1.

(a) (i) >C=C</ carboncarbon double bond / alkene (1) 1

(ii)

CH CH CH H
CH H H H
C C C C
3 3 3
3
(1) (1)


if the structure of but1ene is given as well as one (or both) stereoisomer(s) of
but2ene then (max 1) 2
(iii) no/restricted rotation about C=C bond (1)
some reference to the relevance of bonds or overlapping porbitals/ substit groups
on each carbon atom not the same (1) 2
(iv) CH
3
CH
2
CH=CH
2
(1) accept C
2
H
5
CH=CH
2
1
(b) (i)

CH CH
CH
C O
2 3
3
(1) accept C
2
H
5
for CH
3
CH
2
1
(ii)

CH C O
3
and CH CH
3
OH

(1) (1) 2
(iii) (D:) CH
3
CH
2
COO

(Na
+
) (1)
(E:) CH
3
CH
2
COOH (1)
D and E labels not required 2
(c) (i)

3 3 2
OH
CH CH CHCH
1
(ii) CH
3
CH
2
+
/ C
2
H
5
+
29 (1)
CH
3
CHOH
+
45 (1) not C
2
H
4
OH
+
or C
2
H
5
O
+

if charge(s) is (are) absent or incorrect then penalise (1)
since these are the only products it must be assumed that these are more stable than
the molecular ion / if both 29 and 45 are present this indicates total fracture of the
molecule (1) 3
(d) Hbonding responsible for variable frequency (1)
Hbonding broken as A is mixed with benzene (1)
a recognition that i.r. measures vibration/stretching of the OH group (1)
(some recognition of a modification of OH vibrations due to Hbonding which is then
disrupted can score (2)) max 2
[17]

2. (a) (i) CH
3
Br (1) 1
(ii) Ethoxyethane/ dry (1) ether (1) or ethoxyethane/
ether (1) iodine catalyst (1) 2
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(b) (i)
H C
H
H
C C
H H
H H
C
H
O

or CH
3
CH
2
CHO but not C
3
H
7
CHO (1) 1
(ii)

OH
C C C C C
H H H
H
H
H
H
H H H H
or formulae as above 1
(c) (i) Iodoform / CHl
3
(1) 1
(ii)

H C
H
H
C C
H H
H H
C
H
O Na
+
1
(d)

C C C C
H H H
H
H
H
C H
H
H H O
1
(e) (i) m/e 86 CH
3
COCH
2
CH
2
CH
3
+
(1)
m/e 43 CH
3
CH
2
CH
2
+
(1)
CH
3
CO
+
If charges absent/incorrect (1) or compressed formulae (1) 3
(ii) Strong peak at about 1700 cm
1
(1) shows C =O (1) 2
[13]

3. (a)
N N C
H H O
C
O
n

Correct structure if linkage(1)
Some evidence of continuation of molecule(1) 2
(b) Peak at A : C=O (1)
Peak at B : C O (1)
Spectrum is that of benzene 1,4- dicarboxylic acid (1) 3
(c) (i) To prevent the volatile reactant / dimethyl benzene boiling off (1)
(ii) Because the diacid is soluble in hot water (1)
(iii) M.Pt not sharp
or different from / not consistent with / less than data book (1) 3
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(d) (i)
C C
F F H H F F H H
F F H H F F H H
C C C C C C
n n
or

(or H...F...F...H on chain)
Correct repeating structure(1)
Some evidence of continuation of molecule(1) 2
(ii) Kevlar : condensation(1)
PDFE : addition (1) 2
(e) (i) more carbon dioxide per kJ of energy (1)
therefore more global warming/ more greenhouse gas produced (1) 2
(ii) Some reference to need for special arrangements for filling tank /
dangerous in the event of a crash /more weight as gas tank
weighs more than petrol tank / more likely to leak because gas
under pressure(1) 1
[15]

