OCR A-Level Chemistry AS Depth in chemistry (02), June 2018: Question 6
9 marks · Medium difficulty · Structured Questions
Analyze reactions of compound C (1,1-dichloroethene) including hydration, electrophilic addition of bromine, and addition polymerisation.
Practise this questionQuestion
Question text
6 Two reactions of compound C are shown in the flowchart below.
H Cl
C C
H Cl
Compound C
Reaction 1 Reaction 2
H Cl H Cl
H C C OH H C C Cl
H Cl Br Br
Compound D
(a) State the reagents and conditions for reaction 1.
… [1]
(b) In reaction 2, compound C reacts with bromine to form compound D.
(i) Give the systematic name of compound D.
… [1]
(ii) Outline the mechanism for reaction 2.
Include curly arrows, charges and relevant dipoles.
[3]
(c) Compound C forms an addition polymer E.
(i) Write a balanced equation for this reaction.
Show displayed formulae.
[2]
(ii) State one advantage and one disadvantage of using combustion as a method for the
disposal of waste polymer E.
Advantage …
Disadvantage …
… [2]
Mark scheme
Show the mark scheme
Question Answer Marks
6 (a) steam 1
AND
Acid/H+ (catalyst)
(b) (i) 1,2-dibromo-1,1-dichloroethane 1
H032/02 Mark scheme June 2018
Question Answer Marks Guidance
6 (b) (ii) 3 ANNOTATE ANSWER WITH TICKS AND CROSSES
ETC
For curly arrows, ALLOW straight or snake-like arrows
and small gaps (see examples):
1st curly arrow must
go to a Br atom of Br–Br
AND
start from, OR be traced back to any point across
width of C=C
1st curly arrow (from ANY alkene)
Curly arrow from double bond to Br of Br–Br
DO NOT ALLOW partial charge on C=C
2nd curly arrow
2nd curly arrow must
Correct dipole on Br–Br +
AND curly arrow for breaking of Br–Br bond start from, OR be traced back to, any part of Br–
Br – bond
AND go to Br –
3rd curly arrow
Correct carbocation with + charge on C with 3 bonds
AND curly arrow from Br– to C+ of carbocation
DO NOT ALLOW δ+ on C of carbocation
X
H Cl 3rd curly arrow must
H Cl H Cl +
go to the C of carbocation
C C H C C Cl AND
H C C Cl start from, OR be traced back to any point across
width of lone pair on :Br–
H Cl Br
Br OR start from – charge on Br– ion
Brδ+
Br OR Br
δ− 19
Br
i.e. ALLOW carbonium + on either C atom
DO NOT ALLOW half headed or double headed arrows but (Lone pair NOT needed if curly arrow shown
from – charge on Br–)
allow ECF if seen more than once
H032/02 Mark scheme June 2018
6 (c) (i) 20 2 For repeat unit,
displayed formula required
‘side bonds’ required on either side of repeat unit from
C atoms
ALLOW section containing more than one repeat unit
Correct polymer with side links and brackets
Equation balanced with n DO NOT ALLOW ECF from incorrect repeat unit
n on LHS at any height to the left of the formula
TAKE CARE of ‘n’ position on both sides of equation. n on RHS must be subscript
(c) (ii) Advantage (1 mark) 2
Energy production / (energy) used to produce electricity ALLOW reduced use of fossil fuels
Disadvantage (1 mark) ALLOW less landfill / less harm to wildlife
Formation of HCl/products of combustion cause acid rain
OR
Formation of CO2/gases that cause global warming / ALLOW chlorine/Cl OR Cl2
greenhouse gases
OR ALLOW toxic/poisonous waste products
Formation of CO
Total 9
How to answer it
Reactions of Alkenes and Addition Polymers
This question assesses your core knowledge of alkene chemistry, specifically electrophilic addition mechanisms, hydration conditions, IUPAC nomenclature for halogenoalkanes, and the formation and disposal of addition polymers. You will need to demonstrate precision with curly arrows, dipoles, displayed formulae, and balanced equations.
Part (a): Reagents and Conditions for Reaction 1
Hydration of an Alkene to form an Alcohol
✅ Correct Answer
Steam ( H₂O(g) ) AND Acid / H⁺ catalyst (e.g., concentrated H₃PO₄ or H₂SO₄ ).
💡 Key Knowledge
Reaction 1 is an industrial hydration reaction used to convert alkenes into alcohols. Both reagents/conditions must be stated to secure the single mark.
❌ Common Errors
Writing "water" instead of "steam" (since industrial hydration uses gaseous water at high temperature and pressure). Omitting the catalyst description will also lose the mark.
Part (b)(i): Systematic Nomenclature
Naming Compound D
✅ Correct Answer
1,2-dibromo-1,1-dichloroethane
🧠 Exam Technique
Number the longest carbon chain starting from the end that gives the lowest locant numbers for substituents. Remember to list substituents alphabetically ( bromo before chloro ), ignoring number prefixes like di-.
Part (b)(ii): Electrophilic Addition Mechanism
Mechanism for Reaction 2 (Bromination of Compound C)
✅ Correct Answer
- 1st curly arrow: From the C=C double bond to the δ⁺ Br atom of the Br-Br bond.
- 2nd curly arrow: Representing heterolytic fission of the Br-Br bond, going from the bond to the δ⁻ Br atom, showing δ⁺ Br and δ⁻ Br dipoles correctly labeled.
- 3rd curly arrow: From the lone pair (or minus charge) on the resulting bromide ion ( :Br⁻ ) to the positively charged carbon ( C⁺ ) of the carbocation intermediate.
❌ Common Errors
Starting the first curly arrow from a carbon atom instead of the C=C bond. Failing to include intermediate partial charges ( δ⁺ / δ⁻ ) on the halogen molecule, or showing a partial charge on the carbocation carbon instead of a full + sign.
Part (c)(i): Polymerisation Equation
Balanced Equation with Displayed Formulae
✅ Correct Answer
Equation showing n molecules of the monomer with a C=C double bond reacting to form the repeat unit enclosed in square brackets with an n subscript on the right, and 'side bonds' extending through the brackets.
🧠 Exam Technique
Ensure n is placed correctly: as a full-size coefficient on the reactant monomer on the LHS, and as a subscript outside the right-hand bracket on the RHS.
❌ Common Errors
Leaving the double bond in the polymer chain, forgetting the extending 'side bonds' passing through the brackets, or drawing skeletal/condensed structures instead of fully displayed formulae.
Part (c)(ii): Disposal of Polymers
Advantages and Disadvantages of Combustion
✅ Correct Answer
Advantage: Energy / electricity generation, or reduced use of fossil fuels.
Disadvantage: Formation of toxic gases like HCl / Cl₂ causing acid rain, or formation of greenhouse gases like CO₂ causing global warming.
💡 Key Knowledge
Because Compound C contains chlorine atoms, combustion produces acidic hydrogen chloride gas ( HCl ), which is a key environmental hazard distinct from standard hydrocarbon combustion.
Topics
Module 4: Core organic chemistry · 4.1 Basic concepts and hydrocarbons · 4.2 Alcohols, haloalkanes and analysis
Question and mark scheme from the OCR A-Level Chemistry examination, AS Depth in chemistry (02), June 2018. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.