Barr Beacon School

A-level Chemistry (7404/7405)

3.3.4 Alkenes
Past Paper Questions

Name _______________________________

Questions All Attempted: 

Green Pen: 
Used examiners report to annotate: 

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Q1.The correct systematic name for is

A 2-ethyl-3,4-dimethylpent-2-ene

B 4-ethyl-2,3-dimethylpent-3-ene

C 2,3,4-trirnethylhex-3-ene

D 3,4,5-trimethylhex-3-ene
(Total 1 mark)

Q2.Which statement about E-1,2-dichloroethene is correct?

A It has the same boiling point as Z-1,2-dichloroethene.

B It forms a polymer with the same repeating unit

as Z-1,2-dichloroethene.

C It has the same IR spectrum as Z-1,2-dichloroethene

in the range 400–1500 cm−1.

D It has a molecular ion peak different from that of

Z-1,2-dichloroethene in its mass spectrum.

(Total 1 mark)

Q3.The correct name for the alkene monomer which forms the polymer shown below is

A 2-methyl-3-ethylpropene

B 2-methylpent-2-ene

C 2-methylpent-3-ene

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

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Q4. The reaction of bromine with an alkene is used in a test to show that the alkene is unsaturated.

(a) State what is meant by the term unsaturated as applied to an alkene.

......................................................................................................................
(1)

(b) Name and outline a mechanism for the reaction of bromine with but-2-ene.

Name of mechanism ....................................................................................

Mechanism

(5)

(c) But-2-ene can exist as a pair of stereoisomers.

(i) State what is meant by the term stereoisomers.

.............................................................................................................

.............................................................................................................

.............................................................................................................
(2)

(ii) Draw the structure of (E)-but-2-ene.

.............................................................................................................
(1)
(Total 9 marks)

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Q5. Alkenes are useful intermediates in the synthesis of organic compounds.

(a) (i) Complete the elimination mechanism by drawing appropriate curly arrows.

(3)

(ii) Draw structures for the E and Z stereoisomers of hex-3-ene.

E isomer of hex-3-ene Z isomer of hex-3-ene

(2)

(iii) State the meaning of the term stereoisomers.

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................
(2)

(b) The equation for the first reaction in the conversion of hex-3-ene into hexan-3-ol is shown
below.

CH CH CH=CHCH CH
3 2 2 3 + H SO 2 4 CH CH CH CH(OSO OH)CH CH
3 2 2 2 2 3

Outline a mechanism for this reaction.

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(4)
(Total 11 marks)

Q6. It is possible to convert but-1-ene into its structural isomer but-2-ene.

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

........................................................................................................................
(1)

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

CH CH CH=CH
3 2 2 + HBr CH CH CHBrCH
3 2 3

Outline a mechanism for this reaction.

(4)

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

CH CH CHBrCH
3 2 + KOH CH CH=CHCH
3 3 + KBr + HO
2

CH 3

Outline a mechanism for this reaction.

(3)
(Total 8 marks)

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Q7. In which of the following is a curly arrow used incorrectly?

D
(Total 1 mark)

Q8. (a) Compounds with double bonds between carbon atoms can exhibit geometrical
isomerism.

(i) Draw structures for the two geometrical isomers of 1,2-dichloroethene.

Isomer 1 Isomer 2

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(ii) What feature of the double bond prevents isomer 1 from changing into isomer 2?

.............................................................................................................
(3)

(b) When 2-chloropropane reacts with sodium hydroxide, two different reactions occur.
Each reaction produces a different organic product.

(i) Outline a mechanism for Reaction 1 and state the role of the hydroxide ion in this
reaction.

Mechanism

Role of the hydroxide ion ....................................................................

(ii) Outline a mechanism for Reaction 2 and state the role of the hydroxide ion in this
reaction.

Mechanism

Role of the hydroxide ion ....................................................................

(7)
(Total 10 marks)

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Q9. The table below shows the structures of three isomers with the molecular formula C H O 5 10

Isomer 1

(E)-pent-3-en-2-ol

Isomer 2

pentanal

Isomer 3

(a) Complete the table by naming Isomer 3.

(1)

(b) State the type of structural isomerism shown by these three isomers.

.....................................................................................................................
(1)

(c) The compound (Z)-pent-3-en-2-ol is a stereoisomer of (E)-pent-3-en-2-ol.

(i) Draw the structure of (Z)-pent-3-en-2-ol.

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(1)

(ii) Identify the feature of the double bond in (E)-pent-3-en-2-ol and that in
(Z)-pent-3-en-2-ol that causes these two compounds to be stereoisomers.

.............................................................................................................
(1)

(d) A chemical test can be used to distinguish between separate samples of Isomer 2 and
Isomer 3.
Identify a suitable reagent for the test.
State what you would observe with Isomer 2 and with Isomer 3.

Test reagent ...............................................................................................

Observation with Isomer 2...........................................................................

.....................................................................................................................

Observation with Isomer 3............................................................................

.....................................................................................................................
(3)

(e) The following is the infrared spectrum of one of the isomers 1, 2 or 3.

(i) Deduce which of the isomers (1, 2 or 3) would give this infrared spectrum. You may
find it helpful to refer to Table 1 on the Data Sheet.

