1.	(a)	(i)	– *CH(CH3)–   (1)	1
(ii)	(the three) OH groups   (1)
allow adrenalin to form more hydrogen bonds with water 
(than does benzedrine)  (1)	2
 
(b)	(i)		1
Can use R in place of C6H5CH2CH(CH3)– in both (i) and (ii)
 
(ii)		1
 
(iii)	
	substitution(s) in ring at any position(s)   (1)
production of amide   (1)	2
 
(d)		2
 
(e)	(i)	(CH(CH3)–NH2)+   (1)	1
(ii)	(CH2–NH–CH3)+ / (CH(OH)CH2)+  (1)
	max 1 for (e) if no charges shown
must show some structure in answers ie. C2H5N(0)	1
[11]

2.	(a)	(i)	Has two isomers that are non–superimposable (1)
mirror images (1) not stand alone
or
The molecule does not have a plane of symmetry
or
The molecule contains a single (1) asymmetric carbon	2
atom (1)
 
(ii)	
	One correct 3 –D diagram (1)
second molecule mirror image of first as drawn (1)
Stand alone provided two tetrahedral mirror image drawn of C4H9OH	2
 
(iii)	Rotates the plane of plane polarised (monochromatic) light (1)
in opposite directions (1)
Consequential on mention of polarised light
or
Use polarimeter (1)
measure rotation (of plane of polarised light) in opposite
directions (1)	2
 
(b)	(i)	CH3COOH    +    C2H5OH  CH3COOC2H5     +     H2O (1)	1
Any valid ester equation scores the mark but must be
actual molecules not ROH or RCOOH
Equilibrium sign not important
 
(ii)	double alcohol / alcohol at each end (1)
double acid / acid at each end (1)
or
Alcohol group at one end and acid group at the other (2)
Could be shown on an equation or as diagrams
React at each end / illustrate with equation or diagram to
show production of a long chain polyester (1)	3
 
(iii)	Esters react with alkalis/ ester linkages are hydrolysed (1)
conc / hot will attack polyesters / coat will be damaged (1)
too slowly to be a problem (1)
Second mark consequential on first	2
 
(iv)	Acyl chlorides / acid chlorides / acid halides / RCOCl / acid 
anhydride (1)	1
Not specific reagent
[13]

3.	(a)	(i)	CH3CH(NH2)COOH + HCl ® CH3CH(NH3+Cl-)COOH (1)	1
Cl- can be separated but then changes must be shown

(ii)	CH3CH(NH2)COOH + NaOH ® CH3CH(NH2)COO-Na+ + H2O	1
charges optional but if shown must be correct
 
(b)	·	Exists as zwitterion (or diagram) (1)
•	Strong attraction between oppositely charged ions (1)	2
 
(c)	(i)	2 unambiguous 3-D diagrams (2)	2

Must show attachment to correct atoms
 
(ii)	Rotates the plane of (plane) polarised (monochromatic) light (1)
in opposite directions (1) consequential on mention of polarised light
or
Use polarimeter (1)
measure rotation (of plane of polarised light) in opposite
directions (1)	2
 
(d)	(i)	diagram of but-1-ene (1)
	CH3CH2CH==CH2 or	
	or C2H5CH=CH2
diagram of but-2-ene (1)	2
	CH3CH ==CHCH3 or	
 
(ii)	geometric (or cis-trans) (1)

diagram of cis- but-2-ene (1)	3
diagram of trans-but-2-ene (1)
[13]

4.	(a)	
•	Identification of chiral centre (1)
	2 diagrams to show two isomers of non-superimposable molecules
•	3D diagram (1)
mirror image (1)
Distinguish by rotation of the plane of (plane)-polarised light (1)	4
	NB could identify their own real molecule.- correctly shown.
Not necessarily Ibuprofen
 
(b)	(i)	COOH is present anyway – absorbs at app 280and 1700
If A is present – nothing else
If B – peak at 3600
or
A spectrum will include 1700 but not 3600
B will include 3600
Marking points
identification of groups to note (1)
link to peaks in spectrum (1)
how to distinguish (1)	3
 
(ii)	Correct test (1)
PCl5
or
2,4 dinitrophenylhydrazine
or dilute sulphuric acid plus potassium dichromate(VI)
or sodium hydroxide and iodine
2 correct observations (1)	2
 
(iii)	 or sodium salt
	1 correct COOH group scores 1 mark
2 correct COOH groups score 2 marks	2
 
(c)	(i)	25.75 ´ 2/1000 mol of NaOH left (1) so
(100 - 51.50)/1000 mol reacted (1)
0.0485 mol of acid in 50 tablets (1)
0.0485 ´ 206/50 (1) = 0.1998 g per tablet (0.200)
199.8 mg / 200 mg (1) 3 or 4 sig figs	5
 
