T1-2P2 [156 marks]

[1 mark]
1a.

Markscheme
compounds with same structural/displayed formula but different arrangements of atoms (in space);

Do not accept different 3D structures.

Do not allow similar instead of same.

Examiners report
This was the least popular question in Section B. In part (a) (i), some candidates gave a definition of structural isomers instead of
stereoisomers.

[4 marks]
1b.

Markscheme
6.93 × 10−312.01
Mass of C: 44.01
= 1.89 × 10−3/0.00189 (g) and
2× 1.01 × 2.83 × 10−3
Mass of H: 18.02
= 3.17 × 10− 4/0.000317 (g);

Mass of O: 3.00 × 10−3 − 1.89 × 10−3 − 3.17 × 10− 4 = 7.93 × 10− 4/0.000793 (g);
1.89 × 10−3
nC : 12.01
= 1.57 × 10− 4/0.000157 (mol) and
3.17 × 10−4
nH : 1.01
= 3.14 × 10− 4/0.000314 (mol) and
7.93 × 10−4
nO : 16.00
= 4.96 × 10−5/0.0000496 (mol);

Empirical formula = C 3H6O;

Allow C19H38O6.

Award [4] for correct final answer if alternative working is used.

Award [1 max] for C3H6O/C19H38O6 without working.

Examiners report
Part (b) (i) proved to be very challenging for candidates. A large majority of candidates in fact did not know how to even commence the
problem. There were a number of G2 comments all of who stated that it would have been better if the ratios of the amounts of C, H and
O were in fact closer to whole number ratios.

[1 mark]
1c.

Markscheme
C 6H12O2;

Examiners report
In part (ii) of the question the molar mass of the ester was given as 116.18 g mol− 1, which meant that taking the experimental data
given in (b) (i), the empirical formula is in fact C 3H6O, with the associated molecular formula of C 6H12O2. The better students realised
this and typically gave an answer of C 3H6O. However, a very small minority did in fact use a scaling factor to suggest an empirical
formula of C 19H38O6, which was also accepted. In general however for this question, candidates tended to score either scored full
marks for parts (i) and (ii), or zero.
 [2 marks]
1d.

Markscheme
Accept either one of the following two E2 mechanisms:

OR

curly arrow going from lone pair/negative charge on O in HO− to H on β–C;

Do not allow curly arrow originating on H in HO –.

curly arrow going from CH bond to form C=C bond;

curly arrow showing Br leaving;

formation of organic product H2C =CH(CH2CH3)/H(CH3)C=CH(CH3) and

Br− and H2O;

For this reaction since a strong negatively charged base, HO – is used, resultant mechanism will be E2. However, accept the
corresponding E1 mechanism.

If E1, allow the following mechanism:

OR
 curly arrow showing Br leaving;

representation of secondary carbocation;

curly arrow going from lone pair on O in H2O to H on C adjacent to

C + and curly arrow going from CH bond to form C=C bond;
+
formation of organic product (H3C)CH=CH(CH3) / H2C =CH(CH2CH3) and Br− and H3O ;

For E1 HO– is an alternative to H 2O, but if used, H2O forms instead of H 3O+.

Examiners report
In part (iii), some candidates did not show the 3D nature of the two enantiomers which was necessary for M1 and only gave 2D
representations. It was encouraging to see a greater percentage of candidates however using tapered (wedge/dash) representations.
For M2, many did not mention the fact that the two optical isomers rotate the plane of polarized light in opposite directions. Some did not
state plane.

[9 marks]
2a.

Markscheme
(i) Empirical formula:

simplest (whole number) ratio of atoms/moles of each element present in a compound/molecule;

Molecular formula:

actual numbers of atoms/moles of each element present in a compound/molecule / whole number multiple of empirical formula;

(ii) n(C) = 4.54 (mol), n(H) = 9.11 (mol) and n(O) = 2.27 (mol);
C 2H4O;
Accept other valid method for calculation.

(iii) C 4H8O2;
(iv) CH3CH2CH2COOH;
Accept full or condensed structural formulas.

(v) CH3CH2COOCH3/CH3COOCH2CH3/HCOOCH2CH2CH3/HCOOCH(CH3)2;
Accept full or condensed structural formulas.

(vi) Stronger bond:

C=O/double bond;

Longer bond:

C–O/single bond;
 Examiners report
There were some vague and convoluted definitions in (a)(i) but thereafter the calculations were well done. Where difficulty was found,
was in the formula of an ester in (v), (AS 10.1.11).

[5 marks]
2b.

