type of mechanism for the reaction of this isomer of C3H7Cl with aqueous sodium hydroxide.

[1]
b(ii).

Sketch the mechanism using curly arrows to represent the movement of electrons.

[4]
b(iii).

Write an equation for the complete combustion of the compound C3H8O formed in (a)(iv).

[1]
c(i).

Determine the enthalpy of combustion of this compound, in kJ mol−1, using data from section 11 of the data booklet.

[3]
c(ii).

State the reagents for the conversion of the compound C3H8O formed in (a)(iv) into C3H6O.

[1]
d(i).

Explain why the compound C3H8O, produced in (a)(iv), has a higher boiling point than compound C3H6O, produced in d(i).

[2]
d(ii).

Explain why the 1H NMR spectrum of C3H6O, produced in (d)(i), shows only one signal.

[1]
d(iii).

Propene is often polymerized. Draw a section of the resulting polymer, showing two repeating units.

[1]
e.



Biochemical oxygen demand (BOD) can be determined by the Winkler Method.

A 25.00 cm3 sample of water was treated according to the Winkler Method.

Step I:   2Mn2+ (aq) + O2 (g) + 4OH− (aq) → 2MnO2 (s) + 2H2O (l)

Step II:  MnO2 (s) + 2I− (aq) + 4H+ (aq) → Mn2+ (aq) + I2 (aq) + 2H2O (l)

Step III: 2S2O32− (aq) + I2 (aq) → 2I− (aq) + S4O62− (aq)

The iodine produced was titrated with 37.50 cm3 of 5.000 × 10−4 mol dm−3 Na2S2O3.

Outline what is measured by BOD.

[1]
a.

A student dissolved 0.1240 ± 0.0001 g of Na2S2O3 to make 1000.0 ± 0.4 cm3 of solution to use in the Winkler Method.

Determine the percentage uncertainty in the molar concentration.

[2]
b.

Calculate the amount, in moles of Na2S2O3 used in the titration.

[1]
c(i).

Deduce the mole ratio of O2 consumed in step I to S2O32− used in step III.

[1]
c(ii).

Calculate the concentration of dissolved oxygen, in mol dm−3, in the sample.

[2]
c(iii).

The three steps of the Winkler Method are redox reactions.

Deduce the reduction half-equation for step II.

[1]
c(iv).

Suggest a reason that the Winkler Method used to measure biochemical oxygen demand (BOD) must be done at constant temperature.

[1]
c(v).



An organic compound containing carbon, hydrogen and oxygen has 62.02 % carbon and 10.43 % hydrogen by mass.

Determine the empirical formula of the compound, showing your working.

[3]
a.

The infrared spectrum of the compound is shown. Deduce the functional group of the compound.

[1]
b.

The mass spectrum of the compound is shown. Deduce the relative molecular mass of the compound.

[1]
c.

The compound could not be oxidized using acidifi ed potassium dichromate(VI).

Deduce the structural formula of the compound.

[1]
d.



Carbon forms many compounds.

C60 and diamond are allotropes of carbon.

Chlorine reacts with methane.

CH4 (g) + Cl2 (g) → CH3Cl (g) + HCl (g)

Outline two differences between the bonding of carbon atoms in C60 and diamond.

[2]
a(i).

Explain why C60 and diamond sublime at different temperatures and pressures.

[2]
a(ii).

State two features showing that propane and butane are members of the same homologous series.

[2]
b.

Describe a test and the expected result to indicate the presence of carbon–carbon double bonds.

[2]
c.

Draw the full structural formula of (Z)-but-2-ene.

[1]
d(i).

Write the equation for the reaction between but-2-ene and hydrogen bromide.

[1]
d(ii).

State the type of reaction.

[1]
d(iii).

Suggest two differences in the 1H NMR of but-2-ene and the organic product from (d)(ii).

[2]
d(iv).

Predict, giving a reason, the major product of reaction between but-1-ene and steam.

[2]
d(v).