(ii)	0.0485/50 ´ 6.023 ´ 1023 (1) = 5.84 ´ 1020 (1)	2

(d)	·	At pH=3 equilibrium pushed back in favour of undissociated
	acid molecules (1)
•	So acid is insoluble because large benzene carboxylic acid
molecules are insoluble (1)
At pH=8 salt is formed (1)
Ionic bonding results in increase solubility (1)	4
 
(e)	-COOH (1)
warm with a little conc sulphuric acid (1)
ester (1)	3
[25]

5.	(a)	(i)	Homolytic - even separation of electrons when a bond breaks / one
electron from bonding pair goes to each atom when (a covalent) 
bond breaks (1) could be shown as diagrams 
Free radical - species with one unpaired electron (1)	2
 
(ii)	
1 mark for correct repeating unit 1 mark for evidence of	2
continuing structure
 
(iii)	·	Combustion - produces large volume of carbon dioxide
	contributing to global warming / may produce toxic products (1)
•	Landfill - may result in
very slow decomposition producing flammable gases which must be
managed / unsightly / uses up large areas of land (1)	2
 
(iv)	Low softening point (1)
makes it easy to mould into new shapes / can be turned into expanded 
polystyrene (1)
Or
Glassy like appearance (1)
Makes it suitable for attractive contexts (1)	2
 
(b)	(i)		3
 
(ii)	Add bromine water / bromine in organic solvent (1)
No change of specified colour (1)
Allow valid alternative such as KMnO4 with named acid or alkali	2
 
(c)	(i)	3 marks for developing evidence:
•	Formula suggests that benzene has three double C-C bonds 
and three single C-C bonds (1)
Summation of bond enthalpy of three double and three single 
bonds plus six carbon hydrogen (1)
gives value for enthalpy of formation less than measured value (1)
	2 marks for actual structure
•	Actual structure has electrons delocalised in a p orbital (1)
Each carbon bonded to two other carbons by s bond (1)	5
 
(ii)	Substitution enables delocalisation to be preserved (1)
energetically more favourable than addition (1)	2
[20]

6.	(a)	All three compounds can form hydrogen bonds to water molecules	1
(b)	Brady’s reagent / 2,4 DNP (1)
Red–yellow/ yellow/red–orange / orange precipitate / crystals solid (1)	2
 
(c)	(i)	Benedict’s solution
OR acidified potassium / sodium dichromat(VI)
OR potassium manganate(VII)	1
(ii)	Blue to red
OR orange to green / blue
OR purple to colourless	1
(iii)	C–H (stretching) frequency for an aldehyde
OR
carbonyl, C=O, frequency different value	1

(d)	Na2CO3(aq) + 2CH3CH2CO2H(aq)/(I) ® 2CH3CH2CO2Na(aq) + CO2(g) + H2O(l)
Reactants (1)	2
Products (1)
 
(e)	Sodium	)
sodium hydroxide	)  Anytwo
sodium hydrogencarbonate	)
sodium oxide	)	2
[10]

7.	(a)	(i)	It is non-superimposable on mirror image/ it has a single asymmetric
carbon atom	1
(ii)	rotates the plane (of polarisation) (1)
of (plane–) polarised (monochromatic) light (1)
OR
Use a polarimeter (1)
rotates the plane (of polarisation) of the light (1)	2
(iii)	product is an equimolar mixture/racemic mixture (1)
so rotations cancel (1)	2
 
(b)	– NH3 +Cl– on the amino group (1)
–COO– Na+ on the carboxyl group (1)	2
(c)	Zwifterion’s structure (1)
There is ionic attraction between adjacent zwitterions (1)	2
 
(d)	(i)	(polymer formed by) elimination/ removal of a small molecule/ water
(between two monomers)	1
(ii)	any CIOC***COCl (1) and H2N*CH2*NH2 (1)	2
(iii)	structure consequential on answer to (ii) showing amide link (1)
and extension of the chain (1)	2
(iv)	

	CONH drawn out (1)
	Show 3 units (1)	2
[16]

8.	(a)		6
solution	X	Y	
Sodium
carbonate	fizzing/ effervescence/ bubbles (1)	no reaction /
no bubbles (1)	
Brady’s reagent (2,4-dinitro
phenyl hydrazine)	no change/
(stays) yellow/orange (1)	yellow /orange / orange-red or
yellow-orange precipitate /
(crystalline) solid (1)	
Potassium
dichromate +
sulphuric acid	no change
/(stays) orange (1)	Goes from orange to green/
brownish green/dull green (1)	
 
(b)	(i)		1

Do not allow if bond is obviously to wrong atom from benzene
ring
 
(ii)		1

(iii)	Undisplayed ester + unchanged – CHO (1)
Correctly displayed for both groups (1)	2

(iv)	sulphuric acid / hydrochloric acid	1
(v)	Cl (and O) electronegative/electron withdrawing (1)
So Cd+ is more/ very susceptible to nucleophilic attack/ more d+/
more electrophilic (1)	2

