A Level Chemistry 9701 Paper 22, May/June 2023

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9701/22 · May/June 2023

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1

The melting points of some solids are shown in Table 1.1. Table 1.1

solidmelting point/K
magnesium923
phosphorus317
sodium chloride1074
sulfur392
a(i)

State the type of bonding present in magnesium and in sodium chloride. bonding in magnesium ...................................................................................................... bonding in sodium chloride ...............................................................................................

[1]
a(ii)

Explain the difference in the melting points of magnesium and sodium chloride.

[1]
a(iii)

Explain the difference in the melting points of phosphorus and sulfur in terms of structure and bonding.

[2]
b(i)

Define electronegativity.

[1]
b(ii)

Explain why electronegativity increases across a period.

[2]
b(iii)

Name the strongest intermolecular force that exists between NH3(l) molecules.

[1]
b(iv)

Draw a diagram to show the formation of the strongest intermolecular force between two molecules of NH3(l). Include any relevant lone pairs of electrons and dipoles.

[2]
b(v)

The melting points of ice and ammonia are shown in Table 1.2. Table 1.2

solidmelting point/K
ice273
ammonia195

Suggest two reasons for the difference in the melting points of ice and ammonia.

[2]
2

Chlorine is a reactive element. It forms many compounds.

a(i)

Complete Table 2.1 to show the maximum oxidation number of the elements Na to P in their chlorides. Table 2.1

elementNaMgAlSiP
maximum oxidation number
[1]
a(ii)

State what determines the maximum oxidation number of elements in Period 3.

[1]
b(i)

An excess of cold water is added to the chloride of silicon. Write an equation for the reaction between an excess of cold water and the chloride of silicon.

[1]
b(ii)

Suggest the pH of the solution produced in (b)(i).

[1]
c(i)

An excess of cold water is added to the chloride of phosphorus. Write an equation for the reaction between an excess of cold water and the chloride of phosphorus.

[1]
c(ii)

Suggest the pH of the solution produced in (c)(i).

[1]
d(i)

Write an equation for the reaction of chlorine with water.

[1]
d(ii)

Write an equation for the reaction of chlorine with hot NaOH(aq).

[1]
e(i)

Bleach is used as a cleaning product to kill bacteria. It is made by adding compounds like sodium chlorate(I), NaClO, to water. Identify the formula of the ion present in bleach that kills bacteria.

[1]
e(ii)

Sodium chlorate(I), NaClO, reacts with hydrogen peroxide to produce sodium chloride, water and oxygen gas. Construct an equation for this reaction.

[1]
e(iii)

A sample of bleach W contains an unknown concentration of sodium chlorate(I). 10.0 cm3 of W is diluted with distilled water to make a total volume of 100 cm3 of bleach solution. 25.0 cm3 of this diluted bleach solution is added to an excess of hydrogen peroxide and the volume of gas produced measured under room conditions. The experiment is repeated and on average 25.0 cm3 of diluted bleach solution produces 42.0 cm3 of gas. Calculate the concentration, in g dm−3, of sodium chlorate(I) in W.

[3]
3

Fig. 3.1 describes a sequence of reactions that can be used to produce a food additive, compound Y, from CH3CH2Cl. CH3CH2Cl→step 1CH3CH2CNX→dilute acidstep 2CH3CH2COOH→Ca(s)step 3Y Fig. 3.1

Figure 1 of 1 for question 3
a(i)

State the reagent and conditions for step 1 in Fig. 3.1.

[1]
a(ii)

Give the systematic name of X.

[1]
a(iii)

Identify the type of reaction that occurs when dilute acid is added to X in step 2.

[1]
a(iv)

In step 3, Y and a gas are produced. Construct an equation for step 3.

[2]
b

CH3CH2COOH can also be formed from propan-1-ol and potassium dichromate(VI). State the conditions required.

[1]
c

Complete Table 3.1 to show the number of sigma bonds (σ) and pi bonds (π) present in a molecule of X. Table 3.1

type of bondnumber of bonds in X
sigma (σ)
pi (π)
[2]
4

In industry, ethanol is made by reacting ethene with steam in the presence of H3PO4. reaction 1C2H4(g)+H2O(g)⇌C2H5OH(g)

Figure 1 of 2 for question 4
Figure 2 of 2 for question 4
a

Use the bond energy values in Table 4.1 to calculate the enthalpy change, ΔHr, for reaction 1. Table 4.1

bondbond energy / kJ mol−1
C–C350
C=C610
C≡C840
C–H410
C–O360
C=O740
O–H460

ΔHr=..............................kJ mol−1

[2]
b

Reaction 1 reaches equilibrium at constant temperature and pressure. Deduce what effect increasing the pressure will have on the amount of ethanol in the new equilibrium mixture. Use Le Chatelier’s principle to explain your answer. effect of increasing pressure ..................................................................................................... explanation ............................................................................................................................... ...................................................................................................................................................

