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AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 1

DISTILLATION OF PETROLEUM
a) (i)

Mixture of alkanes with a wide range of Mr (1)

(ii) Middle East crude has a relatively high proportion of alkanes of high Mr (1)
b) (i)

Mixture of alkanes / compounds (1)


of similar boiling point (1)

(ii) Boiling point (1)


c) Sketch to show:
furnace for partial vaporisation of crude oil (1)
fractionating column (1)
any indication of trays and bubble caps (1)
injection of feedstock (1)
(superheated) steam injected at base of column (1)
Maximum 3 marks
d) (i)

Cool / 110 C at top to hot / 340 C at bottom (1)

(ii) Petroleum gases from top of column (1)


Light gasoline / petrol from top or near top (1)
Then, in decreasing order:
heavy gasoline / naphtha (1)
Half marks if shown at
kerosene / paraffin (1)
incorrect levels
diesel fuel / DERV (1)
lubricating oil (1)
Maximum 4 marks
e) Material
Use

Bitumen (1)
Road surfacing / for making fuel oil (1)

f) Industrial operation is continuous (1)


Laboratory operation is a batch process (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 2

CRACKING
a) (i)

Insufficiently volatile / does not fully vaporise in the cylinder (1)

(ii) CH3(CH2)8CH3 CH3(CH2)6CH3 + CH2 = CH2 (1)


CH3(CH2)8CH3 CH3(CH2)5CH3 + CH3CH = CH2 (1)
(iii) Lower alkanes are useful as petrol (1)
Lower alkenes can be polymerised (1)
Or one example of polymerisation (1)
Alkenes are used as feedstock for the petrochemical industry (1)
Or one example of this (1)
b)
Thermal cracking

Catalytic cracking

Conditions

High temperature ()
High pressure ()

High temperature ()
Slight pressure ()
Zeolite / alumino-silicate catalyst (1)

Type of bond breaking

Homolytic (1)

Heterolytic (1)

Type of reaction intermediate

Free radicals (1)

Carbonium ions / carbocations (1)

Principal products

Alkenes (1)

Motor fuels / arenes (1)

c) Reaction occurs on the surface of a catalyst (1)


With prolonged use the surface becomes coated / inefficient / will not properly adsorb reactants (1)
so the catalyst must be replaced (1)
Maximum 2 marks

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 3

FUELS
a) (i)

Methane -882/16 = - 55.1 kJ g-1 (1)


Octane -5512/114 = - 48.4 kJ g-1 (1)

(ii) Volume problem if CH4 is gaseous (1)


Cost / weight / escape problem if CH4 is liquid (1)
Transfer / refuelling problem for gaseous fuels (1)
Maximum 2 marks
b) (i)

Ignition during the upward stroke of the piston / before the petrol-air mixture is fully compressed (1)
leading to loss of power (1) and increased engine wear (1)

(ii) The percentage of 2,2,4-trimethylpentane / iso-octane (1)


in a mixture of 2,2,4-trimethylpentane and heptane (1)
with the same combustion characteristics as the fuel being tested (1)
c) (i)

Benzene

Carcinogenic / causes cancer (1)

Tetraethyllead

Exhaust emissions are poisonous / cause brain damage in children (1)

(ii) Method

Reforming / rearrangement / isomerisation (1)

Example

Accept any example of an unbranched alkane changing to a branched chain isomer (1)

Or Method

Cyclisation / ring formation (1)

Example

CH3(CH2)4CH3

+ H2 (1)
CH3

Or
d) (i)

CH3(CH2)5CH3

+ H2 (1)

Compression ignition / no spark plug (1)

(ii) Higher alkanes / higher Mr / higher b.p. / greater chain length (1)
(iii) Particulate carbon (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 4
EPOXYETHANE AND ETHANE-1,2-DIOL

a) (i)

O
2CH2 = CH2(g) + O2(g) 2CH2 CH2(g) (1)

