1.

From the evidence, candidates may have identified compound F as propanone, propanal or
propanoic acid
If F is propanone or propanoic acid, then maximum score = 7; but if F is propanal then
maximum score = 6
The mark scheme for F = propanone and propanal is shown below.
mass spec of E– Remember to check the spectrum
Quality of Written Communication – mass spec gives M+ or molecular ion of 60 OR mass
spec gives parent ion of 60 OR highest m/z (ALLOW m/e) value is 60
m/z = 45 indicates loss of CH3
OR m/z = 45 indicates presence of CH3CHOH
OR CH2CH2OH OR C2H5O

IR of F – Remember to check the spectrum

IR shows no broad absorption between 2500 to 3300 cm–1 so no O—H bond
OR no broad absorption between 2500 to 3300 cm–1 so not a carboxylic acid
IR shows absorption at 1700 cm–1 due to a C=O bond
OR absorption at 1700 cm–1 indicates a ketone OR aldehyde present

Identification and equation

F is CH3COCH3 OR propanone
E is CH3CHOHCH3 OR propan-2-ol
CH3CHOHCH3 + [O] → CH3COCH3 + H2O

If F has been incorrectly identified as propanal, mark identification and equation as ECF, so
max = 2
ALLOW E is CH3CH2CH2OH
ALLOW: CH3CH2CH2OH + [O] → CH3CH2CHO + H2O

The mark scheme for F = propanoic acid is shown below.

mass spec of E– Remember to check the spectrum
QWC – mass spec gives M+ or molecular ion of 60
OR mass spec gives parent ion of 60
OR highest m/z (OR m/e) value is 60
m/z = 45 indicates loss of CH3
OR m/z = 45 indicates presence of CH3CHOH
OR CH2CH2OH OR C2H5O

[Link] 1
 IR of F– Remember to check the spectrum
IR shows (broad) absorption somewhere between 3500 and 2500 cm–1 suggests carboxylic acid
OR O–H bond
IR shows absorption at 1700 cm–1 due to C=O
OR absorption at 1700 cm–1 indicates a carboxylic acid

Identification and equation

F is CH3CH2COOH OR propanoic acid
E is CH3CH2CH2OH OR propan-1-ol
CH3CH2CH2OH + 2[O] → CH3CH2COOH + H2O

Extra guidance for marking of question

If E has not been identified OR if F has been identified as a ketone or aldehyde, use the first
mark scheme
If F has been identified as a carboxylic acid, use the second mark scheme

Mass spec
These two marking points stand as independent marks whichever compounds have been
identified.
The positive sign for fragment ions is not required. IGNORE negative charge.
The mass spec may well be on the actual spectrum.

IR mark
These stand as independent marks whichever compounds have been identified.
The IR analysis may well be on the actual spectrum.

Identification marks
If both structure and name are given they must both be correct but allow ‘propanol’ drawn with
the correct structure because the position number of the –OH has been clearly identified
ALLOW ECF for identification of F e.g. if E is pentan-2-ol then an answer of
pentan-2-one for F will be given a mark as ECF
ALLOW identification marks for E and F from equation

[Link] 2
 Equation mark
ALLOW ECF for any correct equation showing the oxidation of any alcohol to the appropriate
product.
ALLOW molecular formulae in equations,
i.e. C3H7OH + [O] → C2H5CHO + H2O ; C3H8O + [O] → C3H6O + H2O ;
C3H7OH + [O] → C2H5COH + H2O
[7]

2. (a) method 1:
fermentation of sugars or carbohydrates OR reaction with
yeast with sugar or carbohydrates
C6H12O6 → 2C2H5OH + 2CO2
method 2:
hydration of ethene OR reaction of ethene with water OR
reaction of steam with ethene
C2H4 + H2O → C2H5OH
ALLOW sugar from equation
ALLOW C2H6O in equation
ALLOW correct multiples
IGNORE state symbols
ALLOW ethene from the equation
IGNORE mention of any catalyst
ALLOW C2H6O in equation OR H2O over the arrow
ALLOW correct multiples
IGNORE state symbols
4

