Q1.

The skeletal formulas of two compounds are shown.

Which method would distinguish between samples of these compounds?

A comparing fingerprint regions of their infrared spectra

B obtaining molecular masses from their high resolution

mass spectra
C warming with acidified potassium dichromate(VI)
solution
D warming with Tollens’ reagent

(Total 1 mark)

Q2.
Which compound forms a racemic mixture when reacted with KCN followed by dilute acid?

A HCHO

B CH3CHO

C CH3COCH3

D (CH3CH2)2CO
(Total 1 mark)
Q3.
This question is about rates of reaction.
Iodine and propanone react together in an acid-catalysed reaction

CH3COCH3(aq) + I2(aq) → CH3COCH2I(aq) + HI(aq)

A student completed a series of experiments to determine the order of reaction with respect to
iodine.

Method
• Transfer 25 cm3 of 1.0 mol dm–3 propanone solution into a conical flask.
• Add 10 cm3 of 1.0 mol dm–3 HCl(aq)
• Add 25 cm3 of 5.0 × 10–3 mol dm–3 I2(aq) and start a timer.
• At intervals of 1 minute, remove a 1.0 cm3 sample of the mixture and add each sample to
a separate beaker containing an excess of NaHCO3(aq)
• Titrate the contents of each beaker with a standard solution of sodium thiosulfate and
record the volume of sodium thiosulfate used.

(a) Suggest why the 1.0 cm3 portions of the reaction mixture are added to an excess of
NaHCO3 solution.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(b) Suggest why the order of this reaction with respect to propanone can be ignored in this
experiment.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
The volume of sodium thiosulfate solution used in each titration is proportional to the
concentration of iodine in each beaker.

The table below shows the results of the experiment.

Time / Volume of sodium

minutes thiosulfate solution / cm3

1 41

2 35

3 24

4 22

5 16

6 10

(c) Use the results in the table above to draw a graph of volume of sodium thiosulfate solution
against time.

Draw a line of best fit.

(3)
(d) Explain how the graph shows that the reaction is zero-order with respect to iodine in the
reaction between propanone and iodine.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) The Arrhenius equation can be written as

The figure below shows a graph of ln k against for the reaction

2 HI(g) → H2(g) + I2(g)

Use the figure above to calculate a value for the activation energy (Ea), in kJ mol−1, for this
reaction.

The gas constant R = 8.31 J K−1 mol−1

Ea ____________________ kJ mol−1
(3)
(Total 12 marks)
Q4.
Which statement about the industrial production of ethanol from ethene at 300 °C is correct?

C2H4(g) + H2O(g) ⇌ C2H5OH(g) ΔH = –46 kJ mol–1

A An increase in pressure decreases the equilibrium

yield of ethanol.
B An increase in pressure increases the value of Kc

C An increase in temperature increases the equilibrium

yield of ethanol.
D An increase in temperature decreases the value of Kc

(Total 1 mark)

Q5.
This question is about gaseous equilibria.

The diagram below shows the effect of pressure on the percentage yield of a reaction at
equilibrium at two different temperatures.

(a) Explain how the diagram shows that the forward reaction in this equilibrium is exothermic.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(b) State whether the forward reaction in this equilibrium results in an increase, decrease or
no change in the amount, in moles, of gas.

Explain your answer.

Tick (✓) one box.

increase

decrease

no change

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Explain why using a catalyst has no effect on the percentage yield.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

Hydrogen and nitrogen react to form ammonia.

3 H2(g) + N2(g) ⇌ 2 NH3(g)

At 745 K, the equilibrium constant, Kc = 0.118 mol–2 dm6

(d) At 745 K, 0.150 dm3 of an equilibrium mixture contains 0.0285 mol of hydrogen and
0.0870 mol of nitrogen.

Calculate the amount, in moles, of ammonia present in this equilibrium mixture.

Amount of ammonia __________ mol

 (5)

(e) Calculate the value, at 745 K, for the equilibrium constant Kc for this dissociation of
ammonia to give hydrogen and nitrogen.

State the units.