[2]
c(i)

The mechanism for reaction 1 can be described in three steps. Steps 1 and 2 for reaction 1 are shown in Fig. 4.1. Describe the behaviour of H3PO4 in step 1 in Fig. 4.1. Explain your answer.

[1]
c(ii)

Identify the species that behaves as an electrophile in step 2 in Fig. 4.1. Explain your answer.

[1]
c(iii)

Complete Fig. 4.2 to show the mechanism for step 3 of reaction 1. Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate.

[2]
c(iv)

Describe how a catalyst affects a reaction. Explain your answer.

[2]
c(v)

Use Fig. 4.1 and Fig. 4.2 to justify why H3PO4 is described as a catalyst in reaction 1.

[1]
c(vi)

Propene also reacts with steam. A mixture of organic products is produced. Explain why propan-2-ol is produced in the higher yield.

[2]
d

Describe the covalent bonds present between the carbon atoms in an ethene molecule by completing Table 4.2. Table 4.2

sigma (σ)pi (π)
type of orbitals involved in bond
how the orbitals overlap
[2]
5
Figure 1 of 2 for question 5
Figure 2 of 2 for question 5
a

Describe structural isomerism.

[1]
b(i)

A and B are structural isomers with molecular formula C5H10O. They are both straight-chained molecules with only one functional group. Table 5.1 describes observations when separate samples of A and B are added to different reagents. Table 5.1

reagentAB
2,4-dinitrophenylhydrazine (2,4-DNPH reagent)orange precipitate appearsorange precipitate appears
Tollens’ reagentsilver mirror appearsno reaction
alkaline I2(aq)no reactionno reaction

Name the functional group present in both A and B.

[1]
b(ii)

Draw the structures of A and B in the boxes.

[2]
c(i)

C is a structural isomer of A and B. C is straight chained and has two functional groups. C shows only one type of stereoisomerism. Table 5.2 describes observations when separate samples of C are added to different reagents. Table 5.2

reagentC
2,4-dinitrophenylhydrazine (2,4-DNPH reagent)no reaction
Br2(aq)orange to colourless
alkaline I2(aq)yellow precipitate appears

Draw the structure of C in the box.

[2]
c(ii)

Name the type of stereoisomerism shown by molecules of C.

[1]
d(i)

D reacts in the presence of a sulfuric acid catalyst to form E and water. The structure of E is shown in Fig. 5.1. Name the functional group present in E.

[1]
d(ii)

Identify the type of reaction that occurs when D reacts to form E.

[1]
d(iii)

Draw the structure of D in the box.

[1]
d(iv)

The infrared spectrum of E is shown in Fig. 5.2. Table 5.3

bondfunctional groups containing the bondcharacteristic infrared absorption range (in wavenumbers)/ cm−1
C–Ohydroxy, ester1040–1300
C=Caromatic compound, alkene1500–1680
C=Oamide<br>carbonyl, carboxyl<br>ester1640–1690<br>1670–1740<br>1710–1750
C≡Nnitrile2200–2250
C–Halkane2850–2950
N–Hamine, amide3300–3500
O–Hcarboxyl<br>hydroxy2500–3000<br>3200–3600

Use Fig. 5.2 and Table 5.3 to predict two differences in the absorptions above 1500 cm−1 of the infrared spectrum of D compared to E. Explain your answer.

[2]

Mark scheme

9701/22 · May/June 2023

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1a(i) · 1 mark

  • 1 mark

    bonding in magnesium – metallic AND bonding in sodium chloride – ionic

1a(ii) · 1 mark

  • 1 mark

    bonds in NaCl are stronger than bonds in Mg

1a(iii) · 2 marks

  • M1

    S8 / molecules of sulfur have more electrons (than P4 / molecules of phosphorus)

  • M2

    S has stronger instantaneous dipole–induced dipole forces (than phosphorus / P)

1b(i) · 1 mark

  • 1 mark

    power of an atom to attract electrons to itself

1b(ii) · 2 marks

  • 1 mark

    Two of: increase in nuclear charge; similar shielding; (so) increase in nuclear attraction for bonding / outer / valence electrons OR bonding / outer / valence electron(s) are more strongly attracted to nucleus

  • 1 mark

    All three correct

1b(iii) · 1 mark

  • 1 mark

    hydrogen bond

1b(iv) · 2 marks

  • M1

    link shown as a dashed line between the lone pair of electrons from N of one NH3 to one H on other NH3

  • M2

    minimum 3 correct partial charges (on adjacent atoms) over two NH3 molecules EITHER δ–N—δ+H - - - δ–N OR δ+H - - -δ–N—δ+H

1b(v) · 2 marks

  • M1

    O is more electronegative than N

  • M2

    two H-bonds per water molecule : 1 per ammonia molecule.