Markscheme
(i) methoxyethane/ CH3OCH2CH3 as there are only dipole-dipole forces (and van der Waals’ forces) between molecules;

propan-1-ol has hydrogen bonding between molecules;

hydrogen bonding is stronger than dipole-dipole forces;

(ii) propan-1-ol/ CH3CH2CH2OH as it has a smaller hydrocarbon chain;

the longer (non-polar) carbon chain in hexan-1-ol decreases the attraction between the alcohol and the (polar) water molecules /
OWTTE;

Examiners report
The answers to (b)(i) were reasonable, although it was common to state that the intermolecular bonding in methoxyethane is van der
Waals‘. Some G2s took issue with the examination of ethers in organic chemistry; it was, in fact, examined under AS 4.3.2. In (ii), some
mentioned a “larger molecule” rather than a “longer chain” and few were able to explain the attraction (or lack thereof) between the
organic molecule and water.

2c. [6 marks]

Markscheme
graphite:

forms flat hexagonal rings / layers of carbon atoms each (covalently) bonded to 3 other carbon atoms / trigonal planar around C / C has
sp2 hybridization;
layers are held together by weak intermolecular/van der Waals’ forces;

layers can slide over each other;

delocalization of electrons / free moving electrons;

diamond:

all carbon atoms are (covalently) bonded to 4 other carbon atoms / tetrahedral around C / C has sp3 hybridization;

strong covalent bonds;

no delocalized electrons / OWTTE;

Examiners report
Part (c) suggested that there is work to be done on understanding the structures of graphite and diamond. One particular mark lost was
not to state that the reason diamond is hard is because the covalent bonds are strong.

3. [1 mark]

Markscheme
C

Examiners report
[N/A]
4. [1 mark]

Markscheme
D

Examiners report
One respondent stated in the G2 form that technically 1 atm is not standard pressure.

In Table 2 of the Data Booklet the conversion “ 1 atm = 1.01 × 105 Pa” is given, so students should be familiar that 1 atm or
1.01 × 105 Pa can be used for standard pressure.
This question proved to be the most difficult in the paper with only 9.95% of the candidates opting for the correct response D, the vast
majority, 75.79%, chose response C thinking that choice I is incorrect. Candidates should know that the sodium ion is Na+ (assessment
statement 4.1.3) so they should be able to deduce the oxidation number of hydrogen to be −1 (assessment statement 9.1.2) and that
H− is the negative ion in sodium hydride, NaH. Although hydrogen is usually assigned the oxidation number of +1, in metallic hydrides
the oxidation number of hydrogen is −1.

[1 mark]
5.

Markscheme
D

Examiners report
[N/A]

[1 mark]
6.

Markscheme
C

Examiners report
[N/A]

[1 mark]
7.

Markscheme
D

Examiners report
[N/A]

[2 marks]
8a.

Markscheme
0.675 (g) ± 0.002 (g);

Percentage uncertainty: 0.3%;

Accept answers correct to one, two or three significant figures for percentage uncertainty.
 Examiners report
Many students lost easy marks as they forgot to propagate uncertainties.

[3 marks]
8b.

Markscheme
In 25.0 cm 3: n HA = 1.21 × 10−3 (mol);

In 100 cm 3: n HA = 4.84 × 10−3 (mol);

M (= 0.675
) = 139 (g mol− 1);
4.84 × 10−3

Award [3] for correct final answer.

Accept suitable alternative methods.

Examiners report
Many candidates struggled with the concept of mole and the dilution factor added to the difficulty.

[2 marks]
8c.

Markscheme
n C : ( 70.56
12.01
=) 5.88 and nO : ( 23.50
16
=) 1.47 and n H : ( 5.94
1.01
=) 5.88

C 4H4O;
Award [2] for correct final answer.

Accept answers using integer values of molar mass.

Examiners report
Most students determined the empirical formula correctly.

8d. [1 mark]

Markscheme
weak acids partially dissociated/ionized and strong acids completely dissociated/ionized (in solution/water) / OWTTE;

Examiners report
Weak and strong acids were generally correctly defined, though sometimes they were defined in terms of pH.
8e. [2 marks]

Markscheme
strong acids have greater electrical conductivity / weak acids have lower electrical conductivity;

OR

adding a reactive metal / carbonate / hydrogen carbonate;

Accept correct example.

stronger effervescence with strong acids / weaker with weak acids / OWTTE;

OR

adding a strong base;

Accept correct example.

strong acid would increase more in temperature / weak acids increase less in temperature;

Examiners report
The conductivity test appeared frequently and was well described. Many candidates used a strong based, but then went on to describe
a titration method.

