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Date	November 2020	Marks available	1	Reference code	20N.2.sl.TZ0.1
Level	SL	Paper	2	Time zone	TZ0
Command term	Predict and Justify	Question number	1	Adapted from	N/A

Question

Chlorine undergoes many reactions.

$2.67 g$ of manganese(IV) oxide was added to $200.0 {cm}^{3}$ of $2.00 mol {dm}^{- 3} HCl$ .

${MnO}_{2} (s) + 4 HCl (aq) \to {Cl}_{2} (g) + 2 H_{2} O (l) + {MnCl}_{2} (aq)$

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

${Cl}_{2} (g) + H_{2} O (l) ⇌ HClO (aq) + HCl (aq)$

${CCl}_{2} F_{2}$ 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.

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 ${dm}^{3}$ , 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 ${MnO}_{2}$ and ${MnCl}_{2}$ .

[2]

b(v).

Deduce, referring to oxidation states, whether ${MnO}_{2}$ 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 $HClO (aq)$ 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).

Write the equation for the reaction of chloroethane with a dilute aqueous solution of sodium hydroxide.

[1]

d(iii).

Deduce the nucleophile for the reaction in d(iii).

[1]

d(iv).

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

[1]

d(v).

Deduce the number of signals and their chemical shifts in the ${}_{1}H NMR$ spectrum of ethoxyethane. Use section 27 of the data booklet.

[2]

d(vi).

Calculate the percentage by mass of chlorine in ${CCl}_{2} F_{2}$ .

[2]

e(i).

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

[1]

e(ii).

Markscheme

$1 s^{2} 2 s^{2} 2 p^{6} 3 s^{2} 3 p^{5}$ ✔

Do not accept condensed electron configuration.

a(i).

${Cl}^{-}$ AND more «electron–electron» repulsion ✔

Accept $C l^{-}$ AND has an extra electron.

a(ii).

$Cl$ 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 ✔

a(iii).

«two major» isotopes «of atomic mass $35$ and $37$ » ✔

a(iv).

«diatomic» molecule composed of «two» chlorine-37 atoms ✔

chlorine-37 is the least abundant «isotope»
OR
low probability of two ${}_{37}{Cl}$ «isotopes» occurring in a molecule ✔

a(v).

$« \frac{2.67 g}{86.94 g {mol}^{- 1}} = » 0.0307 « mol »$ ✔

b(i).

$« n_{HCl} = 2.00 mol {dm}^{- 3} \times 0.2000 {dm}^{3} » = 0.400 mol$ ✔

$« \frac{0.400}{4} = » 0.100 mol$ AND ${MnO}_{2}$ is the limiting reactant ✔

Accept other valid methods of determining the limiting reactant in M2.

b(ii).

$« 0.0307 mol \times 4 = 0.123 mol »$

$« 0.400 mol - 0.123 mol = » 0.277 « mol »$ ✔

b(iii).

$« 0.0307 mol \times 22.7 {dm}^{3} {mol}^{- 1} = » 0.697 « {dm}^{3} »$ ✔

Accept methods employing $p V = n R T$ .

b(iv).

${MnO}_{2} : + 4$ ✔

${MnCl}_{2} : + 2$ ✔

b(v).

oxidizing agent AND oxidation state of $Mn$ changes from $+ 4$ to $+ 2$ /decreases ✔

b(vi).

partially dissociates/ionizes «in water» ✔

c(i).

${ClO}^{-}$ ✔

c(ii).

$« [H^{+}] = 10^{- 3.61} = » 2.5 \times 10^{- 4} « mol {dm}^{- 3} »$ ✔

c(iii).

«free radical» substitution/ $S_{R}$ ✔

Do not accept electrophilic or nucleophilic substitution.

d(i).

chloroethane AND $C - Cl$ bond is weaker/ $324 kJ {mol}^{- 1}$ than $C - H$ bond/ $414 kJ {mol}^{- 1}$
OR
chloroethane AND contains a polar bond ✔

Accept “chloroethane AND polar”.

d(ii).