............................................................................................................. (1)

(ii) Identify two features of the infrared spectrum that support your deduction.
In each case, identify the functional group responsible.

Feature 1 and functional group ...........................................................

.............................................................................................................

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.............................................................................................................

.............................................................................................................

Feature 2 and functional group ...........................................................

.............................................................................................................

.............................................................................................................

............................................................................................................. (2)
(Total 10 marks)

Q10. Consider the following scheme of reactions.

(a) Give the IUPAC name for compound P and that for compound Q.

P .....................................................................................................................

Q ....................................................................................................................
(2)

(b) The conversion of P into Q in Reaction 1 uses HCl

Name and outline a mechanism for this reaction.

........................................................................................................................

(5)

(c) The conversion of Q into R in Reaction 2 uses NH3

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Name and outline a mechanism for this reaction.

........................................................................................................................

(5)

(d) State the type of reaction shown by Reaction 3.

Identify a reagent for this reaction.

Give one condition necessary for a high yield of product when Q is converted into P.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................( 3)

(e) Hydrogen bromide (HBr) could be used in the overall conversion of P into R, instead of using HCl
Hydrogen bromide is made by the reaction of NaBr with concentrated phosphoric acid.
Concentrated sulfuric acid is not used to make HBr from NaBr

Write an equation for the reaction of NaBr with H3PO4 to produce HBr and Na3PO4 only.

Identify two toxic gases that are formed, together with HBr, when NaBr reacts with
concentrated H2SO4

State the role of H2SO4 in the formation of these two toxic gases.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

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........................................................................................................................
(4)
(Total 19 marks)

Q11. The alkene (Z)-3-methylpent-2-ene reacts with hydrogen bromide as shown below.

(a) (i) Name the major product P.

.............................................................................................................
(1)

(ii) Name the mechanism for these reactions.

.............................................................................................................
(1)

(iii) Draw the displayed formula for the minor product Q and state the type of structural
isomerism shown by P and Q.

Displayed formula for Q

Type of structural isomerism ..............................................................

(2)

(iv) Draw the structure of the (E)-stereoisomer of 3-methylpent-2-ene.

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(1)

(b) The infrared spectra of two compounds R and S are shown below. R and S have the
molecular formula C H and are structural isomers of 3-methylpent-2-ene. R is an
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unsaturated hydrocarbon and S is a saturated hydrocarbon.

Spectrum 1

Spectrum 2

(i) Identify the infrared Spectrum 1 or 2 that represents compound R.

Use information from the infrared spectra to give one reason for your answer.
You may find it helpful to refer to Table 1 on the Data Sheet.
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R is represented by Spectrum ................

Reason ...............................................................................................

............................................................................................................. (2)

(ii) State the type of structural isomerism shown by R and S.

.............................................................................................................
(1)

(iii) Name one possible compound which could be S.

.............................................................................................................
(1)
(Total 9 marks)

Q12. Dodecane (C12H26) is a hydrocarbon found in the naphtha fraction of crude oil. Dodecane can be
used as a starting material to produce a wide variety of useful products. The scheme below
shows how one such product, polymer Y, can be produced from dodecane.

(a) Name the homologous series that both C2H4 and C4H8 belong to.
Draw a functional group isomer of C4H8 that does not belong to this homologous series.

Name ...........................................................................................................

Functional group isomer

(2)

(b) Identify compound X.

........................................................................................................................
(1)

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(c) Name polymer Y.

........................................................................................................................
(1)

(d) Reaction 1 is an example of thermal cracking and is carried out at a temperature of

750 °C.

State one other reaction condition needed.

........................................................................................................................ (1)

(e) Reaction 2 is exothermic. A typical compromise temperature of 200 °C is used industrially

for this reaction.

Explain the effect of a change of temperature on both the position of equilibrium and the
rate of reaction, and justify why a compromise temperature is used industrially.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................ (6)
(Total 11 marks)

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Q13. Consider the following reactions.

(a) Name and outline a mechanism for Reaction 1.

Name of mechanism .........................................................................................................

Mechanism

(5)
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(b) Name and outline a mechanism for Reaction 2.

Name of mechanism .........................................................................................................

Mechanism

(5)

(c) State the type of reaction in Reaction 3.

Give the name of substance X.

........................................................................................................................

........................................................................................................................

........................................................................................................................
(2)

(d) The haloalkane produced in Reaction 1 can be converted back into propene in an
elimination reaction using ethanolic potassium hydroxide.

CH CHBrCH
3 3 H C=CHCH
2 3

Outline a mechanism for this conversion.

(3)
(Total 15 marks)

Q14.The alkene (E)-but-2-enenitrile is used to make acrylic plastics.

The structure of (E)-but-2-enenitrile is

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(a) (i) Draw the structure of (Z)-but-2-enenitrile.

(1)

(ii) Identify the feature of the double bond in the E and Z isomers that causes them to
be stereoisomers.

...............................................................................................................

...............................................................................................................

...............................................................................................................
(1)

(b) Draw the repeating unit of the polyalkene formed by addition polymerisation of (E)-but-2-
enenitrile.