(ii) Silver (1)


(iii) To relieve the pressure / by Le Chateliers principle (1)
equilibrium is disturbed to the side with fewer gas molecules (1)
(iv) Risk of explosive oxidation if too much ethene is present (1)
b) (i)

The C O C bond angle is only 60 (1)


the ring is strained / strain is relieved when the ring opens up (1)

(ii) CH2

O + CH3OH

CH2

CH2OH
(1)
CH2OCH3

(iii) CH2
O + CH3O(CH2) 2OH CH3O(CH2)2O(CH2)2OH (1)
CH2
c) The molecule hydrogen bonds with water through two OH groups (1)
there is little loss through vaporisation (1)
d) (i)

A chemical reaction in which two reactants undergo addition (1)


with subsequent elimination of a small molecule, such as H2O (1)

(ii)
C

O
O

H
(1)

O
O

(iii) Instead of one molecule of acid reacting with one molecule of the diol, one acid molecule reacts with the OH
groups of two diol molecules (1)
Or explained by formulae (1)
e) Hydraulic fluid / brake fluid (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 5

ADDITION POLYMERS
a) Monomer
Addition polymer

Simple compound / alkene / substituted alkene from which a polymer is derived (1)
A compound made by molecules of an unsaturated compound joining together in an addition
reaction (1)
Compound of high relative molecular mass / derived from a high number of monomer
molecules (1)
with a long chain of repeat units (1)

High polymer

b) (i)

LDPE Polymer chain is highly branched (1)


HDPE No chain branching / completely linear structure (1)

(ii) High temperatures / 100 300 C (1)


Very high pressures / 1000 2000 atm (1)
O2 catalyst / other catalyst which can give free radicals (1)
(iii) Triethylaluminium and titanium(IV) chloride (1)
Accept other valid examples.
(iv) Higher melting point / softening point (1)
More transparent (1)
Tougher / higher impact strength (1)
Maximum 2 marks
c) (i)

CH3

CH3

n CH=CH2 CH

CH2

(2)

Deduct 1 mark for each error. Bonds must pass through curved brackets.
(ii) Use
Crates / food containers / fibre for string, ropes, blankets, etc (1)
Advantage Tough / no odour (as appropriate) (1)
d) (i)

CH3
CH2 C

(1)

COOCH3
(ii)
CH3 CH3
C

(2)

CH3 H

Deduct 1 mark for each error.

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 6

POLY(CHLOROETHENE)
a)

Cl

H
C C

n
H

Cl

(1)
n

b) Polyvinyl chloride (1)


c) Polarisation of CCl bonds (1)
leads to dipole-dipole attractive forces between molecules of polymer (1)
These are stronger (1)
than the van der Waals attractive forces between molecules of poly(ethene) (1)
Maximum 3 marks
d) (i)

By incorporation of a plasticiser / oily liquid / named plasticiser, e.g. dibutyl phthalate (1)

(ii) Unplasticised poly(chloroethene) is hard / brittle (1)


Or plasticised poly(chloroethene) is soft (1)
(iii) Resistant to weathering / does not depolymerise readily / non-biodegradable (1)
(iv) Fire resistance (1)
e) Use poly(ethene) (1)
Poly(chloroethene) could undergo nucleophilic substitution / hydrolysis (1)
with OH replacing Cl / to give the corresponding alcohol (1)
Poly(ethene) resists attack by NaOH / OH- ions (1)
because it has no polarised bonds / no sites for nucleophilic attack (1)
Maximum 4 marks
f) Incineration gives HCl(g) / dioxins which are toxic (1)
Poly(chloroethene) is not biodegradable (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 7

HALOALKANES AS SYNTHETIC INTERMEDIATES


a) B = Ethene (1)
C = Ethyl hydrogen sulphate (1)
D = Ethanol (1)
E = Ethanoic acid (1)
F = Propanenitrile (1)
G = Propanoic acid (1)
b)
C

