Name: ________________________

3.3.4 Alkenes Class: ________________________

Date: ________________________

Time: 65 minutes

Marks: 60 marks

Comments:

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 Propene reacts with concentrated sulfuric acid to form two isomers, E and F.
1.
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)

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 (b)  Draw the structure of F.

(1)

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

___________________________________________________________________

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(2)
(Total 8 marks)

But-1-ene reacts with a reagent of the form HY to form a saturated compound.

2.
(a) Suggest a reagent of the form HY which reacts with but-1-ene.

___________________________________________________________________
(1)

(b) Name and draw a mechanism for the reaction in part (a).

Name of mechanism __________________________________________________

Mechanism

(5)

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 (c) Explain how three isomeric products are formed when HY reacts with but-1-ene.

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(3)
(Total 9 marks)

The correct name for the alkene monomer which forms the polymer shown below is
3.

A 2-methyl-3-ethylpropene

B 2-methylpent-2-ene

C 2-methylpent-3-ene

D 4-methylpent-2-ene
(Total 1 mark)

It is possible to convert but-1-ene into its structural isomer but-2-ene.

4.
(a) State the type of structural isomerism shown by but-1-ene and but-2-ene.

___________________________________________________________________
(1)

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 (b) The first stage in this conversion involves the reaction of hydrogen bromide with but-1-ene.

CH3CH2CH=CH2 + HBr CH3CH2CHBrCH3

Outline a mechanism for this reaction.

(4)

(c) The second stage is to convert 2-bromobutane into but-2-ene.

CH3CH2CHBrCHCH3 + KOH CH3CH=CHCH3 + KBr + H 2O

Outline a mechanism for this reaction.

(3)
(Total 8 marks)

The alkene 3-methylpent-2-ene (CH3CH=C(CH3)CH2CH3) reacts with hydrogen bromide to form

5. a mixture of 3-bromo-3-methylpentane and 2-bromo-3-methylpentane.

(a) The alkene 3-methylpent-2-ene (CH3CH=C(CH3)CH2CH3) exists as E and Z

stereoisomers.

Draw the structure of Z-3-methylpent-2-ene.

(1)

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 (b) Name and outline the mechanism for the formation of 3-bromo-3-methylpentane from this
reaction of 3-methylpent-2-ene with hydrogen bromide.

Explain why more 3-bromo-3-methylpentane is formed in this reaction than 2-bromo-

3-methylpentane.

___________________________________________________________________

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(7)
(Total 8 marks)

The repeating unit of a polymer is

6.

Which of the following molecules would form a polymer containing this repeating unit?

A But-1-ene

B E-but-2-ene

C Z-but-2-ene

D Methylpropene

(Total 1 mark)

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 2-Methyl but-2-ene reacts with concentrated sulfuric acid to form two different products.
7.
(a) Outline a mechanism for this reaction to show the formation of the major product.

(4)

(b) Draw the structure of the minor product of this reaction.

(1)

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 (c) Explain why the two products are formed in different amounts.

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(2)
(Total 7 marks)

A student prepared cyclohexene by heating cyclohexanol with concentrated phosphoric acid. The
8. cyclohexene produced was distilled off from the reaction mixture.

(a)  Complete the diagram of the apparatus used to distil the cyclohexene from the reaction
mixture at 83 °C.

(2)

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(b)  The distillate was shaken with saturated sodium chloride solution. The cyclohexene was
separated from the aqueous solution using a separating funnel.

State why cyclohexene can be separated from the aqueous solution using the separating
funnel.

___________________________________________________________________

___________________________________________________________________
(1)

(c)  The cyclohexene separated in part (b) was obtained as a cloudy liquid.
The student dried this cyclohexene by adding a few lumps of anhydrous calcium chloride
and allowing the mixture to stand.

Give one observation that the student made to confirm that the cyclohexene was dry.

___________________________________________________________________

___________________________________________________________________
(1)

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(d)  In this preparation, the student added an excess of concentrated phosphoric acid to 14.4 g
of cyclohexanol (Mr = 100.0).
The student obtained 4.15 cm3 of cyclohexene (Mr = 82.0).
Density of cyclohexene = 0.810 g cm–3

Calculate the percentage yield of cyclohexene obtained.

Give your answer to the appropriate number of significant figures.

