Name: ________________________

Alkenes
Class: ________________________

Date: ________________________

Time: 60 minutes

Marks: 53 marks

Comments:

Page 1 of 18
Q1.
This question is about 2-methylbut-1-ene.

(a) Name the mechanism for the reaction of 2-methylbut-1-ene with concentrated
sulfuric acid.

Outline the mechanism for this reaction to form the major product.

Name of mechanism _________________________________________________

Outline of mechanism to form major product

(5)

(b) Draw the structure of the minor product formed in the reaction in part (a)

Explain why this is the minor product.

Structure of minor product

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Draw the skeletal formula of a functional group isomer of 2-methylbut-1-ene.

Page 2 of 18
 (1)

(d) 2-methylbut-1-ene can form a polymer.

State the type of polymerisation.

Draw the repeating unit for the polymer formed.

Type of polymerisation _______________________________________________

Repeating unit

(2)
(Total 11 marks)

Q2.
Alkenes react with bromine (Br2)

(a) Name and outline the mechanism for the reaction of cyclohexene with Br2

Name of mechanism __________________________________________________

Outline of mechanism

(5)

Page 3 of 18
 (b) Explain why there is an attraction between a C=C double bond and Br2

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Draw the skeletal formula of the halogenoalkane formed when buta-1,3-diene
(CH2=CHCH=CH2) reacts with an excess of Br2

(1)
(Total 9 marks)

Q3.
Prop-2-en-1-ol is a natural chemical found in garlic. It is also used in the production of
plasticisers.

(a) Prop-2-en-1-ol can be prepared by reacting 3-chloroprop-1-ene with dilute aqueous

sodium hydroxide.

Name the mechanism for this reaction.

___________________________________________________________________
(1)

(b) Prop-2-en-1-ol can also be formed from HOCH2CH2CH2OH in the presence of an

acid catalyst.

Page 4 of 18
 HOCH2CH2CH2OH ⟶ CH2=CHCH2OH + H2O

Name and outline a mechanism for this reaction.

Name of mechanism __________________________________________________

Outline of mechanism

(4)

(c) Prop-2-en-1-ol forms an addition polymer.

Draw the repeating unit of poly(prop-2-en-1-ol).

(1)

(d) The figure below shows the infrared spectrum of a functional group isomer of
prop-2-en-1-ol.

Page 5 of 18
 This isomer reacts with acidified potassium dichromate(VI) to form a green solution.

Draw the structure of this isomer.

(1)
(Total 7 marks)

Q4.
Propene reacts with concentrated sulfuric acid to form two isomers, E and F.

The structure of E is shown.

(a) Name and outline the mechanism for the formation of E in this reaction.

Name of mechanism __________________________________________________

Mechanism

(5)

(b) Draw the structure of F.

Page 6 of 18
 (1)

(c) Explain why more of isomer E than isomer F is formed in this reaction.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)

Q5.
Which statement about poly(ethene) is correct?

A It has a lower relative molecular mass than ethene.

B It has a lower density than ethene at standard

temperature and pressure.
C It has a higher melting point than ethene.

D It decolourises bromine water.

(Total 1 mark)

Q6.
A polymer is formed from the monomer CH2 = CHCN

Which statement is not correct?

A The monomer is propanenitrile.

B The monomer is unsaturated.

C The polymer is an addition polymer.

Page 7 of 18
 D
The polymer has the repeating unit
(Total 1 mark)

Q7.
This question is about poly(propene).

(a) The three key steps in the manufacture of poly(propene) from crude oil are shown.

Naphtha is a mixture of alkanes with 6 to 12 carbon atoms per molecule.

For each step, name the process and state briefly the purpose of the process that
leads to the formation of poly(propene).

Step 1

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________

Step 2

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________

Step 3

Name _____________________________________________________________

Purpose ___________________________________________________________

___________________________________________________________________

___________________________________________________________________
(6)

(b) Poly(propene) is not biodegradable because it is unreactive.

Explain why poly(propene) is unreactive.

___________________________________________________________________

Page 8 of 18
 ___________________________________________________________________

___________________________________________________________________
(1)

(c) Scientists are developing new polymers, including some that are biodegradable.

Suggest why it is beneficial for some polymers to be biodegradable.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 8 marks)

Q8.
This question is about poly(chloroethene), commonly known as PVC.

