Topic 10 Paper 2 [147 marks]

1a. [1 mark]
Chloroquine is a medication used to prevent and treat malaria.

Draw a circle around the secondary amino group in chloroquine.

Markscheme

✔
1b. [1 mark]
Determine the index of hydrogen deficiency, IHD, of chloroquine.

Markscheme
seven/7 ✔
1c. [1 mark]
Compare, giving a reason, the length of the carbon-nitrogen bond in the ring to the length
of the carbon-N1 bond.

Markscheme
«bond in ring is» shorter AND more electrons are shared
OR
«bond in ring is» shorter AND partial double/multiple bonding/bond order 1.5 ✔
1d. [1 mark]
State, giving a reason, whether carbon or nitrogen is the most electronegative element.

Markscheme
nitrogen AND larger number of protons/nuclear charge/Zeff
OR
nitrogen AND smaller «atomic» radius ✔

Accept nitrogen AND further along period.

1e. [2 marks]
Chloroquine can be synthesized by reacting 4,7-dichloroquinoline with another reactant, B.
 4,7-dichloroquinoline chloroquine
Deduce the structure of B.

Markscheme

primary amine/–NH2 ✔
rest of structure ✔

Do not penalize using “N1”.

1f. [1 mark]
This reaction can be done with a copper catalyst. State the ground-state
electron configuration for copper.
Markscheme
1s22s22p63s23p64s13d10 / 1s22s22p63s23p63d104s1
OR
[Ar]4s13d10 / [Ar]3d104s1 ✔
1g. [1 mark]
Annotate the Maxwell–Boltzmann distribution curve showing the activation energies, Ea,
for the catalysed and uncatalysed reactions.
Markscheme

both Ea values marked AND left one labelled catalysed ✔

1h. [1 mark]
Explain, referring to the Maxwell–Boltzmann distribution curve, the effect of a catalyst on a
chemical reaction.

Markscheme
increases rate AND there is a greater area under the curve past activation energy
OR
increases rate AND greater proportion of/more molecules have «kinetic» E ≥ Ea «(cat) than
Ea (uncat)» ✔

Do not award a mark for general statements about catalysts such as “provides alternative
pathway” or “lowers Ea”.
2a. [3 marks]
An organic compound, A, reacts with ethanoic acid to produce B using
concentrated sulfuric acid as a catalyst.
Deduce the structural and empirical formulas of B.

Markscheme
Structure:

ester functional group ✔

rest of structure ✔

Empirical Formula:
C3H5O ✔

Accept condensed/skeletal formula.

2b. [2 marks]
Explain, with reference to Le Châ telier’s principle, the effect of using dilute rather than
concentrated sulfuric acid as the catalyst on the yield of the reaction.

Markscheme
dilute adds «excess» water
OR
water is a product ✔

shift left AND decreases yield ✔

2c. [2 marks]
Explain, with reference to intermolecular forces, why B is more volatile than A.

Markscheme
A has hydrogen bonding/bonds «and dipole-dipole and London/dispersion forces» AND B
has dipole-dipole «and London/dispersion forces»
OR
A has hydrogen bonding/bonds AND B does not ✔

intermolecular forces are weaker in B

OR
hydrogen bonding/bonds stronger «than dipole-dipole» ✔
2d. [1 mark]
Compound A can also react with bromine. Describe the change observed if A is reacted
with bromine.

Markscheme
brown/orange/red/yellow to colourless ✔

Do not accept clear for colourless.

3a. [1 mark]
Magnesium is a reactive metal often found in alloys.
Magnesium can be produced by the electrolysis of molten magnesium chloride.
Write the half-equation for the formation of magnesium.

Markscheme
Mg2+ + 2 e- → Mg ✔

Do not penalize missing charge on electron.

Accept equation with equilibrium arrows.
3b. [2 marks]
Suggest an experiment that shows that magnesium is more reactive than zinc, giving the
observation that would confirm this.

Markscheme
Alternative 1
put Mg in Zn2+(aq) ✔
Zn/«black» layer forms «on surface of Mg» ✔

Award [1 max] for “no reaction when Zn placed in Mg2+(aq)”.