${CH}_{3} {CH}_{2} Cl (l) + {OH}^{-} (aq) \to {CH}_{3} {CH}_{2} OH (aq) + {Cl}^{-} (aq)$
OR
${CH}_{3} {CH}_{2} Cl (l) + NaOH (aq) \to {CH}_{3} {CH}_{2} OH (aq) + NaCl (aq)$ ✔

Accept use of $C_{2} H_{5} C l$ and $C_{2} H_{5} O H / C_{2} H_{6} O$ in the equation.

d(iii).

hydroxide «ion»/ ${OH}^{-}$ ✔

Do not accept $N a O H$ .

d(iv).

/ ${CH}_{3} {CH}_{2} {OCH}_{2} {CH}_{3}$ ✔

Accept $(C H_{3} C H_{2})_{2} O$ .

d(v).

$2$ «signals» ✔

$0.9 - 1.0 « ppm »$ AND $3.3 - 3.7 « ppm »$ ✔

Accept any values in the ranges.

Award [1 max] for two incorrect chemical shifts.

d(vi).

$« M ({CCl}_{2} F_{2}) = » 120.91 « g {mol}^{- 1} »$ ✔

$\frac{2 \times 35.45 g {mol}^{- 1}}{120.91 g {mol}^{- 1}} \times 100 % = » 58.64 « % »$ ✔

Award [2] for correct final answer.

e(i).

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 $C F C$ as greenhouse gas or product of fossil fuel combustion.

Accept reference to specific measures, such as agreement on banning use/manufacture of $C F C$ s.

e(ii).

Examiners report

Most candidates wrote the electron configuration of chlorine correctly.

a(i).

Only half of the candidates deduced that the chloride ion has a larger radius than the chlorine atom with a valid reason. Many candidates struggled with this question and decided that the extra electron in the chloride ion caused a greater attraction between the nucleus and the outer electrons.

a(ii).

Only about a third of the candidates identified the extra proton in the chlorine nucleus as the cause of the smaller atomic radius when compared to the sulfur atom, and only the stronger candidates also compared the shielding or the number of shells in the two atoms. Many candidates had a poor understanding of factors affecting atomic radius and could not explain the difference.

a(iii).

About 60% of the candidates recognized that the peaks at m/z 35 and 37 in the mass spectrum of chlorine are due to its isotopes. A few students wrote 'isomers' instead of 'isotopes'.

a(iv).

This was the lowest scoring question on the paper, that was also left blank by 10% of the candidates. About 20% of the candidates identified the peak at m/z = 74 to be due to a molecule made up of two 37Cl atoms. And only very few candidates commented that the low abundance of the peak was due to the low abundance of the 37Cl isotope. A common incorrect answer was that chlorine has an isotope of mass number 74.

a(v).

Most candidates were able to determine the number of moles of MnO₂ using the mass.

b(i).

It was pleasing that the majority of the candidates were able to determine the limiting reactant by using the stoichiometric ratio.

b(ii).

Half of the candidates were able to determine the amount of excess reactant. Some candidates who determined the limiting reactant in the previous part correctly, forgot to use the stoichiometric ratio in this part, and ended up with incorrect answers.

b(iii).

60% of the candidates determined the volume of chlorine produced correctly. Some candidates made mistakes in the units when using PV = nRT and had a power of 10 error.

b(iv).

The majority of candidates were able to determine the oxidation states of Mn in the two compounds correctly.

b(v).

Less than half of the candidates were awarded the mark. Some did identify MnO2 as the oxidizing agent but did not give the explanation in terms of oxidation state as required in the question. Other candidates did not have an understanding of oxidizing and reducing agents.

b(vi).

A very well answered question - 80% of candidates understood what is meant by the term weak acid. Incorrect answers included 'acids that have high pH'.

c(i).

Half of the candidates deduced the formula of the conjugate base of hypochlorous acid. Incorrect answers included H₂O and HCl.

c(ii).