(c)	(i)	Electrophiles / electrophilic	1
(ii)	Brd+/ Br+/ Brd+– Brd–	1
(iii)	Any substitution product with Br on benzene ring, and other	1
groups unchanged
(iv)	lone pairs / electrons on phenolic group make ring more	1
negative than in benzene / lone pairs on OH donated to ring
[17]

9.	(a)	(i)	Add Brady’s Reagent / 2,4-dinitrophenylhydrazine (1)
Yellow/orange precipitate / crystals/ solid produced (1)	2
(ii)	CH3CH2COCH3 (1)
Butanone (1)	2
(iii)	
 (1)	1
 
(b)	(i)	Esters (1)	1
(ii)	CH3CH2CH2CO2CH2CH3 + H2O (1)	1
(iii)	Ethyl butanoate (1)	1
(iv)	Nucleophile/ nucleophilic (1)	1
 
(c)	Cloudy/misty/steamy fumes/vapour/gas	1
(d)	Cl is more electron withdrawing/electronegative (1)
Which makes carbonyl carbon more electrophilic/positive/susceptible to
nucleophilic attack
OR Cl is a better leaving group (than OH)
as Cl– is more stable (than –H) (1)	2
[12]

10.	(a)	Ethylmagnesium bromide of formula, or any other halide NOT C2H5BrMg, (1)
Dry ether / ethoxyethane
Followed by hydrolysis / acid / water (1)
	Grignard reagent / named reagent with incorrect alkyl group scores (0) for (1)
reagent but can score both condition marks.
If halogenoalkane given as reagent, can score 1st mark if Mg included under	3
conditions.
 
(b)	(i)	Observation
effervescence/ bubbles/ fizzing (1)
NOT gas evolved
	2C2H5COOH + Na2CO3 ® 2C2H5COONa + CO2 + H2O (1)	2
 
(ii)	Observation
	steamy/ misty/ white fumes (1)
NOT smoke
C2H5COOH + PCl5 ® C2H5COCl + POCl3 + HCl (1)	2
 
(c)	Reagents potassium dichromate ((VI)) / K2Cr2O7, (1)
sulphuric acid / H2SO4 / hydrochloric acid / HCl but conseq. on an oxidising (1)
agent
ALLOW acidified potassium dichromate / H+ and Cr2O72– (2)
ALLOW acidified dichromate ions (2)
Acidified dichromate (without ion) scores just (1)
ACCEPT
Potassium manganate(VII) / potassium permanganate / KMnO4 / Tollens’* / 
Fehling’s* (1)
Acidified / alkaline* / neutral (1)	2
(*) need to acidify to liberate free acid for 2nd mark
 
(d)	(i)	Reagent	Condition
	(any one of)	(to match)
HCN	and KCN
HCN or KCN	(buffered between) pH between 6 and 9
KCN	+ acid / H+ NOT excess
HCN	+ base / OH– NOT excess (2)
	Type of reaction
	Nucleophilic addition   - both words needed (1)	3
 
(ii)	Reagent	Condition
	(any one of)	(to match)
Hydrogen	Pt / Ni / Pd (catalyst) – IGNORE ref to temp.
Sodium	(in) ethanol
Lithium aluminium hydride	dry ether / ethoxyethane
Sodium borohydride	(in) aqueous / water / ethanol / methanol (2)
	Type of reaction
	Reduction
ACCEPT redox / hydrogenation (not addition)
ACCEPT nucleophilic addition if metal hydrides used (1)	3

(e)	(i)		2

(ii)	

	OR

	OR

	NOT

		1

(f)	Optical
NOT stereo (1)

ALLOW – C2H5 for – CH2CH3
 
	MUST show the two as object and mirror image (2)

	but NOT

	C must not be bonded to H in OH group
Near-miss molecule plus mirror image (1)	3
The two solid lines in 3D structure must not be at 180 °
[21]

11.	(a)	(i)	 (1)  Butanal  /  butan-1-al  (1)
	(1)  (2-) methylpropanal / (2-)methylpropan-1-al (1) NOT methylpropan-2-al	
	Aldehyde must be displayed but rest of molecule not
displayed (1 out of 2) 
	Name must match correct compound. No marks for correctly
naming an incorrect compound	4

(ii)	Any one from
	Infrared spectra   (1)
different in ‘fingerprint’
OR differences in frequencies/wavelengths absorbed
OR different peak/trough patterns  (1)
NOT different peaks/troughs
	Measure Boiling point  (1)
Different boiling points and suggest why e.g.straight chain
higher boiling point  (1)
 
	nmr spectra   (1)
A + B would have a different number of peaks (1)
	Mass spec  (1)
Different fragmentation pattern  (1)
	X-ray diffraction  (1)
Electron density  maps identify branching (1)
	Prepare 2,4-dinitrophenylhydrazone  (1)
and measure melting point  (1)
NOT measure melting point	2
 