Explain the mechanism of the reaction between 1-bromopropane, CH3CH2CH2Br, and aqueous sodium hydroxide, NaOH (aq), using curly arrows to represent the movement of electron pairs.

[4]
e(i).

Deduce the splitting pattern in the 1H NMR spectrum for 1-bromopropane.

[1]
e(ii).

Calculate the enthalpy change of the reaction, ΔH, using section 11 of the data booklet.

[3]
f(i).

Draw and label an enthalpy level diagram for this reaction.

[2]
f(ii).



Carbonated water is produced when carbon dioxide is dissolved in water under pressure. The following equilibria are established.

Equilibrium (1)  CO2 (g)  CO2 (aq)

Equilibrium (2)  CO2 (aq) + H2O (l) H+ (aq) + HCO3 (aq)

Carbon dioxide acts as a weak acid.

Soda water has sodium hydrogencarbonate, NaHCO3, dissolved in the carbonated water.

Distinguish between a weak and strong acid.

Weak acid: 

Strong acid: 

[1]
a(i).

The hydrogencarbonate ion, produced in Equilibrium (2), can also act as an acid.

State the formula of its conjugate base.

[1]
a(ii).

When a bottle of carbonated water is opened, these equilibria are disturbed.

State, giving a reason, how a decrease in pressure affects the position of Equilibrium (1).

[1]
b.

At 298 K the concentration of aqueous carbon dioxide in carbonated water is 0.200 mol dm−3 and the pKa for Equilibrium (2) is 6.36.

Calculate the pH of carbonated water.

[3]
c.

Identify the type of bonding in sodium hydrogencarbonate.

Between sodium and hydrogencarbonate:

Between hydrogen and oxygen in hydrogencarbonate:

[2]
d(i).

Predict, referring to Equilibrium (2), how the added sodium hydrogencarbonate affects the pH.(Assume pressure and temperature remain constant.)

[2]
d(ii).

100.0cm3 of soda water contains 3.0 × 10−2g NaHCO3.

Calculate the concentration of NaHCO3 in mol dm−3.

[2]
d(iii).

The uncertainty of the 100.0cm3 volumetric flask used to make the solution was ±0.6cm3.

Calculate the maximum percentage uncertainty in the mass of NaHCO3 so that the concentration of the solution is correct to ±1.0 %.

[1]
d(iv).

The reaction of the hydroxide ion with carbon dioxide and with the hydrogencarbonate ion can be represented by Equations 3 and 4.

Equation (3)     OH (aq) + CO2 (g) → HCO3 (aq)
Equation (4)     OH (aq) + HCO
3 (aq) → H2O (l) + CO32− (aq)

Discuss how these equations show the difference between a Lewis base and a Brønsted–Lowry base.

 

Equation (3):

Equation (4):

[2]
e.

Aqueous sodium hydrogencarbonate has a pH of approximately 7 at 298 K.

Sketch a graph of pH against volume when 25.0cm3 of 0.100 mol dm−3 NaOH (aq) is gradually added to 10.0cm3 of 0.0500 mol dm−3 NaHCO3 (aq).

[2]
f.



Xylene is a derivative of benzene. One isomer is 1,4-dimethylbenzene.

Xylene, like benzene, can be nitrated.

Bromine reacts with alkanes.

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

 

[2]
a.

Draw the structure of one other isomer of xylene which retains the benzene ring.

[1]
b.

Write the equation for the production of the active nitrating agent from concentrated sulfuric and nitric acids.

[1]
c(i).

Explain the mechanism for the nitration of benzene, using curly arrows to indicate the movement of electron pairs.

[4]
c(ii).

Identify the initiation step of the reaction and its conditions.

[2]
d(i).

1,4-dimethylbenzene reacts as a substituted alkane. Draw the structures of the two products of the overall reaction when one molecule of bromine reacts with one molecule of 1,4-dimethylbenzene.

[2]
d(ii).

The organic product is not optically active. Discuss whether or not the organic product is a racemic mixture.

[1]
e.