9a. [2 marks]

Markscheme
( Mass ofMC =) 139
68.08
= 2;
4H4O

C 8H8O2;
Award [2] for correct final answer.

Examiners report
Errors were carried forward in the marking of (d).

9b. [2 marks]

Markscheme
solution which resists change in pH / changes pH slightly / keeps pH constant / OWTTE;

when small amounts of acid or base are added;

Examiners report
The common error in defining a buffer solution in (f) (i) was to omit “small” in the addition of acid or alkali whilst in (ii) candidates needed
to be more specific about the volume of acid added for full credit.

[2 marks]
9c.

Markscheme
less effective at higher temperatures / more effective between 24 °C and 40 °C than > 40 °C;

pH changes more if the same volume of acid is added at high(er) temperature / OWTTE;
 Examiners report
The common error in defining a buffer solution in (f) (i) was to omit “small” in the addition of acid or alkali whilst in (ii) candidates needed
to be more specific about the volume of acid added for full credit.

10a. [2 marks]

Markscheme
alkene;

alcohol;

Allow hydroxyl (group) but not hydroxide.

ketone;

Accept carbonyl.

Examiners report
Question 7 was answered by relatively few candidates, but those who chose this question were usually well-prepared. In a) (i) and (ii)
most candidates correctly identified two functional groups in cortisone, but some incorrectly named the ketone group as an aldehyde.

[1 mark]
10b.

Markscheme
correctly drawn circle around each of the two functional groups and labelled

1 and 2;

Mark can be scored for (ii) without labels (1 and 2) only if no answer is given in (i).

Apply ECF from (incorrect) functional groups in (i).

Examiners report
Question 7 was answered by relatively few candidates, but those who chose this question were usually well-prepared. In a) (i) and (ii)
most candidates correctly identified two functional groups in cortisone, but some incorrectly named the ketone group as an aldehyde.

[1 mark]
10c.

Markscheme
compounds with same molecular formula but different arrangements of atoms;

Allow compounds with same molecular formula but different structural formulas.

Examiners report
In b) the definition of isomers was reasonably well answered.

10d. [1 mark]

Markscheme
but-2-ene;

Allow 2-butene.
 Examiners report
Most correctly named but-2-ene in c) (i). Some mistakenly said butene which was insufficient.

10e. [1 mark]

Markscheme
;

Examiners report
In c) (ii) most candidates drew the structure of but-1-ene although some drew the original compound.

10f. [2 marks]

Markscheme
Q: CH3CH(OH)CH2CH ;

R: CH3CH2CH2CH3;

Condensed or full structural formulas may be given.

Examiners report
In c) (iii) several candidates identified the product as butan-1-ol rather than butan-2-ol.

[1 mark]
10g.

Markscheme
platinum / palladium / nickel;

Allow Pt / Pd / Ni.

Examiners report
Nearly all identified butane as the second compound and correctly identified a suitable catalyst for this reaction in (c) (iv).
 [4 marks]
10h.

Markscheme
Since secondary bromoalkane could be either S N1 and SN2 so allow S N1 or SN2 for M1 –M4.

SN1:

curly arrow showing Br leaving;

Do not allow arrow originating from C to C–Br bond.

representation of secondary carbocation;

curly arrow going from lone pair/negative charge on O in HO – to C+;

Do not allow arrow originating on H in OH –.

formation of CH3CH(OH)CH2CH3 and Br–;

Allow formation of NaBr instead of Br –.

OR

SN2:

curly arrow going from lone pair/negative charge on O in HO – to C;

Do not allow curly arrow originating on H in OH –.

curly arrow showing Br leaving;

Accept curly arrow either going from bond between C and Br to Br in 2-bromobutane or in the transition state.

Do not allow arrow originating from C to C – Br bond.

representation of transition state showing negative charge, square brackets and partial bonds;

Do not penalize if HO and Br are not at 180° to each other.

Do not award M3 if OH—C bond is represented.

formation of CH3CH(OH)CH2CH3 and Br–;

Allow formation of NaBr instead of Br –.

Examiners report
The mechanism required in c) (v) was either S N1 or SN2. Several candidates produced very clear, correct mechanisms. A few lost
marks for incorrectly having a curly arrow from H instead of O in the nucleophile, or for neglecting to show the curly arrow showing Br
leaving, or for omitting the negative charge on the transition state in SN2.
10i. [1 mark]

Markscheme
H3CCOCH2CH3;

Condensed or full structural formula may be given.

Apply ECF from (c)(iii).