2 NH3(g) ⇌ 3 H2(g) + N2(g)

Value _______________

Units _______________
(2)
(Total 13 marks)

Q6.
1-Methylcyclohexene and limonene are cyclic alkenes with a citrus smell.
1-Methylcyclohexene is manufactured and used in the chemical industry.
Limonene is found naturally in orange peel.

(a) 1-Methylcyclohexene reacts with HBr to form two structural isomers.

The major product is 1-bromo-1-methylcyclohexane.

Name and outline the mechanism for the formation of this major product.

Name of mechanism __________________________________________

Outline of mechanism
 (5)

(b) Draw the skeletal formula of the minor product formed in the reaction in part (a).

Explain why the products are formed in different amounts.

Skeletal formula

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(4)

(c) Draw the structure of the major product when an excess of HBr reacts with limonene.

(1)
(Total 10 marks)
Q7.
What is the IUPAC name of the major product of the reaction between 2-ethylbut-1-ene and
hydrogen bromide?

A 1-bromo-2-ethylbutane

B 2-bromo-2-ethylbutane

C 2-bromo-2-methylpentane

D 3-bromo-3-methylpentane

(Total 1 mark)

Q8.
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.

(1)

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

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)
Q9.
The alkene (E)-but-2-enenitrile is used to make acrylic plastics.
The structure of (E)-but-2-enenitrile is

(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.

Feature 1 ___________________________________________________________

___________________________________________________________________

___________________________________________________________________

Feature 2 ___________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 5 marks)
Q10.
Use the Data Booklet to help you answer this question about amino acids.
The diagram shows parts of two polypeptide chains in a beta-pleated sheet of a protein.

(a) The polypeptide chains are held together by hydrogen bonding as shown in the diagram.

Explain how these hydrogen bonds form.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(b) A different type of bond can form between two polypeptide chains when the chains each
contain the amino acid cysteine.

Complete the structure to show the bond that forms between the side chains of two
cysteine molecules.

(1)

(c) The type of bond in part (b) between two polypeptide chains influences the three-
dimensional structure of the protein.

Name this type of protein structure.

___________________________________________________________________
(1)
 (d) Draw the structure of the zwitterion of a dipeptide formed by alanine and serine.
(2) (Total 6 marks)

Q11.
This question is about the preparation of 2,3,3-trimethylbut-1-ene.

The preparation is done by heating the alcohol with concentrated phosphoric acid, that acts as
a catalyst.

The figure below shows the apparatus used.

The distillate is collected in the range 77–82 °C

(a) Explain why the water should enter the condenser at the bottom and not at the top.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(b) Name and complete the mechanism for this reaction.

Name of mechanism _________________________________________________

(4)

(c) In a similar experiment, 12.0 cm3 of 2,3,3-trimethylbutan-1-ol (Mr = 116.0) produces 6.12 g
of 2,3,3-trimethylbut-1-ene.

Calculate the percentage yield.

density of 2,3,3-trimethylbutan-1-ol = 0.818 g cm–3

Percentage yield ____________________

(5)
(Total 11 marks)
Q12.
This question is about compound Z, with molecular formula C7H12O3

Figure 1 shows the infrared spectrum of Z.

Figure 1

(a) Identify the bond that causes the absorption at 1725 cm–1

___________________________________________________________________

Figure 2 shows the 13C NMR spectrum of Z.

Figure 2

(1)

(b) How many different carbon environments are there in a molecule of Z?

5 6 7 8

Tick ✓ one
box
(1)

(c) State the type of carbon environment that causes the peak at ẟ = 174 ppm

Use Table C in the Data Booklet to help you answer this question.
 ___________________________________________________________________ (1)

(d) the table below shows data from the 1H NMR spectrum for compound Z.

Chemical shift ẟ /
4.10 2.60 2.56 2.19 1.26
ppm

Integration ratio 2 2 2 3 3

Splitting pattern quartet triplet triplet singlet triplet

Explain what can be deduced from the splitting patterns and chemical shift values for the
peaks at ẟ = 4.10 ppm and at ẟ = 1.26 ppm

Deduce the part of the structure of Z that causes the peaks at

ẟ = 4.10 ppm and ẟ = 1.26 ppm

Use Table B in the Data Booklet to help you answer this question.

