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INTERNATIONAL A-LEVEL
CHEMISTRY (9620)
Unit 4: Organic 2 and Physical 2
Friday 7 June 2024 07:00 GMT Time allowed: 1 hour 30 minutes
Materials
For this paper you must have: For Examiner’s Use
• the Periodic Table/Data Sheet, provided as an insert Question Mark
• a ruler with millimetre measurements
1
• a scientific calculator, which you are expected to use where appropriate.
2
Instructions 3
• Use black ink or black ball-point pen.
4
• Fill in the boxes at the top of this page.
• Answer all questions. 5
• You must answer the questions in the spaces provided. Do not write 6
outside the box around each page or on blank pages. 7
• If you need extra space for your answer(s), use the lined pages at the end of
8
this book. Write the question number against your answer(s).
• All working must be shown. 9
• Do all rough work in this book. Cross through any work you do not want 10
to be marked.
TOTAL
Information
• The marks for questions are shown in brackets.
• The maximum mark for this paper is 80.
*JuN24CH0401*
IB/G/Jun24/G4002/E11 CH04
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Answer all questions in the spaces provided. box
0 1 This question is about the equilibrium
–1
CO(g) + 2 H2(g) ⇌ CH3OH(g) ΔH = –203 kJ mol
In one experiment, a mixture of 0.850 mol of carbon monoxide and
1.44 mol of hydrogen is allowed to reach equilibrium at a fixed temperature.
At equilibrium, 0.280 mol of methanol is formed.
The total pressure of the equilibrium mixture is 190 kPa
0 1 . 1 Calculate the amount, in mol, of carbon monoxide and of hydrogen in the
equilibrium mixture.
[2 marks]
Amount of carbon monoxide mol
Amount of hydrogen mol
0 1 . 2 In a different experiment, the equilibrium amount of methanol is 0.260 mol,
of carbon monoxide is 0.350 mol and of hydrogen is 0.550 mol.
The total pressure of the equilibrium mixture is 190 kPa
Calculate the partial pressure of hydrogen, in kPa, in the equilibrium mixture.
[2 marks]
Partial pressure of hydrogen kPa
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0 1 . 3 Write an expression for the equilibrium constant (Kp) for this reaction. box
[1 mark]
Kp
0 1 . 4 The experiment is done at two different temperatures, T1 and T2.
The equilibrium constant (Kp) is determined at each temperature.
The results are shown in Table 1.
Table 1
–2
Temperature Kp / kPa
–5
T1 4.50 × 10
–6
T2 8.95 × 10
Explain how you can deduce that T2 is the higher temperature.
[2 marks]
Turn over for the next question
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0 2 This question is about rates of reaction. box
0 2 . 1 Explain what is meant by the order of a reaction with respect to an
individual substance.
[1 mark]
Compounds A and B react together as shown
A+B → C
The initial rates of the reaction are found for different initial concentrations of A and B.
Table 2 shows data from this reaction.
Table 2
Initial rate /
Experiment [A] / mol dm–3 [B] / mol dm–3
mol dm–3 s–1
1 0.100 0.150 3.68 × 10–5
2 0.300 0.150 3.31 × 10–4
3 0.200 0.300 2.94 × 10–4
0 2 . 2 Deduce the order of the reaction with respect to A and the order of the reaction with
respect to B.
[2 marks]
Order with respect to A
Order with respect to B
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0 2 . 3 The rate of reaction between compound D and compound E is investigated.
The reaction is first order with respect to D and first order with respect to E.
–5 –3 –1
In one experiment, the initial rate is 7.10 × 10 mol dm s when the
–3
initial concentration of D is 0.160 mol dm and the initial concentration
–3
of E is 0.220 mol dm
Calculate the value of the rate constant, k, at this temperature.
Give the units of k
[3 marks]
Units 6
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*05*
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0 3 This question is about the effect of temperature on the rate of a reaction. box
The Arrhenius equation can be written
−Ea
ln k = + ln A
RT
A compound decomposes when heated.
Table 3 shows the value of the rate constant at different temperatures for this
decomposition.