Examiners report
In c) (vi) some candidates thought that an aldehyde formed from oxidation of an alcohol under reflux. Error carried forward was applied
if candidates had given butan-1-ol as the product in c) (iii) and then drew and named butanoic acid here.

[1 mark]
10j.

Markscheme
butan-2-one;

Allow 2-butanone or butanone.

Examiners report
[N/A]

10k. [1 mark]

Markscheme
representation of polymer showing two repeating units;

Brackets not necessary but continuation bonds must be given.

No penalty if methyl groups given on same side.

Examiners report
Drawing two repeating units of the polymer made from but-2-ene caused many problems in c) (viii).

10l. [3 marks]

Markscheme
n C : ( 76.84
12.01
) = 6.398 mol and nH : ( 12.92
1.01
) = 12.79 mol and

n O : ( 10.24
16.00
) = 0.6400 mol;

Allow integer values for atomic masses.

dividing across by lowest number to give integer values;

C 10H20O;
Award [3] for correct final answer.
 Examiners report
Parts d) (i) and (ii) were extremely well answered with most candidates determining the empirical and molecular formulas correctly.

10m. [1 mark]

Markscheme
−
(M (C 10H20O) = 156.30 (gmol 1), therefore empirical formula = molecular

formula =) C 10H20O;

Examiners report
Parts d) (i) and (ii) were extremely well answered with most candidates determining the empirical and molecular formulas correctly.

11a. [1 mark]

Markscheme
compounds with same structural formula but different arrangements of atoms in space;

Award [1] if correct description of geometric and optical isomers given.

Examiners report
A reasonably popular question and often well done. In (a), some weaker candidates did not understand the idea of a stereoisomer.

[1 mark]
11b.

Markscheme
1: sp 2 and 2: sp 3;

Examiners report
(b) and (c) were well done.

11c. [1 mark]

Markscheme
amine;

benzene ring;

Allow phenyl (group).

Do not allow just benzene.

alkene / chloroalkene;

chloro;

ether / phenyl ether;

Ethers not required as per guide but allow if given.

 Examiners report
(b) and (c) were well done.

11d. [2 marks]

Markscheme

Examiners report
In (d), most scored full marks though some gave cis.

[2 marks]
11e.

Markscheme
trans-but-2-ene and cis-but-2-ene;

Allow trans 2-butene and cis 2-butene.

Do not accept just 2-butene or 2-butene.

but-1-ene;

Allow 1-butene.

Examiners report
In (d), most scored full marks though some gave cis. In (ii), many did not gain marks for but-2-ene.
 [4 marks]
11f.

Markscheme
Q: CH3CHBrCH2CH3;

R: CH3CH(OH)CH2CH3;

S: CH3CHBrCHBrCH3;

T: CH3CH(OH)CH2CH3;

Condensed or full structural formulas may be given.

Examiners report
In (d), most scored full marks though some gave cis.

11g. [1 mark]

Markscheme
H3CCOCH2CH3;
Condensed or full structural formula may be given.

Examiners report
In (d), most scored full marks though some gave cis.

[1 mark]
11h.

Markscheme
butan-2-one;

Allow 2-butanone or butanone.

Accept butan-2-one if (v) is incorrect but also apply ECF.

Examiners report
In (d), most scored full marks though some gave cis.
 [4 marks]
11i.

Markscheme
mC : (1.755 × 10− 1 × 12.01)/(44.01) = 4.790 × 10− 2 g and
mH : (7.187 × 10− 2 × 2 × 1.01)/(18.02) = 8.056 × 10−3 g;
mO : (6.234 × 10− 2 − 8.056 × 10−3 − 4.790 × 10− 2) = 6.384 × 10−3 g;
(nC = 3.988 × 10−3 and nH = 2 × 3.988 × 10−3 and nO = 3.988 × 10−3 hence empirical formula = ) C 10H20O;

(M (C 10H20O) = 156.30 (g mol− 1), therefore molecular formula =) C 10H20O;

OR

n CO 2 = ( 1.755 ) = 3.988 × 10−3 and nH2O = ( 7.187 ) = 3.988 × 10−3;

−1 −1
× 10 × 10
44.01 18.02

mO : (6.234 × 10− 2 − 8.056 × 10−3 − 4.790 × 10− 2) = 6.384 × 10−3 g;

(nC = 3.988 × 10−3 and nH = 2 × 3.988 × 10−3 and nO = 3.988 × 10−3 hence empirical formula = ) C 10H20O;

(M (C 10H20O) = 156.30 (g mol− 1), therefore molecular formula =) C 10H20O;

Allow alternative working to be used.

Award [3 max] for C10H20O if no working shown.

