1.

(i) When calcium oxide and coke are heated in an electric furnace, the products are carbon
monoxide and calcium dicarbide (CaC
2
). Write the equation for this reaction.
CaO + 3C CaC
2
+ CO (1)
(ii) Addition of water to calcium dicarbide leads to the formation of calcium hydroxide and
ethyne (ethyne has the formula C
2
H
2
and is the starting point for the manufacture of a
variety of substances, including rayon and PVC). Write the equation for the production
of ethyne
.
CaC
2
+ 2H
2
O Ca(OH)
2
/CaO
2
H
2
+ C
2
H
2
(1)
(iii)

Until recently most ethyne was made in industry by the method in (ii). Today, ethyne is
produced in industry by heating methane (CH
4
) alone at a high temperature for 0.01
second. Write an equation for this reaction.
2CH
4
C
2
H
2
+ 3H
2
(1)
(iv) Draw a diagram showing the electron arrangement in the dicarbide ion C
2
2
.

Triple bond with correct total number of electrons (2)
(5)

2. (a) Benzene and methylbenzene may be separated by fractional distillation. Sketch the
general form of the boiling point/composition diagram for such a mixture and use it to
explain the basis on which fractional distillation rests.
0 1
b.p. of benzene
temperature
/C
b.p. of methylbenzene
mole fraction of methylbenzene

vapour line (1)
liquid line (1)
tie line (1)
vapour richer in more volatile component (1) must be a verbal statement
repeat tie lines (1)
distillate is benzene () and residue is methylbenzene () must be a
verbal statement
(6)


(b) (i) All lighter (more volatile) fractions from petroleum distillation are useful as fuels.
Suggest two reasons why the liquid fractions with 8 to 12 carbon atoms per
molecule are used as motor fuels, rather than the gaseous ones containing from one
to four carbon atoms.
higher AH
c
per mole / greater amount of energy per mole (1)
greater density or words to that effect / some reference to volume occupied
(1)
possible hazard of carrying compressed gases (1)
discussion on the presence of branched chains in liquids (1) (max 2)
(2)
(ii) Benzene is added to unleaded petrol to compensate for the absence of tetraethyl
lead. Both compounds are hazardous; which hazard is associated with benzene,
other than its flammability?
carcinogenic or words to that effect (1) not just toxic
(1)
(iii) Suggest two reasons why unleaded fuel has been promoted by government and the
petroleum industry.
lead toxic (1)
another reason eg effect on childrens intelligence (1)
reference to poisoning of catalytic converters (1) (max 2)
(2)
(Total 11 marks)

3. (a) All lighter (more volatile) fractions from petroleum distillation are useful as fuels.
Suggest two reasons why the liquid fractions with 8 to 12 carbon atoms per molecule are
used as motor fuels, rather than the gaseous ones containing from one to four carbon
atoms.
higher AH
c
per mole / greater amount of energy per mole (1)
greater density or words to that effect / some reference to volume occupied (1)
possible hazard of carrying compressed gases (1)
discussion on the presence of branched chains in liquids (1) (max 2)
(2)
(b) Benzene is added to unleaded petrol to compensate for the absence of tetraethyl lead.
Both compounds are hazardous; which hazard is associated with benzene, other than its
flammability?
carcinogenic or words to that effect (1) not just toxic
(1)
(c) Tetraethyl lead or benzene are added to petrol to prevent pre-ignition.
What is pre-ignition, and why is it a problem?
mixture in cylinder ignites before piston reaches top of stroke/ before
maximum compression/before spark (1) not just a restatement of pre-ignition
engine damage or power loss or loss of efficiency (1) not just pinking or
knocking unless explanation given
(2)


(d) Suggest two reasons why unleaded fuel has been promoted by government and the
petroleum industry.
lead toxic (1)
another reason eg effect on childrens intelligence (1)
reference to poisoning of catalytic converters (1) (max 2)
(2)
(Total 7 marks)

4. (a) When excess methane reacts with chlorine, the main product is chloromethane.
(i) Under what conditions does this reaction occur?
sunlight / UC (1)
(1)
(ii) Give the mechanism for this reaction.
(initiation) CICI CI