(1)

(c) Consider the infrared spectrum of (E)-but-2-enenitrile.

Wavenumber / cm −1

Identify two features of the infrared spectrum that support the fact that this is the infrared
spectrum for but-2-enenitrile.
You may find it helpful to refer to Table 1 on the Data Sheet.
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Feature 1 .......................................................................................................

........................................................................................................................

........................................................................................................................

Feature 2 .......................................................................................................

........................................................................................................................

........................................................................................................................
(2)
(Total 5 marks)

Q15. The following pairs of compounds can be distinguished by simple test−tube reactions.

For each pair of compounds, give a reagent (or combination of reagents) that, when added
separately to each compound, could be used to distinguish between them.
State what is observed in each case.

(a) Butan−2−ol and 2−methylpropan−2−ol

Reagent .........................................................................................................

Observation with butan−2−ol

........................................................................................................................

........................................................................................................................

Observation with 2−methylpropan−2−ol

........................................................................................................................

........................................................................................................................ (3)

(b) Propane and propene

Reagent .........................................................................................................

Observation with propane

........................................................................................................................

........................................................................................................................
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Observation with propene

........................................................................................................................

........................................................................................................................ (3)

(c) Aqueous silver nitrate and aqueous sodium nitrate

Reagent .........................................................................................................

Observation with aqueous silver nitrate

........................................................................................................................

........................................................................................................................

Observation with aqueous sodium nitrate

........................................................................................................................

........................................................................................................................ (3)

(d) Aqueous magnesium chloride and aqueous barium chloride

Reagent .........................................................................................................

Observation with aqueous magnesium chloride

........................................................................................................................

........................................................................................................................

Observation with aqueous barium chloride

........................................................................................................................

........................................................................................................................
(3)
(Total 12 marks)

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Mark Scheme
M1.C
[1]

M2.B
[1]

M3.B
[1]

M4. (a) Contains a C=C OR a double bond

1

(b) Electrophilic addition

Both words needed
1
Mechanism:

Ignore partial negative charge on the double bond.

M2 Penalise partial charges on bromine if wrong way and penalise
formal charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond.
M1 Must show an arrow from the double bond towards oneof the Br atoms on a Br-Br
molecule.
Deduct 1 mark for sticks.
M2 Must show the breaking of the Br-Br bond.
M3 Is for the structure of the secondary carbocation with Br substituent.
M4 Must show an arrow from the lone pair of electrons on anegatively charged bromide
ion towards the positivelycharged carbon atom.
Deduct 1 mark for wrong reactant, but mark consequentially.If
HBr, mark the mechanism consequentially and deduct one markIf
but-1-ene, mark the mechanism consequentially and deduct one
mark.If both HBr and but-1-ene, mark the mechanism
consequentially and deduct ONLY one mark.
4

(c) (i) M1 Compounds with the same structural formula

Penalise M1 if “same structure”Ignore references to “same
molecular formula” or “same empirical formula”
1
M2 With atoms/bonds/groups arranged differently in
spaceORatoms/bonds/groups have different spatialarrangements/ different
orientation.
Mark independently.
1

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(ii)
Award credit provided it is obvious that the candidate is drawing
the trans isomer.
Do not penalise poor C–C bonds
Trigonal planar structure not essential
1
[9]

M5. (a) (i)

Penalise one mark from their total if half-headed arrows are used
Penalise M3 for formal charge on C of the C-Br or incorrect partial
charges on C-Br
Ignore other partial charges

M1 must show an arrow from the lone pair on oxygen of a negatively charged
hydroxide ion to the correct H atom
Penalise once only in any part of the mechanism for a line and two
dots to show a bond.
M2 must show an arrow from the correct C–H bond to the correct C–C bond.Only
award if an arrow is shown attacking the H atom of the correct C–Hbond in M1
M3 is independent but CE=0 if nucleophilic substitution
N.B these are double-headed arrows
3

(ii)
Award 1 mark if both correct stereoisomers but in the wrong
places
Accept no other alkenes.
Be reasonably lenient on the bonds to ethyl (or to CH2CH3) since
the question is about E and Z positions but penalise once only if
connection is clearly to the CH3 of CH2CH3
Accept linear structures
2

(iii) M1 (Compounds / molecules with) the same structural formula

Penalise M1 if “same structure”
M2 with atoms/bonds/groups arranged differently in space
Ignore references to “same molecular formula” or “same empirical
formula” or any reference to “displayed formula”
ORatoms/bonds/groups that have different spatial arrangements / different
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orientation.
Mark independently
2

(b)
M1must show an arrow from the double bond towards the H atom of the H – O bond OR
HO on a compound with molecular formula for H2SO4
M1 could be to an H+ ion and M2 an independent O – H bond break on a compound with
molecular formula for H2SO4
M1 Ignore partial negative charge on the double bond.
M2 must show the breaking of the O – H bond.
M2 Penalise partial charges on O – H bond if wrong way and
penalise formal charges
In M2 do not penalise incorrect structures for H2SO4
M3 is for the structure of the carbocation.
M4 must show an arrow from the lone pair of electrons on the correct oxygen of the
negatively charged ion towards a correct (positively charged) carbon atom.
M4 NOT HSO4–
For M4, credit as shown or –:OSO3H ONLY with the negative
charge anywhere on this ion
OR correctly drawn out with the negative charge placed correctly
on oxygen
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
NB The arrows here are double-headed
Max 3 of any 4 marks for wrong organic reactant or wrong organic
product (if shown)
Accept the correct use of “sticks”
4
[11]