Table 3
Rate constant k Temperature 1 –1
–1 ln k /K
/s /K T
5 –3
8.68 × 10 13.67 278 3.60 × 10
6 –3
2.20 × 10 14.60 298 3.36 × 10
15.42 318
7 –3
1.01 × 10 16.13 338 2.96 × 10
7 –3
1.92 × 10 16.77 358 2.79 × 10
0 3 . 1 Complete Table 3.
Give values to 3 significant figures.
[2 marks]
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1
0 3 . 2 Plot a graph of ln k against box
T
[2 marks]
–1
0 3 . 3 Use your graph to calculate a value for the activation energy (Ea), in kJ mol , for
this reaction.
–1 –1
The gas constant, R = 8.31 J K mol
[3 marks]
Ea kJ mol
–1
7
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0 4 This question is about carbonyl compounds. box
Compound F (C3H6O) reacts with Fehling’s solution to form a red precipitate.
0 4 . 1 Draw the skeletal formula of F.
[1 mark]
0 4 . 2 Identify the organic product formed when F reacts with Fehling’s solution.
[1 mark]
Butanone reacts with NaBH4 in aqueous solution to form butan-2-ol.
0 4 . 3 Name and outline the mechanism for this reaction.
[4 marks]
Name of mechanism
Mechanism
*08*
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0 4 . 4 The product from the reaction between butanone and NaBH4 is dried. box
State how infrared spectroscopy can show that the reaction between butanone and
NaBH4 is complete.
Use Table A on the Chemistry Data Sheet.
[1 mark]
Turn over for the next question
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*09*
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0 5 This question is about polymers. box
A section of a condensation polymer, G, is shown.
Polymer G
0 5 . 1 Name this type of condensation polymer.
[1 mark]
0 5 . 2 Draw displayed formulas for each of the two monomers used to make polymer G.
[2 marks]
Monomer 1
Monomer 2
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0 5 . 3 Explain why polymer G is biodegradable. box
[2 marks]
A different type of polymer can be formed from the monomer H.
0 5 . 4 Draw the repeating unit of this polymer.
[1 mark]
13
0 5 . 5 Draw an isomer of H that only has two peaks in its C NMR spectrum.
[1 mark]
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0 6 This question is about the reactions of methylbenzene. box
0 6 . 1 Compound J can be made from methylbenzene, propanoyl chloride and
another reagent.
J
This reagent reacts with propanoyl chloride to make the reactive intermediate that
reacts with methylbenzene.
Identify this reagent.
Write an equation for the formation of this reactive intermediate.
[2 marks]
Reagent
Equation
*12*
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Compound K is formed when methylbenzene reacts with the reactive box
+
intermediate NO2
K
+
0 6 . 2 Write an equation to show how NO2 is formed from concentrated nitric acid and
concentrated sulfuric acid.
[1 mark]
+
0 6 . 3 Name and outline the mechanism for the reaction of NO2 with methylbenzene to
form K.
[4 marks]
Name of mechanism
Mechanism
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0 7 This question is about the synthesis of aspirin. box
Aspirin can be prepared from salicylic acid by Reaction 1 or Reaction 2.
0 7 . 1 Explain why Reaction 2 has the higher atom economy.
[1 mark]
0 7 . 2 Companies that manufacture aspirin need to consider factors other than atom
economy before deciding which reaction to use.
Give one other factor that needs to be considered.
[1 mark]
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Aspirin made by either reaction is impure. box
0 7 . 3 Give two ways that the melting point of impure aspirin would differ from the melting
point of pure aspirin.
[2 marks]
Difference 1
Difference 2
Question 7 continues on the next page
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Impure aspirin can be purified using the following steps. box
Step 1 A small volume of ethanol is heated using a water bath.
Step 2 An impure sample of aspirin is dissolved in a minimum volume of the
hot ethanol.
Step 3 The mixture is filtered while hot.
Step 4 The filtrate is cooled in ice.
Step 5 The crystals formed are collected by filtration and washed with a small
amount of ice-cold ethanol.
0 7 . 4 State why a water bath is used to heat the ethanol in Step 1.
[1 mark]
0 7 . 5 State why the mixture is filtered in Step 3.
[1 mark]
0 7 . 6 State why the crystals are washed in Step 5.
[1 mark]
0 7 . 7 State why the ethanol used in Step 5 is ice-cold.