4. (a) (i) impurities lower / change the melting point /(impure solid)
melts over a range of temperatures
or the pure solid has a sharp melting point (1) 1
(ii) C=O / carbonyl responsible for peak at 1720cm
1
(1) 1
(iii) because of hydrogen bonding (1)
between (alcohol) molecules (1) 2
(iv) A is CH
3
CH
2
CH
2
CHO (1) or in full
B is CH
3
CH
2
CH
2
CH
2
OH (1) or in full
Incorrect B can score consequentially on A being a carbonyl from data 2
(b) (i) Reagent: potassium hydroxide / sodium hydroxide (1) or
KOH / NaOH
Solvent: ethanol/alcohol (1) but aqueous alcohol(0) 2
(ii) CH
3
CH
2
CH=CH
2
or in full (1)
if answer incorrect, consequential on B in (a)(iv) 1
(iii) CH
3
CH
2
CHBrCH
3
or in full (1)
consequential on D in (b)(ii) 1
(iv) Because CH
3
CH
2
CH
+
CH
3
/secondary ion / secondary intermediate is more stable
than the CH
3
CH
2
CH
2
CH
2
+
/primary ion / primary intermediate (1)
(do not allow Markovnikov as the reason) 1
[11]

5. (a) Peak 1 m/e 77: C
6
H
5
+
(1)
Peak 2 m/e 105: C
6
H
5
CO
+
(1)
Peak 3 m/e 134: C
6
H
5
COCH
2
CH
3
+
(1)
if + left off penalize only once 3
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(b) (i) IR spectrum number 2 1
(ii) Because of the broad peak at 3320cm
1
caused by OH / because peak at
3320 is OH / because it does not have a peak at 1750 and is only one
without C O 1
(iii) The other has a peak at approx. 1700 cm
1
caused by C=O 1
(c) (i) C 1 (brown) goes colourless 1 2
(ii) B 1 silver mirror / black precipitate 1 2
(iii) A (1) and B (1) red/orange/yellow ppt 1 3
(iv) C
6
H
5
CHBrCHBrCH
2
OH 1
(v) C
6
H
5
CH
2
CH
2
COO

but allow the carboxylic acid as product

consequential 1
(d) (i) Reagent: propanoyl chloride / C
2
H
5
COCl (1)
Conditions: dry / anhydrous (1)
aluminium chloride /iron (III) chloride (1) 3
(ii) C
2
H
5
COCl +AlCl
3
[C
2
H
5
CO]
+
+[AlCl
4
]

(1) for electrophile(1) for eqn

Allow
C H C Cl AlCl
O
2 5 3
+
2
[20]

6. (a) (i) Magnesium(1)
Dry Ether (1) 2
(ii) (Solid) carbon dioxide(1) then /followed by dilute HCl (1) 2
Carbon dioxide and dil HCl scores 1 mark
Any named mineral acid can score
Ignore state of carbon dioxide
(b) (i) (ether) flammable(1)
No naked flames/ use water bath / heating mantle(1) 2
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(ii) This is a diagrammatic representation of a set up that could be used.
The marks are for the particular elements not their orientation
Some means of adding bromoethane safely.
Or
Calcium chloride drying tube
Magnesium
+
ether
+
(iodine)
Reflux condenser
Water bath /
heating mantle
This mark lost if
Bunsen present
or heat

Marking
Flask +Reflux condenser (1)
Water bath / heating mantle(1) Consequential on first mark
Some means of excluding water vapour e.g. calcium chloride
guard tube or some means of adding reactants without danger (1) 4
Overall diagram(1) this must work and this must be safe
i.e. not closed show as Q
(c)
3 3 5 3 2 2
O O
CH CH C CH CH C OH +PCl Cl +POCl +HCl

structure of acid chloride showing at least expansion of COCl (1)
products (1) 2
(d)
C H
2 5
(1)
O
C

2,4dnp reacts with carbonyl group (1)
this carbonyl compound is a ketone and cannot be oxidised
by/ cannot reduce ammoniacal silver nitrate(1) 3
This is consequential on B being shown as a ketone
(e) (i) C H
2 5
(1)
OH
C
H