M6.(a) Position(al) (isomerism)

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

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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

(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]

M7.C
[1]

M8. (a) (i)

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(ii) restricted rotation OR no rotation OR cannot rotate (1)

3

(b) (i) Mechanism:

M1 and M2 independent
Curly arrows must be from a bond or a lone pair
Do not penalise sticks
Penalise M1 if precedes (penalise this once)
Penalise incorrect δ+ δ– for M2
Penalise + on C atom for M2
Only allow M1 for incorrect haloalkane
Role of the hydroxide ion: nucleophile (1) electron pair
donor lone pair donor
NOT nucleophilic substitution

(ii) Mechanism:

Only allow M1 and M2 for incorrect haloalkane unless RE on (i)

+ charge on H on molecule, penalise M1
M3 independentM2 must be to correct C–C
M1 must be correct H atom
Credit M1 and M2 via carbocation mechanism
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No marks after any attack of C by OH–
Role of the hydroxide ion: base (1) proton
acceptor accepts H+
7
[10]

M9. (a) Pentan-2-one

ONLY but ignore absence of hyphens
1
(b) Functional group (isomerism)
Both words needed
1

(c) (i)

Award credit provided it is obvious that the candidate is drawing

the Z / cis isomer
The group needs to be CHOHCH3 but do not penalise poor C–C
bonds or absence of brackets around OH
Trigonal planar structure not essential
1

(ii) Restricted rotation (about the C=C)

OR
No (free) rotation (about the C=C)
1

(d)
M1 Tollens’ (reagent) M1 Fehling’s (solution) / Benedict’s
(Credit ammoniacal silver nitrate OR (Penalise Cu2+(aq) or CuSO4 but
a description of making Tollens’) mark M2 and M3)
(Do not credit Ag+, AgNO3 or
[Ag(NH3)2+] or “the silver mirror test”
on their own, butmark M2 and M3)
M2 silver mirror M2 Red solid/precipitate
OR black solid or black precipitate (Credit orange or brown solid)
M3 (stays) colourless M3 (stays) blue
OR OR
no (observed) change / no reaction no (observed) change / no reaction

If M1 is blank CE = 0, for the clip

Check the partial reagents listed and if M1 has a totally incorrect
reagent, CE = 0 for the clip
Allow the following alternatives
M1 (acidified) potassium dichromate(VI) (solution); mark on from
incomplete formulae or incorrect oxidation state
M2 (turns) green
M3 (stays) orange / no (observed) change / no reaction
OR
M1 (acidified) potassium manganate(VII) (solution);

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mark on from incomplete formulae or incorrect oxidation state
M2 (turns) colourless
M3 (stays) purple / no (observed) change / no reaction
In all cases for M3
Ignore “nothing (happens)”
Ignore “no observation”
3

(e) (i) Spectrum is for Isomer 1

or named or correctly identified
The explanation marks in (e)(ii) depend on correctly identifying
Isomer 1.
The identification should be unambiguous but candidates should
not be penalised for an imperfect or incomplete name. They may
say “the alcohol” or the “alkene” or the “E isomer”
1

(ii) If Isomer 1 is correctly identified, award any two from

• (Strong / broad) absorption / peak in the range3230 to 3550 cm–1 or specified
value in this rangeor marked correctly on spectrumand(characteristic
absorption / peak for) OH group /alcohol group
• No absorption / peak in range 1680 to 1750 cm–1 orabsence marked correctly
on spectrumand(No absorption / peak for a) C=O group / carbonyl group /
carbon-oxygen double bond
• Absorption / peak in the range 1620 to 1680 cm–1or specified value in this
range or marked correctlyon spectrumand
(characteristic absorption / peak for) C=C group/ alkene / carbon-carbon
double bond
If 6(e)(i) is incorrect or blank, CE=0
Allow the words “dip” OR “spike” OR “trough” OR “low
transmittance” as alternatives for absorption.
Ignore reference to other absorptions e.g. C-H, C-O
2
[10]

M10.(a) P 3,3−dimethylbut−1−ene
OR
accept 3,3−dimethylbutene
Ignore absence of commas, hyphens and gaps
Require correct spelling
Q 3−chloro−2,2−dimethylbutane
OR
accept 2−chloro−3,3−dimethylbutane
In Q, “chloro” must come before “dimethyl”
2

(b) M1 Electrophilic addition

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M2 must show an arrow from the double bond towards the H atom of HCl
M3 must show the breaking of the H−Cl bond
M4 is for the structure of the carbocation
M5 must show an arrow from the lone pair of electrons on the negatively charged
chloride ion towards the positively charged carbon atom on their carbocation.
NB The arrows here are double−headed
M1 both words required
For the mechanism
M3 Penalise incorrect partial charge on H−Cl bond and penalise
formal charges
Ignore partial negative charge on the double bond.
Maximum 3 of 4 marks for a correct mechanism using HBr or
the wrong organic reactant or wrong organic product (if shown) or
a primary carbocation
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
Credit the correct use of “sticks”
For M5, credit attack on a partially positively charged carbocation
structure, but penalise M4
5