+ CI

(1)
(propagation) CI

+ HCH
3
CIH +

CH
3
(1)
CICI +

CH
3
CI

+ CICH
3
(1)
(termination) eg CI

+ CI

CI
2
(1)
if correct use of half arrow these take place of

does not have to be on the C atom ie CH

3

is acceptable.
(4)
(b) Heptane and octane are liquids at room temperature with boiling points of 98C and
126C respectively.
(i) What type of intermolecular forces of attraction are present in such liquids?
van der Waals/dispersion / induced dipole-induced dipole /
instantaneous dipole (1)
(1)
(ii) On the axes below, sketch a graph of how the boiling points of various mixtures of
these two liquids vary with composition. Show clearly the composition of the
liquid and vapour phases.
0
Temperature
mole fraction of heptane
1


lines correct shape () and labels ()
there must be 2 curves without a max or min in the diagram
the liquid line must not be straight
correct orientation according to axes (1)
(2)
(iii) By what process would a mixture containing a mole fraction of 0.5 heptane be

separated into pure heptane and pure octane?
fractional distillation (1)
(1)
(c) Liquid alkanes such as heptane and octane occur in petrol used as fuel to drive cards.
(i) Give two reasons why liquid fuels are generally preferred to gaseous ones.
any TWO from:
liquids have smaller volume can carry more fuel OWTTE (1)
(ie some reference to volume and consequence)
gases would need high pressures and therefore more likely escape (1)
(ie some reference to pressure and reason)
liquids easier to transfer (1) (max 2)
(2)
(ii) The combustion characteristics of fuels for internal combustion engines in cars can
be considerably improved by adding branched chain alkanes, cycloalkanes,
aromatic hydrocarbons or tetraethyl lead(IV) (lead tetraethyl). Two of these are
now considered to be hazardous to health. Select these two and identify the health
hazard with which each is associated.
aromatics () carcinogenic ()
lead compounds () lead poisoning etc ()
hazard is consequential on compound chosen
(2)
(Total 13 marks)

5. Liquid alkanes such as heptane and octane occur in petrol used as fuel to drive cards.
(i) Give two reasons why liquid fuels are generally preferred to gaseous ones.
any TWO from:
liquids have smaller volume can carry more fuel OWTTE (1)
(ie some reference to volume and consequence)
gases would need high pressures and therefore more likely escape (1)
(ie some reference to pressure and reason)
liquids easier to transfer (1) (max 2)
(2)
(ii) The combustion characteristics of fuels for internal combustion engines in cars can be
considerably improved by adding branched chain alkanes, cycloalkanes, aromatic
hydrocarbons or tetraethyl lead(IV) (lead tetraethyl). Two of these are now considered to
be hazardous to health. Select these two and identify the health hazard with which each
is associated.
aromatics () carcinogenic ()
lead compounds () lead poisoning etc ()
hazard is consequential on compound chosen
(2)
(Total 4 marks)



6. One use of nitric acid is to make inorganic nitrate fertilisers such as ammonium nitrate. Organic
compounds, e.g. urea, are also used. Discuss the relative merits of these compounds as
nitrogenous fertilisers.
TEMPERATURE:
increase t moves equilibrium right (1)
AH (+) (1)
and increases rate (1)
k.e. of molecules increased / more molecules have E
A
(1)
PRESSURE:
increase pressure no effect on equilibrium position (1)
same number moles of gas on each side (1)
increases rate (1)
ECONOMICS:
and the following related to the economics of the process:
recognition of need to move equilibrium right (1)
and increase rate (1)
not reference to catalyst
(Total 4 marks)