A well answered question. It was pleasing to see that 70% of the candidates were able to calculate [H⁺] from the given pH.

c(iii).

More than half of the candidates identified the type of reaction between ethane and chlorine as a substitution reaction. A few candidates lost the marks for writing 'electrophilic substitution' or 'nucleophilic substitutions'.

d(i).

This was a challenging question that was answered correctly by only 30% of the candidates. A variety of incorrect answers were seen such as 'chlorine is a halogen and hence it is reactive', and 'ethane is more reactive because it is an alkane'. For students who answered correctly, the polarity was the most frequently given reason.

d(ii).

Half of the candidates wrote the correct equation for the hydrolysis of chloroethane. Incorrect answers often included carbon dioxide and water as the products.

d(iii).

This was a highly discriminating question. Only 30% of the candidates were able to identify the hydroxide ion as the nucleophile in the hydrolysis of chloroethane. Incorrect answers included NaOH where the ion was not specified. 14% of the candidates left this question blank.

d(iv).

Half of the candidates were able to give the structural formula of ethoxyethane. Incorrect answers included methoxymethane, ketones and esters.

d(v).

Nearly half of the candidates were able to identify the number of signals obtained in the 1H NMR spectrum of ethoxyethane, obtaining the first mark of this question. Many candidates were awarded the mark as 'error carried forward' from an incorrect structure of ethoxyethane. The second mark for this question required candidates to look up values of chemical shift from the data booklet. Nearly a third of the candidates were able to match the chemical environments of the hydrogen atoms in ethoxyethane to those listed in the data booklet successfully.

d(vi).

This was the highest scoring question in the paper. The majority of candidates were able to calculate the percentage by mass of chlorine in CCl₂F₂. Mistakes included incorrect rounding and arithmetic errors.

e(i).

This nature of science question was well answered by half of the candidates. Some teachers commented that the wording was rather vague. Incorrect answers were mainly assuming that CFCs were related to the combustion of fuels and greenhouse gas emissions.

e(ii).

Syllabus sections

Core » Topic 10: Organic chemistry » 10.2 Functional group chemistry

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Calculate the standard enthalpy change for the reaction, ΔH ^θ, using section 12 of the data booklet.
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State a suitable oxidizing agent for the oxidation of propan-2-ol in an acidified aqueous solution.
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Identify the initiation step of the reaction and its conditions.
17M.3.hl.TZ1.9a:
Deduce the repeating unit of the polymer and the other product of the reaction.
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16N.2.sl.TZ0.5b:
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(i) State an equation and the condition required for the reaction of 1 mol of propane with 1 mol of bromine.

(ii) State an equation for the reaction of 1 mol of propene with 1 mol of bromine.

(iii) State the type of each reaction with bromine.

Propane:

Propene:
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18N.1.sl.TZ0.24:
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II. (CH₃)₃CCH₂OH

III. CH₃CH₂CH(OH)CH₃

A. I and II only

B. I and III only

C. II and III only

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State the organic product of the reaction between 1-chlorobutane, CH₃CH₂CH₂CH₂Cl, and aqueous sodium hydroxide.
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Write an equation for the complete combustion of ethyne.
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D. –CH₂–CH₂–
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Deduce the type of chemical reaction and the reagents used to distinguish between these compounds.
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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.
17N.1.sl.TZ0.25:
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B. CH₃CH₂CH(OH)CH₃

C. (CH₃)₃COH

D. CH₃(CH₂)₂COOH
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17N.2.sl.TZ0.6b:
Explain, with the help of equations, the mechanism of the free-radical substitution reaction of ethane with bromine in presence of sunlight.
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19M.2.hl.TZ1.1d(i):
Identify the initiation step of the reaction and its conditions.
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18M.1.sl.TZ1.27:
Which compound could be formed when CH₃CH₂CH₂OH is heated with acidified potassium dichromate(VI)?