C2H6SO4

Reagent(s)

Concentrated H2SO4

(1)

Reagent(s)

Water

(1)

Conditions

Room temp. / 10-30 0C

(1)

Conditions

Warm / 30 - 40 0C

(1)

Reagent(s)
B

(1)

Concentrated H2SO4

C2H4
Conditions

170 - 180 C

C2H6O

(1)

Reagent(s)

Alcoholic KOH / NaOH

(1)

Reagent(s)

Aqueous NaOH / KOH

(1)

Conditions

Heat / boil

(1)

Conditions

Heat / boil under reflux

(1)

A C2H5Br

Reagent(s)

KCN / NaCN

(1)

Conditions

Heat / boil in aq. ethanol

(1)

Reagent(s)
F C3H5N
Conditions

Reagent(s)

Na2Cr2O7 + dil. H2SO4

(1)

Conditions

Heat / boil under reflux

(1)

Dilute H2SO4 / HCl(aq)

(1)

Heat / boil under reflux

(1)

C2H4O2

C3H6O2

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 8

CFCs
a) (i)
(ii)

Chlorofluorocarbon (1)
Cl F
Cl C

(1) (Accept CHCl2CHF2)

H H
(iii) In refrigerators / air conditioning units (1)
In the manufacture of expanded polystyrene (1)
Sprays for muscular sports injuries (1)
As cleaners (1)
Maximum 2 marks
b) (i)

An atom or group of atoms with an unpaired electron (1)

(ii) CF bond is stronger than the CCl bond (1)


because the F atom is smaller than the Cl atom / the CF bond is shorter than the C Cl bond (1)
Cl + O3 ClO + O2 (1)

(iii) Reaction 1

Reaction 2

ClO + O Cl + O2 (1)

(iv) The Cl free radical is catalyst (1)


and is not used up (1)
The Cl free radical which is used in Reaction 1 reappears as a product in Reaction 2 (1)
Because Cl free radicals are regenerated, they are available to bring about further change (1)
Maximum 2 marks
(v) At high altitudes the concentrations of the gaseous reactants are very low (1)
c) (i)

Greater intensity of ultraviolet light reaching the Earths surface (1)


can lead to skin cancer (1)

(ii) Contribute to the greenhouse effect (1)


(iii) Butane / ammonia / dinitrogen monoxide (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 9

USES OF OTHER ORGANIC HALOGENOCOMPOUNDS


a) (i)

Paint / electrodeposited metals will not adhere to a greasy surface (1)

(ii) Precaution
Reason

Efficient fume extraction (1)


Vapour is highly toxic / causes liver damage (1)

(iii) Dry cleaning (1)


b) (i)

Durability / resistance to weathering (1)


Low maintenance costs / does not need painting (1)
Fire resistance (1)

(ii) Name
Use
c) (i)

Poly(tetrafluoroethene) / PTFE (1)


Non-stick pans (1)

Slow to break down in the environment / effective for a long time (1)

(ii) Can enter the food chain (1)


d) (i)

Forms a blanket of non-flammable vapour (1)


which excludes air / oxygen (1)

(ii) Foam extinguishers may cause a short circuit / BCF cannot do so (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 10

FERMENTATION
a) (i)

Glucose / fructose (1)

(ii) In the absence of air / oxygen (1)


(iii) C6H12O6 2C2H5OH + 2CO2 (2)
Award (1) for reactant and (1) for products if balance is correct.
(iv) Catalyst (1)
b) (i)

Gas syringe (1)

Flexible tube

Thermostatically controlled water bath (1)

Sugar solution + yeast

(ii)
Rate

(1)