% yield _________________________
(5)

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 (e)  Cyclohexene reacts with bromine.

Complete the mechanism for this reaction.

(3)
(Total 12 marks)

This structure shows a section of a polymer chain formed from the random polymerisation of two
9. 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)

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 What is the empirical formula of 4-hydroxypent-2-ene?
10.

A C5H12O

B C5H10O

C CH2O

D C5H9OH

(Total 1 mark)

Which statement is not correct about CH2═C(CH3)CH2Br?

11.
A It displays E-Z isomerism.

B It forms an addition polymer.

C It reacts with electrophiles.

D It decolourises bromine water.

(Total 1 mark)

Which statement is correct about poly(chloroethene)?

12.
A It has the empirical formula CHCl

B It decolourises bromine water.

C Its brittleness is reduced by plasticisers.

D Its polymer chain contains alternate single and double bonds.

(Total 1 mark)

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 Which is the major product of the reaction between 2-methylbut-2-ene and iodine monochloride
13. (ICl)?

(Total 1 mark)

Which alkene reacts with hydrogen bromide to give 2-bromo-3-methylbutane as the major
14. product?

A (CH3)2C=CHCH3

B CH3CH2CH=CHCH3

C CH3CH2C(CH3)=CH2

D (CH3)2CHCH=CH2

(Total 1 mark)

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Mark schemes

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 (a)  M1 electrophilic addition
1.

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 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

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 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]

(a) HBr OR HCl OR H2SO4

2.
Allow HI or HY
1

(b) Electrophilic addition

1

Allow consequential marking on acid in 12.1 and allow use of HY

4

(c) The major product exists as a pair of enantiomers

1

The third isomer is 1-bromobutane (minor product)

1

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 Because it is obtained via primary carbocation
1
[9]

B
3.
[1]

(a) Position(al) (isomerism)

4. 1

(b)

Penalise one mark from their total if half-headed arrows are used

M1 must show an arrow from the double bond towards the H atom of the H–Br
molecule
M1 Ignore partial negative charge on the double bond.

M2 must show the breaking of the H–Br bond.

M2 Penalise partial charges on H–Br bond if wrong way and
penalise formal charges

M3 is for the structure of the secondary carbocation.

Penalise M3 if there is a bond drawn to the positive charge

M4 must show an arrow from the lone pair of electrons on the negatively charged
bromide ion towards the positively charged carbon atom of either a primary or
secondary carbocation.
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
Maximum any 3 of 4 marks for wrong reactant or primary
carbocation.
If Br2 is used, maximum 2 marks for their mechanism
Do not penalise the use of “sticks”

NB The arrows here are double-headed

4

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(c)

Penalise one mark from their total if half-headed arrows are used

M1 must show an arrow from the lone pair on oxygen of a negatively charged
hydroxide ion to a correct H atom
Penalise M1 if covalent KOH

M2 must show an arrow from a C–H bond adjacent to the C–Br bond towards
the appropriate C–C bond. Only award if an arrow is shown attacking the
H atom of an adjacent C–H (in M1)

M3 is independent provided it is from their original molecule.

Penalise M3 for formal charge on C of the C–Br or incorrect partial
charges on C–Br
Penalise M3 if an extra arrow is drawn from the Br of the C–Br bond
to, for example, K+
Ignore other partial charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond.
Maximum any 2 of 3 marks for wrong reactant or wrong product
(if shown) or a mechanism that leads to but-1-ene
Accept the correct use of “sticks” for the molecule except for the
C–H being attacked

Award full marks for an E1 mechanism in which M2 is on the correct carbocation.

NB The arrows here are double-headed

3
[8]

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5.
(a)

Must show all 4 groups bonded to C=C

Allow CH3− for methyl group; allow C2H5 for ethyl group
Allow correct structure of the style

Allow correct skeletal structure

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(b) M1 electrophilic addition

NB the arrows here are double-headed

1

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

atom of the H-Br molecule
1

M3 must show the breaking of the H-Br bond

1

M4 is for the structure of the tertiary carbocation

1

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

negatively charged bromide ion towards the positively
charged atom (of either a secondary or) of a tertiary
carbocation
1