(c) M1 Nucleophilic substitution

For M1, both words required.
Accept phonetic spelling

M2 must show an arrow from the lone pair of electrons on the nitrogen atom of an
ammonia molecule to the correct C atom
M3 must show the movement of a pair of electrons from the C− Cl bond to the Cl
atom. Mark M3 independently provided it is from their original molecule
M4 is for the structure of the alkylammonium ion, which could be a condensed
formula. A positive charge must be shown on, or close to, the N atom.
M5 is for an arrow from the N−H bond to the N atom
Award full marks for an SN1 mechanism in which M2 is the attack of the ammonia
on the intermediate carbocation
NB These are double-headed arrows
For the mechanism
Penalise M2 if NH3 is negatively charged.
Penalise M3 for formal charge on C of the C−Cl or incorrect partial
charges on C−Cl
Penalise M3 for an additional arrow from the Cl to something else
The second mole of ammonia is not essential for M5; therefore
ignore any species here
Penalise once only for a line and two dots to show a bond
Maximum 3 of 4 marks for the mechanism for wrong organic
reactant OR wrong organic product if shown
Accept the correct use of “sticks”
5

(d) M1 (base) elimination

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M1 Dehydrohalogenation
M2 KOH OR NaOH
M3 Must be consequential on a correct reagent in M2, but if incomplete or
inaccurate attempt at reagent (e.g. hydroxide ion), penalise M2 only and mark on
Any one from
• high temperature OR hot OR heat / boil under reflux
• concentrated
• alcohol / ethanol (as a solvent) / (ethanolic conditions)
M3 not “reflux” alone
M3 if a temperature is stated it must be in the range 78C to 200 °C
Ignore “pressure”
3

(e) M1
3NaBr + H3PO4 3HBr + Na3PO4
M1 Credit correct ionic species in the equation
M2 and M3
SO2 and Br2 identified
M4
Concentrated sulfuric acid
• is an oxidising agent
• oxidises the bromide (ion) or Br− or NaBr or HBr
• is an electron acceptor
In M2 and M3 the two gases need to be identified. If equations are
used using sulfuric acid and the toxic gases are not identified
clearly, allow one mark for the formulas of SO2 and Br2
• apply the list principle as appropriate but ignore any
reference to HBr
• the marks are for identifying the two gases either by
name or formula
4
[19]

M11. (a) (i) 3-bromo-3-methylpentane ONLY

Must be correct spelling but ignore hyphens and commas
1

(ii) Electrophilic addition (reaction)

Both words needed
Accept phonetic spelling
1

(iii) M1 Displayed formula of 2-bromo-3-methylpentane

All the bonds must be drawn out but ignore bond angles
M2 Position(al) (isomerism)
Do not forget to award this mark
2

(iv) Structure of (E)-3-methylpent-2-ene

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The arrangement of groups around the double bond must be clear

with the ethyl group attached in the correct order. Ignore bond
angles.
Accept C2H5 for ethyl
Be lenient on C ─ C bonds. The main issue here is whether they
have drawn an (E) isomer.
Accept “sticks” for C ─ H bonds and correct skeletal formula
1

(b) (i) M1 R is represented by Spectrum 2

M2 Spectrum 2 shows an infrared absorption/spike/dip/trough/peak with any
value(s)/range within the range 1620 to1680 (cm–1) OR this range
quoted/identified and thisis due to C=C OR this information could be a
correctly labelled absorptionon the spectrum
OR Spectrum 1 does not have an infrared absorption in range1620 to 1680
(cm–1) and does not contain C=C.
Award M1 if it is obvious that they are referring to the second
spectrum (or the bottom one)
M2 depends on a correct M1
Ignore other correctly labelled peaks
Ignore reference to “double bond” or “alkene”
2

(ii) Functional group (isomerism)

1

(iii) Cyclohexane
OR
Methylcyclopentane etc.
Named correctly
Ignore structures and ignore numbers on the methyl group of
methylcyclopentane
1
[9]

M12.(a) Alkenes
1

Correctly drawn molecule of cyclobutane or methyl cyclopropane,

need not be displayed formula
1

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(b) C6H14 (or correct alkane structure with 6 carbons)
Allow hexane or any other correctly named alkane with 6 carbons
1

(c) Poly(but-2-ene)
1

(d) High pressure

Allow pressure ࣙ MPa
Mention of catalyst loses the mark
1

(e) This question is marked using levels of response. Refer to the Mark Scheme
Instructions for Examiners for guidance on how to mark this question.
Level 3
All stages are covered and the explanation of each stage is generally correct and
virtually complete.
Answer communicates the whole process coherently and shows a logical
progression from stage 1 and stage 2 (in either order) to stage 3.
5–6 marks