I. CH₃CH₂CHO

II. CH₃CH₂COOH

III. CH₃COCH₃

A. I and II only

B. I and III only

C. II and III only

D. I, II and III
21N.2.sl.TZ0.4a(i): Identify the type of reaction.
19N.2.hl.TZ0.3a(i): State the type of reaction.
19N.2.hl.TZ0.3c(i):
Write an equation for the complete combustion of the compound C₃H₈O formed in (a)(iv).
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17M.2.hl.TZ2.7b.ii:
Deduce the structural formula of the main organic product when hex-1-ene reacts with hydrogen bromide.
19N.3.hl.TZ0.5a:
Draw the structure of the monomers of Kevlar^® if the by-product of the condensation polymerization is hydrogen chloride.
19N.3.sl.TZ0.14a:
Write the equation for the complete combustion of ethanol.
17M.2.sl.TZ1.6b:
State the typical reactions that benzene and cyclohexene undergo with bromine.
17M.2.sl.TZ1.6a:
Discuss the physical evidence for the structure of benzene.
18M.2.hl.TZ1.3b:
Ethyne reacts with chlorine in a similar way to ethene. Formulate equations for the following reactions.
18M.2.sl.TZ1.3a.i:
Ethyne, like ethene, undergoes hydrogenation to form ethane. State the conditions required.
19M.1.hl.TZ2.33:
Methane reacts with chlorine in sunlight.

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

Which type of reaction occurs?

A. free-radical substitution

B. electrophilic substitution

C. nucleophilic substitution

D. electrophilic addition
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17M.2.hl.TZ2.7b.i:
Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.
19M.2.sl.TZ2.1a:
Write an equation for the complete combustion of ethyne.
17M.2.sl.TZ2.6c:
Polyvinyl chloride (PVC) is a polymer with the following structure.

State the structural formula for the monomer of PVC.
17M.2.sl.TZ1.5a:
Ethane, C₂H₆, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.
17M.2.sl.TZ2.6b:
Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.
19N.2.hl.TZ0.3d(i):
State the reagents for the conversion of the compound C₃H₈O formed in (a)(iv) into C₃H₆O.
19N.1.sl.TZ0.28: Which compound cannot undergo addition polymerization?
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19M.2.hl.TZ2.6a:
Draw the repeating unit of polyphenylethene.
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20N.1.sl.TZ0.27: Which mechanism does benzene most readily undergo? A. Nucleophilic substitution B. ...
17M.2.hl.TZ2.2a.v:
Identify one organic functional group that can react with acidified K₂Cr₂O₇(aq).
22M.2.sl.TZ1.3d(ii): Deduce the structural formula of the repeating unit of the polymer formed from this alkene.
19M.2.sl.TZ2.1c(i):
Product A contains a carbon–carbon double bond. State the type of reactions that compounds containing this bond are likely to undergo.
19M.2.hl.TZ1.2f(ii):
Formulate the equation for the complete combustion of benzoic acid in oxygen using only integer coefficients.
19N.2.sl.TZ0.3d(i):
State the reagents and conditions for the conversion of the compound C₂H₆O, produced in (b), into C₂H₄O.
19M.2.hl.TZ1.1d(ii):
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.
19N.3.hl.TZ0.24c:
Explain how redox chemistry is used to measure the ethanol concentration in a breathalyser.
21M.1.sl.TZ1.26: What is formed in a propagation step of the substitution reaction between bromine and...
21M.1.sl.TZ1.27:
Which monomer would produce the polymer shown?

A. ${CF}_{3} {CCl}_{2} F$

B. ${CF}_{3} CClHF$

C. ${CF}_{2} CClF$

D. ${CF}_{2} {CF}_{2}$
21M.2.hl.TZ1.5d: A white solid was formed when ethene was subjected to high pressure. Deduce the type of...
21M.2.hl.TZ1.5c: Suggest two possible products of the incomplete combustion of ethene that would not be formed...
21M.2.hl.TZ1.5e(iii): 2-bromopropane can be converted directly to propan-2-ol. Identify the reagent required.
21M.1.sl.TZ2.26:
Which monomer forms the polymer shown?