(b)	(i)	2,4-dinitrophenylhydrazine / 2,4-DNP(h) / Brady’s reagent  (1)
	orange/yellow/orange-red/yellow-orange precipitate/crystals
[a solid must be mentioned]   (1)
NOT ‘Red’
2nd mark dependent on 1st	2
 
(ii)	(Heat with) Benedict’s reagent/Fehling’s reagent    (1)
	Result for C       remains blue    (1)
ALLOW no change if blue mentioned somewhere
	Result for A and B  orange/red/green/yellow/brown
precipitate/crystals [a solid must be mentioned]   (1)
	OR
Acidified dichromate (1)
Result for C remains orange  (1)
Result for A + B green/blue  (1)
Same rules as above but precipitate not needed 
	2nd and 3rd marks dependent on 1st	3

(c)	(i)	

	Any two
ALLOW fully displayed 

NOT CH2CH2CH2CHOH etc	2
 
(ii)	Esters
NOT esterification	1
 
(iii)	e.g.

	ester group  - must be displayed   (1)
rest of molecule - need not be fully displayed   (1)
- 2nd mark dependent on 1st
ALLOW TE from CH2CH2CH2CHOH etc in (c)(i) for 2 marks in (iii)
	If enol in (c)(i) max 2 (out of 5) for (c)  ie (ii) and ester displayed
in (iii) can be awarded	2
[16]

12.	(a)	Yellow/orange solid/precipitate/crystals formed	1
Reject red
 
(b)	F : CH3CH(CH3)CHO (1)
G : CH3CH2COCH3 (1)
H : e.g. CH2(=)CHCH2CH2OH (1)	3
H : other alkenols and cyclic alcohols, e.g.
cyclobutanol / correct enols / cyclic ethers (1)
Allow displayed formulae

(c)	(i)	Prevents reagents/products from boiling/volatilising /evaporating
away/being lost to the surroundings
Reactants have greater chance of reacting since they condense and
rejoin the mixture	1
Accept reduces the risk of fire; (1)
Accept prevents potentially harmful vapours from entering the lab (1)
 
(ii)	Ethyl butanoate	1
 
(iii)	Ethanol (1)
Sodium butanoate (1)	2
Accept T.E. from (ii)
Reject butanoic acid
 
(iv)	Hydrolysis / saponification	1
Reject hydration
[9]

13.	(a)
	1
 
(b)	ester	1
 
(c)	(i)	Moles: C2H5OH: 3.75 (1)
	Moles: HCOOC2H5 : 2.50 and moles H2O : 2.50 (1) for both	2
 
(ii)		1
Reject obviously round brackets “( )”

(iii)	 (1)
Must have clearly divided moles of each component by
0.485 for 1st mark e.g.
[HCOOC2H5] = [H2O] = 5.16 (mol dm–3)
and [HCOOH] = 1.03 (mol dm–3)
and [C2H5OH] = 7.73 (mol dm–3)
	= 3.33 (1) stand alone mark
	IGNORE sig.figs.	2
Accept  = 3.33 only scores (2) if it is stated that V cancels either here or in (iv)
If [H2O] omitted in (ii), then answer
Kc = 0.647 mol–1 dm3
(2) but this will give
Kc = 1.33 mol–1 dm3 with V omitted from calculation (1)
Reject 1st mark if 485 used as V in expression
 
(iv)	No, (as) equal numbers of moles on both sides
OR volumes cancel
OR mol dm–3 cancel
OR units cancel
OR crossing out units to show they cancel	1
Accept “equal powers/moles on both sides”
OR “powers cancel”
Mark CQ on Kc expression in (ii)
Reject “concentrations cancel”
 
(d)	(i)	(as reaction) endothermic (1)
Accept exothermic in backward direction (or words to that effect)
	Kc decreases (1)
If state exothermic in forward direction, 1 mark only (out of 4) for CQ “increase in Kc”
	numerator in quotient (has to) decrease
OR denominator in quotient (has to) increase
OR fraction (has to) decrease (1)
	yield of HCOOC2H5 decreases (1)	4

(ii)	no effect as catalysts do not affect (the value of) K
OR
no effect as catalysts do not affect the position of equilibrium
OR
no effect as catalysts do not affect the yield
OR
No effect as catalysts increase the rate of the forward and
backward reactions equally/to the same extent
OR
no effect as catalysts only increase the rate
OR
no effect as catalysts only alter the rate
	“no effect” can be stated or implied
IGNORE any references to activation energy	1
Reject just “catalysts increase rate”
[13]

14.	(a)	(i)	effervescence (1)
COOH present/acid/ acidic/contains H+ (1)
	[if wrong gas is identified second mark is lost]	2
Accept bubbles, fizzing
Reject gas/CO2 evolved
Reject just ‘acid-base reaction’
 