Level 2
All stages are covered but the explanation of each stage may be incomplete or may
contain inaccuracies OR two stages are covered and the explanations are generally
correct and virtually complete.
Answer is mainly coherent and shows progression. Some steps in each stage may
be out of order and incomplete.
3–4 marks

Level 1
Two stages are covered but the explanation of each stage may be incomplete or
may contain inaccuracies, OR only one stage is covered but the explanation is
generally correct and virtually complete.
Answer includes isolated statements but these are not presented in a logical order
or show confused reasoning.
1–2 marks

Level 0
Insufficient correct chemistry to gain a mark.
0 marks
Indicative chemistry content
Stage 1: consider effect of higher temperature on yield
(Or vice versa for lower temperature)
• Le Chatelier’s principle predicts that equilibrium shifts to
oppose any increase in temperature
• Exothermic reaction, so equilibrium shifts in endothermic
direction / to the left
• So a Higher T will reduce yield

Stage 2: consider effect of higher temperature on rate

(Or vice versa for lower temperature)
• At higher temperature, more high energy molecules
• more collisions have E>Ea
• So rate of reaction increases / time to reach equilibrium
decreases
Stage 3: conclusion
Industrial conditions chosen to achieve (cost-effective) balance of
suitable yield at reasonable rate
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[11]

M13.(a) M1 electrophilic addition

For M1, both words required
Accept phonetic spelling

For the mechanism

M2 Ignore partial negative charge on the double bond
M2 must show an arrow from the double bond towards the H atom of the H–Br
molecule
M3 Penalise partial charges on H–Br bond if wrong way and
penalise formal charges
M3 must show the breaking of the H–Br bond
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
M5 must show an arrow from the lone pair of electrons on the negatively charged
bromide ion towards the correct (positively charged) carbon atom
Maximum any 3 of 4 marks for the mechanism for wrong
(organic) reactant OR wrong organic product (if shown) OR
primary carbocation
Accept the correct use of sticks
NB These are double-headed arrows
5

(b) M1 Nucleophilic substitution

For M1, both words required
Accept phonetic spelling

For the mechanism

Penalise M2 if NH3 is negatively charged
M2 must show an arrow from the lone pair of electrons on the nitrogen atom of an
ammonia molecule to the correct C atom
Penalise M3 for formal charge on C of the C−Br or incorrect partial
charges on C−Br
Penalise M3 for an additional arrow from the Br to something else
M3 must show the movement of a pair of electrons from the C–Br bond to the Br
atom. Mark M3 independently provided it is from their original molecule
The second mole of ammonia is not essential for M5; therefore
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ignore any species here
M4 is for the structure of the alkylammonium ion, which could be a condensed
formula. A positive charge must be shown on / or close to, the N atom
Penalise once only for a line and two dots to show a bond
M5 is for an arrow from the N–H bond to the N atom
Maximum any 3 of 4 marks for the mechanism for wrong
organic reactant OR wrong organic product if shown
Award full marks for an SN1 mechanism in which M2 is the attack of the ammonia
on the intermediate carbocation
Accept the correct use of “sticks”
NB These are double-headed arrows
5

(c) M1 (addition) polymerisation OR poly-addition

Ignore “additional”
Credit polyprop-1-ene and polypropylene
M2 poly(propene) / polypropene
Penalise “condensation polymerisation”
2

(d)

Penalise M1 if covalent KOH

M1 must show an arrow from the lone pair on the oxygen of a negatively charged
hydroxide ion to a correct H atom
Penalise M3 for formal charge on C of C–Br or incorrect partial
charges on C−Br.
M2 must show an arrow from a correct C–H bond adjacent to the C–Br bond to the
appropriate C–C bond. Only award if an arrow is shown attacking the H atom of a
correct C−H bond in M1
Ignore other partial charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
M3 is independent provided it is from their original molecule, but CE=0 if
nucleophilic substitution
Maximum any 2 of 3 marks for wrong organic reactant
Award full marks for an E1 mechanism in which M3 is on the correct carbocation.
Accept the correct use of “sticks” for the molecule except for the
C–H being attacked
NB These are double-headed arrows
3
[15]

M14.(a) (i) Structure of (Z)-but-2-enenitrile with or without either or both of the CH 3 and the CN
groups displayed

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Penalise C−NC
Do not penalise C−H3C
Ignore bond angles.
1

(ii) Restricted rotation / no (free) rotation about the double bond / about the C=C
OR does not rotate (about the double bond)
Must use the word rotate / rotation.
1

(b) Repeating unit of polyalkene

All the bonds relevant to the unit must be drawn out including
those on either side of the unit. There is no need to expand either
the CH3 or the CN
Penalise C−NC
Penalise “sticks”.
Ignore brackets.
Penalise “n”
1

(c) Feature 1Absorption / peak in the range 2220 to 2260 cm−1 or specified value in this
range or marked correctly on spectrumand(characteristic absorption / peak for) C≡N
/ CN group / nitrile / cyanide group
Allow the words “dip” OR “spike” OR “trough” OR “low
transmittance” as alternatives for absorption.
Allow a peak at 2200 cm−1 to 2220 cm−1 in this case.
Feature 2Absorption / peak in the range 1620 to 1680 cm−1 or specified value in this
range or marked correctly on spectrumand(characteristic absorption / peak for) C=C
group / alkene / carbon-carbon double bond
Ignore reference to other absorptions eg C-H
Either order.
2
[5]