Alternative 2
place both metals in acid ✔
bubbles evolve more rapidly from Mg
OR
Mg dissolves faster ✔

Alternative 3
construct a cell with Mg and Zn electrodes ✔
bulb lights up
OR
shows (+) voltage
OR
size/mass of Mg(s) decreases «over time»
OR
size/mass of Zn increases «over time»

Accept “electrons flow from Mg to Zn”.

Accept Mg is negative electrode/anode
OR
Zn is positive electrode/cathode

Accept other correct methods.

3c. [1 mark]
Organomagnesium compounds can react with carbonyl compounds. One overall equation
is:

State the name of Compound A, applying International Union of Pure and Applied
Chemistry (IUPAC) rules.

Markscheme
propanone ✔

Accept 2-propanone and propan-2-one.

3d. [1 mark]
Identify the strongest force between the molecules of Compound B.
Markscheme
hydrogen bonds ✔
3e. [1 mark]
Compound B can also be prepared by reacting an alkene with water.
Draw the structural formula of the alkene required.

Markscheme

3f. [1 mark]
Deduce the structural formula of the repeating unit of the polymer formed from this alkene.
Markscheme

Do not penalize missing brackets or n.

Do not award mark if continuation bonds are not shown.
3g. [1 mark]
Deduce what would be observed when Compound B is warmed with acidified aqueous
potassium dichromate (VI).

Markscheme
no change «in colour/appearance/solution» ✔
3h. [1 mark]
Iodomethane is used to prepare CH3Mg I . It can also be converted into methanol:
CH3 I + HO– → CH3OH + I –
Identify the type of reaction.

Markscheme
«nucleophilic» substitution
OR
SN2 ✔

Accept “hydrolysis”.
Accept SN1
3i. [2 marks]
Outline the requirements for a collision between reactants to yield products.

Markscheme
energy/E ≥ activation energy/Ea ✔
correct orientation «of reacting particles»
OR
correct geometry «of reacting particles» ✔
3j. [1 mark]
The polarity of the carbon–halogen bond, C–X, facilitates attack by HO –.
Outline, giving a reason, how the bond polarity changes going down group 17.

Markscheme
decreases/less polar AND electronegativity «of the halogen» decreases ✔

Accept “decreases” AND a correct comparison of the electronegativity of two halogens.

Accept “decreases” AND “attraction for valence electrons decreases”.
4a. [1 mark]
Carbon forms many compounds.
C60 and diamond are allotropes of carbon.
Outline one difference between the bonding of carbon atoms in C60 and diamond.

Markscheme
C60 fullerene: «each carbon is» bonded to 3 C AND diamond: bonded to 4 C
OR
C60 fullerene: delocalized/resonance AND diamond: not delocalized/no resonance
OR
C60 fullerene: single and double bonds AND diamond: single bonds ✔

Accept “C60 fullerene: sp2 AND diamond: sp3”.

Accept “C60 fullerene: trigonal planar geometry / bond angles between 109.5°/109°/108°–
120° AND diamond: tetrahedral geometry / bond angle 109.5°/109°”.
Accept "bonds in fullerene are shorter/stronger/have higher bond order".
4b. [2 marks]
Explain why C60 and diamond sublime at different temperatures and pressures.

Markscheme
diamond giant/network covalent AND sublimes at higher temperature ✔
C60 molecular/London/dispersion/intermolecular «forces» ✔

Accept “diamond has strong covalent bonds AND require more energy to break «than
intermolecular forces»” for M1.
4c. [2 marks]
State two features showing that propane and butane are members of the same homologous
series.

Markscheme
same general formula / CnH2n+2 ✔
differ by CH2/common structural unit ✔
Accept "similar chemical properties".
Accept “gradation/gradual change in physical properties”.
4d. [2 marks]
Describe a test and the expected result to indicate the presence of carbon–carbon double
bonds.

Markscheme
ALTERNATIVE 1:
Test:
add bromine «water»/Br2 (aq) ✔
Result:
«orange/brown/yellow» to colourless/decolourised ✔

Do not accept “clear” for M2.