7. (a) (i) use of mixed acid increases concentration of NO
2
+
/ creates NO
2
+
(1)
electrophile or some comment on the way H
2
SO
4
does this (1)
OR
full equation (2) 2
(ii) (reaction exothermic and) temperature must not rise (1)
some indication that the temperature
must be kept down not too exothermic 1
(iii) too much conversion to dinitrobenzene otherwise /
to prevent further nitration (1)
if this is not mentioned in (iii) but then given in
(iv) the mark can be awarded 1
(iv) optimum rate / good yield (1) 1
(v) acid and benzene immiscible / there are 2 layers / maintain mixing of reactants (1)
so rate slow if not mixed or ensure reactants are in contact (1) 2
(vi) removes/dilutes most of the acid remaining (1)
if this is not mentioned in (vi) but then given in
(vii) the mark can be awarded 1
(vii) removes residual acid dissolved in nitrobenzene (1) 1
(viii) separates nitrobenzene from other volatile constituents / this is the temperature over
which pure nitrobenzene will distill (1) 1
(b) tin / tin(II) chloride / Fe (1)
(concentrated) HCl (1) ignore any reference to concentration of HCl this mark is
conditional on tin / tin(II) chloride / Fe or Sn
2+
being given heat (1) this mark is
conditional on both reagents being correct not LiAlH
4
which gives other products 3


(c) (i)

NH CO NHCO

enough to make structure clear
amide links (1) correct 1,3 position of ring (1)
some idea of extension required (ie the end groups must not be terminated)
brackets not necessary 2
(ii) polyamide or condensation (1) 1
(iii) acid chlorides (much) more reactive / more easily reacted (1)
give faster polymerisation / better yield (1) 2
(iv) add SOCl
2
/ PCl
5
/ PCl
3
(1)
COCl
COCl
(1)
2
[20]

8. (a) (i) D (1) 1
(ii) ionic (1) hydration energies of ions (OWTTE) / water is polar (1) 2
(b) (i) B (1) 1
(ii) B has long alkyl etc chain i.e. focussing on the C
15
H
31
group /
A and C have more sites for H bonding (1) 1
(c) (i) esterification (1) 1
(ii) acid (catalyst) (1) H
+
acceptable heat under reflux (1)
or
conc (1) sulphuric acid (1) 2
(iii) A to B: C
15
H
31
CO
2
H or the acid chloride (1) not C
16
H
32
O
2
C to D: NaOH / NaHCO
3
/ Na
2
CO
3
(1) 2
(d) (i) dissolve in min () quantity
hot () suitable solvent
filter when hot () cool () to crystallise
filter () wash () dry () (3 max 3) 3
(ii) determine melting point and compare to known values (1)
or sharp melting point (1)
if spectroscopy mentioned it must be explained fully 1
(e) hydrolysis (1) not saponification 1
[15]



9. (a) H
2
SO
4
+H
2
O HSO
4

+ H
3
O
+
(1)
can be expressed in
acid 1 base 2 base 1 acid 2 (1) words
need identification of pairs by number or letter, not A B A B alone
sulphuric acid acts as proton donor
or water acts as proton acceptor i.e. base(1) 3
(b) (i) both strong acids or both completely dissociated (1) the reaction in both is
H
+
+OH

H
2
O (1); must have equation for second mark 2
(ii) weak (acid) or incompletely dissociated (1)
needs to ionise during reaction which is an endothermic process or some
explanation of this in candidates own words (1) 2
(c) (i) solution resists change in pH (NOT constant pH ) or candidates own words
expressing same idea (1)
for small addition of acid or base (1) 2
(ii) +H
+
: SO
4
2
+H
+
HSO
4

+OH

: HSO
4

+OH

SO
4
2
+H
2
O
accept balanced nonionic equations. 2
(d) (i) Used to introduce hydrophilic or ionic or polar(1)
sulphonate or sulphonic acid group (1)
or introduces sulphonate group (1) into nonpolar
or hydrophobic molecules (1) 2
(ii) Do not form scum (1) (with hard water) and reason e.g. form soluble calcium
or magnesium salts or reference to soap forming insoluble salts (1) or less
detergent is needed (1) [Max 2]
references to lather or environment or clothes cleaner do not score
[15]

10. (a) (i) Restricted / no rotation about the C=C bond (1)
a d
C C
b e
in the case of sorbic acid a =b and d =e ( ) 1

The four groups do not need to be different 2
(ii) Four (1)
two for each double bond (1) 2


(b) (i) A system that resists changes of pH (1)
on the addition of small amounts of H
+
or OH

(1) 2
(ii) RCOOH RCOO

+ H
+
(1)
This equation must show
RCOOK RCOO

+ K
+
(1) or high concentration of sorbate ion from the
complete ionisation of the salt
This equation, if given, must not show
first equilibrium suppressed (1)
When H
+
added : RCOO