M15. (a) M1 acidified potassium dichromate or K2Cr2O7 / H2SO4

OR K2Cr2O7 / H+ OR acidified K2Cr2O7
M2 (orange to) green solution OR goes green
M3 (solution) remains orange or no reaction or no (observed) change
If no reagent or incorrect reagent in M1, CE = 0 and no marks for
M1, M2 or M3
If incomplete / inaccurate attempt at reagent e.g. “dichromate” or
“dichromate(IV)” or incorrect formula or no acid, penalise M1 only
and mark on
For M2 ignore dichromate described as “yellow” or “red”
For M3 ignore “nothing (happens)” or “no observation”
Alternative using KMnO4 / H2SO4
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M1 acidified potassium manganate(VII) / potassium permanganate or KMnO4 /
H2SO4
OR KMnO4 / H+ OR acidified KMnO4
M2 colourless solution OR goes colourless
M3 (solution) remains purple or no reaction or no (observed) change
For M1
If incomplete / inaccurate attempt at reagent e.g. “manganate” or
“manganate(IV)” or incorrect formula or no acid, penalise M1 only
and mark on
Credit alkaline KMnO4 for possible full marks but M2 gives brown
precipitate or solution goes green
3

(b) M1 (Shake with) Br2 OR bromine (water) OR bromine (in CCl4 / organic solvent)
M2 (stays) orange / red / yellow / brown / the same
OR no reaction OR no (observed) change
M3 decolourised / goes colourless / loses its colour / orange to colourless
If no reagent or incorrect reagent in M1, CE = 0 and no marks for
M1, M2 or M3
If incomplete / inaccurate attempt at reagent (e.g. Br), penalise
M1 only and mark on
No credit for combustion observations; CE = 0
For M2 in every case
Ignore “nothing (happens)”
Ignore “no observation”
Ignore “clear”
OR as alternatives
Use KMnO4 / H2SO4
M1 acidified potassium manganate(VII) / potassium permanganate OR KMnO4 /
H2SO4
OR KMnO4 / H+ OR acidified KMnO4
M2 (stays) purple or no reaction or no (observed) change
M3 decolourised / goes colourless / loses its colour
Use iodine
M1 iodine or I2 / KI or iodine solution
M2 no change
M3 decolourised / goes colourless / loses its colour
Use concentrated sulfuric acid
M1 concentrated H2SO4
M2 no change
M3 brown
For M1, it must be a whole reagent and / or correct formula
For M1 penalise incorrect attempt at correct formula, but mark M2
and M3
With potassium manganate(VII)
If incomplete / inaccurate attempt at reagent e.g. “manganate” or
“manganate(IV)” or incorrect formula or no acid, penalise M1 only
and mark on
Credit alkaline / neutral KMnO4 for possible full marks but M3
gives brown precipitate or solution goes green
Apply similar guidance for errors in the formula of iodine or
concentrated sulfuric acid reagent as those used for other
reagents.
3

(c) M1 Any soluble chloride including hydrochloric acid (ignore concentration)

M2 white precipitate or white solid / white suspension
M3 remains colourless or no reaction or no (observed) change or no precipitate or
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clear solution or it remains clear
OR as an alternative
M1 Any soluble iodide including HI
M2 yellow precipitate or yellow solid / yellow suspension
M3 remains colourless or no reaction or no (observed) change or no precipitate or
clear solution or it remains clear
OR as an alternative
M1 Any soluble bromide including HBr
M2 cream precipitate or cream solid / cream suspension
M3 remains colourless or no reaction or no (observed) change or no precipitate or
clear solution or it remains clear
OR as an alternative
M1 NaOH or KOH or any soluble carbonate
M2 brown precipitate or brown solid / brown suspension with NaOH / KOH
(white precipitate / solid / suspension with carbonate)
M3 remains colourless or no reaction or no (observed) change or no precipitate or
clear solution or it remains clear
If no reagent or incorrect reagent or insoluble chloride in M1, CE =
0 and no marks for M1, M2 or M3
Allow chlorine water
If incomplete reagent (e.g. chloride ions) or inaccurate attempt at
formula of chosen chloride, or chlorine, penalise M1 only and
mark on
For M2 require the word “white” and some reference to a solid.
Ignore “cloudy solution” OR “suspension” (similarly for the
alternatives)
For M3
Ignore “nothing (happens)”
Ignore “no observation”
Ignore “clear” on its own
Ignore “dissolves”
3