Examiners report
(e) (i) also was very well answered compared to some recent sessions.

[1 mark]
11j.

Markscheme
chiral (carbon/centre/atom) / (tetrahedral) carbon surrounded by four

different groups;

Accept chiral compound or chiral molecule.

Examiners report
[N/A]

11k. [1 mark]

Markscheme
polarimeter and (enantiomers) rotate plane of polarized light in (equal and) opposite directions;

Examiners report
Perhaps too much was expected in (iii) for one mark and students either omitted polarimeter or did not refer to plane polarised light.
11l. [2 marks]

Markscheme
Physical properties:

identical except for rotation of plane polarized light;

Accept “identical” as different optical properties assessed in (iii).

Do not accept similar.

Chemical properties:

identical unless they interact with other optically active/chiral compounds/reagents/solvents / identical with achiral
compounds/reagents/solvents / OWTTE;

Allow different physiological effects/taste.

Examiners report
In (iv), few scored both marks.

[1 mark]
12.

Markscheme
B

Examiners report
Some teachers were worried about the use of a skeletal formula for the benzene ring. Certainly skeletal formulas are not on the syllabus
but the benzene ring is.

13. [1 mark]

Markscheme
D

Examiners report
[N/A]

[1 mark]
14.

Markscheme
B

Examiners report
One respondent commented that the question is unfair if candidates are not given the formula of the molecules. The examiners expect
knowledge of simple molecules such as those in this question.
 [1 mark]
15a.

Markscheme
hydroxyl and carbonyl;

Accept alcohol as an alternative to hydroxyl and/or ketone as an alternative to carbonyl.

Allow hydroxy, but not hydroxide as an alternative to hydroxyl.

Examiners report
The functional groups in fructose proved a challenge for only the weakest candidates, with mistaking the carbonyl group for “aldehyde”
being the most common error. Please note that to prepare new candidates for the 2016 syllabus, the markscheme was later altered to
include the correct naming of functional groups following IUPAC guidelines. Many students could also correctly convert the structural
formula into an empirical formula in Part (b) and then went on to correctly determine the percentage by mass of each element in Part
(c), though sometimes only with the help of ECF. Writing the correct combustion equation was difficult for only the weaker candidates.

15b. [1 mark]

Markscheme
CH2O;

Examiners report
The functional groups in fructose proved a challenge for only the weakest candidates, with mistaking the carbonyl group for “aldehyde”
being the most common error. Please note that to prepare new candidates for the 2016 syllabus, the markscheme was later altered to
include the correct naming of functional groups following IUPAC guidelines. Many students could also correctly convert the structural
formula into an empirical formula in Part (b) and then went on to correctly determine the percentage by mass of each element in Part
(c), though sometimes only with the help of ECF. Writing the correct combustion equation was difficult for only the weaker candidates.

15c. [2 marks]

Markscheme
C: ( 12.01
30.03
× 100 =) 39.99/40.0%

H: ( 30.03
2.02
× 100 =) 6.73/6.7%

O: ( 16.00
30.03
× 100 =) 53.28/53.3%;

Award [2] if all three are correct, and [1] if two are correct.

Accept if the third value is obtained by subtracting the other two percentages from 100%.

Do not penalize if integer values of relative atomic masses are used.

Examiners report
The functional groups in fructose proved a challenge for only the weakest candidates, with mistaking the carbonyl group for “aldehyde”
being the most common error. Please note that to prepare new candidates for the 2016 syllabus, the markscheme was later altered to
include the correct naming of functional groups following IUPAC guidelines. Many students could also correctly convert the structural
formula into an empirical formula in Part (b) and then went on to correctly determine the percentage by mass of each element in Part
(c), though sometimes only with the help of ECF. Writing the correct combustion equation was difficult for only the weaker candidates.
 [2 marks]
15d.

Markscheme
C 6H12O6 + 6O2 → 6CO2 + 6H2O
correct formulas of reactants and products;

correct balancing;

M2 can only be scored if M1 correct.

Examiners report
The functional groups in fructose proved a challenge for only the weakest candidates, with mistaking the carbonyl group for “aldehyde”
being the most common error. Please note that to prepare new candidates for the 2016 syllabus, the markscheme was later altered to
include the correct naming of functional groups following IUPAC guidelines. Many students could also correctly convert the structural
formula into an empirical formula in Part (b) and then went on to correctly determine the percentage by mass of each element in Part
(c), though sometimes only with the help of ECF. Writing the correct combustion equation was difficult for only the weaker candidates.

[3 marks]
16.