(b) (i) (CH3)2CO OR

H3C

C O

H3C
(CH3)2CHOH + [O] → (CH3)2CO + H2O
If name and formula given both need to be correct
ALLOW propanone OR acetone
IGNORE propone
NOT incorrect named compound
ALLOW C3H8O + [O] → C3H6O + H2O
ALLOW O instead of [O]
ALLOW correct multiples
IGNORE state symbols
2

[Link] 3
 (ii) CH3CH2COOH OR propanoic acid

Any number or range of numbers between 1750–1640 (cm–1)

for C=O
Any number or range of numbers between 2500–3300 (cm–1)
for O–H
ALLOW C=O and O—H marks independent of compound
identified i.e. stand alone marks
ALLOW correct bonds shown by the appropriate absorption on
the IR spectrum
IGNORE reference to C—O bond
3

(c) (i) 2-methylpropan-2-ol

ALLOW methylpropan-2-ol OR tertiarybutanol
1

(ii) ester
1

(iii) CH3CO2C(CH3)3 OR CH3COOC(CH3)3

OR
O

H3C C

O C(CH3)3
ester group shown
rest of molecule
ALLOW skeletal formula OR displayed formula
ALLOW ester linkage even if rest of structure is wrong
2
[13]

[Link] 4
3. (a) (i)
H H
δ+ δ
C2 H 5 C I C2H5 C OH + I–

H H

OH–
C–I curly arrow from the bond not from carbon atom
curly arrow from the OH-
correct partial charges on C—I
no need to show any lone pairs on oxygen but must have a clear
negative sign rather than partial negative charge
IGNORE lone pairs
IGNORE products of this reaction
ALLOW curly arrow from a negative charge or from any part
of hydroxide ion
If SN1 mechanism is given then use the mark scheme below
correct partial charges on C—I
C–I curly arrow from the bond not from carbon atom
curly arrow from the OH- to the correct carbocation
H
δ+ δ
C2H 5 C

C2H5 C+ OH–

H
3

(ii) nucleophilic substitution

1

[Link] 5
 (b) C–I bonds broken more easily
C–I bonds are weaker OR have less bond enthalpy OR C–I
bonds are longer
ALLOW ora e.g. C—Br bonds are stronger OR broken
less easily
2
[6]

4. from IR absorption, J contains O–H OR from IR J is an

alcohol
70.59 13.72 15.69
C:H:O= : :
12.0 1.0 16.0
OR 5.8825 : 13.72 : 0.9806
empirical formula = C6H14O
(from mass spectrum), Mr = 102
evidence that it has been shown that the empirical formula is
the molecular formulae e.g. Mr of C6H14O = 102 so empirical
formula is molecular formula

OH

OH

OH

[Link] 6
 One mark for each correct structure
This is a QWC mark
ALLOW two marks for correct empirical formula with no
working out
This is a QWC mark
ALLOW structural or displayed formulae
IGNORE incorrect names
ALLOW one minor slip in drawing structures e.g. one missing
hydrogen but ALLOW ecf for bigger slips such as showing just
sticks and no hydrogen atoms
ALLOW bond to H in OH
ALLOW one mark for three isomers of C6H13OH whether
branched or unbranched as a catch mark if no other mark has
been awarded for the structures
If more than three isomers of C6H13OH drawn
• 1 branched and 3 unbranched award two marks
• any other combination award one mark
ALLOW one mark for hexan-1-ol, hexan-2-ol and hexan-3-ol if
structures not drawn
[8]

5. (i) Any two realistic fragments,

e.g. CH3+: 15; C2H5+: 29; C3H7+: 43; C4H9+: 57; OH+: 17, etc. (1) (1)
Do not penalise missing charge. 2
(ii) breathalysers/monitoring of air pollution, MOT emission testing, etc. (1) 1
[3]