(d) M1 Any soluble sulfate including (dilute or aqueous) sulfuric acid

M2 remains colourless or no reaction or no (observed) change or no precipitate or
clear solution or it remains clear
M3 white precipitate or white solid / white suspension
If no reagent or incorrect reagent or insoluble sulfate in M1, CE =
0 and no marks for M1, M2 or M3
Accept MgSO4 and CaSO4 but not barium, lead or silver sulfates
If concentrated sulfuric acid or incomplete reagent (e.g. sulfate
ions) or inaccurate attempt at formula of chosen sulfate, penalise
M1 only and mark on
For M3 (or M2 in the alternative) require the word “white” and
some reference to a solid.
Ignore “cloudy solution” OR “suspension”
For M2 (or M3 in the alternative)
Ignore “nothing (happens)”
Ignore “no observation”
Ignore “clear” on its own
Ignore “dissolves”
OR as an alternative
M1 NaOH or KOH
M2 white precipitate or white solid / white suspension
M3 remains colourless or no reaction or no (observed) change or no precipitate or
clear solution or it remains clear
If incomplete reagent (e.g. hydroxide ions) or inaccurate attempt at
formula of chosen hydroxide, penalise M1 only and mark on
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If M1 uses NH3 (dilute or concentrated) penalise M1 only and
mark on
3
[12]

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E4. This question was generally well answered. The mechanism in part (b) discriminated well
with the full range of marks scored and 60% of the candidates scoring at least 3 marks. The
new part of the Specification tested in part (c)(ii) was answered well.

E5. Providing the students with the basic information for the elimination reaction in part (a)(i)
enabled most students to score at least one mark and more than half scored full marks.
Structures of E and Z isomers were generally well understood and many students could score
at least one mark in their answers to the meaning of the term stereoisomers.
The mechanism in part (b) is demanding and discriminated very well

E6.The two mechanisms in parts (b) and (c) continue to challenge some and full marks were scored
by fewer than 60% of the students in both cases.

E8. Part (a) proved straightforward for most candidates, although some of the weakest did have
problems in knowing which compounds they were trying to draw. While the most able found part
(b) of this question relatively trivial and scored full marks, it is clear that mechanisms continue to
be a challenge for the less able candidates. Almost all of the candidates attempted the
questions and a large majority were able to score at least 3 of the 7 marks available in part (b).
The usual difficulties associated with the position and direction of curly arrows and either
incomplete hydroxide ions or attempts to use an apparently covalent sodium hydroxide resulted
in the loss of marks. The mechanism in (b)(ii) is one of the more demanding parts of the
specification and the weakest candidates struggled to score any marks here.

E9. This was a relatively high-scoring question, although the correct name was only given by
33% of the candidates in part (a). Infrared spectroscopy is an area which candidates are finding
very accessible and although 90% identified the correct isomer in part (e), only 51% were able
to obtain both marks in part (e)(ii).

E10.Part (a) was answered quite well. The naming of P and Q was a challenge for some with a
demand both for correct spelling and correct use of the alphabet for functional groups and this
led to only 48% scoring both marks. This question included two curly arrow mechanisms and
these questions always result in the best discrimination of student performance. Part (b) and
part (c) provided an excellent distribution across the full range of marks with the usual errors
seen, such as an incorrect carbocation in part (b), a negative charge on ammonia in part (c)
and, in both parts, a failure to use either a lone pair of electrons or a bond as the origin of a pair
of electrons. It was essential in part (d) to identify a reagent, in order to be able to access the
reaction condition mark and some excellent responses were seen. It is worth reminding
students that as a general guide, a reagent is something that you get out of a bottle; for
example, sodium hydroxide and not hydroxide ion. Part (e) also discriminated well with most
students able to write the equation and then to identify sulfur dioxide as one of the toxic gases.

E11. The usual mistakes were made in naming but parts (a)(i) and (ii) were high scoring. In part
(a)(iii) many candidates were unable to draw a correct displayed formula and the type of
isomerism was frequently incorrect. Many candidates had little difficulty in part (a)(iv) with
drawing the (E) isomer. Part (b)(i) was well answered with 84% gaining some credit, even
though a correctly assigned spectrum needed a reason, which included both the particular
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bonding and the infrared range. The type of structural isomerism was less well answered and
only a quarter of the candidates recognised that it must be cyclohexane.

E13.Organic reaction mechanisms discriminate well. Schools and colleges still need to heed the
advice that full marks will only be awarded in a mechanism such as that in part (b) if the positive
charge on the intermediate alkylammonium ion is placed on the N atom and not on or adjacent
to a hydrogen atom. Over 80% scored at least 3 marks on both parts (a) and (b). A surprising
number of students were unable to name substance X correctly in part (c).

E14.This was a straightforward question but care was needed in presenting structures. It has been a
feature of the general guidance for many years that we are lenient with C–H C (for C–CH ) but
3 3

not with C–HO (for C–OH) and not with C–NC (for C–CN). This question was no exception. As
a consequence, some marks were lost in parts (a)(i) and (b) by poorly presented structures. In
part (b) the structure of the repeating unit was required and answers which included “n” were
not accepted as these answers indicated the structure of the polymer.
Infrared spectroscopy questions are high scoring and in almost a third of all students scored
both marks in part (b).

E15.This was a high demand question, since it requires application of chemistry from the specification
and a failure to provide a suitable test reagent leads to the loss of three marks in each part. The
number of possible answers to distinguish silver nitrate in part (c) was considerable and partial
credit was awarded for test reagents that were unsuitable for test-tube tests, but which led to
correct chemical observations. Less than one third of students scored all three marks on part (c)
and part (d), whereas three quarters scored full marks on part (b).

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