+ H
+
RCOOH (1)
When OH

added : RCOOH + OH

RCOO

+ H
2
O reducing the effect of
the addition of the OH

(1)
Judge quality of language at this point but show it at the end of the question
as a whole (1)
4max
+
Q of L
(c) (i)
CH CH CH CH CHCOOH + 2 Br CH CH CH CH CHCOOH
Br Br Br Br
( ) 1
3 3 2

product can be shown as CH
3
(CHBr)
4
COOH 1
(ii) Molar mass of sorbic acid =(6 12) +8 +(2 16) =112 g mol
1
(1)
amount of sorbic acid = 7.00/112 =0.0625 mol (1)
amount of bromine = 0.0625 2 =0.125 mol (1)
concentration of bromine solution =0.125/0.125
=1.00 mol dm
3
(1) 4
(d) (i) Aqueous ethanol favours substitution whereas pure ethanol
favours elimination (1) 1
(ii)
CH CH CH CH CHCOOH
OH OH OH OH
( ) 1
3
can also show ----COO

This is consequential on (c)(i) 1
(iii) Large number of OH groups on product will hydrogen bond with water so
soluble (1)
Nonpolar chain in bromo compound inhibits solubility/ cannot hydrogen bond
extensively with solvent /only one OH group / intermolecular bonds stronger than
bonds formed with water (1) 2


(e) (i) Long hydrophobic chain with polar end (1) 1
(ii)
C H COOCH
3 C H COONa + CHOH
C H COOCH + 3NaOH
C H COOCH
17
17
17
17
35
35
35
35
2
2
2
2
2
( ) 1
( ) 1
CH OH
CH OH

Any plausible fat will do but it must be an ester of glycerol for full marks. If ester is
not of glycerol but has at least two acid groups max 2
Use of R in place of Cl
7
H
35
is acceptable 3
[25]

11. (a) (i) correct structure (1)
If greater than 5 carbon atoms in chain but substituents at
2,2,4-trimethyl- then give (1), otherwise (0) 2
(ii) structural isomers (1) 1
(iii) 2C
8
H
18
+ 25O
2
16CO
2
+ 18H
2
O
products (1) balancing (1) 2
(iv) 2:125 or 1:62.5 (1) (2:25 scores zero)
consequential on equation given in (iii) 1
(b) comment on need for or hazards involved with use of pressurised storage (1)
or
more energy per unit volume or mass (1) 1
(c) (i) lead is poisonous / ruins catalyst in catalytic converters (1) 1
(ii) RON may not be maintained
or
fuel can cause pinking / knocking / pre-ignition (1) 1
(iii) benzene is carcinogenic (1) 1
(d) (i) 4.6/12 =4.55 9.1/1 =9.1 36.4/16 =2.275 (1)
4.55/2.275 =2 9.1/2.275 =4
C
2
H
4
O (1) 2
(ii) CH
3
CHO (1)
Reasoning based on MS (1) and IR (1)
e.g. Molecular ion is M
r
=44 so C
2
H
4
O
+
is molecular ion (1)
IR wave number at 1720 cm
1
shows C=O group (1) 3
[15]

12. Liquefaction or condensation (1)
Fractional Distillation (1)
Nitrogen boils off first or how the air is liquefied or that CO
2
/ H
2
O removed first (1)
[3]

13. (a) (i) 2 14 100 /60 (1) = 46.67 / 46.7% (1) 2

(ii) - Low(er) solubility / not easily leached
- non-explosive
- neutral
- less osmotic pressure / less scorching
- slow release Any two for 1 mark each
2
(b) Condensation polymerisation formed of a multiple unit with elimination of a simple
molecules (1)
Diagram (1)
e.g.
Cl C
C
C
C
Cl
N N
+ H N N H
O H H
H H
O
O O