(a) Give an equation, showing structural formulas, for the conversion of chloroethene
into poly(chloroethene).

(3)

(b) State what you would observe if bromine water was added to poly(chloroethene).
Explain this observation.

Observation _________________________________________________________

Explanation _________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(c) Plasticisers are often added during the manufacture of PVC. The structure of the
plasticiser DEHP is shown.

Page 9 of 18
 Deduce the molecular formula of DEHP and state why a plasticiser is added to PVC.

Molecular formula ____________________________________________________

Why a plasticiser is added _____________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 7 marks)

Q9.
This structure shows a section of a polymer chain formed from the random polymerisation
of two different monomers.

Which pair of monomers could produce this polymer?

A CH2=CHF and CH2=CHCF3

B CH2=CH2 and CHF=CHCF3

C CH2=CH2 and CH2=CHCF3

D CH2=CHF and CHCF3=CHF

(Total 1 mark)

Page 10 of 18
Mark schemes

Q1.
(a) Electrophilic addition

NB Allow fully displayed or other structural formulae

if H2O used as electrophile − max 4 ONLY

M2 must show an arrow from = of C=C towards the H atom of the H−O
bond or HO that is part of H−O−S−… on a compound with molecular
formula H2SO4

M2 could have arrow to H+ in which case M3 would be for an

independent H−O bond break on a compound with formula H2SO4

M3: must use an arrow to show the breaking of the H−O bond
M3 ignore partial charges unless wrong

M4: is for the correct carbocation structure

NOT M4 if primary carbocation shown.

M5: must show an arrow from a lone pair of electrons on the correct
oxygen of the negatively charged ion towards the positively charged
carbon atom
M5 NOT HSO4
credit as shown or as: OSO3H − in which case negative
charge can be shown anywhere ECF from H2SO3 in M2

NB: The arrows are double-headed

IGNORE subsequent use of water to hydrolyse
hydrogensulfate
M1M2M3M4M5

(b)

If tertiary shown here allow as ECF for M1 if primary shown

in (a)

Page 11 of 18
 M1

(major) product formed via more stable carbocation OR tertiary

carbocation more stable (than primary)
Must be clear refers to intermediate and not product
M2

Due to electron-releasing character / (positive) inductive effect of three

alkyl groups (as opposed to one)
Primary has one e− donating alkyl group
M3

(c) Skeletal formula of cycloalkane

ignore structure of 2-methylbut-1-ene

1

(d) Addition (polymerisation)

Not additional
Penalise incorrect attachment of ethyl group
Must have trailing bonds
Ignore n and brackets
Ignore structure of 2-methylbut-1-ene
M1M2
[11]

Q2.
(a) M1 electrophilic addition

All arrows are double-headed. Penalise one mark from the

total for M2-5 if half headed arrows are used.
Do not penalise the “correct” use of “sticks”
Penalise only once in any part of the mechanism for a line
and two dots to show a bond
1

Page 12 of 18
 M2 must show an arrow from the double bond towards a Br atom in a Br–Br
molecule
M2 ignore partial negative charges on the double bond
1

M3 must show the breaking of the Br–Br bond

M3 penalise incorrect partial charges on the Br–Br bond and
penalise formal charges
Penalise M4 if there is a bond drawn to the positive charge
1

M4 is for the structure of the correct carbocation

1

M5 must show an arrow from the lone pair of electrons on the Br– towards
the positively charged atom of their carbocation
Max 3 of 4 marks (M2-5) for wrong organic reactant or
wrong carbocation (ignore structure of product)
For M5, credit attack on a partially positively charged
carbocation structure, but penalise M4 for the structure of the
carbocation
1

(b) M1 C=C electron rich / area of high electron density

M1 ignore idea that C=C is negative or highly electronegative
1

M2 Br-Br becomes polarised

1

M3 δ+ Br attracted to C=C
1

(c)

Must be skeletal structure

1
[9]