ALTERNATIVE 2:
Test:
add «acidified» KMnO4 ✔
Result:
«purple» to colourless/decolourised/brown ✔

Accept “colour change” for M2.

ALTERNATIVE 3:
Test:
add iodine / I 2 ✔
Result:
«brown» to colourless/decolourised ✔
4e. [1 mark]
But-2-ene reacts with hydrogen bromide.
Draw the full structural formula of but-2-ene.

Markscheme

Accept

4f. [1 mark]
Write the equation for the reaction between but-2-ene and hydrogen bromide.

Markscheme
CH3CH=CHCH3 (g) + HBr (g) → CH3CH2CHBrCH3 (l)
OR
C4H8 (g) + HBr (g) → C4H9Br (l) ✔
4g. [1 mark]
State the type of reaction.

Markscheme
«electrophilic» addition/EA ✔

Do not accept nucleophilic or free radical addition.

4h. [2 marks]
Suggest two differences in the 1H NMR of but-2-ene and the organic product from (d)(ii).
Markscheme
ALTERNATIVE 1: Any two of:
but-2-ene: 2 signals AND product: 4 signals ✔
but-2-ene: «area ratio» 3:1/6:2 AND product: «area ratio» 3:3:2:1 ✔
product: «has signal at» 3.5-4.4 ppm «and but-2-ene: does not» ✔
but-2-ene: «has signal at» 4.5-6.0 ppm «and product: does not» ✔

ALTERNATIVE 2:
but-2-ene: doublet AND quartet/multiplet/4 ✔
product: doublet AND triplet AND quintet/5/multiplet AND sextet/6/multiplet ✔

Accept “product «has signal at» 1.3–1.4 ppm «and but-2-ene: does not»”.
4i. [3 marks]
Chlorine reacts with methane.
CH4 (g) + Cl2 (g) → CH3Cl (g) + HCl (g)
Calculate the enthalpy change of the reaction, ΔH, using section 11 of the data booklet.
Markscheme
bond breaking: C–H + Cl–Cl / 414 «kJ mol–1» + 242 «kJ mol–1»/656 «kJ»
OR
bond breaking: 4C–H + Cl–Cl / 4 × 414 «kJ mol–1» + 242 «kJ mol–1» / 1898 «kJ» ✔

bond forming: «C–Cl + H–Cl / 324 kJ mol–1 + 431 kJ mol–1» / 755 «kJ»
OR
bond forming: «3C–H + C–Cl + H–Cl / 3 × 414 «kJ mol–1» + 324 «kJ mol–1» + 431 kJ mol–1» /
1997 «kJ» ✔

«ΔH = bond breaking – bond forming = 656 kJ – 755 kJ» = –99 «kJ» ✔

Award [3] for correct final answer.

Award [2 max] for 99 «kJ».
4j. [2 marks]
Draw and label an enthalpy level diagram for this reaction.
Markscheme

reactants at higher enthalpy than products ✔

ΔH/-99 «kJ» labelled on arrow from reactants to products

OR
activation energy/Ea labelled on arrow from reactant to top of energy profile ✔

Accept a double headed arrow between reactants and products labelled as ΔH for M2.
5a. [1 mark]
1-chloropentane reacts with aqueous sodium hydroxide.
Identify the type of reaction.

Markscheme
«nucleophilic» substitution/SN2 ✔

Do not accept if “electrophilic” or “free radical” substitution is stated.

5b. [1 mark]
Outline the role of the hydroxide ion in this reaction.
Markscheme
«acts as a» nucleophile/Lewis base
OR
donates/provides lone pair «of electrons»
OR
attacks the «partially» positive carbon ✔
5c. [2 marks]
Suggest, with a reason, why 1-iodopentane reacts faster than 1-chloropentane under the
same conditions. Use section 11 of the data booklet for consistency.

Markscheme
bond enthalpy C–I lower than C–Cl
OR
C–I bond weaker than C–Cl ✔

«weaker bond» broken more easily/with less energy

OR
lower Ea «for weaker bonds» ✔

Accept the bond enthalpy values for C–I and C–Cl for M1.
5d. [2 marks]
The reaction was repeated at a lower temperature.
Sketch labelled Maxwell–Boltzmann energy distribution curves at the original temperature
(T1) and the new lower temperature (T2).