Or formation of a polyester
Polyamide - polymer containing
C NH
O

/ -CONH- / -NHCO-(1)
Quality of language (1) 4
(c) Ammonia is the stronger base because ammonium ion is the weaker acid (1)
or
The weaker the acid, the stronger is its conjugate base (1)
Therefore (NH
4
+
weaker acid / smaller K
a
) ammonia is stronger base (1)
or
Ka for NH
4
+
is less than Ka for conjugate acid of urea (1)
therefore the ammonia is the stronger base (1)
ammonia is stronger base alone = (0) 2
(d) (i) Bromine (1)
NOT aq
NaOH (1)
Order of adding/addition and heat (1) 3
(ii) NH
2
NH
2
(1) 1


(e) (i) Ammonium nitrate is a solid / not a gas (1) 1
(ii) K
P
=P
NH3
. P
HNO3
(1)
P
NH3
=\15.7 =3.96 atm (1)
3.96 atm =3.96 1/50 moles of ammonia
= 0.079 moles (1)
Moles of NH
4
NO
3
=8.00/80 =0.100 (1)
% dissoc =0.079/0.1 100 =79% (1) 5
(iii) Energy level of product higher than energy level of reactant =thermodynamically
stable (1)
Reaction 1 exothermic therefore thermodynamically unstable /
product more thermodynamically stable than reactants (1)
Reaction 2 endothermic therefore thermodynamically stable /
products less thermodynamically stable than reactants (1)
High activation energy means kinetically stable (1)
Correct statement about either or both being kinetically stable (1) 5
[25]

14. (a) (280/2 =)140 (1)
5510/114 (1) =()48.3 (1) 3
(b) Eg. Hydrogen
- Less pollution (1)
- Greater energy per unit mass (1)
- renewable resource (1)
Eg. Octane
- Liquid easily transported (1)
- More readily available (1)
The two reasons must relate to thesame fuel no mark for fuel itself 2
(c) The answer requires a disadvantage for the fuel chosen in part (b)
Hydrogen needs to be made using electricity / idea of storage problems developed (1)
Octane (air) pollution or non-renewable(1) 1
[6]

15. (a) (i) Valid diagram 4 carbons overall C
4
H
10
(2)
(ii) Valid diagram 4 carbons C =C (2) 4
(b) Valid chlorine substituted product for the structure given in (a)
HCl (2) 2
(c) Any chlorine addition product for the structure given in (b)
Correctly drawn (2) 2


(d) Bromine solution added to unknown
Red/orange colour of bromine
Goes colourless (3) 3
(e) (i) Repeating unit of CH
2

No double bonds shown (2)
(ii) Electrophilic addition (1)
(iii) Any valid use e.g. packaging, containers, electrical insulation, piping, guttering.
Any other valid use (1) 4
[15]

16. (a) (i) enthalpy change /heat energy released
on complete combustion of 1 mole of substance
under standard conditions (3)
(ii) activation energy needed to be present
before reaction can proceed at reasonable rate (2)
(iii) methane plus oxygen at higher level than products
activation energy peak shown
. H shown on diagram (consequential on above) (3) 8
(b) (i) 2C
2
H
18
+25O2 16CO
2
+18H
2
O
1 mark for correct species 1mark for correct balance (2)
(ii) 1 mole of octane needs 12.5 moles of oxygen
1 mole of octane needs 12.5 5 moles of air (1)
1 mole of octane needs 12.5 5 24 dm of air =1500 dm(1) (2)
(iii) 890/16 (1)
=55.6 kJ (1) (2)
(iv) 890/24
=37.1 kJ (2)
(v) More energy per unit of volume
Methane difficult to liquefy/containers for compressed gases heavy
Plus 1 mark for clarity of argument and communication of ideas (3) 11
(c) Source of hydrogen
Source of heat (energy)to run process (2) 2
[21]



17. (a) (i) Rate =k[ (CH
3
)
3
CBr] (1)
CH C Br CH C CH C OH
CH CH CH
CH CH CH
+
:OH
3 3 3
3
3 3 3
3 3

(1) (1)

The hydroxide ion acts as a nucleophile (1)
The rate equation indicates the species involved in the rate determining step (1)
Only the halogenoalkane is involved in the rate equation,
the first step is the rate determining step/the production of
the carbocation (1) Max 6
(ii) Rate of reaction decrease I Br Cl (1)
Because the bond strengths for the CHal bond increase in this order (1) 2
(b)
CH CHCH CH
2 2 3
3
3
3
3
C C
C C
CH
CH
CH
CH
H
H
H
H
(3)
C C