Temperature

(iii) Rate of reaction / fermentation increases with temperature (1)


until higher temperatures denature the enzyme (1)
c) Brazil has a warm climate ()
with a high intensity of sunlight for long periods ()
Therefore sugar cane (accept plants) grows quickly ()
Brazil has little reserves of mineral oil ()
and cannot afford using scarce foreign currency to purchase oil ()
Maximum 2 marks
d) Rapid (1)
Synthetic ethanol contains fewer impurities (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 11

SYNTHETIC ETHANOL PROCESS


a) (i)

CH2 = CH2(g) + H2O(g) CH3CH2OH(g) (1)

(ii) Electrophilic () addition ()


b) (i)

Carbocation / carbonium ion (1)

(ii) Arrow bottom left (should be encircled) should point from the bond to the O atom (1)
c) Advantage
Disadvantage
d) (i)

Increased rate of reaction / attaining equilibrium (1)


Lower yield of ethanol at equilibrium (1)

Higher yield of ethanol at equilibrium (1)


Equilibrium is disturbed to the side with fewer gas molecules (1)
so as to relieve the pressure / in accordance with Le Chateliers principle (1)

(ii) Higher power costs for the compressor (1)


High cost of constructing / maintaining thick-walled pressure vessels (1)
e) (i)

So that it presents a larger surface area to the reactants (1)

(ii) No effect (1)


f) Cool / condense to give aqueous ethanol (1)
Concentrate by fractional distillation (1)
Add methanol (1)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 12

ETHANOL AS A FUEL
a) (i)

C8H18(l) + 12O2(g) 8CO2(g) + 9H2O(l) (1)

(ii) C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l) (1)


b) (i)

m (C8H18) = 1000 x 0.72 = 720 g ()


n (C8H18) = 720/114 = 6.316 mol ()
enthalpy change = -5512 x 6.316 34,800 kJ (1)

(ii) m (C2H5OH) = 1000 x 0.79 = 790 g ()


n (C2H5OH) = 790/46 = 17.17 mol ()
enthalpy change = -1371 x 17.17 23,500 kJ mol-1 (1)
c) (i)

6.316 mol C8H18 6.316 x 8 = 50.53 mol CO2 (1)


m (CO2) = 50.53 x 44 = 2223 g CO2 (1)

(ii) 17.17 mol C2H5OH 17.17 x 2 = 34.34 mol CO2 (1)


m (CO2) = 34.34 x 44 = 1511 g CO2 (1)
d) (i)

2223/34800 = 0.0639 g kJ-1 (1)

(ii) 1511/23500 = 0.0643 g kJ-1 (1)


Comment

Similar masses of CO2 in both cases, therefore a similar impact on the environment (1)

e) Ethene originates from crude oil / fossil fuel / petroleum (1)


on combustion ethanol releases additional CO2 to the atmosphere (1)
Using ethanol made by fermentation recycles CO2 (1)
(No marks for greenhouse effect unless related to CO2 in the atmosphere)

AS Level

TOPIC 15 ANSWERS & MARK SCHEMES


QUESTIONSHEET 13

DISPOSAL OF ORGANIC WASTE


a) (i)

A huge range of plastics is in common use (1)


Separation is virtually impossible (1)

(ii) Paper can be pulped (1)


Vegetable waste can be composted (1)
b) Detrimental to the environment because of the large quantity of waste involved (1)
Toxic substances from industrial waste may contaminate surrounding land / enter the water table (1)
Microbiological reactions in the waste may produce toxic substances (1)
Maximum 2 marks
c) Domestic heating projects (1)
Generating electricity, using a steam turbine (1)
d) (i)

Chlorinated materials (1)


produce toxic compounds / dioxins (1)

(ii) Incomplete combustion (1)


leading to carbon monoxide / soot (1)
e) Sulphur-containing materials produce SO2 / SO3 / oxides of sulphur (1)
Nitrogen-containing materials produce NO2 / oxides of nitrogen (1)
These gases cause acid rain (1)
f) Most noxious gases / named examples are acidic (1)
they can be removed by passing over a base / scrubbing with an alkaline solution (1)