Markscheme

peak at T1 to right of AND lower than T2 ✔

lines begin at origin AND T1 must finish above T2 ✔
5e. [2 marks]
Explain the effect of lowering the temperature on the rate of the reaction.
Markscheme
«rate is» lower AND «average» kinetic energy of molecules is lower
OR
«rate is» lower AND less frequent collisions
OR
«rate is» lower AND fewer collisions per unit time ✔
«rate is» lower AND fewer/smaller fraction of molecules/collisions have the E ≥ Ea ✔

Lower «rate» needs to be mentioned once only.

Do not accept “fewer collisions” without reference to time/frequency/probability for M1.
6a. [2 marks]
Alkanes undergo combustion and substitution.
Determine the molar enthalpy of combustion of an alkane if 8.75 × 10 −4 moles are burned,
raising the temperature of 20.0 g of water by 57.3 °C.
Markscheme
«q = mcΔT = 20.0 g × 4.18 J g−1 °C−1 × 57.3 °C =» 4790 «J» ✔
4790 J
Hc =¿
« 1000 » –5470 «kJ mol–1» ✔
−4
8.75 ×10 mol

Award [2] for correct final answer.

Accept answers in the range –5470 to –5480 «kJ mol−1».
Accept correct answer in any units, e.g. –5.47 «MJ mol−1» or 5.47 x 106 «J mol−1».
6b. [3 marks]
Formulate equations for the two propagation steps and one termination step in the
formation of chloroethane from ethane.

Markscheme
Cl· + C2H6 → ·C2H5 + HCl ✔
·C2H5 + Cl2 → Cl· + C2H5Cl ✔

·C2H5 + Cl· → C2H5Cl

OR
Cl· + Cl· → Cl2
OR
·C2H5 + ·C2H5 → C4H10 ✔

Do not penalize incorrectly placed radical sign, eg C2H5·.

7a. [1 mark]
Ethanol is obtained by the hydration of ethene, C2H4.
State the class of compound to which ethene belongs.

Markscheme
alkene ✔
7b. [1 mark]
State the molecular formula of the next member of the homologous series to which ethene
belongs.

Markscheme
C3H6 ✔
Accept structural formula.
7c. [1 mark]
Justify why ethene has only a single signal in its 1H NMR spectrum.

Markscheme
hydrogen atoms/protons in same chemical environment ✔
Accept “all H atoms/protons are equivalent”.
Accept “symmetrical”
7d. [1 mark]
Suggest two possible products of the incomplete combustion of ethene that would not be
formed by complete combustion.

Markscheme
carbon monoxide/CO AND carbon/C/soot ✔
7e. [1 mark]
A white solid was formed when ethene was subjected to high pressure.
Deduce the type of reaction that occurred.

Markscheme
«addition» polymerization ✔
8a. [2 marks]
Organic chemistry can be used to synthesize a variety of products.
Several compounds can be synthesized from but-2-ene. Draw the structure of the final
product for each of the following chemical reactions.
Markscheme

Penalize missing hydrogens in displayed structural formulas once only.

Accept condensed structural formulas: CH3CH(OH)CH2CH3 / CH3CH2CH2CH3 or skeletal
structures.
8b. [3 marks]
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)

Markscheme
Bonds broken:
2(C–C) + 1(C=C) + 8(C–H) + 6O=O / 2(346) + 1(614) + 8(414) + 6(498) / 7606 «kJ» ✓
Bonds formed:
8(C=O) + 8(O–H) / 8(804) + 8(463) / 10 136 «kJ» ✓
Enthalpy change:
«Bonds broken – Bonds formed = 7606 kJ – 10 136 kJ =» –2530 «kJ» ✓

Award [2 max] for «+» 2530 «kJ».

Award [3] for correct final answer.
8c. [2 marks]
Write the equation and name the organic product when ethanol reacts with methanoic
acid.

