Q1.Glucose Can Decompose in The Presence of Microorganisms To Form A Range of Products

Dubai English Speaking College
Q1.Glucose can decompose in the presence of microorganisms to form a range of products.

One of these is a carboxylic acid (Mr = 88.0) containing 40.9% carbon and 4.5% hydrogen
by mass.
(a)
Deduce the empirical and molecular formulas of the carboxylic acid formed.
Empirical formula = ...................... Molecular formula = ......................

(4)
(b)
Ethanol is formed by the fermentation of glucose.

A student carried out this fermentation reaction in a beaker using an aqueous
solution of glucose at a temperature of 25 C in the presence of yeast.
Write an equation for the reaction occurring during fermentation.
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(1)
(c)
In industry, this fermentation reaction is carried out at 35 C rather than 25 C.

Suggest one advantage and one disadvantage for industry of carrying out the
fermentation at this higher temperature.
Advantage ......................................................................................................
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Disadvantage .................................................................................................
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(2)
(d)
The method used by the student in part (b) would result in the ethanol being
contaminated by ethanoic acid.
How does this contamination occur?
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(1)
(e)
Give two differences between the infrared spectrum of a carboxylic acid and that of
an alcohol other than in their fingerprint regions.
Use Table A on the Data Sheet.
Difference 1 ...................................................................................................
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Difference 2 ...................................................................................................
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(2)
(Total 10 marks)
Q2.Alcohol A (CH3)2CHCH(OH)CH3 undergoes reactions separately with acidified potassium

dichromate(VI) and with concentrated sulfuric acid.
(a)
Deduce the IUPAC name for alcohol A.

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(1)
(b)
Draw the structure of the organic product, B, formed when A is oxidised in the
reaction with acidified potassium dichromate(VI).
(1)
(c)
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Two isomeric alkenes, C and D, are formed when A is dehydrated in the reaction
with concentrated sulfuric acid.
Name the mechanism for this dehydration reaction.

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(1)
(d)
Draw the structure of each isomer.

Isomer C
Isomer D
(2)
(e)
Name the type of structural isomerism shown by C and D.

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(1)
(f)
List alcohol A, product B and isomer C in order of increasing boiling point.

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(1)
(g)
Draw the structure of the isomer of A that is not oxidised by acidified potassium
dichromate(VI).
(1)
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(h)
Draw the structure of the isomer of A that cannot be dehydrated to form an alkene
by reaction with concentrated sulfuric acid.
(1)
(Total 9 marks)
Q3.Ethanol can be oxidised by acidified potassium dichromate(VI) to ethanoic acid in a two-step

process.
ethanol
(a)
ethanal
ethanoic acid
In order to ensure that the oxidation to ethanoic acid is complete, the reaction is
carried out under reflux.
Describe what happens when a reaction mixture is refluxed and why it is necessary,
in this case, for complete oxidation to ethanoic acid.
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(3)
(b)
Write a half-equation for the overall oxidation of ethanol into ethanoic acid.
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(1)
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(c)
The boiling points of the organic compounds in a reaction mixture are shown in the
following table.
Compound
Boiling point / C
ethanol
ethanal
ethanoic acid
78
21
118
Use these data to describe how you would obtain a sample of ethanal from a
mixture of these three compounds. Include in your answer a description of the
apparatus you would use and how you would minimise the loss of ethanal. Your
description of the apparatus can be either a description in words or a labelled
sketch.
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(5)
(d)
Use your knowledge of structure and bonding to explain why it is possible to

separate ethanal in this way.
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(2)
(e)
A student obtained a sample of a liquid using the apparatus in part (c).

Describe how the student could use chemical tests to confirm that the liquid
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contained ethanal and did not contain ethanoic acid.

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(5)
(Total 16 marks)
Q4.Ethanol is an important fuel.

(a)
A dilute aqueous solution of ethanol can be produced by the fermentation of an

aqueous solution of glucose.
It is claimed that the ethanol obtained from this solution is a carbon-neutral biofuel.
Write an equation for this fermentation reaction.
Give two other essential conditions for this reaction to produce a good yield of
ethanol.
Name a process used to produce a much more concentrated solution of ethanol
from a dilute aqueous solution.
State the meaning of the term carbon-neutral in the context of this biofuel.
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(5)
(b)
A student carried out a laboratory experiment to determine the enthalpy change

when a sample of ethanol was burned. The heat produced was used to warm some
water in a copper calorimeter. The student found that the temperature of 75.0 g of
water increased by 5.50 C when 2.40 10 mol of pure ethanol was burned in air.
3
Use the students results to calculate a value, in kJ mol , for the enthalpy change
when one mole of ethanol is burned.
(The specific heat capacity of water is 4.18 J K g )
1
Deduce two reasons why the students value for the standard enthalpy of
combustion of ethanol is different from a Data Book value of 1279 kJ mol .
1
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(5)
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(c)
Mean bond enthalpies can be used to calculate enthalpies of reaction.

