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 question

Question

An exam question showing a reaction flowchart for compound C (1,1-dichloroethene). Reaction 1 converts compound C into an alcohol (1,1-dichloroethanol or similar via hydration), and Reaction 2 converts compound C into compound D (1,2-dibromo-1,1-dichloroethane) with bromine. Parts (a), (b)(i), (b)(ii), (c)(i), and (c)(ii) ask for reagents, naming, mechanisms, polymerisation equations, and advantages/disadvantages of polymer combustion.
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 The mark scheme for the question detailing acceptable answers for reaction 1 reagents, systematic naming of compound D, the electrophilic addition mechanism with curly arrows and dipoles, the addition polymerisation equation using displayed formulae, and advantages/disadvantages of combustion.

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

What this question tests

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.

Marks available: 1

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-.

Marks available: 1

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.

Marks available: 3

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.

Marks available: 2

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.

Marks available: 2

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.