Markscheme
1
(i) ratio of average/mean mass of atom to of mass of C–12 (isotope) / average/mean mass of atom on scale where one atom of
12
1
C–12 has mass of 12 / weighted average/mean mass of isotopes of element compared to of mass of C–12 / OWTTE;
12

Award no mark if “element” is used instead of “atom” in first two alternatives.

1
Allow “mass of an atom relative to the mass of of C–12”.
12

(ii) (Ar =) 0.7899 × 24 + 0.1000 × 25 + 0.1101 × 26;

24.32;

Award [2] for correct final answer.

Award [1 max] for 24.31 with correct working.

Award [0] for 24.31 (Data Booklet value) if working is incorrect or no working is shown.

Final answer must be to 2 decimal places to score [2].

Examiners report
In 2(a) the processes in the spectrometer were generally well described although many candidates did not mention that positive ions
are formed. Relative atomic mass was defined poorly in (b)(i) but the atomic mass was generally calculated correctly. Most candidates
gave their answers to the required two decimal places. Even though relative atomic mass was asked for, most candidates stated units
for Ar.

[2 marks]
17.

Markscheme
(Ar =) 0.7899 × 24 + 0.1000 × 25 + 0.1101 × 26;
24.32;

Award [2] for correct final answer.

Award [1 max] for 24.31 with correct working.

Award [0] for 24.31 (Data Booklet value) if working is incorrect or no working is shown.

Final answer must be to 2 decimal places to score [2].

 Examiners report
This question generally scored well. The processes involved in a mass spectrometer were well understood; except for the importance of
forming a cation. The calculation of Ar and the requirement to give an answer to two decimal places was performed very well.

[3 marks]
18a.

Markscheme
M(CH3COOH) (= (4 × 1.01) + (2 × 12.01) + (2 × 16.00)) = 60.06 (g mol− 1);
Accept 60 (g mol –1).

mass (CH3COOH) (= 5.00 × 1.05) = 5.25 (g);

5.25
60.06
= 0.0874 (mol);

Award [3] for correct final answer.

Accept 0.0875 (comes from using Mr = 60 g mol –1).

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[3 marks]
18b.

Markscheme
0.05
percentage uncertainty in volume of ethanoic acid = 100 × 5.00
= 1%;
0.62
percentage uncertainty in total volume = 100 × 50
= 1.24%;

total percentage uncertainty = 1 + 1.24 = 2.24%;

Accept rounding down to 2.2/2%.

 Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

18c. [1 mark]

Markscheme
±0.1/0.10 (cm3);
Do not accept without ±.

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[1 mark]
18d.

Markscheme
26.00 (cm3);
 Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[1 mark]
18e.

Markscheme
[CH3COOC2H5][H2O]
(K c =) [C ;
2H5OH][C H3COOH]

Do not penalize minor errors in formulas.

[esther][water]
Accept (K c =) .
[ethanol/alcohol][(ethanoic) acid]

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.
 [1 mark]
18f.

Markscheme
0.828× 1.80
(K c =) 0.884 × 0.920
= 1.83;

If assumed [CH 3COOH] = 0.884 mol dm -3, answer is 1.91 – allow this even if an answer was obtained for (iii).

If (ii) given as mean titre (26.5 cm 3) then ECF answer comes to 1.79.

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

18g. [1 mark]

Markscheme
repeat the titration a day/week later (and result should be the same) / OWTTE;

Accept “concentrations/physical properties/macroscopic properties of the system do not change”.

 Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[1 mark]
18h.

Markscheme
enthalpy change/ ΔH for the reaction is (very) small / OWTTE;

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.
 [2 marks]
18i.

Markscheme
decreases (the amount of ethanoic acid converted);

Accept “increases amount of ethanoic acid present at equilibrium” / OWTTE.

(adding product) shifts position of equilibrium towards reactants/LHS / increases

the rate of the reverse reaction / OWTTE;

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[2 marks]
18j.

Markscheme
ethyl ethanoate/ CH3COOC 2H5/ester;

forms only weak hydrogen bonds (to water);

Allow “does not hydrogen bond to water” / “hydrocarbon sections too long” / OWTTE.

M2 can only be given only if M1 correct.

 Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.

[1 mark]
18k.

Markscheme
(large excess of) water will shift the position of equilibrium (far to the left) / OWTTE;

Accept any other chemically sound response, such as “dissociation of ethanoic acid would affect equilibrium”.