(ii)	Decolourises (1)
OR brown/orange/yellow to colourless
Reject “clear” used instead of “colourless”
	compound contains C=C / unsaturated (1)
Accept alkene
Reject just ‘double bond’
	white precipitate so is a phenol (1)	3
Accept activated benzene ring/OH on benzene ring

(b)	(i)	Four (1)
(Two) cis/trans (or geometric), and (two) chiral/optical
isomers/ enantiomers (1)
OR
Two cis-trans/geometric isomers (1)
Two optical isomers/enantiomers (1)
OR
cis-trans/geometric isomers and
optical isomers/enantiomers (1 only)	2
Accept correct description of the idea of cis-trans or optical isomerism without the name
Reject rotates plane of plane-polarised light
 
(ii)	Molecule has a chiral centre/chiral carbon/carbon with
four different groups (1)
	having non-superimposable mirror images (1)	2
Reject asymmetric carbon atom/chiral molecule
 
(c)	QWC
	NaOH (solution) (1)
Accept W identified as secondary halogenoalkane (1) so no NaOH needed (1) for first two marks
	acidify with /add excess HNO3 (1)
[If HCl is added here, only the NaOH mark can score]
Accept neutralise with nitric acid
Reject just “add HNO3”
	add silver nitrate (solution) (1)
	white precipitate (1)
	soluble in dilute/aqueous ammonia (1)
Accept “dilute and concentrated ammonia”
Reject “concentrated ammonia” alone
	If no NaOH max (4)
	If HNO3 added only before NaOH, or no acid is added at all, then
can score 3rd, 4th and 5th marks
	If order of addition is NaOH, AgNO3, HNO3 can score (5)
	If no NaOH and no HNO3, can score last 3 marks
	If any reagent other than silver nitrate, including ammoniacal
silver nitrate, is used only the 1st and 2nd marks can score	5
[14]

15.	(a)	(i)	Pairs:	acid NH4+ /ammonium ion and base NH3 /ammonia
	acid H3O+ / hydronium ion and base H2O / water	1
Accept hydroxonium ion
 
(ii)	Ka =  ignore lower case k	1
Accept Ka = 
Reject answers including [H2O]
 
(iii)	[H3O+] = 10–5 mol dm–3 (1)
	Assumption ionization of NH4+ (negligibly) small (1)
	Assumption [NH3] = [H3O+] (1)
Accept [NH4+] = [NH4Cl] or NH4Cl totally ionized
	thus [NH4Cl] = (1 × 10–5)2 / 5.62 × 10–10
= 0.178 mol dm–3 (1)
Answer to 2 or more S.F.	4
 
(iv)	QWC
	methyl red (1)
	indicator constant or pKIn must be near the endpoint pH
OR indicator constant or pKIn must be near 5 (1)
2nd mark conditional on correct indicator	2
Accept pKIn in the steep part of the graph or it is a weak base-strong acid titration
 
(b)	CN– + H2O  HCN + OH–
IGNORE state symbols	1
Accept “→” instead of ““
 
(c)	(i)	nucleophilic addition	1

(ii)

(1) for both arrows	(1) for intermediate
	
	OR for second step
		3
Fish hook arrows (penalise once)
 
•	Ignore the groups attached to the carbonyl carbon throughout
•	The intermediate is not consequential on their first step
•	The minus of the cyanide ion can be on either the C or the N
•	The arrow can start from the minus of –CN in step 1 (but not
from the minus of CN–) and can start from the minus of O– in step 2
•	The arrow from the bond must not go past the O atom
•	Lone pairs not essential
•	Single step addition of HCN or initial attack by H+/HCN scores zero
•	Autoionisation of C=O can only score the last two marks ie max 2
 
(iii)	QWC
	if too acidic too small a concentration of cyanide ions (1)
Accept not enough / too little CN–
	if too alkaline too little HCN to donate the proton in the last step
OR H+ ion concentration too low (1)	2

(d)	(i)	rate = k[CH3CH2CH2Cl] [CN–]
Must be an equation
Must be [ ] NOT ( )
Ignore upper case K	1
Accept ‘R’ or ‘r’ for rate C3H7Cl] / [1-chloropropane]/ [chloropropane]
Accept [cyanide ion]/[cyanide]
Reject [KCN]
 
(ii)

•	Must have partial bonds in transition state
•	CN and Cl must be on opposite sides of central C in the
transition state
•	Accept negative charge on N of cyanide ion	3
Mechanism based on SN1 scores 0
Reject fish hook arrows (penalise once)
Reject arrow from N of CN
[19]

16.	(a)	(i)		1
Accept [H3O+] in place of [H+]
allow one set of sq brackets to be missing

(ii)	[H+]2 = 1.3 × 10–3 × 0.001 (1)
	= 1.3 × 10–6
	[H+] = √1.3 × 10–6
	1.14 × 10–3 (1)
	pH = –log 1.14 × 10–3 = 2.9(4) (1)
	[IGNORE SF]	3
 