This is consequential on a ketone being shown in (d) 1
(ii) The lithium aluminium hydride would react with any water (1) 1
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(f) B has absorption peak in region 1680 1750 showing carbonyl (1)
but peak in region of 3250 3550 is present ( not present in B)
showing alcohol group / allow broad peak if range omitted (1)
comparison between two spectra(1) 3
(g) (i) P
4
+10Cl
2
4PCl
5
Allow
P
4
PCl
3
PCl
5
for species (1) for balancing (1)
If start with P
2
or P allow one mark for balanced equation 2
(ii) Oxidation number of phosphorus changes from 5 to 3 (1)
Oxidation number of chlorine changes from 1 to 0 (1)
Change of oxidation number is redox (1) 3
[25]

7. (a)
CH CH
CH CO H
C C CH H H
2
3 3
3 2

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)
PCl
5

or
2,4 dinitrophenylhydrazine
or dilute sulphuric acid plus potassium dichromate(VI)
or sodium hydroxide and iodine
2 correct observations (1) 2
(iii)
COOH HOOC
or sodium salt
1 correct COOH group scores 1 mark
2 correct COOH groups score2 marks 2
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(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 10
23
(1) =5.84 10
20
(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]

8. (a) (i)
chiral centre
1
(ii) rotation of plane of polarisation (of plane) polarised
(monochromatic) light 1
(b) 2,4-dinitrophenylhydrazine (1) orange / red / yellow ppt (1)
NOT DNP OR DNPH
Warm ammoniacal silver nitrate / Fehlings / Benedicts / K
2
Cr
2
O
7
+H
2
SO
4
(1) no silver mirror / red ppt OR stays blue / stays orange (1) 4
(c) Amount of carvone used
=2.70g/ 150 g mol
1
=0.018 mol (1)
amount of hydrogen used
=0.864 dm
3
/24 dm
3
mol
1
=0.036 mol (1)
Ratio carvone : hydrogen is 12 (1)
therefore two / / double / both C=C bonds reduced per molecule (1)
and so the structure is
O
(1) 5
(d) (i) Dry (1) ethoxyethane (1) 2
(ii) Attack by H

/ AIH
4

/ or by nucleophilic addition (1)

C=O polar, C=C nonpolar (1) 2
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(iii) Carvone shows peak near 1700 cm
1
(1)
characteristic of C=O / because it is a ketone (1)
Z shows (broad) peak around 3300 cm
1
due to O H group (from
reduction of C=O) (1) 3
(e) Several possibilities:
NaOH (1) C
6
H
5
OH +NaOH C
6
H
5
ONa +H
2
O (1) ethanol no reaction
(1);
OR
(aqueous) bromine (1)
C
6
H
5
OH +3Br
2
C
6
H
3
Br
3
OH +3HBr (ignore substitution pattern if
structural formulae are used) (1) ethanol no reaction (1)
OR conc sulphuric acid
nitration
Rhalogen (Friedel Crafts)
Phosphorus (V) chloride
Potassium dichromate(VI) / sulphuric acid
ethanoic acid (+conc H
2
SO
4
) 3
[21]

9. Tests on Compound C
(a) (i) 3
Observations Inferences
red unchanged (1)
blue red (1)
acidic (1)
(ii) 3
Observations Inferences
brown colour discharged (1)
white ppt (1)
Phenolic OH / phenol (1)
(iii) 1
Observations
Purple/ lilac solution
Tests on Compound D
(a) 4
Observations Inferences
D soluble / miscible (1)
effervescence (1)
polar (1)
carboxylic acid (1)
(b) 3
Observations Inferences
fruity smell (1) ester (1)
D contains COOH (1) do
not allow COOH without ref
to ester
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(c) IR spectrum
[C =O] str 1710 cm
1