[1 mark]
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Turn over for the next question box
DO NOT WRITE ON THIS PAGE
ANSWER IN THE SPACES PROVIDED
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0 8 This question is about esters. box
0 8 . 1 Give a use of esters.
[1 mark]
13 1
The structure of ester L can be confirmed using C NMR and H NMR spectroscopy.
13
0 8 . 2 State the number of peaks in the C NMR spectrum of L.
[1 mark]
1
Table 4 shows data for the H NMR spectrum of L.
Table 4
Chemical shift / ppm 1.2 2.6 3.7
Integration value
0 8 . 3 Complete Table 4 to show the integration values for each peak.
Use Table B on the Chemistry Data Sheet.
[1 mark]
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0 8 . 4 In Figure 1, two of the H atoms are marked a and b. These H atoms are in different box
1
environments and produce different peaks in the H NMR spectrum.
Figure 1
Give the spin-spin splitting pattern that is observed for the peaks that are
produced by Ha and Hb
[2 marks]
Ha spin-spin splitting pattern
Hb spin-spin splitting pattern
0 8 . 5 Acid hydrolysis of ester L produces methanol and compound M.
Identify M.
Give a reagent that can be used to confirm the functional group in M.
State an observation that is made when M reacts with this reagent.
[3 marks]
Identity of M
Reagent
Observation
8
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*19*
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0 9 A synthetic route to form the amine N is shown. box
0 9 . 1 Identify the reagent for Step 1.
Name the mechanism for Step 1.
[2 marks]
Reagent
Name of mechanism
0 9 . 2 Identify a reagent for Step 2.
[1 mark]
Reagent
0 9 . 3 Identify a reagent for Step 3.
State a condition for Step 3.
[2 marks]
Reagent
Condition
0 9 . 4 Amine N can be formed in a one-step synthesis from a halogenoalkane.
Identify the halogenoalkane needed for this one-step synthesis.
[1 mark]
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0 9 . 5 Amine N can be used to form other organic products. box
N can act as a nucleophile and a base.
Explain why N can act as a nucleophile and as a base.
[2 marks]
0 9 . 6 Ethylamine can react with chloromethane to form a secondary amine.
Name the secondary amine.
[1 mark]
0 9 . 7 Give the structure of the final product in the reaction between ethylamine and an
excess of chloromethane.
[1 mark]
10
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1 0 This question is about amino acids and proteins. box
Two amino acids are shown.
alanine threonine
1 0 . 1 Use IUPAC rules to name threonine.
[1 mark]
Most amino acids can exist as optical isomers (enantiomers).
1 0 . 2 State what is meant by the term optical isomers.
Describe how to distinguish between the two optical isomers of alanine.
[3 marks]
Meaning of term
Description
1 0 . 3 Draw 3D representations of the two optical isomers of alanine.
[1 mark]
*22*
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1 0 . 4 Consider the structure of threonine. box
How many optical isomers of threonine are there?
Tick () one box.
[1 mark]
2 4 6 8
Chromatography can be used to identify the compounds in a mixture of amino acids.
A student sets up a thin-layer chromatography (TLC) plate as shown in Figure 2.
Figure 2
1 0 . 5 Give two errors the student made in the experiment shown in Figure 2.
[1 mark]
Error 1
Error 2
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Another student sets up the experiment correctly but uses a longer TLC plate. box
The amino acids cannot be seen as they move up the plate.
1 0 . 6 State how the position of amino acids can be seen on a TLC plate at the end of
the experiment.
[1 mark]
1 0 . 7 State the effect, if any, on the Rf values of using a longer TLC plate.
[1 mark]
Amino acids can react together to form proteins.
A section of a protein chain is shown.
A student hydrolyses this protein with hot sodium hydroxide solution.
1 0 . 8 Draw the products of this hydrolysis.
[2 marks]
Proteins can have primary, secondary and tertiary structures.
1 0 . 9 Give the names of the two types of secondary structures of proteins.
[2 marks]
2 13
END OF QUESTIONS
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ANSWER IN THE SPACES PROVIDED
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Question Additional page, if required.
number Write the question numbers in the left-hand margin.
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Question Additional page, if required.
number Write the question numbers in the left-hand margin.
*27*
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Question Additional page, if required.
number Write the question numbers in the left-hand margin.
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