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.

Practise this question

Question

Question 1 focuses on TNT (2,4,6-trinitrotoluene). Part (a) asks for the reagent(s) used to nitrate aromatic hydrocarbons like toluene. Part (b) states pure TNT has a melting temperature of 80 °C and asks how this is affected if the TNT is slightly damp. Part (c) provides the decomposition equation of TNT (Mr = 227) producing 3/2 N2(g) + 5/2 H2O(g) + 7/2 CO(g) + 7/2 C(s), and asks to calculate the number of moles of gaseous products obtained from the decomposition of 1.00 g of TNT.
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

Show the mark scheme Mark scheme for Question 1: (a) (concentrated) nitric acid and (concentrated) sulfuric acid [1 mark]. (b) Award 1 mark for either 'melting temperature will be lower' or 'it will melt over a range of temperatures'. (c) Moles of TNT = 1.00 / 227 = 0.00441 [1 mark]; moles of gaseous products = 15/2 × 0.00441 = 0.0331 mol [1 mark], error carried forward possible.

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)

What this question tests

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

1 Mark Available

✅ Correct Answer

(Concentrated) nitric acid and (concentrated) sulfuric acid

Mark allocation: [1 mark] for stating both nitric acid and sulfuric acid. Specifying "concentrated" is good practice though placed in brackets in the mark scheme.

💡 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

1 Mark Available

✅ 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

2 Marks Available

📐 Step-by-Step Calculation

Step 1: Calculate moles of reactant (TNT)
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)
Award [1 mark] for calculating moles of TNT = 0.00441 mol.
Step 2: Determine total moles of GASEOUS products per mole of TNT
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!
Step 3: Calculate total moles of gaseous products
Moles of gas = 7.5 × 0.004405... = 0.03304 mol (or 0.0331 mol to 3 s.f.)
Award [1 mark] for total gas moles = 0.0331 mol (error carried forward, ecf, allowed if step 1 was incorrect).

✅ 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.