A. ${CH(Cl)=CH(CH}_{3})$

B. ${CH}_{2} {=C(Cl)CH}_{3}$

C. ${(CH}_{3})_{2} CHCl$

D. ${CH}_{2} =CHCl$
19M.2.sl.TZ1.2b(ii):
Formulate the equation for the complete combustion of benzoic acid in oxygen using only integer coefficients.
19M.2.hl.TZ2.1d(i):
Suggest the reagents and conditions required to ensure a good yield of product B.

Reagents:

Conditions:
20N.2.sl.TZ0.1d(iii):
Write the equation for the reaction of chloroethane with a dilute aqueous solution of sodium hydroxide.
21M.1.hl.TZ2.37:
Which can be reduced to a secondary alcohol?

A. C₂H₅COOH

B. CH₃CH₂OCH₃

C. (CH₃)₂CHCHO

D. CH₃COC₂H₅
17M.2.sl.TZ1.5b:
Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.
17N.2.sl.TZ0.6a.ii:
State the observation expected for each reaction giving your reasons.
21M.2.sl.TZ1.5d: A white solid was formed when ethene was subjected to high pressure. Deduce the type of...
21M.2.sl.TZ1.5c: Suggest two possible products of the incomplete combustion of ethene that would not be formed...
21M.2.sl.TZ2.4a:
Several compounds can be synthesized from but-2-ene. Draw the structure of the final product for each of the following chemical reactions.
21M.2.sl.TZ2.4d:
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.
21M.2.hl.TZ2.4a:
Several compounds can be synthesized from but-2-ene. Draw the structure of the final product for each of the following chemical reactions.
21M.2.hl.TZ2.5c:
Write the equation and name the organic product when ethanol reacts with methanoic acid.
21M.2.hl.TZ2.5b:
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.
17M.2.sl.TZ2.6a:
Using relevant equations, show the initiation and the propagation steps for this reaction.
20N.2.sl.TZ0.1d(iv):
Deduce the nucleophile for the reaction in d(iii).
20N.2.sl.TZ0.1d(i):
State the type of reaction occurring when ethane reacts with chlorine to produce chloroethane.
20N.2.hl.TZ0.1d(ii):
Predict, giving a reason, whether ethane or chloroethane is more reactive.
22M.2.hl.TZ2.8c:
Describe a test and the expected result to indicate the presence of carbon–carbon double bonds.
22M.2.sl.TZ2.4c:
Describe a test and the expected result to indicate the presence of carbon–carbon double bonds.
21M.1.sl.TZ2.27:
Which is a propagation step in the free-radical substitution mechanism of ethane with chlorine?

A. C $l$ ₂ → 2 •C $l$

B. •C₂H₅ + C $l$ ₂ → C₂H₅C $l$ + •C $l$

C. •C₂H₅ + •C $l$ → C₂H₅C $l$

D. C₂H₆ + •C $l$ → C₂H₅C $l$ + •H
22M.2.hl.TZ1.5d(i): Identify the type of reaction.
20N.1.hl.TZ0.34:
Which molecule can be oxidized to a carboxylic acid by acidified potassium dichromate(VI)?

A. Propan-1-ol

B. Propan-2-ol

C. 2-methylpropan-2-ol

D. Propanone
22M.1.sl.TZ2.22:
Which combination best describes what is happening to chloromethane, CH₃Cl, in the equation below?

CH₃Cl (g) + H₂(g) $⇌$ CH₄(g) + HCl (g)

A. Oxidation and addition

B. Oxidation and substitution

C. Reduction and addition

D. Reduction and substitution
21N.2.sl.TZ0.4a(ii): Outline the role of the hydroxide ion in this reaction.
21N.2.hl.TZ0.10b(ii): State the type of reaction which occurs between but-1-ene and hydrogen iodide at room...
21N.2.sl.TZ0.7b: Formulate equations for the two propagation steps and one termination step in the formation...

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