(i)
Give the meaning of the term mean bond enthalpy.

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(2)
(ii)
Consider the mean bond enthalpy data in the following table.
Mean bond enthalpy /

kJ mol
1
CH
CC
CO
O=O
C=O
OH
412
348
360
to be
calculated
805
463
Use the data in the table above and the equation shown to calculate a value
for the bond enthalpy for the O=O double bond in an oxygen molecule.
CH CH OH(g) + 3O (g)
2CO (g) + 3H O(g) H = 1279 kJ mol
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(3)
(Total 15 marks)
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Q5.Ethanoic acid, propyl ethanoate and propan-1-ol are all colourless liquids. Esters do not
give a positive result with any of the usual tests for functional groups.
State how you could use chemical tests to show the presence of ethanoic acid and
propan-1-ol in a mixture of the acid, the alcohol and the ester.
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(Total 4 marks)
Q6.A sample of 2-methylpropan-2-ol was contaminated with butan-2-ol. The student separated
the two alcohols using chromatography.
Identify a reagent or combination of reagents that the student could use to distinguish
between these alcohols. State what would be observed for each alcohol.
Reagent(s) ..............................................................................................................
Observation with 2-methylpropan-2-ol ....................................................................
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Observation with butan-2-ol ....................................................................................
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(Total 3 marks)
Q7.In each of the following questions, you should draw the structure of the compound in the
space provided.
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(a)
Draw the structure of the alkene that would form 1,2-dibromo-3-methylbutane when
reacted with bromine.
(1)
(b)
Draw the structure of the alcohol with molecular formula C H O that is resistant to
oxidation by acidified potassium dichromate(VI).
4
10
(1)
(c)
Draw the structure of the alkene that has a peak, due to its molecular ion, at m/z =
42 in its mass spectrum.
(1)
(d)
Draw the structure of the organic product with Mr = 73, made from the reaction
between 2-bromobutane and ammonia.
(1)
(Total 4 marks)
Q8.Glucose is an organic molecule. Glucose can exist in different forms in aqueous solution.
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(a)
In aqueous solution, some glucose molecules have the following structure.
(i)
Deduce the empirical formula of glucose.

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(1)
(ii)
Consider the infrared spectrum of solid glucose.
Wavenumber / cm
State why it is possible to suggest that in the solid state very few molecules
have the structure shown.
You may find it helpful to refer to Table 1 on the Data Sheet.
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(1)
(b)
In the absence of oxygen, an aqueous solution of glucose can be fermented to

produce ethanol for use in alcoholic drinks.
Write an equation for this fermentation reaction.
Give two other essential conditions for the production of ethanol in this fermentation.
Equation
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Condition 1 ......................................................................................................
Condition 2 ......................................................................................................
(3)
(c)
Any ethanol present in the breath of a drinker can be detected by using a

breathalyser.
The ethanol is converted into ethanoic acid. The breathalyser has negative and
positive electrodes. A current is measured and displayed in terms of alcohol content.
The overall redox equation is as follows
CH CH OH(I) + O (g)
3
(i)
CH COOH(I) + H O(I)
3
Draw the displayed formula for ethanoic acid.
(1)
(ii)
Deduce a half-equation for the reduction of atmospheric oxygen to water in

acidic solution at one electrode of the breathalyser.
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(1)
(iii)
Deduce a half-equation for the oxidation of ethanol in water to ethanoic acid at

the other electrode of the breathalyser.
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(1)
(iv)
The earliest breathalysers used laboratory chemicals to oxidise the ethanol to

ethanoic acid. Detection was by a colour change.
Identify a reagent or combination of reagents that you would use in the
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laboratory to oxidise ethanol to ethanoic acid.

State the colour change that you would expect to see.
Reagent or combination of reagents .......................................................
Colour change .........................................................................................
(2)
(d)
The fermentation of glucose from crops is the main method for the production of
ethanol. The product is called bioethanol. The European Union has declared that
bioethanol is carbon-neutral.
(i)
State the meaning of the term carbon-neutral.