Peak at ẟ = 4.10 ppm _________________________________________________

___________________________________________________________________

___________________________________________________________________

Peak at ẟ = 1.26 ppm _________________________________________________

___________________________________________________________________

___________________________________________________________________

Part of structure

(5)

(e) Deduce the part of the structure of Z that causes the peak at ẟ = 2.19 ppm

Part of structure

(1)
Figure 3 shows the 1H NMR spectrum of compound Z.

Figure 3

(f) Suggest why it would be difficult to determine the structure of Z using the spectrum in
Figure 3, without the information in the table in part (d).

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(g) Deduce the structure of Z.

(1)
(Total 11 marks)
Q13.
This question is about the primary amine CH3CH2CH2NH2

(a) The amine CH3CH2CH2NH2 reacts with CH3COCl

Name and outline a mechanism for this reaction.

Give the IUPAC name of the organic product.

___________________________________________________________________

___________________________________________________________________
(6)

(b) Isomers of CH3CH2CH2NH2 include another primary amine, a secondary amine and a
tertiary amine.

(i) Draw the structures of these three isomers.

Label each structure as primary, secondary or tertiary.

(3)
 (ii) Use Table 1 on the Data Sheet to explain how you could use infrared spectra in the
range outside the fingerprint region to distinguish between the secondary amine and
the tertiary amine.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(c) The amine CH3CH2CH2NH2 can be prepared by two different routes.

Route A is a two-stage process and starts from CH3CH2Br.

Route B is a one-stage process and starts from CH3CH2CH2Br.

(i) Identify the intermediate compound in Route A.

Give the reagents and conditions for both stages in Route A and the single stage in
Route B.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(7)
 (ii) Give one disadvantage of Route A and one disadvantage of Route B.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)
(Total 20 marks)

Q14.
This question is about the reaction scheme shown.

(a) State the reagents needed for step 1 and the reagents needed for step 2.

step 1 _____________________________________________________________

___________________________________________________________________

step 2 _____________________________________________________________

___________________________________________________________________
(3)

(b) Give the name of the mechanism for the reaction in step 3.

___________________________________________________________________
(1)
(c) Name the reagent for step 4.

State a necessary condition for step 4.

Reagent ___________________________________________________________

Condition __________________________________________________________
(2)

(d) Amine A is formed in step 2 and amine B is formed in step 5.

Explain why the yield of B in step 5 is less than the yield of A in step 2.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(e) Explain why amine B is a stronger base than amine A.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)
(Total 10 marks)
Q15.
The concentration of dilute hydrochloric acid can be found by titration using a standard solution
of barium hydroxide.

(a) Calculate the mass, in g, of solid barium hydroxide (Mr = 171.3) needed to prepare 250
cm3 of 0.100 mol dm–3 barium hydroxide solution.

Mass ____________________ g
(1)

(b) The mass of barium hydroxide from part (a) is dissolved in a beaker containing 150 cm3 of
distilled water.

Describe how this solution is used to make 250 cm3 of the

0.100 mol dm–3 barium hydroxide solution.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Before the first titration, the 25 cm3 pipette is rinsed with a small volume of the 0.100 mol
dm–3 barium hydroxide solution.

State why it is good practice to rinse the pipette in this way.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(d) Hydrochloric acid is added to the burette using a funnel.

State why it is good practice to remove the funnel from the burette before the titration.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e) In a different experiment, 0.952 g of solid barium hydroxide is used to make 250 cm 3 of
standard barium hydroxide solution.

25.0 cm3 of this barium hydroxide solution reacts with exactly

24.50 cm3 of hydrochloric acid.

Calculate the concentration of the hydrochloric acid.

Concentration ____________________ mol dm–3

(3)

(f) The uncertainty in the 25.0 cm3 of solution from the pipette is ±0.05 cm3

The total uncertainty in the 24.50 cm3 of solution from the burette is ±0.15 cm3

Calculate the total percentage error in using the pipette and burette.