Markscheme
Equation:
CH3CH2OH + HCOOH ⇌ HCOOCH2CH3 + H2O ✓
Product name:
ethyl methanoate ✓
Accept equation without equilibrium arrows.
Accept equation with molecular formulas (C2H6O + CH2O2 ⇌ C3H6O2 + H2O) only if product
name is correct.
8d. [2 marks]
Oxidation of ethanol with potassium dichromate, K2Cr2O7, can form two different organic
products. Determine the names of the organic products and the methods used to isolate
them.
Markscheme
ethanal AND distillation ✓
ethanoic acid AND reflux «followed by distillation» ✓

Award [1 max] for both products OR both methods.

8e. [2 marks]
Combustion analysis of an unknown organic compound indicated that it contained only
carbon, hydrogen and oxygen.
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.
Markscheme
m/z 58:
molar/«relative» molecular mass/weight/Mr «is 58 g mol−1/58» ✓

m/z 43:
«loses» methyl/CH3 «fragment»
OR
COCH3+ «fragment» ✓

Do not penalize missing charge on the fragments.

Accept molecular ion «peak»/ CH3COCH3+/C3H6O+.
Accept any C2H3O+ fragment/ CH3CH2CH2+/C3H7+.
8f. [1 mark]
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.

Markscheme
C=O ✓

Accept carbonyl/C=C.
8g. [2 marks]
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).

Markscheme
Information deduced from 1H NMR:
«one signal indicates» one hydrogen environment/symmetrical structure
OR
«chemical shift of 2.2 indicates» H on C next to carbonyl ✓

Compound:
propanone/CH3COCH3 ✓

Accept “one type of hydrogen”.

Accept .
9a. [1 mark]
Chlorine undergoes many reactions.
State the full electron configuration of the chlorine atom.

Markscheme
2 2 6 2 5
1s 2s 2 p 3s 3 p ✔
Do not accept condensed electron configuration.
9b. [1 mark]
State, giving a reason, whether the chlorine atom or the chloride ion has a larger radius.

Markscheme
−¿¿
Cl AND more «electron–electron» repulsion ✔

−¿ ¿
Accept C l AND has an extra electron.
9c. [2 marks]
Outline why the chlorine atom has a smaller atomic radius than the sulfur atom.

Markscheme
Cl has a greater nuclear charge/number of protons/ Z eff «causing a stronger pull on the
outer electrons» ✔
same number of shells
OR
same «outer» energy level
OR
similar shielding ✔
9d. [1 mark]
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 .

Markscheme
«two major» isotopes «of atomic mass 35 and 37 » ✔
9e. [2 marks]
Explain the presence and relative abundance of the peak at m/ z=74 .
Markscheme
«diatomic» molecule composed of «two» chlorine-37 atoms ✔
chlorine-37 is the least abundant «isotope»
OR
low probability of two Cl37 «isotopes» occurring in a molecule ✔
9f. [1 mark]
2.67 g of manganese(IV) oxide was added to 200.0 cm3 of 2.00 mol d m−3 HCl.
MnO2 ( s ) +4 HCl ( aq ) → Cl 2 ( g ) +2 H 2 O ( l ) + MnCl 2 ( aq )

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

Markscheme
2.67 g
¿ −1
=¿ 0.0307 ≪mol≫¿ ✔
86.94 g mol
9g. [2 marks]
Determine the limiting reactant, showing your calculations.
Markscheme
−3 3
¿ n HCl=2.00 mol dm × 0.2000 dm ≫¿ 0.400 mol ✔
0.400
¿ =¿ 0.100 mol AND MnO2 is the limiting reactant ✔
4
Accept other valid methods of determining the limiting reactant in M2.
9h. [1 mark]
Determine the excess amount, in mol , of the other reactant.

Markscheme
¿ 0.0307 mol × 4=0.123 mol ≫¿
¿ 0.400 mol 0.123 mol=¿ 0.277 ≪mol≫¿ ✔
9i. [1 mark]
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.

Markscheme
3 −1 3
¿ 0.0307 mol × 22.7 dm mol =¿ 0.697≪dm ≫¿ ✔

Accept methods employing pV =nRT .

9j. [2 marks]
State the oxidation state of manganese in MnO2 and MnCl 2.
Markscheme
MnO2 :+ 4 ✔

MnCl 2 :+2 ✔

9k. [1 mark]
Deduce, referring to oxidation states, whether MnO2 is an oxidizing or reducing agent.