2a(i) · 1 mark

  • 1 mark

    Na: (+)1, Mg: (+)2, Al: (+)3, Si: (+)4, P: (+)5 (All correct for one mark)

2a(ii) · 1 mark

  • 1 mark

    number of outer/valence electrons

2b(i) · 1 mark

  • 1 mark

    SiCl4 + 2H2O → SiO2 + 4HCl

2b(ii) · 1 mark

  • 1 mark

    1–4

2c(i) · 1 mark

  • 1 mark

    PCl5 + 4H2O → 5HCl + H3PO4

2c(ii) · 1 mark

  • 1 mark

    1–4

2d(i) · 1 mark

  • 1 mark

    Cl2 + H2O ⇌ HOCl + HCl

2d(ii) · 1 mark

  • 1 mark

    3Cl2 + 6NaOH → 5NaCl + NaClO3 + 3H2O

2e(i) · 1 mark

  • 1 mark

    ClO–

2e(ii) · 1 mark

  • 1 mark

    NaClO + H2O2 → O2 + NaCl + H2O

2e(iii) · 3 marks

  • M1

    (show how to calculate) mol O2 gas 42 cm3 gas = 42 / 24000 mol oxygen gas (= 1.75 × 10–3 mol)

  • M2

    (process to find) amount NaClO in 10 cm3 sample = 100 cm3 (diluted) bleach M1 x 4 (= 4 × 1.75 × 10–3 mol in 10 cm–3 = 0.007)

  • M3

    correct calculation using M2 to find concentration = (M2 /10) × 1000 × 74.5 = 52.2 (g / dm3)

3a(i) · 1 mark

  • 1 mark

    KCN in ethanol + heat

3a(ii) · 1 mark

  • 1 mark

    propanenitrile

3a(iii) · 1 mark

  • 1 mark

    (acid) hydrolysis

3a(iv) · 2 marks

  • M1

    H2 as product

  • M2

    balanced equation based on correct formula of Y: 2 CH3CH2COOH + Ca → (CH3CH2COO)2Ca + H2

3b · 1 mark

  • 1 mark

    acid (conditions) / H+(aq) AND heat under reflux

3c · 2 marks

  • 1 mark

    sigma σ = 8

  • 1 mark

    pi π = 2

4a · 2 marks

  • 1 mark

    Two correct steps in Method 1 or Method 2

  • 1 mark

    Three correct steps in Method 1 or Method 2

4b · 2 marks

  • M1

    amount ethanol increases

  • M2

    equilibrium moves to right AND to produce fewer moles gas OR smaller amount of gas (to reduce the pressure)

4c(i) · 1 mark

  • 1 mark

    acid AND it donates a proton / H+

4c(ii) · 1 mark

  • 1 mark

    (CH3CH2)+ OR CH3C+H2 AND accepts a pair of electrons

4c(iii) · 2 marks

  • M1

    arrow from bond of one of the O-H to O of the cation

  • M2

    arrow from lone pair on O of the anion to between H of H-O

4c(iv) · 2 marks

  • M1

    a catalyst increases rate of reaction

  • M2

    by producing an alternative reaction pathway with lower activation energy

4c(v) · 1 mark

  • 1 mark

    it is regenerated OR it is reformed

4c(vi) · 2 marks

  • M1

    (propan-2-ol is produced via a) more stable carbocation OR more stable intermediate OR (CH3)2C+H is more stable

  • M2

    (positive) inductive effect of more alkyl/methyl groups OR more electron donating alkyl / methyl groups OR greater electron donating effect of two alkyl / two methyl groups

4d · 2 marks

  • 1 mark

    Two correct entries in table

  • 1 mark

    Four correct entries in table

5a · 1 mark

  • 1 mark

    molecules / isomers with the same molecular formula / same number of atoms of each element AND different structural formulae / different structures

5b(i) · 1 mark

  • 1 mark

    carbonyl (group)

5b(ii) · 2 marks

  • 1 mark

    Structure A correctly drawn

  • 1 mark

    Structure B correctly drawn

5c(i) · 2 marks

  • M1

    CH3CH(OH) present

  • M2

    five carbons in a straight chain AND molecular formula C5H10O AND 1 C=C structure which shows only one type of stereoisomerism

5c(ii) · 1 mark

  • 1 mark

    optical

5d(i) · 1 mark

  • 1 mark

    ester

5d(ii) · 1 mark

  • 1 mark

    condensation

5d(iii) · 1 mark

  • 1 mark

    Correct skeletal structure of monomer D (4-hydroxypentanoic acid)

5d(iv) · 2 marks

  • 1 mark

    First correct difference from table

  • 1 mark

    Second correct difference from table

Questions

  1. 1
    Question 112 marks
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  2. 2
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  3. 3
    Question 38 marks
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    Question 415 marks
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  5. 5
    Question 512 marks
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