Percentage error ____________________

(1)
(Total 10 marks)
Q16.
Test-tube reactions can be used to identify the functional groups in organic molecules.

You are provided with samples of each of the four compounds.

Describe how you could distinguish between all four compounds using the minimum number of
tests on each compound.

You should describe what would be observed in each test.

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________
(Total 6 marks)
Mark schemes

Q1.
A
comparing fingerprint regions of their infrared spectra
[1]

Q2.
B
[1]

Q3.
(a) The sodium hydrogencarbonate solution neutralises the acid (catalyst)
M1

So stops the reaction

M2

(b) The concentration/amount of propanone is much larger than/200 times

larger than the concentration/amount of iodine
M1

Concentration of propanone is (almost) constant

The change in concentration in propanone is negligible
M2

(c)

M1
 Suitable axes (plotted points must take up at least half of the grid)
M2

For all points correctly plotted to ± 1/2 small square

For straight line of best fit which avoids the anomalous plot M1
M3

(d) The graph is a straight line / has a constant gradient

M1

So the rate of reaction does not change as the concentration (of iodine)
changes / the iodine is being used up at a constant rate.
Correct rate vs conc graph scores M2
M2

(e) Gradient = (−14.1 − −2.8) / (0.00180 − 0.00128)

= −11.3 / 0.00052
= −21731
Allow -21330 to -22130
M1

Gradient = −Ea / R
−Ea = their answer x 8.31 ( = 180583 J mol-1)
M2

Ea = M2 ÷ 1000 (= 181 kJ mol-1)

M3
[12]

Q4.
D
An increase in temperature decreases the value of Kc
[1]

Q5.
(a) Lower yield at higher temperature
Allow converse arguments

Higher yield at lower temperature

1

So, equilibrium has shifted backwards/left/in the endothermic direction to

oppose the increase in temperature
So, equilibrium has shifted forwards/right/in the exothermic
direction to oppose the decrease in temperature
1
Ignore reference to pressure

(b) Increase
1

Lower yield at higher pressure

Higher yield at lower pressure
1
 So, equilibrium has shifted backwards/to the side with fewest number of
moles to oppose the increase in pressure
So, equilibrium has shifted forwards/to the side with highest
number of moles to oppose the decrease in pressure
1
Ignore reference to temperature

(c) Increases the rate of forwards and reverse reactions equally

1

(d)
M1: Kc expression
1

0.118 =
M2: converts moles to concentration; divides mole quantities
by 0.150
1

0.118 =
[NH3]2 = 4.69 × 10–4
M3: calculation of [NH3]2
1

[NH3] = 0.0217 mol dm–3

M4 = √M3
1

n(NH3) = 0.0217 × 0.150 = 3.25 × 10–3 mol

M5 = M4 × 0.150 (allow ecf on an incorrect volume used in
M2)
If Kc upside down then can still score 4)
1

(e)
Allow 8.45 − 8.5
1

Units – mol2 dm–6

1
[13]

Q6.
(a) M1 electrophilic addition
 M2 must show an arrow from the double bond towards the
H atom of the HBr molecule

M3 must show the breaking of the H-Br bond

M4 is for the structure of the correct carbocation (the added H does not need to be
shown)

M5 must show an arrow from the lone pair of electrons on the negatively charged
Br towards the positively charged atom of their carbocation drawn
All arrows are double-headed. Penalise one mark from the
total if half headed arrows are used
Do not penalise the “correct” use of “sticks”
Penalise only once in mechanism for a line and two dots to
show a bond
Mechanism can involve skeletal or structural formulae. If
skeletal, do not penalise presence of hydrogen atoms (and
bonds)

Max 3 of 4 marks (M2-5) for wrong organic reactant or

wrong carbocation (ignore structure of product)

Ignore partial negative charges on the double bond in M2

Penalise incorrect partial charges on the H-Br bond or formal

charges in M3

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

For M5, credit attack on a partially positively charged

carbocation structure, but penalise M4 for the structure of
the carbocation.
5

(b) M1
M1 Penalise inclusion of —H bonds

(allow carbonium ion in place of carbocation)