(iii)	Trichloroethanoic, as it has the largest Ka value (1)
	and has (3 electron withdrawing) chlorine atoms to stabilise
the anion formed (on dissociation). (1)	2
 
(b)	(i)

	ester group (1)
rest of molecule (1) dependent on first mark
(must be fully displayed)
methyl chloroethanoate (1)	3
No transferred error for name
 
(ii)	ester(s)	1
Reject ether
 
(iii)	nucleophile, (1)
	as it has a lone pair (of electrons) on the (hydroxyl) oxygen (1)
	which can attack the positive carbonyl carbon on the acid (1)	3
2nd and 3rd marks could be obtained by use of a diagram
Reject attack by CH3O–
 
(iv)	(reflux) heat with NaOH(aq) (1)
(cool) and add HCl(aq) (1)
	OR
reflux (1) [must be in context]
with HCl (1)	2
[15]

17.	(a)	IGNORE ‘alkane’ in any answer
	X : ester (1)
Reject carbonyl
	Y : both alkene and alcohol or hydroxyl (1)
Accept carbon–carbon double bond
Accept “hydroxy”
Reject OH– or “hydroxide”
	Z : both alcohol or hydroxyl and aldehyde (1)	3
Accept “hydroxy”
Reject OH– or “hydroxide” or “carbonyl”
Reject just the formula

(b)	X : no reaction (1)
	Y : no reaction (1)
	Z :

(1) do not award if the bond from the carbon atom is clearly to
the H of the OH group	3
Accept

–O– Na+ or –ONa
Reject any formula with the alcohol group oxidised

(c)	(i)	CH3CH2CH2COONa/CH3CH2CH2COO–Na+/

	Allow C3H7 / C2H5CH2
	CH3OH/
	2
Accept

CH3CH2CH2COO– /
CH3CH2CH2CO2Na /
CH3CH2CH2CO2–Na+
Reject carboxylic acid
Or
…O– ―Na+
 
(ii)	

/CH2(OH)CH2CH2CH(CN)OH
/ CH2(OH)CH2CH2CH(OH)CN (1)	1
[9]

18.	methanal
Accept formaldehyde
Accept metanal
Reject methanol
Reject methone
[1]

19.	(a)

	Ketone + five carbon atoms (could be straight chain) (1)
Branched chain + rest of molecule (1)	2
Allow 1 CH3 group not displayed
Reject aldehyde
Reject if any hydrogen atoms missing (1 max)
 
(b)	2-methylbutan(e)-3-one/
3-methylbutan(e)-2-one
Ignore punctuation	1
Accept 2-methylbutanone
Accept 3-methylbutanone
Allow TE from (a) provided it is a ketone
e.g. pentan-2-one, pentan-3-one
Reject 2-methylbuta(-3)one
Reject 2-methylbut(-3-)one
Reject 2-methylbutan-2-one
Reject methylbutanone
 
(c)	C5H12O	1
Accept C5H11OH
Reject structural or displayed formula

(d)	The reactants don’t distil over before they can react
Owtte	1
Accept higher % of alcohol will be oxidised/not all of the alcohol will react/maximum chance of oxidising
Accept more time to oxidise to condense (any evaporated) reactants
Reject BP of alcohol low
Reject explanation of what happens during refluxing
Reject to get a higher yield
Reject discussion of rate of reaction
[5]

20.	(a)	Can be given in either order
	1st functional group
alkene or C=C or carbon-carbon double bond (1)
Reject just ‘double bond’ or just ‘carbon double bond’
	bromine water/Br2 turns (from orange/brown etc. to)
colourless/decolorised (1)
INITIAL COLOUR NOT REQUIRED
Accept KMnO4
Accept acidified decolorised
Accept alkaline green
Reject ‘clear’ instead of ‘colourless’
 
	2nd functional group
carboxylic (acid)
 (1)
Accept carboxyl
Reject “carbonyl”
	on addition of Na2CO3 or NaHCO3 or CaCO3 or Mg, fizzing occurs (1)
Accept gas evolved which turns limewater milky
OR
or universal indicator/ blue litmus turns red
Reject just “a gas/CO2/H2 evolved” for fizzing
	OR
	(warm with) a named alcohol plus conc. acid (as catalyst),
pleasant/fruity smell
	Ignore references to testing with PCl5	4
 
(b)	(i)	W as it contains an aldehyde group / –CHO group
OR
W can be oxidised (whereas X cannot)
OR
X cannot be oxidised
OR
W as X is a ketone (which cannot be oxidised)	1
Reject W with no reason or an incorrect reason (0)
Contains C=O
 
(ii)	CH2 OHCH2 OH
OR

OR
Ethan(e)-1-2-diol	1
Accept (CH2OH)2
 
(iii)

OR
HOOCCOOH
OR
Ethanedioic acid/oxalic acid	1
Accept (COOH)2
Accept ethan(e)-1,2-dioic acid or ethandioic acid
Reject any other name