Orbital overlap shown as diagram or words equivalent (1)
prevents free rotation (1)
The OH

is a base /removes H
+
(1) 6
(c)
C
C
C
H H
H
H
COOCH
COOCH
COOCH
+ 3KOH 3C H COO K + CHOH
CH OH
CH OH
2
2
2
2
35 35
35
35
17 17
17
17
+
(1) (1)

Stoichiometry LHS (1) (No need for charges)
Product is a soap (1). 4
[18]

18. (a) (i) 2H
2
+O
2
2H
2
O
formulae(1) balancing (1)
(ii) C
2
H
5
OH +3O
2
2CO
2
+3H
2
O
formulae(1) balancing (1) 4


(b) H
2
gives more heat per gram or more heat per / ethanol gives
less (1)
H
2
cheaper / ethanol more expensive(1)
H
2
is gas and so difficult to store/transport because it needs to
be under pressure or needs a strong container (1)
Ethanol liquid needs no special storage conditions (1)
H
2
gives only water which is not a pollutant (1)
ethanol gives CO
2
which is a greenhouse gas / leads to global
warming (1)
Ethanol can be a renewable resource needs to be qualified
(1)
e.g made from sugar or made by fermentation
Full marks can only be obtained for an answer that
includes a clear discussion of the advantages and Max
disadvantages of both types of fuels 5
[9]

19. (a) Group of compounds with the same general
formula(1) that
differ by CH
2
- (1)
Same or similar chemical properties / same 3
functional group (1)
(b) (i)
CH H
C C
H H
3
At least one repeat unit (1)
evidence of extension of chain (1) 2
consequential on correct repeat unit
(ii) CH
2
(1)
empirical formula of propene/ the repeat unit (1)
since polymer made by addition reaction / no loss of
small molecules (1) 3
(c) Different chain lengths / areas of crystalline and amorphous structure(1) 1
(d) (i) C-F bond strong / high bond enthalpy / bond not 1
easily broken / steric hindrance by fluorine around carbon (1)
(ii) Nonstick coatings e.g. in saucepans, in pipes, on skis,
stainproofing of fabrics, waterproof clothing. (1) 1
(e) Only single / sigma bonds in ethane(1)
Ethene also has t bond (1)
t bond weaker (and breaks) / electrons in t bond 3
more accessible(1)
[14]

20. (a) Spectra shows three types / environment of hydrogen (1)
Each peak related to type of hydrogen in ethanol (1)
References to mass spec score zero 2


(b) (i) Conc. sulphuric acid would produce (some) bromine(1)
50% acid produces HBr only (1) 2
(ii) Ammonia(1) heat in sealed tube / under pressure(1)
or
Concentrated ammonia(1) at room temperature(1) 2
(iii) Acid protonates -NH
2
(to -NH
3
+
) / -NH
2
reacts with H
+
( not HCl) (1) 2
ionic more soluble(1)
(c) If 3 steps that works
Correct intermediates score 2 marks
Any 3 correct reagents score 3 1 marks
Any one correct condition scores 1 mark
CH CH OH CH COOH
CH COONH
CH COCl
CH CONH
3 3
3 4
3
3 2
2
(1)
(1) (1)
(2)
(4) (3)
(5)

-
Step Reagent Conditions
1 Potassium dichromate +
named mineral acid or
potassium manganate(VII)
with sulphuric acid
Heat under reflux
2 PCl
3
/ PCl
5
/ SOCl
2
Dry / room
temperature
3 Ammonia Room temperature
4 Ammonia Room temperature
5 Heat
6
If scheme breaks down mark from start to breakdown and from end back
to breakdown and score best of these two marks
names or correct formulae allowed.
Name scores even if formulae then given and wrong
(d) (i)
2
2
2
2
or
O
O
O
O
O
O
C
C
N
N
C
C
(CH )n
(CH )n
(CH )m
(CH )m
C
C
N
N
H
H
H
H
(1) 1