Q3.
(a) nucleophilic substitution
1

(b) M1 elimination

Page 13 of 18
 1

M2 arrow from lone pair on O to H+

1

M3 1st intermediate and arrow from C–O+H2 bond to O

1

M4 2nd intermediate (carbocation) and arrow from a correct

C–H bond to correct C–C to form C=C
Max 2 of 3 marks (M2-4) for wrong organic reactant (ignore
structure of product)
M3 and M4 can be scored in one concurrent step:
M3 for correct intermediate and arrow from C–O+H2 bond to
O
M4 for arrow from a correct C–H bond to correct C–C to form
C=C 1

(c)

Any correct structural representation

Ignore any brackets and/or n
1

(d)

Page 14 of 18
 Structure in any form
1
[7]

Q4.
(a) M1 electrophilic addition

All arrows are double-headed. Penalise one mark

from the total for M2-5 if half headed arrows are
used.
Do not penalise the "correct" use of "sticks"
Penalise only once in any part of the mechanism
for a line and two dots to show a bond
1

M2 must show an arrow from the double bond towards the H

atom of the H2SO4 molecule
For M2/3, the full structure of H2SO4 does not
need to be shown, but the key features for the
mechanism should be shown and the formula
must be correct. Penalise only once in M2/3 an
incorrect but genuine attempt at the structure of
sulfuric acid
M2 ignore partial negative charges on the double
bond
1

M3 must show the breaking of the H-O bond in H2SO4

M3 penalise incorrect partial charges on the H–O
bond and penalise formal charges
1

M4 is for the structure of the correct carbocation

Penalise M4 if there is a bond drawn to the
positive charge
1

M5 must show an arrow from the lone pair of electrons on

the negatively charged oxygen of HSO4– towards the
positively charged atom of their carbocation drawn
Max 3 of 4 marks (M2-5) for wrong organic

Page 15 of 18
 reactant or wrong carbocation (ignore structure of
product)
1
If attack is shown from C=C to H+ rather than
H2SO4, then allow M2 but not M3
For M5, credit attack on a partially positively
charged carbocation structure, but penalise M4
for the structure of the carbocation.
For M5, the full structure of HSO4– is not essential, but attack must
come from a lone pair on an individual oxygen on HSO4–, but the –
sign could by anywhere on the ion (e.g.: OSO3H–)

(b)

Any correct structural formula, including OSO3H

bonded through O to correct C
1

(c) M1 idea that E is formed from/via more stable carbocation

M1-2 Allow carbonium ion in place of carbocation
1

M2 idea that 2y carbocation is more stable than 1y carbocation

M2 Allow descriptions in terms of number of alkyl
groups attached to positive C atom
1
Ignore reference to inductive effect
Penalise M1 if answer suggests that the products
are carbocations (but could score M2)
In order to access M1 and/or M2 there must be
some reference to carbocations (carbonium ions)
by name or structure or description
[8]

Q5.
C
It has a higher melting point than ethene
[1]

Q6.
A
The monomer is propanenitrile
[1]

Page 16 of 18
Q7.
(a) Step 1

M1 fractional distillation
1

M2 separated into mixtures of compounds with similar boiling points /

similar sized molecules
M2 to separate naphtha from other compounds; to separate
compounds by chain length / size / boiling point
1

Step 2

M3 (thermal) cracking
M3 not catalytic cracking
1

M4 to make alkenes / propene / shorter molecules

1

Step 3

M5 (addition) polymerisation
M5 not condensation polymerisation 1
1

M6 molecules joined together or to produce long chain molecule

For each step the two marks are independent
1

(b) no polar bonds (in chain) / non-polar

Do not allow if only C-H bonds mentioned as non polar
1

(c) to prevent build-up of waste (in landfill) OR they can be broken down by
natural processes
1
[8]

Q8.
(a) M1 structure of chloroethene
Allow any correct structural representations of monomer and
polymer
1

M2 structure of PVC
M2 allow correct repeating unit, but penalise incorrect use of
bracket in M3
1

M3 correct use of n on both sides of equation

Page 17 of 18
 M2 and M3 could score as ECF from incorrect M1
1

(b) M1 no reaction / yellow-orange

M1 ignore brown; ignore red; ignore ‘nothing’; ignore ‘no
observation’
1

M2 polymer is saturated / does not contain double bond(s)

1

(c) M1 C24H38O4
M2 allow make less brittle; ignore making more elastic
1

M2 makes it more flexible

1
[7]

Q9.
A
[1]

Page 18 of 18