(c)	(i)

(2) for a correct structure
IF STRUCTURE IS INCORRECT, BUT A CORRECT ESTER
LINKAGE IS FULLY DRAWN (1)
	the correct repeat unit must contain only 4 carbon and 4 oxygen atoms	2
Accept CQ polyester on basis of monomers in (b)(ii) and (iii)
Accept –CH2CH2–
instead of

in relevant part of structure
only (1) if STRUCTURE IS CORRECT, BUT the ester linkage has been written as COO/CO2
 
(ii)	Condensation	1
[10]

21.	First two marks:
	For correct reagent (ignore all state symbols) (1)
For correct condition(s), but only if with matching reagent (1)
Reagent	Condition	
HCN	Catalyst of CN–	
HCN	KCN	
KCN	HCN	
HCN or KCN	any stated pH or pH
range between 5 and 9	
KCN	+ (named) acid / H+	
HCN	+ (named) base / OH–	
	[Note: The intermediate compound CH3CH(OH)CN does not have to be identified.]
	Hydrolysis of –CN group to –COOH group:
	IGNORE MENTION OF “HEAT / REFLUX”
 
	Second two (only available if correct reagent has previously been given):
	EITHER
Name or formula of a mineral acid (1)
Boil or heat (1)
Second mark dependent on first mark being awarded
Accept “H+”
Accept “warm”
Reject conc H2SO4 (0)
	IGNORE MENTION OF “REFLUX”
	OR
Name or formula of correct alkali AND boil/heat (1)
“Acidify” / H+ or name/formula of any acid (1)
Accept OH– AND boil /heat/warm (1)
	IGNORE MENTION OF “REFLUX”	4
[4]

22.	(a)	Aldehyde(s)	1

(b)	(blue to) red (1)
precipitate/solid (1)	2
Accept green/yellow/ brown/orange instead of red
[3]

23.	(a)	(i)	Contains two double bonds /2 C=C / 1 × C=C and 1 × C=O	1
Accept triple bond
Reject a double bond
Reject does not contain a benzene ring
Reject alkene
Reject double bonds
 
(ii)	Does not contain an –OH group	1
Accept “Not an alcohol”
Reject “Not a hydroxide”
OR
Accept “Not an hydroxyl”
OR
“hydroxyl”
OR
“Not an alcohol nor a carboxylic acid/nor a phenol”
Reject “Not a carboxylic acid”
Reject “Not a phenol”
 
(iii)	Contains one C=C/ a C=C bond	1
 
(iv)	“Aldehyde or ketone” (both needed)
OR
carbonyl compound	1
Accept C=O
 
(v)	Aldehyde	1
Accept CHO
OR

(vi)	Has the same two groups across (on opposite sides) a C=C	1
May be shown in a diagram OR in (vii)
 
(vii)	Alkene and aldehyde groups anywhere in molecule
[but must have 6 carbons, 10 hydrogens and 1 oxygen] (1)
	Trans and rest of molecule (1)
	2
Accept CH3CH2CH2–
 
(b)	(i)	Nickel / platinum and hydrogen (1)
	Lithium tetrahydridoaluminate((III)) (1)
	Either order	2
Accept formulae
Accept Lithium aluminium
Accept hydride
Ignore solvent unless water – then reject
Accept sodium tetrahydridoborate((III))/borohydride
Reject sodium and ethanol
 
(ii)	(primary) alcohol	1
Accept hydroxyl OR hydroxyl
Reject OH
OR hydroxide
OR OH–
[11]

24.	(a)	Electrophilic substitution (1)
IGNORE extras eg Friedel Craft, alkylation UNLESS contradictory
	1-chloro-(2)-methylpropane (1)
IGNORE punctuation
Accept (2)-methyl-1-chloropropane
Accept CH3CH(CH3)CH2Cl/CH(CH3)2CH2Cl
Accept “Bromo”/”iodo” for “chloro”
Reject 1-methyl-2-chloropropane
Reject missing “1” from position of Cl in name
	Catalyst
AlCl3/aluminium chloride (1)	3
Accept Al2Cl6, AlBr3, FeBr3
 
(b)	LiAlH4 is a source of H– / hydride ion (1)
	Hydrogen might reduce/attack benzene ring/ H– won’t attack
region of negative charge/ H– can attack (δ+) C in keto group (1)	2
Reject comments on conditions or safety eg temperature, pressure
Reject LiAlH4/H– is a more powerful reducing agent
Reject H– is a nucleophile/a stronger nucleophile
Reject any mention of attack on carboxylate ion (for 2nd mark)