Markscheme
oxidizing agent AND oxidation state of Mn changes from + 4 to +2/decreases ✔
9l. [1 mark]
Chlorine gas reacts with water to produce hypochlorous acid and hydrochloric acid.
Cl2 ( g ) + H 2 O ( l ) ⇌ HClO ( aq ) + HCl ( aq )

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

Markscheme
partially dissociates/ionizes «in water» ✔
9m. [1 mark]
State the formula of the conjugate base of hypochlorous acid.

Markscheme
−¿ ¿
ClO ✔
9n. [1 mark]
Calculate the concentration of H +¿ (aq) ¿ in a HClO ( aq ) solution with a pH=3.61.

Markscheme
¿¿ ✔
9o. [1 mark]
State the type of reaction occurring when ethane reacts with chlorine to produce
chloroethane.

Markscheme
«free radical» substitution/ S R ✔

Do not accept electrophilic or nucleophilic substitution.

9p. [1 mark]
Predict, giving a reason, whether ethane or chloroethane is more reactive.

Markscheme
chloroethane AND CCl bond is weaker/324 kJ mol−1 than CH bond/414 kJ mol−1
OR
chloroethane AND contains a polar bond ✔

Accept “chloroethane AND polar”.

9q. [1 mark]
Write the equation for the reaction of chloroethane with a dilute aqueous solution of
sodium hydroxide.

Markscheme
¿OR
CH 3 CH 2 Cl (l )+ NaOH ( aq ) →CH 3 CH 2 OH ( aq )+ NaCl ( aq ) ✔

Accept use of C 2 H 5 Cl and C 2 H 5 OH /C 2 H 6 O in the equation.

9r. [1 mark]
Deduce the nucleophile for the reaction in d(iii).

Markscheme
−¿¿
hydroxide «ion»/OH ✔
Do not accept NaOH .
9s. [1 mark]
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion. Draw the
structural formula of ethoxyethane

Markscheme

CH 3 CH 2 OCH 2 CH 3

/ ✔

Accept ( C H 3 C H 2 )2 O.

9t. [2 marks]
Deduce the number of signals and their chemical shifts in the H1 NMR spectrum of
ethoxyethane. Use section 27 of the data booklet.
Markscheme
2 «signals» ✔
0.91 .0≪ ppm≫¿ AND 3.33 .7≪ ppm≫¿✔

Accept any values in the ranges.

Award [1 max] for two incorrect chemical shifts.
9u. [2 marks]
CCl2 F2 is a common chlorofluorocarbon, CFC .

Calculate the percentage by mass of chlorine in CCl2 F2.

Markscheme
−1
¿ M ( CCl2 F 2 )=¿ 120.91≪ g mol ≫¿ ✔
−1
2× 35.45 g mol
−1
×100 %=¿58.64 ≪%≫¿ ✔
120.91 g mol

Award [2] for correct final answer.

9v. [1 mark]
Comment on how international cooperation has contributed to the lowering of CFC
emissions responsible for ozone depletion.
Markscheme
Any of:
research «collaboration» for alternative technologies «to replace CFC s»
OR
technologies «developed»/data could be shared
OR
political pressure/Montreal Protocol/governments passing legislations ✔

Do not accept just “collaboration”.

Do not accept any reference to CFC as greenhouse gas or product of fossil fuel combustion.
Accept reference to specific measures, such as agreement on banning use/manufacture of
CFC s.
10a. [2 marks]
Compound A is in equilibrium with compound B.

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

Markscheme
Electron domain geometry: tetrahedral ✔
Molecular geometry: bent/V-shaped ✔
10b. [1 mark]
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.

Markscheme
B AND C=O absorption/1750≪cm−1 ≫¿
OR
B AND absence of OH /3200−3600≪cm−1 absorption≫¿ ✔

Accept any value between 1700−1750 c m−1.

10c. [2 marks]
Compound A and B are isomers. Draw two other structural isomers with the formula
C 3 H 6 O.
Markscheme
Accept any two C 3 H 6 O isomers except for propanone and propen-2-ol:
 ✔✔

Penalize missing hydrogens in displayed structural formulas once only.