M6 3-bromo-3-methylpentane is formed from 3y carbocation

OR
2-bromo-3-methylpentane is formed from 2y carbocation
1

M7 3y carbocation more stable than 2y

1
M2-M5 Penalise one mark from their total if half-headed arrows are
used
M2 Ignore partial negative charge on the double bond
M3 Penalise incorrect partial charges on H-Br bond and penalise
formal charges
Penalise M4 if there is a bond drawn to the positive charge
Penalise only once in any part of the mechanism for a line and two
dots to show a bond
Max 3 of any 4 marks (M2-5) for wrong organic reactant or wrong
organic product (if shown) or secondary carbocation
Max 2 of any 4 marks in the mechanism for use of bromine
Do not penalise the “correct” use of “sticks”
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 For M5, credit attack on a partially positively charged carbocation
structure but penalise M4
M6 is high demand and must refer to product being formed
from/via correct class of carbocation
M7 is high demand and must be clear answer refers to stability
of carbocations (intermediates) not products
Candidate that states that products are carbocations would
lose M6 and M7
M6,7 allow carbonium ion in place of carbocation; or a description
of carbocation in terms of alkyl groups/ number of carbon atoms
joined to a positive C

When asked to outline a mechanism, candidates are expected to

draw a mechanism with curly arrows (specification 3.3.1.2). On this
occasion only we would allow a detailed description as shown.
M2 must describe the movement of a pair of electrons / curly arrow
from the C=C towards the H atom of the H-Br molecule
M3 must describe the breaking of the H-Br bond with the bonding
pair of electrons moving to the Br / curly arrow from H-Br bond to Br
M4 is for the structure of the tertiary carbocation (i.e. positive C
bonded to one methyl and two ethyl groups)
M5 must describe the movement of a pair of electrons from the Br−
ion to the positive C atom of the carbocation / curly arrow from the
lone pair of electrons on the negatively charged bromide ion
towards the positively charged C atom (of either a secondary or) of
a tertiary carbocation
[8]

D
6. [1]

(a)
7.

M1, M2 and M4 are awarded for the three curly arrows shown on the mechanism
(1 mark for each correct)

M3 is for the structure of the carbocation intermediate

4

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 (b)

Correct answers include:

• the displayed formula
• structural formulae such as CH 3CH(CH3)CH(OSO3H)CH3
• skeletal formulae such as

(c) The major product is formed via a tertiary carbocation intermediate and the minor
product is formed via a secondary carbocation intermediate
1

The tertiary carbocation is more stable than the secondary carbocation

1
[7]

(a)  Thermometer and bung in flask with bulb level with side arm.
8.
Must be cross section diagram with no gaps at joints
1

Condenser jacket with water in at bottom and out at top.

1

(b)  Liquids are immiscible

Allow don’t mix, forms two layers (stated or implied)
Allow it is insoluble
Ignore density or reference to solutions
1

(c)  Liquid goes clear / not cloudy

Ignore colourless
1

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 (d)
Via moles Via mass Via volume
Amount cyclohexanol Amount cyclohexanol Amount cyclohexanol M1
(= 14.4/100) = 0.144 mol (= 14.4/100) = 0.144 mol (= 14.4/100) = 0.144 mol

Mass cyclohexene formed
= 4.15 x 0.81 = 3.36 g
Mass of cyclohexene
Mass cyclohexene formed
expected (= 0.144 × 82.0 = M2
= 4.15 x 0.81 = 3.36 g
11.808 g ) OR M1 × 82

volume of cyclohexene
amount cyclohexene mass of cyclohexene
expected
obtained expected
(= 11.808/0.810 = M3
(= 3.36/82.0 = 0.0410 mol) (= 0.144 × 82.0 = 11.808 g)
14.577cm3)
OR M2/82.0 OR = M1 × 82.0
OR M2/0.810

M4

= 28.5% (must be 3 sf) = 28.5% (must be 3 sf) = 28.5% (must be 3 sf)

Only award M5 if answer is to 3sf and follows some attempt at % yield calculation in M4 M5

(e)

Lose M1 if
Full charges on Br−Br
OR
Wrong partial charges on Br−Br
OR
Arrow is to Br+ ion (formed in a preliminary step)
Any C shown in the ring must have the correct number of hydrogens
attached to score M2
3
[12]

A
9.
[1]

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 B
10.
[1]

A
11.
It displays E-Z isomerism
[1]

C
12.
[1]

C
13.
[1]

D
14.
[1]

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