(CH
2
)n or m represents a sensible unit which may be a benzene ring


(ii) H
2
N(CH
2
)
n
NH
2
and ClOC(CH
2
)
m
COCl
(1) (1) 2
Consequential on (i)
Allow caprolactan (2 marks)
or cyclic compound
H
2
N(CH
2
)
n
COCl scores 2 marks
(iii) Toxic if burnt/ non-biodegradable(1) 1
[18]

21. (a) (i) H F H F
C C C C
H F H F
(n) (n)

Min 2 carbon (1) 2 3
extension shown for both of them(1).
(ii) Mixture of different chain lengths
or
Areas of crystalline and amorphous structure(1) 1
(b) - C-F bond extremely strong / requires a lot of energy to break (1)
- so resistant to hydrolysis or some specified chemical attack (1) 2
(c) - Strong C-Cl means herbicide is persistent in environment / non-
biodegradable / hard to breakdown (1)
- useful for herbicidal effect (1)
but potentially toxic / harmful (1) 3
[9]

22. (a) (i) C
2
H
6
+Br
2
C
2
H
5
Br +HBr (1)
C
2
H
4
+Br
2
CH
2
BrCH
2
Br ALLOW C
2
H
4
Br
2
(1) 2
IGNORE STATE SYMBOLS
(ii) (Free) radical / homolytic (1) substitution (1)
Electrophilic (1) addition (1) 4
(b) (i) H H
C ( ) C
n
H Cl
1
(ii)
one Any
NOT
|
|
|
|
|
|
|
|
|
|
.
|
bags carrier / PVC / plastic
flooring
cables electrical on coating
bottles
clothing
frames door or window
pipes Water
1


(iii) Persists in the environment / persisting as litter
OR non-biodegradable / not broken down by bacteria (1)
because of strong C-Cl bond (1)
OR
combustion / burning (1)
produces toxic gases /acidic gases/HCI (1)
NOT chlorine 2
[10]

23. (a)
C C
F F
F F

Allow one carbon atom but not three or more unless two are bracketed together 1
(b) Resistant/ inert/ unreactive to foods/ cleaning materials
high melting/softening point/ nonflammable/ nontoxic/ stable at high
temperatures 1
(c) Persists in the environment / occupies sites for long time / many sites needed
Allow nonbiodegradable 1
(d) must be related to (c)
CF bond strong so difficult to break chemically / biologically
If nonbiodegradable used in (c), must refer to biological breakdown 1
[4]

24. (a) (i) nucleophilic substitution (1) 2
aqueous (1) Ignore heat under reflux here
Allow aqueous ethanol
(ii) elimination (1)
ethanolic / alcoholic (1)
heat (under reflux) (1) not h.u.r. , not warm 3
(b) (i) nCH
2
=CHCl ( CH
2
CHCl

n

ns (1) must balance
structure of product clearly shown with continuation bonds (1) 2
(ii) Electrical insulation / water pipes / guttering / window frames /
flooring/ specified clothing (1)
Do not allow buckets, bottles etc 1
(iii) Either
Remain in landfill sites (1)
not biodegradable / strong CCl bond (1) (both are stand-alone marks)
or
If incinerated (1)
produce toxic fumes (1) (consequential on incineration)
if specified, must be correct eg HCl or dioxins, not chlorine 2


(c) (i) 61.0/12 15.3/1 23.7/14 i.e. divide by A
r
(1)
5.08/1.69 15.3/1.69 1.69/1.69 i.e. divide by 1.69 to give 3:9:1 (1)
or
% C,H and N calculated from given formula (1)
which are the same as the data (1) 2
(ii) Ammonia (1) (Not formula)
CH
3
CHBrCH
3
+2NH
3
CH
3
CH(NH
2
)CH
3
/C
3
H
9
N +NH
4
Br
Organic species (1) (consequential on reasonably correct reagent)
balancing of equation as above (1) 3
(iii)
Br C C C H
H
H
H
H
H
H

All bonds must be shown 1
[16]

25. (a) enthalpy/heat (not energy) change for one mole of a compound / substance (1)
to be formed from its elements (1)
in standard states or under standard conditions of 1atm pressure and stated
temperature (298 K). (1) 3
(b) (i) AH
c
=[(394) +(2 286)] (75)]
=891 kJ mol
1