M2 idea that 1-bromo-1-methylcyclohexane is formed

 from/via or has more stable carbocation
M2 and M3 must refer to stability of carbocations (ignore
reference to stability of products)

M3 idea that major product from tertiary carbocation rather

than secondary carbocation
M3 allow descriptions in terms of number of alkyl groups
attached to positive C atom

M4 idea of stability from greater (positive) inductive effect

(from more alkyl/C groups) or more electron-releasing
alkyl/C groups
M4 must be a comparison
4

(c)

Any correct form of the structure

1
[10]

Q7.
D
3-bromo-3-methylpentane
[1]

Q8.
(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
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]

Q9.
(a) (i) Structure of (Z)-but-2-enenitrile with or without either or both of the CH 3 and
the CN groups displayed

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 1
Absorption / peak in the range 2220 to 2260 cm−1 or specified value in this
range or marked correctly on spectrum
 and
(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 2
Absorption / peak in the range 1620 to 1680 cm−1 or specified value in this
range or marked correctly on spectrum
and
(characteristic absorption / peak for) C=C group / alkene / carbon-carbon
double bond
Ignore reference to other absorptions eg C-H
Either order.
2
[5]

Q10.
(a) electron deficient H
Allow H delta plus / slightly positive
M1

(Which attracts) lone pair/electron pair on O

Penalise lone pair/electron pair donation
M2

(b)
Penalise dashed/dotted S—S
Ignore extra additions to structures
1

(c) Tertiary or Quaternary

Allow 3° or 4°
do not penalise minor error in spelling e.g. Quarternary
1

(d)

OR
 Incorrect peptide bond CE=0
M1 for correct dipeptide
M2 for correct charges
Ignore additional dipeptide in working
Allow –CONH— or –COHN—
1
1
[6]

Q11.
(a) M1 idea of ensuring condenser fills with water

M2 idea that condenser is cool(er) or

ensuring (more) vapour condenses

2

(b) M1 elimination

M1 ignore dehydration; ignore reference to acid-catalysed

M2 correct protonated intermediate with OH2+

M3 loss of H2O: correct arrow from middle of C-O bond to the O

M4 loss of H+: correct arrow from middle of correct C-H

bond to correct C-C bond
M2 + charge anywhere on OH2 group
M3 and M4 can be two separate steps or all in one step - if
two steps shown then the correct carbocation is part of M4
Ignore structure of product
For M3/4, penalise extra arrows on the original structure (or
elsewhere) that contradict “correct” ones
4

(c) Correct answer scores 5

M1 mass of alcohol = 12 × 0.818 (= 9.816 g)

M2 amount of alcohol = (= 0.0846 mol)

 M3 Mr of alkene = 98(.0)

M4 mass of alkene expected = M2 × M3 (= 8.29 g)

M5 % yield = × 100 = 73.8% (at least 2sf)

Alternative

M4 mol of alkene formed = (= 0.0624 mol)

M5 % yield = × 100 = 73.8% (at least 2sf)

Allow ECF at each stage

M5 should be an attempt at (their) mass (or moles) of alkene

achieved divided by their mass (or moles) of alkene
expected x 100
5
[11]

Q12.
(a) C=O
1

(b) Tick in the box for 7 ONLY

1

(c)

Ignore acids
1

(d) M1 (Quartet) because neighbouring C has 3H

M2 (At ẟ = 4.1 ppm) because connected to single bonded O of ester or

M3 (Triplet) because neighbouring C has 2H

M4 (At ẟ = 1.26 ppm) because R2CH2 or RCH3

M5

Ignore use of integration

5

(e)
 1

(f) Cannot deduce splitting patterns of peaks (at about ẟ = 2.60)

Or

No integration values
Allow
Peaks at ẟ = 2.60 and ẟ = 2.56 ppm overlap
OR
spectrum at ẟ = 2.60 is second order
1

(g)

1
[11]