10d. [1 mark]
The equilibrium constant, K c , for the conversion of A to B is 1.0 ×108 in water at 298 K .
Deduce, giving a reason, which compound, A or B, is present in greater concentration when
equilibrium is reached.
Markscheme
B AND K c is greater than 1/large ✔

11a. [1 mark]
Nickel catalyses the conversion of propanone to propan-2-ol.

Outline how a catalyst increases the rate of reaction.

Markscheme
provides an alternative pathway/mechanism AND lower E a ✔

Accept description of how catalyst lowers E a (e.g. “reactants adsorb on surface «of catalyst»”,
“reactant bonds weaken «when adsorbed»”).
11b. [2 marks]
Explain why an increase in temperature increases the rate of reaction.
Markscheme
more/greater proportion of molecules with E ≥ Ea ✔
greater frequency/probability/chance of collisions «between the molecules»
OR
more collision per unit of time/second ✔
11c. [3 marks]
Discuss, referring to intermolecular forces present, the relative volatility of propanone and
propan-2-ol.

Markscheme
hydrogen bonding/bonds «and dipole–dipole and London/dispersion forces are present
in» propan-2-ol ✔
dipole–dipole «and London/dispersion are present in» propanone ✔
propan-2-ol less volatile AND hydrogen bonding/bonds stronger «than dipole–dipole »
OR
propan-2-ol less volatile AND «sum of all» intermolecular forces stronger ✔
11d. [1 mark]
The diagram shows an unlabelled voltaic cell for the reaction
¿
Label the diagram with the species in the equation.

Markscheme

11e. [1 mark]
Suggest a metal that could replace nickel in a new half-cell and reverse the electron flow.
Use section 25 of the data booklet.
Markscheme
Bi/Cu/ Ag/ Pd/ Hg/ Pt / Au ✔
Accept Sb OR As.
11f. [2 marks]
Describe the bonding in metals.

Markscheme
electrostatic attraction ✔
between «a lattice of» metal/positive ions/cations AND «a sea of» delocalized electrons ✔

Accept “mobile/free electrons”.

11g. [1 mark]
Nickel alloys are used in aircraft gas turbines. Suggest a physical property altered by the
addition of another metal to nickel.
Markscheme
Any of:
malleability/hardness
OR
«tensile» strength/ductility
OR
density
OR
thermal/electrical conductivity
OR
melting point
OR
thermal expansion ✔

Do not accept corrosion/reactivity or any chemical property.

Accept other specific physical properties.
12a. [1 mark]
The following shows some compounds which can be made from ethene, C 2H4.
ethene (C2H4) → C2H5Cl → C2H6O → C2H4O
State the type of reaction which converts ethene into C2H5Cl.

Markscheme
«electrophilic» addition ✔
NOTE: Do not accept “nucleophilic addition” or “free radical addition”.
Do not accept “halogenation”.
12b. [1 mark]
Write an equation for the reaction of C2H5Cl with aqueous sodium hydroxide to produce a
C2H6O compound, showing structural formulas.
Markscheme
CH3CH2Cl (g) + OH− (aq) → CH3CH2OH (aq) + Cl− (aq)
OR
CH3CH2Cl (g) + NaOH (aq) → CH3CH2OH (aq) + NaCl (aq) ✔
12c. [1 mark]
Write an equation for the complete combustion of the organic product in (b).

Markscheme
C2H6O (g) + 3O2 (g) → 2CO2 (g) + 3H2O (g)
OR
CH3CH2OH (g) + 3O2 (g) → 2CO2 (g) + 3H2O (g) ✔
12d. [3 marks]
Determine the enthalpy of combustion of the organic product in (b), in kJ mol −1, using data
from section 11 of the data booklet.