[OH] str 3000 cm
1
(br) (2) 2
bands given must relate to the carboxylic acid.
(d)
-COOR / C
O
O
1
[17]

10. ALLOW correct names or formulae. If both given, both must be correct.
Condition marks are dependent on correct or nearly correct reagents.
(a) (i) aluminium chloride / AlCl
3
/ Al
2
Cl
6
/ iron(III) chloride / FeCl
3
OR the equivalent bromides 1
(ii) First step
Potassium dichromate +sulphuric acid
OR acidified dichromate
OR H
+
+Cr
2
O
7
2
OR (potassium) manganate(VII) / permanganate +acid / alkali /
neutral (1)
heat / reflux (1)
Intermediate: CH
3
COOH / CH
3
CO
2
H (1)
Second step
PCl
5
/ PCl
3
/ SOCl
2
(1) 4
(b) (i) LiAlH
4
(1)
dry ether / ethoxyethane (followed by hydrolysis). (1)
OR
NaBH
4
(1)
aqueous ethanol / water (1)
OR
Na (1)
ethanol (1)
OR
H
2
(1)
Pt OR Ni
+
heat OR Ni +specified temperature (1) 2
(ii) KMnO
4
(1)
sodium hydroxide / alkali (1) )
ALLOW KOH ) Both conditions dependent on
Heat (1) ) KMnO
4
OR
I
2
(1)
NaOH (1)
warm (1) 3
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(c) (i) A spectrum shows bond due to C =O at 1680 1700 (cm
1
) (1)
Can be given as a range or number within this range
NOT 1750
NOT 1680 1750
QWC
B spectrum shows bond due to OH at 3230 - 3550 (cm
1
) (1)
A has no OH / no bond at 3230 3550
OR B has no C=O bond / no bond at 1680 - 1700 (1)
Can be given as a range or number within this range
ALLOW 1750 if already penalised in first marking point 3
(ii) IR spectra due to bonds present (1)
Same bonds / functional groups in both isomers (1) 2
(d) (i) Iodine / I
2
/ sodium iodate(I) / NaOI / NaIO / iodate(I) / OI

/ IO

1
(ii) C
6
H
5
COCH
3
+3I
2
+4OH

C
6
H
5
COO

+CHI
3
+3I

+3H
2
O
OR
C
6
H
5
COCH
3
+3I
2
+4NaOH C
6
H
5
COONa +CHI
3
+3NaI +3H
2
O
CHI
3
on RHS (1)
NOT CH
3
I
All remaining species correct (1)
Balance (1) dependent on 2
nd
mark 3
(iii) (Hydrolyse with) NaOH / alkali (1)
acidify / neutralise with HNO
3
/ excess HNO
3
(1)
NOT just add
add silver nitrate (solution) (1)
yellow ppt (1)
If no hydrolysis 1 max for last 3 points correct 4
[23]

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11. (a) (i) C
6
H
5
O

Na
+
/ C
6
H
5
ONa / C
6
H
5
O

1
Do not allow covalent O-Na
(ii)
1
No other Isomer allowed
OR

IGNORE bond to H of OH
(iii)
1
No ring substitution allowed
(b) (i) NaNO
2
/ sodium nitrate / nitrate(III) (1)
conc aq / dil HCl / hydrochloric acid (1)
NOT HCI
Any temperature between 0 - 10 C
OR range between 0 - 10 C (1)
NOT less than 10 C
IGNORE everything before phenylamine eg starting from benzene
Conditions are dependent on correct or nearly correct reagents 3
(ii)

Correct diazonium ion (1) if -
+
N=N the +must be on correct N
Correct equation (1)
IGNORE position of OH group
Can include Cl

if equation is balanced
ALLOW +C
6
H
5
OH . +H
+
2
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(iii) Alkaline / alkali / sodium hydroxide / NaOH / KOH / potassium hydroxide /
sodium carbonate / sodium hydrogencarbonate
IGNORE temperature 1
[9]


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