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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	Draw	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 » 10.1 Fundamentals of organic chemistry

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State the name of product B, applying IUPAC rules.
18M.2.hl.TZ1.3d:
One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.
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.
20N.1.hl.TZ0.40:
Which compound with the molecular formula $C_{4} H_{8} O$ has this high resolution ${}_{1}H NMR$ ?

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A. but-3-en-2-ol, ${CH}_{2} = CHCH (OH) {CH}_{3}$

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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.
17M.3.sl.TZ1.10b.i:
Describe the difference in their structures.
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18M.3.sl.TZ2.2a:
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20N.2.hl.TZ0.2e:
Compound A and B are isomers. Draw two other structural isomers with the formula $C_{3} H_{6} O$ .
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18M.3.sl.TZ2.2b.i:
The above ball and stick model is a substituted pyridine molecule (made of carbon, hydrogen, nitrogen, bromine and chlorine atoms). All atoms are shown and represented according to their relative atomic size.

Label each ball in the diagram, excluding hydrogens, as a carbon, C, nitrogen, N, bromine, Br, or chlorine, Cl.
17M.2.hl.TZ2.2a.v:
Identify one organic functional group that can react with acidified K₂Cr₂O₇(aq).
17M.2.hl.TZ2.7a.ii:
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.
17M.2.hl.TZ1.6c.i:
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.
20N.3.sl.TZ0.9b: State a class of organic compounds found in gasoline.
19N.3.hl.TZ0.24b:
Describe a technique for the detection of steroids in blood and urine.
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22M.2.sl.TZ1.3c(i):
State the name of Compound A, applying International Union of Pure and Applied Chemistry (IUPAC) rules.
17M.3.hl.TZ2.20a.iii:
Suggest two absorbances, other than the absorbances due to the ring structure and C–H bonds, that would be present in the infrared (IR) spectrum of aspirin.
17M.2.sl.TZ1.5c.i:
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.
19N.3.hl.TZ0.24c:
Explain how redox chemistry is used to measure the ethanol concentration in a breathalyser.
21M.1.sl.TZ1.25: What is the name of this compound, applying IUPAC rules? A. 4-methylhex-2-ene B. ...
18M.3.sl.TZ2.2b.iii:
Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.
20N.3.hl.TZ0.11b: State a class of organic compounds found in gasoline.
20N.3.hl.TZ0.11e(iii):
Suggest a wavenumber absorbed by methane gas.
21M.2.hl.TZ1.5a(ii): State the molecular formula of the next member of the homologous series to which ethene belongs.
21M.2.hl.TZ1.5a(i): State the class of compound to which ethene belongs.
21M.1.sl.TZ2.24: Which is in the same homologous series as CH3OCH3? A. CH3COCH3 B. CH3COOCH3 C. ...
21M.1.sl.TZ2.28:
Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

I. mass
II. infrared
III. ¹H NMR

A. I and II only

B. I and III only

C. II and III only

D. I, II and III
18M.2.sl.TZ2.7a:
The Kekulé structure of benzene suggests it should readily undergo addition reactions.

Discuss two pieces of evidence, one physical and one chemical, which suggest this is not the structure of benzene.
21M.2.sl.TZ1.5a(i): State the class of compound to which ethene belongs.
21M.2.sl.TZ1.5a(ii): State the molecular formula of the next member of the homologous series to which ethene belongs.
20N.2.sl.TZ0.4c: Discuss, referring to intermolecular forces present, the relative volatility of propanone and...
21M.2.sl.TZ2.4c:
Write the equation and name the organic product when ethanol reacts with methanoic acid.
20N.2.sl.TZ0.2c:
Compound A and B are isomers. Draw two other structural isomers with the formula $C_{3} H_{6} O$ .
17M.2.sl.TZ2.6a:
Using relevant equations, show the initiation and the propagation steps for this reaction.
20N.2.hl.TZ0.1d(iv):
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion.
Draw the structural formula of ethoxyethane
20N.2.hl.TZ0.2d:
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.
19M.2.hl.TZ1.1b:
Draw the structure of one other isomer of xylene which retains the benzene ring.
20N.2.hl.TZ0.4c: Discuss, referring to intermolecular forces present, the relative volatility of propanone and...
20N.2.sl.TZ0.2b:
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.
20N.3.sl.TZ0.9f(iii):
Suggest a wavenumber absorbed by methane gas.
20N.3.sl.TZ0.14a(i): Name two functional groups that both zanamivir and oseltamivir contain.
22M.2.hl.TZ2.8d(iv):
Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).
22M.2.hl.TZ2.8e(ii):
Deduce the splitting pattern in the ¹H NMR spectrum for 1-bromopropane.
19M.2.hl.TZ2.1c(ii):
Determine the enthalpy change for the reaction, in kJ, to produce A using section 11 of the data booklet.
22M.2.sl.TZ2.4b: State two features showing that propane and butane are members of the same homologous series.
22M.2.sl.TZ2.4d(i): Draw the full structural formula of but-2-ene.
22M.2.sl.TZ2.4d(iv):
Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).
17M.2.hl.TZ1.6c.ii:
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.
18M.2.sl.TZ1.3c:
One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.
17M.2.sl.TZ1.5c.ii:
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.
21M.1.sl.TZ1.24: Which series is in order of increasing boiling point? A. CH2CH2CH3OH CH3COCH3 ...
22M.1.sl.TZ2.26:
Which is a homologous series?

A. C₂H₄, C₃H₅, C₄H₆

B. C₂H₂, C₃H₄, C₄H₆

C. C₂H₂, C₂H₄, C₂H₆

D. C₂H₂, C₄H₄, C₆H₆
21N.1.sl.TZ0.25: What is the name of this substance using IUPAC rules? A. 2-ethyl-1-methylbutan-1-ol B. ...

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