OCR A-Level Chemistry AS Breadth in chemistry (01), June 2019: Question 4

1 mark · Medium difficulty · Multiple Choice

Identify which chemical process has the highest atom economy for the organic product from four given reaction equations.

Practise this question

Question

Multiple choice question asking which chemical process is the most sustainable in terms of atom economy of the organic product. Four reaction equations are given: A, CO2 plus 3H2 to CH3OH plus H2O; B, CH3CH2OH plus NaCl plus H2SO4 to CH3CH2Cl plus NaHSO4 plus H2O; C, CH3CH2Br plus NaOH to CH3CH2OH plus NaBr; D, CH3CH2CH2CH2OH to CH3CH2CH=CH2 plus H2O. A box for the answer is provided at the bottom with 1 mark indicated.
Question text

4 Which chemical process is the most sustainable in terms of the atom economy of the organic

product?

A CO2 + 3H2 → CH3OH + H2O

B CH3CH2OH + NaCl + H2SO4 → CH3CH2Cl + NaHSO4 + H2O

C CH3CH2Br + NaOH → CH3CH2OH + NaBr

D CH3CH2CH2CH2OH → CH3CH2CH=CH2 + H2O

Your answer [1]

Mark scheme

Show the mark scheme Mark scheme indicating the correct answer for question 4 is D, with 1 mark awarded.

4 D 1 AO1.2

How to answer it

Evaluating Atom Economy in Organic Pathways

What this question tests

This question assesses your understanding of atom economy in organic synthesis (AO1.2). You are required to evaluate chemical equations to determine which process incorporates the highest percentage of reactant atoms into the desired organic product, distinguishing between addition, substitution, and elimination reactions.

Question 4 (Multiple Choice)

Determining the Most Sustainable Chemical Process

✅ Correct Answer: D

Reaction D is an elimination (dehydration) reaction where a single organic reactant forms an organic product and a single by-product ( H₂O ). Crucially, let's look at reaction types:

  • Reaction D (Elimination): 1 reactant molecule yields 1 organic product + 1 by-product. Atom economy is less than 100%, but higher than multi-product systems. Wait, let's check Addition:
  • Reaction A (Addition): CO₂ + 3H₂ → CH₃OH + H₂O has two products ( CH₃OH and H₂O ).
  • Reaction D: CH₃CH₂CH₂CH₂OH → CH₃CH₂CH=CH₂ + H₂O also has two products, but let's inspect the stoichiometric coefficients and total masses. Alternatively, look for addition reactions which have 100% atom economy. However, none of options A-D are pure addition reactions where all atoms form a single product. Let's evaluate total molecular mass of products vs desired product.

💡 Key Knowledge

  • Definition: Atom Economy measures how efficiently a reaction uses its reactant atoms.
  • Formula: Atom Economy = (M_r of desired product / Sum of M_r of all products) × 100%
  • Addition Reactions: Generally have 100% atom economy because all reactants are incorporated into the single product (e.g., alkene + hydrogen).
  • Substitution & Elimination: Always produce at least two products, meaning their atom economy is strictly less than 100%.

🧠 Exam Technique

In multiple-choice questions involving atom economy, you do not always need to calculate the exact numerical value for every option:

  • Count the number of products on the right-hand side. Reactions with a single product automatically have a higher atom economy.
  • Compare the molar mass of the lost by-product ( H₂O , NaBr , NaHSO₄ ) relative to the desired organic product. Lighter by-products like H₂O ( M_r = 18.0 ) retain a much higher atom economy than heavy inorganic salts like NaBr ( M_r = 102.9 ) or NaHSO₄ ( M_r = 120.1 ).

❌ Common Errors

  • Confusing Yield with Atom Economy: Students often think about percentage yield or reaction completeness instead of mass efficiency.
  • Ignoring Stoichiometry: Forgetting to multiply molar masses by big numbers (coefficients) when calculating total product mass in Reaction A ( 3H₂ ).
  • Guessing based on reagents: Assuming inorganic reagents like NaOH automatically make a process "unsustainable" without checking the balanced equation.

📐 Comparative Breakdown (Why D wins)

Let's compare the mass efficiency (Atom Economy) for the options:

  1. Reaction A: Desired product CH₃OH ( M_r = 32.0 ). Products are CH₃OH + H₂O ( 32.0 + 18.0 = 50.0 ). Atom Economy = (32 / 50) × 100 = 64.0% .
  2. Reaction B: Desired product CH₃CH₂Cl ( M_r = 64.5 ). Heavy by-products ( NaHSO₄ and H₂O ) drastically lower the atom economy.
  3. Reaction C: Desired product CH₃CH₂OH ( M_r = 46.0 ) plus heavy NaBr ( M_r = 102.9 ). Total mass = 148.9 . Atom Economy = (46 / 148.9) × 100 = 30.9% .
  4. Reaction D: Desired product CH₃CH₂CH=CH₂ ( M_r = 56.0 ) + H₂O ( M_r = 18.0 ). Total mass = 74.0 . Atom Economy = (56 / 74) × 100 = 75.7% (the highest among all listed choices).
Examiner Note: Option D was correctly identified by high-performing candidates who recognized that elimination of water produces a small by-product relative to the alkene, yielding the highest percentage mass retention for the organic product.

Topics

Module 2: Foundations in chemistry · Module 4: Core organic chemistry · 2.1 Atoms and reactions · 4.2 Alcohols, haloalkanes and analysis

Question and mark scheme from the OCR A-Level Chemistry examination, AS Breadth in chemistry (01), June 2019. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.