6. mole ratio = 88.89/12 : 11.1/1 = 7.41 : 11.1 (1)

empirical formula = C2H3 (1)
relative mass of C2H3 = 27.
Mr = 2 × 29 so molecular formula = C4H6 (1)
X reacts with 2 mol H2 so there are 2 double bonds (1)
Possible structure = 1,3-butadiene /

(1)
[5]

7. (a) (i) H+ 1
Cr2O7 2- 1
(ii) Orange to green/black/blue 1

(b) (i) contains a C=O/aldehyde, ketone, carboxylic acid and ester/ 1

[Link] 7
 carbonyl/carbonyl in an aldehyde
(ii) does not contain a O−H/ (hydrogen bonded in a) carboxylic acid 1
(iii) distillation (no mark) because distillation allows loss of volatile 1
components /removes butanal from oxidising mixture
prevents formation of RCOOH/ partial oxidation would be achieved 1
or reverse argument for reflux not being used
in that reflux prevents loss of volatile components
hence complete oxidation would be achieved/RCOOH would be formed

[7]

8. (i) H+ Cr2O72- 2
(ii)
compound E compound F
H3C H H
2[O] H3C
C C + H2 O
C C
H3C CH2 CH2 CH2 OH H3C CH2 CH2 COOH

C 7 H 14 O C 7 H 14 O2

3
(iii) carboxylic acid would have an absorption between
1680 – 1750 cm-1 /1700 cm-1 or 2500 – 3300 cm-1. 1
[6]

9. (a) (i) (volatile components) can escape/distil out 1

ethanal is most volatile/b pt less than 60°C/partial oxidation 1
(ii) (volatile components) cannot escape/ refluxed 1
complete oxidation will be achieved/oxidised to the acid 1

(b) C2H5OH + 2[O] → CH3COOH + H2O

(CH3COOH + H2O ) 2

(c) spectrum C 1
spectrum C only shows absorption at 1700 cm-1 for the C=O 1
the other two spectra contain the OH group absorption at approx 3000 cm-1 1
[9]

10. acrylic acid 1

approx 1700 cm-1 (range 1650 − 1750 ) indicates C=O 1

[Link] 8
 approx 3000 cm-1 (range 2500- 3300) indicates O-H 1
not 3230 − 3550 cm-1
[3]

11. (a) (i) alkene 1

alcohol/hydroxy/hydroxyl 1

(b) (i) I = alkene & II = alcohol… both are needed 1

(ii) decolourised / colourless 1
(iii) 1

OH
Br
Br
(iv) X as shown below 1
100
TRANSMITTANCE%

50

0
4000 3000 2000 1500 1000 500
HAVENUMBER

(c) (i) Ni/Pt/Rh/Pd 1

(ii) compound B is C10H22O 1
(iii) C10H20O + H2 → C10H22O 1
[9]

12. (a) (i) Alkene/C=C 1

Alcohol/ROH/hydroxy/hydroxyl/OH (not OH- or hydroxide) 1
(ii) One of the C in both C=C is joined to two atoms or groups that
are the same 1

[Link] 9
 (b) Observation decolourisation (of Br2) 1
Molecular formula C10H18OBr4 2
C10H18OBr2 gets 1 mark

(c) reagent CH3COOH 1

catalyst H2SO4/H+/HCl (aq) or dilute loses the mark 1

(d) (i) C10H18O + 2[O] → C10H16O2 + H2O 2

1 mark for H2O and 1 mark for 2[O]
(ii) The infra-red spectrum was of compound Y
because absorption between 1680 − 1750 cm-1 indicates a C=O 1
and the absence of a peak between 2500 − 3300 cm-1 shows the absence
of the OH hydrogen bonded in a carboxylic acid 1
[12]

[Link] 10