Q13.
(a) (nucleophilic) addition-elimination
1

M4 for 3 arrows and lp

Allow wrong amine in M1 but penalise in M3

Allow C3H7 in M3

Minus sign on NH3 loses M1 (but not M4 if NH3 also shown here)
• Allow attack by: NH2CH2CH2CH3
• M2 not allowed independent of M1, but allow M1 for
 correct attack on C+
• + rather than δ+ on C=O loses M2
• If Cl lost with C=O breaking, max 1 for M1
• M3 for correct structure with charges but lone pair on O is
part of M4
• 3 arrows in M4 can be shown in two separate steps.
• If M3 drawn twice, mark first answer eg ignore missing + if
missed off second structure
• Only allow M4 after correct / very close M3
• For M4, ignore RNH2 removing H+ but lose M4 for Cl–
removing H+ in mechanism,
• but ignore HCl shown as a product.
4

N-propylethanamide must be this name even if wrong amine used

NOT N-propylethaneamide
1

(b) (i)

Not allow ambiguous C3H7NH2

BEWARE No mark for the original amine CH3CH2CH2NH2
Label and structure must both be correct for each type to
score the mark.
1

Allow C2H5
Penalize wrong number of carbons but otherwise correct,
first time only.
1

(ii) Absorption at 3300−3500 (cm−1) in spectrum

Allow trough, peak, spike.
Ignore absorption at 750 − 1100 for C–C bond in secondary
- this is within fingerprint region.
Allow any number in this range.
If range missing, no further marks.
If range linked to tertiary, no further marks.
1

N–H (bond) (only) present in secondary amine or not present in tertiary

amine
OR
 This peak or N–H absorption (only) present in spectrum of secondary
amine or not present in spectrum of tertiary amine
1

(c) (i) M1 Route A: stage 1 KCN

Apply list principle for extra reagents or catalysts
NOT HCN NOT KCN / acid Not KCN / HCN
1

M2 Aqueous or ethanolic
M2 only scores after correct M1
ignore warm; acid here loses M1 & M2
1

M3 Route A Intermediate CH3CH2CN or propanenitrile

If M3 intermediate wrong, max 2 for M1 & M2 ie no mark for
stage 2

Name alone must be exactly correct to gain M1 but mark on if name

close
But if M3 intermediate close, eg “nitrile” or wrong nitrile, can
award marks in stage 2

correct formula gains M1 (ignore name if close)

If stage 1 correct and intermediate is missing, can award
marks in stage 2

contradiction of name and formula loses mark

stage 1 wrong & intermediate missing, no marks.
1

M4 Route A: stage 2 H2

H loses M4 but mark on

LiAlH4
Apply list principle for extra reagents or catalysts.
M5 only scores after correct M4
Not NaBH4 not Sn or Fe / HCl
Allow (dil) acid after but not with LiAlH4
Penalise conc acid.
1

M5 Ni or Pt or Pd

ether
1

M6 Route B NH3
With acid loses M6 & M7
Apply list principle for extra reagents or catalysts.
1

M7 Excess NH3
Ignore conc, ignore high P, ignore solvent.
1
 (ii) Route A disadv Toxic / poisonous KCN or cyanide or CN− or
HCN

Expensive LiAlH4
ignore acidified

OR lower yield because 2 steps

Allow H2 flammable / explosive etc.
Not just dangerous.
Ignore time reasons.
1

Route B disadv Further reaction / substitution likely

Allow impure product.
1
[20]

Q14.
(a) Step 1 Conc HNO3
M1

Step 1 Conc H2SO4

If conc missing in both allow 1 for HNO3 and H2SO4
M2

Step 2 Sn and HCl

Allow Fe and HCl or Ni and H2
M3

(b) (nucleophilic) addition-elimination

1

(c) Chlorine
Allow Cl2
M1

UV (light)
Allow sunlight / High temp (above 300°C)
M2

(d) In Step 5 further substitution / gives other amine products

1

In Step 2 only one amine

1

(e) In B Alkyl group is electron donating or positive inductive effect

Or In A lone pair (on N partially) delocalised
1

Lone pair on N more available

Lone pair on N less available
1
[10]
Q15.

