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Date	November 2020	Marks available	1	Reference code	20N.2.hl.TZ0.1
Level	HL	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).

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

[2]

e(i).

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

[1]

e(ii).

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

[2]

e(iii).

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).

curly arrow going from lone pair/negative charge on $O$ in ⁻OH to $C$ ✔

curly arrow showing $Cl$ leaving ✔

representation of transition state showing negative charge, square brackets and partial bonds ✔

Accept $O H^{-}$ with or without the lone pair.

Do not accept curly arrows originating on $H$ in $O H^{-}$ .

Accept curly arrows in the transition state.

Do not penalize if $H O$ and $C l$ are not at 180°.

Do not award M3 if $O H - C$ bond is represented.

d(iii).

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

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

d(iv).

2 «signals» ✔

0.9−1.0 AND triplet ✔

3.3−3.7 AND quartet ✔

Accept any values in the ranges.

Award [1] for two correct chemical shifts or two correct splitting patterns.

d(v).

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

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

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).

$O_{3} + Cl \cdot \to O 2 + ClO \cdot$ ✔

$ClO \cdot + O \cdot \to O_{2} + Cl \cdot$
OR
$ClO \cdot + O_{3} \to Cl \cdot + 2 O_{2}$ ✔

Penalize missing/incorrect radical dot (∙) once only.

e(iii).

Examiners report

Well answered question with 90% of candidates correctly identifying the complete electron configuration for chlorine.

a(i).

Most candidates could correctly explain the relative sizes of chlorine atom and chloride ion.

a(ii).

Fairly well answered though some candidates missed M2 for not recognizing the same number of shells affected.

a(iii).

More than 80% could identify that the two peaks in the MS of chlorine are due to different isotopes.

a(iv).

Not well answered. Some candidates were able to identify m/z 74 being due to the m/z of two Cl-37 atoms, however fewer candidates were able to explain the relative abundance of the isotope.

a(v).

Stoichiometric calculations were generally well done and over 90% could calculate mol from a given mass.

b(i).

90% of candidates earned full marks on this 2-mark question involving finding a limiting reactant.

b(ii).

Surprisingly, quite a number of candidates struggled with the quantity of excess reactant despite correctly identifying limiting reactant previously.

b(iii).

Most candidates could find the volume of gas produced in a reaction under standard conditions.

b(iv).

More than 90% could identify the oxidation number of manganese in both MnO₂ and MnCl₂.

b(v).

Most candidates stated that MnO₂ is an oxidizing agent in the reaction but many did not get the mark because there was no reference to oxidation states.

b(vi).

Another well answered 1-mark question where candidates correctly identified a weak acid as an acid which partially dissociates in water.

c(i).

Roughly ⅓ of the candidates failed to identify the conjugate base, perhaps distracted by the fact it was not contained in the equation given.

c(ii).

Vast majority of candidates could calculate the concentration of H⁺ (aq) in a HClO (aq) solution with a pH =3.61.

c(iii).

Many identified the reaction of chlorine with ethane as free-radical substitution, or just substitution, with some erroneously stating nucleophilic or electrophilic substitution.

d(i).

The underlying reasons for the relative reactivity of ethane and chloroethane were not very well known with a few giving erroneous reasons and some stating ethane more reactive.

d(ii).

Few earned full marks for the curly arrow mechanism of the reaction between sodium hydroxide and chloroethane. Mistakes being careless curly arrow drawing, inappropriate –OH notation, curly arrows from the hydrogen or from the carbon to the C–Cl bond, or a method that missed the transition state.

d(iii).

Approximately 60% could draw ethoxyethane however many demonstrated little knowledge of structure of an ether molecule.

d(iv).

A poorly answered question with some getting full marks on this 1HNMR spectrum of ethoxyethane question. Very few could identify all 3 of number of signals, chemical shift, and splitting pattern.

d(v).

Another good example of candidates being well rehearsed in calculations with 90% earning 2/2 on this question of calculation percentage by mass composition.

e(i).

Somewhat disappointing answers on this question about how international cooperation has contributed to the lowering of CFC emissions. Many gave vague answers and some referred to carbon emissions and global warming.

e(ii).

Few could construct the propagation equations showing how CFCs affect ozone, and many lost marks by failing to identify ClO· as a radical.

e(iii).

Syllabus sections

Core » Topic 10: Organic chemistry » 10.1 Fundamentals of organic chemistry

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Explain why the compound C₃H₈O, produced in (a)(iv), has a higher boiling point than compound C₃H₆O, produced in d(i).
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State the typical reactions that benzene and cyclohexene undergo with bromine.
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Discuss the physical evidence for the structure of benzene.
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Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.
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19M.2.sl.TZ2.1c(ii):
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.
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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.
20N.2.sl.TZ0.1d(v):
Ethoxyethane (diethyl ether) can be used as a solvent for this conversion. Draw the structural formula of ethoxyethane
19N.3.hl.TZ0.24c:
Explain how redox chemistry is used to measure the ethanol concentration in a breathalyser.
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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.TZ0.2d:
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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