(c)	Note: although many candidates have calculated the empirical formula,
this is not required.
	Molecular formula of ibuprofen = C13H18O2 (1)
Allow if given at end
	Allow marks for masses and number of moles if answers are
rounded to 2 SF in “OR” but method is correct.
	EITHER
Mr = 206 (1)
	1 g = mol = 4.854 × 10–3 mol
mass CO2 produced from 13 C
= 13 × 44 × 4.854 × 10–3 = 2.78 g (1)
	mass H2O from 18 H
= 9 × 18 × 4.854 × 10–3 = 0.787 g (1)
	OR
Mass C =  = 0.758g
Mass H =  = 0.0873g (1)
	Moles C =  = 0.0632
Moles H = 0.0873 (1)
	Ratio C:H = 0.0632: 0.0873 = 13:18 (1)	4
 
(d)	(i)	(Aspirin and ibuprofen) both contain same (types of)
bond(s)(so absorb at same frequency/wavenumber)	1
Accept list of at least 4 bonds which are present in both
Reject “groups” for “bonds”
 
(ii)	Data is required for mark
	Y = paracetamol
Peak at 3500–3300 (N–H)
IGNORE mention of amine
	OR 3500–3140 (N–H or amide)
	OR 3750–3200 ((phenolic) O–H)
	OR Only Y has peaks above 3000 cm–1 (so must contain
different type of bond to X and Z)	1
Reject C–H in arene = 3030 as present in both
Reject 1700–1630 (amide)

(iii)	57 in Ibuprofen
C4H9+ /CH3CH(CH3)CH2+/CH(CH3)2CH2+
OR
C2O2H+/CCO2H+ (1)
Accept structural or displayed formulae
Do not allow lines at
15 (CH3+)
76 (C6H4+)
43 (C3H7+ or CH3CO+)
45 (COOH+)
as present in both
	Aspirin
59 (1) OCOCH3+ /C2H3O2+ (1)
OR
121 (1) C6H4CO2H+ (1)
OR
180 (1) C9H8O4+ (parent ion) (1)
OR
137 (1) C6H4(CO2H)O+ (1)
	Penalise no/wrong charges once only	3
[14]

25.	D
[1]

26.	(a)	C	1
 
(b)	D	1
 
(c)	B	1
[3]

27.	(a)	A	1
 
(b)	D	1

(c)	A	1
[3]

28.	(a)	B	1
 
(b)	B	1
[2]

29.	(a)	C	1
 
(b)	B	1
[2]

30.	(a)	methyl butanoate
Accept Methyl butaneoate	1
Reject ‘an’ missing
 
(b)	the other three substances can form
intermolecular hydrogen bonds with themselves but the ester cannot.	1
Reject Discussion of London Forces
 
(c)	Hydrolysis	1

(d)	QWC
	Must cover advantages and disadvantages. Must not be contradictory
	Advantages to manufacturers: (any two)
•	not dependent on weather, seasons etc
•	consistent taste /concentration/more consistent
•	quality
•	or alternative ideas
	Disadvantages to consumers : (any two)
•	some people put off by ‘non-natural’ food
•	may not taste the same as natural product which may contain
other impurities
•	unable to describe the product as organic
	or alternative ideas	4
Reject cost with no justification
 
(e)	Kc =  (1)
Accept eq subscripts
		Moles at	Concentration /
	equilibrium	mol dm–3
	butanoic acid = 4.4/88 =	0.05	1.67
methanol	0.05	1.67
ester (methyl butanoate)	0.05	1.67
water	0.95	31.7
	all four equilibrium moles = (1)
Conc at equilibrium = equilibrium moles ÷ 0.030 (1)
	Kc =  (1) = 0.053 (1)
ignore significant figures unless value given to 1 s.f.
	The units cancel because both the top and bottom of the fraction
have units of concentration squared.
Or same number of moles on both sides of the equation (1)	5
Reject absence of square brackets
[12]

31.	(a)	(i)	contains one carbon-carbon double bond
Accept alkene	1

(ii)	is a carbonyl compound / C=O group reduced (to CH(OH))
Accept aldehyde or ketone	1
 
(iii)	is a carbonyl compound
Accept aldehyde or ketone	1
 
(iv)	is a ketone / P is not an aldehyde	1
Reject aldehyde
 
(v)	has two groups on the same side of a C=C
Accept cis isomer	1
 
(b)	(i)	QWC
	3060 alkene (C–H stretching)
2920 alkane (C–H stretching)
1690 ketones (C=O stretching)
1660 alkene (C=C stretching)
	4 Correct ® 3 marks
3 Correct ® 2 marks
2 Correct ® 1 mark	3
 
(ii)	not an aldehyde	1
 
(iii)	QWC
	15 CH3 group (1)
29 C2H5 group (1)
43 no C3H7 group (1)	3
 
(c)

	ketone and Z (1)
rest of molecule (1)
Accept Fully displayed	2
 
(d)	Measure its melting temperature (1)
And compare with data book values (1)	2
[16]

32.	B
[1]

33.	D
[1]

34.	B
[1]

35.	A
[1]

36.	B
[1]

37.	(a)	B	1
 
(b)	B	1
 
(c)	A	1
 
(d)	D	1
[4]