Examiners report
Generally candidates found this question quite challenging and some left quite a number of parts unanswered. The tradition is that the
first question on the paper is a data response question, which often addresses many aspects of the syllabus, and unfortunately
candidates, especially those of average or below average ability, seem to have difficulty in tackling questions of this nature. One other
issue with data response questions is that, of necessity, the data appears at the beginning of the question whilst, mainly because of the
space left for candidates to answer, the later parts of the question referring to these data may not appear until a number of pages into
the paper.

Part (a) concerning density, volume and amount of substance was generally reasonably well answered, but the following parts,
concerning uncertainties, were rarely answered correctly and a number confused precision (uncertainty, either absolute or as a
percentage) and accuracy (percentage error in the value obtained). Many candidates also seemed to lack experimental common sense,
simply taking an average that included an initial titre that was much larger than the concordant second and third titres, rather than
excluding it. This lack of experimental “know how” was also evident in responses to (c) (iii) where it was unusual for the approach to the
question to indicate the candidate had realised that the alkali was neutralising two different acids (HCl and CH3COOH) and again in
part (d) where it was rare for the response to outline a practical solution to the problem, though quite a number of candidates suggested
that the pH would become constant, presumably not realising that the pH would be dominated by the HCl catalyst. Most students could
however carry out the more routine tasks of writing an equilibrium constant expression and determining its value from the data given.
Many candidates were aware of Le Chatelier effects on the position of equilibrium, but a significant number failed to use this information
to answer the question actually asked and the unusual approach to the effect of temperature disconcerted many. Whilst most students
managed to identify the ester as the component of the mixture that was insoluble in water, the reasons given were usually couched in
terms of the polarity of the molecule (many quite polar molecules, halogenoalkanes for example, are insoluble in water) rather than its
inability to form strong hydrogen bonds to water, which is the critical factor. Quite a number of students came up with a valid reason
why water would not be a suitable solvent, though some students appeared to have overlooked the fact the question stated “other
reason”.
19a. [1 mark]

Markscheme

/ OWTTE;

Accept mass of C 5H12O = 88.17 so % of C = ( )

60.05
88.17
× 100 = 68.11,

% of H = ( 12.12 ) × 100 = 13.75 and % of O = ( 16.00 ) × 100 = 18.15.

88.17 88.17

Allow integer values for atomic masses.

Examiners report
The question on empirical formula in (a) posed no difficulty and even the weaker candidates scored the mark. In the spectroscopy
question in (b), some of the better candidates managed to score all 11 marks assigned to this extended response type question. In the
MS, + was often omitted. Many students could not distinguish between observed ions and lost fragments. Only one candidate
mentioned the "fingerprint" region of IR but did not refer to the need to compare with library spectral data. For the IR the majority of
candidates scored all three marks, though the weaker candidates frequently suggested NH bonds and CF bonds even though neither
nitrogen nor fluorine are part of the empirical formula given in the stem of the question. Discussion of the 1H NMR spectrum proved the
most challenging and many candidates did not relate the splitting pattern to the specific carbon fragments. It was disappointing at HL
seeing a number of candidates not including hydrogens in their final answer for the structural formula of 2-methylbutan-2-ol.
 [11 marks]
19b.

Markscheme
Mass spectrum:

molecular ion peak at 88/M + = 88 shows molecular formula is C 5H12O;

absorption at 73 due to (M–CH 3)+ / X contains a methyl group as peak at M–15 / OWTTE;

absorption at 59 due to (M–C 2H5)+ / X contains an ethyl group as peak at M–29;

Penalise once only if + charge omitted.

Accept that X contains a CHO group due to M–29 but in fact it cannot as there are too many hydrogen atoms in the compound for it to
be an aldehyde.

Infrared spectrum:

peak in range at 3200–3600 cm− 1 shows it contains an OH group / OWTTE;

(sharp) peaks just below 3000 cm− 1/in range 2850–3100 cm− 1 due to C–H

absorptions;

lack of peak at approximately 1700 cm− 1 shows it does not contain C=O;

absorption between 1050 and 1410 cm− 1 due to C–O;

Allow “due to alcohol” instead of due to C–O.

Accept “absorption between 1050 and 1410 cm –1 due to ether or ester” although it cannot be either as there is only one O atom and it
has been identified as bonded to H.

fingerprint region specific to compound but needs to be compared with library / OWTTE;
1H NMR spectrum:

(12 protons are in) four different chemical environments (in the ratio 1:2:6:3);

singlet (with integration trace of 1) due to OH proton;

singlet (with integration trace of 6) suggests (two CH3) groups attached to a carbon atom with no Hs attached to it;

quartet (with integration trace of 2) due to CH2 next to CH3;

triplet (with integration trace of 3) due to CH3 next to CH2;

Reference must be made to the association of the splitting pattern (singlet, triplet etc.) to the specific carbon fragments.