891 kJ mol
1
with working (3)
605 kJ mol
1
with working (2)
all other non-typo values (max 1) for 2 286
891 kJ mol
1
with no working (1) 3
(ii) (negative so) exothermic
(consequential on (i)) 1
(c) C
2
H
5
OH +3O
2
2CO
2
+3H
2
O
species (1)
balancing (1) 2
(d) QWC
Must compare the two fuels for full marks
Only datagenerated advantages and disadvantages to score.
- Methane is a gas and ethanol is a liquid plus a valid comment about
storage in vehicle, e.g. methane requires heavy container to store gas
under pressure / large container required to store gas, whereas easy to
store liquid in fuel tank (1)
Any 2 of
- Methane cheaper per kJ of heat released (than ethanol)
- Methane cheaper (per tonne than ethanol)
- Methane produces more heat per gram (than ethanol)
Cheaper / more heat implies a comparison 3


(e) C
2
H
5
OH +[O] CH
3
CHO +H
2
O (1) not CH
3
COH
C
2
H
5
OH +2[O] CH
3
COOH +H
2
O (1) (allow CH
3
CO
2
H)
Allow CH
3
CHO +[O] CH
3
COOH if CH
3
CHO is a product in 1
st
equation 2
(f) conc. H
2
SO
4
/Al
2
O
3
/ conc or syrupy H
3
PO
4
or names (1)
For acids, conditions: heat (if temp stated conc sulphuric 150 C200 C
phosphoric 50 to 100C)
For aluminium oxide, conditions: pass vapour over hot Al
2
O
3
(1) 2
[16]

26. (a) H
2
/ hydrogen NOT H (1)
Ni / nickel
OR platinum / Pt / palladium / Pd (1)
(Ni) 140 180 C / heat (1) 3
OR (Pt / Pd) room temperature
If no reagent but other parts correct (1)
Incorrect reagent (0)
(b) (i)
1
(ii) electrophile / electrophilic IGNORE any reference to addition 1
(c) potassium manganate(VII) / potassium permanganate / MnO
4

/
manganate(VII) ions IGNORE acid or alkali 1
ACCEPT name or formula
(d)

Correct structure (1) only one repeat until identified
Continuation (1)
IGNORE ( )
n
2
[8]



27. (a) (i)

Skeleton (1)
NOT C
3
H
7
NOT just R for side chain unles specify R = CH
3
CH
2
CH
2
Brackets are not essential
Extension (1) conditional on first mark OR C
3
H
7
/ R 2
(ii) nitration
ROOR 2RO
-
(1)
Propogation (1)
(1) (1)

ROCH(CH
2
C
2
H
5
)CH
2
-
+C
2
H
5
CH
2
CH =CH
2

ROCH (CH
2
C
2
H
5
)CH
2
CH (CH
2
C
2
H
5
)CH
2
-
Second propagation step consequential on first step
ALLOW C
3
H
7
OR CH
2
C
2
H
5
(1)

ALLOW any representation of the alkene eg RCH =CH
2
A correct use of single headed curly arrow 4
IGNORE additional incorrect arrows
IGNORE termination steps


(b) (i)

(1) for both arrows (1) for structure of intermediate


(1) Arrow
Lone pair not essential, but if it is shown the arrow must start from it
ALLOW arrow from negative charge
ALLOW arrow to + if written below the C
ALLOW C
3
H
7
/ R
If ethene is used MAX 2 for curly arrows 3
(ii) Structures of the 2 intermediate carbocations / intermediate cation
giving 2-bromopentane is secondary and primary for 1-bromopentane (1)
Secondary cation is more stable than primary CONDITIONAL
on reference to cations (1) 2
(c) (i) Sample in polarimeter / use of crossed polaroids / pass polarised
light through sample (1)
Rotates the plane of (polarisation of plane)-polarised (monochromatic)
light (1)
NOT deflection
NOT reflection 2
(ii) intermediate (carbocation) planar (1)
equal (probability of) attack from either side (1)
(leads to) racemic/ 50:50 / equimolar mixture (1) stand alone 3
[16]