WJEC A-Level Chemistry Unit 4, June 2025: Question 1
4 marks · Easy difficulty · Structured Questions
State the reagents for nitrating aromatic hydrocarbons, explain the effect of impurities on melting point, and calculate the moles of gaseous products from TNT decomposition.
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Question text
1. TNT (2,4,6-trinitrotoluene) is used as an explosive.
CH3
O2N NO2
NO2
TNT
(a) The first stage in its production is the nitration of toluene (methylbenzene).
State the reagent(s) used to nitrate aromatic hydrocarbons such as benzene and
toluene. [1]
(b) The final stage in the production of TNT is its purification. Pure TNT has a melting
temperature of 80°C.
State how this melting temperature will be affected if the TNT is slightly damp. [1]
Examiner
02 only
(c) One equation for the explosive decomposition of TNT is shown below.©WJEC CBAC Ltd.(1410U40-1)
NO2
O N CH 3 N (g) + 5 H O(g) + 7 CO(g) + 7 C(s)
23 2 2 2 2 2 2
NO2
Mr 227
Calculate the number of moles of gaseous products obtained if 1.00g of TNT
decomposes as shown in the equation. [2]
Number of moles = … mol
Mark scheme
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Marks available
Question Marking details
AO1 AO2 AO3 Total Maths Prac
1 (a) (concentrated) nitric acid and (concentrated) sulfuric acid 1 1 1
(b) award (1) for either of following
melting temperature will be lower 1 1 1
it will melt over a range of temperatures
(c) 1.00
moles of TNT = 227 = 0.00441 (1)
moles of gaseous products = 2 × 0.00441 = 0.0331 (1) 2 2 1
ecf possible
How to answer it
Aromatic Chemistry & Stoichiometry: TNT (2,4,6-trinitrotoluene)
This question evaluates your foundational knowledge of aromatic synthesis, practical analytical chemistry techniques, and quantitative stoichiometry involving gaseous products.
- Electrophilic Aromatic Substitution: Identifying the standard nitrating mixture required to introduce -NO₂ groups onto a benzene ring.
- Assessing Purity via Melting Temperature: Understanding the physical effects of impurities (e.g., residual moisture/water) on crystalline solids.
- Stoichiometric Calculations: Calculating molar amounts and interpreting balanced chemical equations with fractional coefficients, paying close attention to state symbols.
Question 1 (a)
Reagents for the Nitration of Arenes
✅ Correct Answer
(Concentrated) nitric acid and (concentrated) sulfuric acid
💡 Key Knowledge
- Electrophile generated: the nitronium ion ( NO₂⁺ ).
- Role of H₂SO₄ : Acts as a Brønsted-Lowry acid catalyst, protonating HNO₃ to generate the active electrophile:
HNO₃ + 2H₂SO₄ ⇌ NO₂⁺ + H₃O⁺ + 2HSO₄⁻
❌ Common Errors
- Omitting sulfuric acid entirely and naming only nitric acid.
- Stating "dilute" acids; dilute acids will not generate the electrophile in sufficient concentration.
- Writing "nitrous acid" ( HNO₂ ) instead of nitric acid ( HNO₃ ).
🧠 Exam Technique
Always state both the specific reagents and their concentrations (e.g., concentrated HNO₃ and concentrated H₂SO₄). Whenever an exam asks for "reagent(s)" in nitration, examiners expect both components of the nitrating mixture.
Question 1 (b)
Effect of Dampness (Impurities) on Melting Temperature
✅ Correct Answer
Award [1 mark] for either of the following:
- The melting temperature will be lower (than 80 °C).
- It will melt over a range of temperatures (rather than a sharp melting point).
💡 Key Knowledge
- A completely pure organic solid has a sharp, well-defined melting temperature.
- Soluble impurities (such as moisture/water in a damp sample) disrupt the regular crystal lattice, weakening intermolecular forces.
- This lattice disruption causes the solid to melt below the literature value and over a broad temperature range.
❌ Common Errors
- Thinking water will "cool" the sample or raise the melting point due to high boiling point of water.
- Stating merely that the melting temperature "changes" without qualifying that it decreases or broadens.
🧠 Exam Technique
Use the standard organic chemistry phrasing: "lowers the melting point and broadens the melting range." Either description scores the single mark, but stating both guarantees you hit the mark scheme terminology.
Question 1 (c)
Stoichiometric Calculation of Gaseous Products
📐 Step-by-Step Calculation
Mass of TNT = 1.00 g, Relative molecular mass (Mᵣ) = 227
Moles of TNT = mass / Mᵣ = 1.00 / 227 = 0.004405... mol (or 4.41 × 10⁻³ mol)
Reaction equation:
TNT → ³/₂ N₂(g) + ⁵/₂ H₂O(g) + ⁷/₂ CO(g) + ⁷/₂ C(s)
Count only products with state symbol (g):
Total gas moles = ³/₂ + ⁵/₂ + ⁷/₂ = 15/2 = 7.5 mol of gas per 1 mole of TNT.
Note: Solid carbon, C(s), must NOT be included!
Moles of gas = 7.5 × 0.004405... = 0.03304 mol (or 0.0331 mol to 3 s.f.)
✅ Summary of Final Answer
Number of moles = 0.0331 mol (or 3.31 × 10⁻² mol)
Acceptable range: 0.0330 to 0.0331 mol based on intermediate rounding.
❌ Common Calculation Traps
- Including solid carbon: Summing all stoichiometric coefficients gives (3 + 5 + 7 + 7)/2 = 11 moles, yielding 0.0485 mol. This loses the second mark because C is a solid, not a gas.
- Premature rounding: Rounding 0.004405 to 0.004 too early can lead to 0.03 mol, which loses marks for precision.
- Forgetting fractional coefficients: Missing the "/2" in the coefficients.
Topics
Organic Chemistry · Physical Chemistry · Practical · 4.2 Aromaticity · 4.8 Organic synthesis and analysis · 1.3 Chemical calculations · A2 Unit 4 practical work
Question and mark scheme from the WJEC A-Level Chemistry examination, Unit 4, June 2025. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.