(X is) 2-methylbutan-2-ol/CH3CH2C(CH3)2OH;

No ECF throughout 2(b).

Examiners report
The question on empirical formula in (a) posed no difficulty and even the weaker candidates scored the mark. In the spectroscopy
question in (b), some of the better candidates managed to score all 11 marks assigned to this extended response type question. In the
MS, + was often omitted. Many students could not distinguish between observed ions and lost fragments. Only one candidate
mentioned the "fingerprint" region of IR but did not refer to the need to compare with library spectral data. For the IR the majority of
candidates scored all three marks, though the weaker candidates frequently suggested NH bonds and CF bonds even though neither
nitrogen nor fluorine are part of the empirical formula given in the stem of the question. Discussion of the 1H NMR spectrum proved the
most challenging and many candidates did not relate the splitting pattern to the specific carbon fragments. It was disappointing at HL
seeing a number of candidates not including hydrogens in their final answer for the structural formula of 2-methylbutan-2-ol.

20. [1 mark]

Markscheme
A

Examiners report
[N/A]
 [1 mark]
21.

Markscheme
D

Examiners report
[N/A]

22. [1 mark]

Markscheme
D

Examiners report
This question was found to be difficult as many candidates did not add the number of protons to the number of electrons. They missed
the word “total” in the stem. What was surprising was the percentage of candidates giving answer A (31%).

[1 mark]
23.

Markscheme
B

Examiners report
This might have taken some time and was, perhaps, more challenging for those reliant on calculators. Nearly 68% of the candidates,
however, gave the correct answer.

[4 marks]
24a.

Markscheme
(i) temperature = 358 K;
M= mRT
/1.17 × 8.31 × (0.40358101) ;
pV ×

(M = ) 86.2 (gmol− 1);

Award [1 max] for correct final answer without working.

(ii) C 6H14;

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates although there were again some very poor answers.
 [2 marks]
24b.

Markscheme
C(CH3)4;
Accept correct name 2,2-dimethylpropane.

Do not penalize missing H atoms.

weakest London/dispersion/van der Waals’/vdW/instantaneous induced dipoleinduced dipole forces because of smallest surface
area/contact

OR

weakest London/dispersion/van der Waals’/vdW/ instantaneous induced dipoleinduced dipole forces because of least distortion of the
electron cloud

OR

weakest London/dispersion/van der Waals’/vdW/ instantaneous induced dipoleinduced dipole forces because polarizability of electrons
(in electron cloud) is less;

Accept other words to that effect but student must mention a correct IMF and a correct reason.

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

[2 marks]
24c.

Markscheme
Ethanal: distill off product as it forms;

Accept distillation.

Ethanoic acid: (heat under) reflux / use excess oxidizing agent;

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

[2 marks]
24d.

Markscheme
Ethanol: –2/–II;

Ethanal: –1/–I;

Do not accept 2– or 1–, but penalize only once.

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.
 [1 mark]
24e.

Markscheme
CH3CH2OH → CH3CHO + 2H+ + 2e− ;
Half-equation required. Do not accept C2H5OH + 2[O] → CH3CHO + H2O.

Accept e for e− .

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

[2 marks]
24f.

Markscheme
3CH3CH2OH(aq) + Cr2O27− (aq) + 8H+ (aq) → 2Cr3+ (aq) + 3CH3CHO(l) + 7H2O(l)
correct reactants and products;

correct balancing;

M2 can only be scored if M1 correct.

Ignore state symbols.

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

[2 marks]
24g.

Markscheme
rate of forward process/reaction = rate of backward/reverse process/reaction;

concentrations of reactants and products remain constant;

no change in macroscopic properties;

closed/isolated system / constant matter/energy;

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.
 24h. [2 marks]

Markscheme
provides alternative pathway (of lower energy);

lowers activation energy (of the reaction) / more particles with E ⩾ Ea;

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

24i. [2 marks]

Markscheme
no effect (on position of equilibrium);

increases rate of forward and reverse reactions (equally);

Examiners report
This was the least popular question however many who chose it were successful in parts. Part (a) that required a calculation of M r was
quite well done. However (b) that asked for the isomer of C 5H12 with the lowest boiling point was not well answered. Identification of the
methods to produce ethanal or ethanoic acid was done well by the strong candidates and others just guessed. Deduction of oxidation
numbers and then writing of redox equations was not well answered. However (d) and (e) about equilibrium were answered well by
many candidates, although there were again some very poor answers.

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