Markscheme
bonds broken:
5(C–H) + C–C + C–O + O–H + 3(O=O)
OR
5(414«kJ mol−1») + 346«kJ mol−1» + 358«kJ mol−1» + 463«kJ mol−1» + 3(498«kJ mol−1») /
4731 «kJ» ✔

bonds formed:
4(C=O) + 6(O–H)
OR
4(804«kJ mol−1») + 6(463«kJ mol−1») / 5994 «kJ» ✔
«ΔH = bonds broken − bonds formed = 4731 − 5994 =» −1263 «kJ mol−1» ✔
NOTE: Award [3] for correct final answer.
12e. [2 marks]
State the reagents and conditions for the conversion of the compound C 2H6O, produced in
(b), into C2H4O.

Markscheme
K2Cr2O7/Cr2O72−/«potassium» dichromate «(VI)» AND acidified/H+
OR
«acidified potassium» manganate(VII) / «H+» KMnO4 / «H+» MnO4− ✔

NOTE: Accept “H2SO4” or “H3PO4” for “H+”.

Do not accept “HCl”.
Accept “permanganate” for “manganate(VII)”.

distil ✔

12f. [2 marks]
Explain why the compound C2H6O, produced in (b), has a higher boiling point than
compound C2H4O, produced in d(i).
Markscheme
C2H6O/ethanol: hydrogen-bonding AND C2H4O/ethanal: no hydrogen-bonding/«only»
dipole–dipole forces ✔

hydrogen bonding stronger «than dipole–dipole» ✔

12g. [1 mark]
Ethene is often polymerized. Draw a section of the resulting polymer, showing two
repeating units.

Markscheme

NOTE: Continuation bonds must be shown.

Ignore square brackets and “n”.
13a. [2 marks]
Xylene is a derivative of benzene. One isomer is 1,4-dimethylbenzene.
State the number of 1H NMR signals for this isomer of xylene and the ratio in which they
appear.
Number of signals:

Ratio:

Markscheme
Number of signals:
2 [✔]
Ratio:
3:2
OR
6 : 4 [✔]

Note: Accept any correct integer or fractional ratio.

Accept ratios in reverse order.
13b. [1 mark]
Draw the structure of one other isomer of xylene which retains the benzene ring.
Markscheme

[✔]
13c. [2 marks]
Bromine reacts with alkanes.
Identify the initiation step of the reaction and its conditions.

Markscheme
Br2 → 2Br• [✔]
«sun»light/UV/hv
OR
high temperature [✔]

Note: Do not penalize missing radical symbol on Br.

Accept “homolytic fission of bromine” for M1.
13d. [2 marks]
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.

Markscheme

[✔]
HBr [✔]

Note: Accept condensed formulae, such as CH3C6H4CH2Br.

Accept skeletal structures.
14a. [1 mark]
Benzoic acid, C6H5COOH, is another derivative of benzene.
Draw the structure of the conjugate base of benzoic acid showing all the atoms and all the
bonds.
Markscheme

[✔]

Note: Accept Kekulé structures.

Negative sign must be shown in correct position- on the O or delocalised over the carboxylate.
14b. [2 marks]
The pH of an aqueous solution of benzoic acid at 298 K is 2.95. Determine the
concentration of hydroxide ions in the solution, using section 2 of the data booklet.
Markscheme
ALTERNATIVE 1:
[H+] «= 10−2.95» = 1.122 × 10−3 «mol dm−3» [✔]
−14 2 −6
1.00× 10 mol d m
«[OH−] = −3 −3 =» 8.91 × 10
−12
«mol dm−3» [✔]
1.22× 10 mol d m

ALTERNATIVE 2:
pOH = «14 − 2.95 =» 11.05 [✔]
«[OH−] = 10−11.05 =» 8.91 × 10−12 «moldm−3» [✔]

Note: Award [2] for correct final answer.

Accept other methods.
14c. [2 marks]
Formulate the equation for the complete combustion of benzoic acid in oxygen using only
integer coefficients.

Markscheme
2C6H5COOH(s) + 15O2 (g) → 14CO2 (g) + 6H2O(l)
correct products [✔]
correct balancing [✔]
14d. [1 mark]
Suggest how benzoic acid, Mr = 122.13, forms an apparent dimer, Mr = 244.26, when
dissolved in a non-polar solvent such as hexane.
Markscheme
«intermolecular» hydrogen bonding [✔]

Note: Accept diagram showing hydrogen bonding.

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