(a) = 4.28 g
Allow 4.3 g
1

(b) M1 Transfers the solution to a volumetric/graduated flask

M2 Add washings using distilled water and make up to the

graduation mark/250 cm3

M3 Invert many times / shake to mix

3

(c) So that the titration is done with known concentration of Ba(OH)2

Allow so that water does not dilute the solution
Allow remove water/prevent contamination
1

(d) Drops of acid could fall into the burette (so no longer know
how much has been added from burette)

OR

Decreases titre
Ignore changes the titre
Do not accept increases titre
1

(e) M1 n Ba(OH)2 in 25 cm3 = = 5.56 x 10-4 mol

M2 n HCl in 24.5 cm3 = 2 x 5.56 x 10-4 = 0.00111 mol

M2 = M1 x 2

M3 Concentration of HCl = = 0.045 mol dm-3

M3 =
3

(f) x 100% = 0.8(1)%

1
[10]

Q16.
This question is marked using Levels of Response. Refer to the Mark Scheme
Instructions for Examiners for guidance.

Level 3 (5 – 6 marks)
All stages are covered and each stage is generally correct and virtually complete.
Answer is communicated coherently and shows a logical progression from Stage 1 to
Stages 2 and 3 to distinguish all the compounds with results for all remaining compounds
stated.
Describing subsequent organic test on product (unnecessary) - limits to lower mark in
level

Level 2 (3 – 4 marks)
All stages are covered but stage(s) may be incomplete or may contain inaccuracies
OR two stages are covered and are generally correct and virtually complete.
Answer is communicated mainly coherently and shows a logical progression from Stage 1
to Stages 2 and 3.
Describing subsequent organic test on product (unnecessary) - limits to lower mark in
level

Level 1 (1 – 2 marks)
Two stages are covered but stage(s) may be incomplete or may contain inaccuracies OR
only one stage is covered but is generally correct and virtually complete.
Answer includes isolated statements but these are not presented in a logical order.

Level 0 (0 marks)
Insufficient correct chemistry to gain a mark.

Indicative chemistry content

Stage 1: An initial test to separate into two groups (2 groups of 2 OR 1 group of 3 and 1
group of 1)

Stage 2: A second test to distinguish within a group or to separate into two further groups

Stage 3: A third test leads to a set of results/observations which distinguishes between all
4 compounds

Tests must include reagent and observation which identifies compound(s)

−
COOH
a) NaHCO3 / Na2CO3 (or correct alternative)
b) effervescence /gas turns limewater milky
c) K and /or M but not L and/or N
-OH and -CHO
d) acidified K2Cr2O7
e) solution turns green
f) K and/or L and/or N but not M
-CHO
g) Fehlings OR Tollens
h) red ppt OR silver mirror
i) N only but not K and/or L and/or M
-Br
j) Silver nitrate
k) cream ppt
l) L and/or N but not K and/or M

Isolated tests on individual compounds - max LEVEL 2

Isolated tests not linked to any compound – max LEVEL 1
Penalise observation if deduction wrong, but allow observation if deduction
incomplete

Alternative tests

-COOH -COOH -OH only

a) named alcohol & a) named indicator m) named carboxylic
H2SO4 b) correct colour acid & H2SO4
b) sweet smell (of c) K and /or M but not n) sweet smell (of
ester) L and/or N ester)
c) K and /or M but not o) K and/or L but not
L and/or N M and /or N

Test Tests
K L M N
for

a) NaHCO3 / Mg
KM ✓ ✘ ✓ ✘
/ Indicator

d) K2Cr2O7 / H+ KLN ✓ ✓ ✘ ✓

g) Fehlings /
N ✘ ✘ ✘ ✓
Tollens

j) AgNO3 see
LN ✘ ✓ ✘ ✓
Note *

a) named
alcohol & KM ✓ ✘ ✓ ✘
H2SO4

m) named
carboxylic KL ✓ ✓ ✘ ✘
acid & H2SO4

Note * allow NaOH then HNO3, AgNO3 as one test; but treat NaOH, AgNO3 without acid as
incomplete,so can mark on.
[6]