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(1)
(ii)
Other than carbon-neutrality, state the main advantage of the use of glucose
from crops as the raw material for the production of ethanol.
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(1)
(iii)
Give one disadvantage of the use of crops for the production of ethanol.
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(1)
(Total 13 marks)
Q9.Baking powder contains sodium hydrogencarbonate and an acid or a mixture of acids. One
acid that may be in baking powder is 2,3-dihydroxybutanedioic acid. This has the
molecular formula C4H6O6 and it is often referred to as tartaric acid.
(a)
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Draw the structural formula of tartaric acid.
(1)
(b)
Write an equation for the reaction of tartaric acid (C4H6O6) with sodium
hydrogencarbonate to form a salt, carbon dioxide and water.
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(1)
(c)
Substances that contain carbonate or hydrogencarbonate ions can be used to

confirm the presence of an acid.
Identify one other substance that could be used to confirm the presence of acid
groups in tartaric acid.
State the observation you would make when this other substance is added to an
aqueous solution of tartaric acid.
Substance ......................................................................................................
Observation ....................................................................................................
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(2)
(d)
It is known that tartaric acid contains alcohol and carboxylic acid functional groups
only.
A test can be used to show that tartaric acid contains secondary alcohol groups, not
tertiary alcohol groups.
(i)
Identify a reagent for this test and state the observation you would make for
each type of alcohol.
Reagent ................................................................................................
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Observation for secondary alcohol .......................................................
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Observation for tertiary alcohol .............................................................
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(3)
(ii)
Suggest why this test cannot be used to distinguish between a primary

alcohol and a secondary alcohol.
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(1)
(e)
Baking powder usually contains starch. Starch is added to absorb any water vapour
that may come into contact with the baking powder when the container is opened.
Deduce a reason why this water vapour needs to be absorbed.
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(1)
(f)
Sodium hydrogencarbonate in baking powder forms carbon dioxide during the

production of bread and cakes.
Suggest one advantage of having an acid in baking powder.
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(1)
(g)
Safety information indicates that tartaric acid and its salts can act as muscle toxins.
These can cause paralysis and possible death.
Suggest one reason why the use of tartaric acid in baking powder is not a hazard to
health.
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(1)
(Total 11 marks)
Q10.Methanol (CH OH) is an important fuel that can be synthesised from carbon dioxide.
3
(a)
The table shows some standard enthalpies of formation.

CO (g)
H (g)
CH OH(g)
H O(g)
394
201
242
H /kJ mol
f
(i)
CO (g)
2
Use these standard enthalpies of formation to calculate a value for the

standard enthalpy change of this synthesis.
3H (g)
2
CH OH(g)
3
H O(g)
2
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(3)
(ii)
State why the standard enthalpy of formation for hydrogen gas is zero.
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(1)
(b)
CO (g)
2
State and explain what happens to the yield of methanol when the total pressure is
increased in this synthesis.
+
3H (g)
CH OH(g)
H O(g)
2
Effect on yield ................................................................................................

Explanation ....................................................................................................
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(3)
(c)
The hydrogen required for this synthesis is formed from methane and steam in a
reversible reaction. The equation for this reaction is shown below.
CH (g) + H O(g)
4
C0(g) + 3H (g)
2
H = +206 kJ mol
State and explain what happens to the yield of hydrogen in this reaction when the
temperature is increased.
Effect on yield ................................................................................................
Explanation ....................................................................................................
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(3)
(d)
The methanol produced by this synthesis has been described as a carbon-neutral

fuel.
(i)
State the meaning of the term carbon-neutral.

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(1)
(ii)
Write an equation for the complete combustion of methanol.
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(1)
(iii)
CO (g)
2
The equation for the synthesis of methanol is shown below.

3H (g)
2
CH OH(g)
3
H O(g)
2
Use this equation and your answer to part (d)(ii) to deduce an equation to
represent the overall chemical change that occurs when methanol behaves as
a carbon-neutral fuel.
Equation ...............................................................................................
(1)
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(e)
A student carried out an experiment to determine the enthalpy change when a

sample of methanol was burned.
The student found that the temperature of 140 g of water increased by 7.5 C when
0.011 mol of methanol was burned in air and the heat produced was used to warm
the water.
Use the students results to calculate a value, in kJ mol , for the enthalpy change
when one mole of methanol was burned.
(The specific heat capacity of water is 4.18 J K g ).
1
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(3)
(Total 16 marks)
Q11.Three different ways of producing ethanol are shown below.
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(a)
Reaction 1 produces a 15% aqueous solution of ethanol.

It is claimed that the ethanol produced in this way is a carbon-neutral biofuel.
Write an equation for Reaction 1 and name the process.
Write an equation for the complete combustion of ethanol.
Explain why the ethanol produced by this process may not be a carbon-neutral
biofuel.
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(5)
(b)
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Give a reagent and conditions for Reaction 2.
CH CH Br
3
CH CH OH
3
Name and outline a mechanism for Reaction 2.
Suggest one reason, other than safety, why this method is not used in industry to
make ethanol.
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(6)
(c)
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Reaction 3 is used in industry.
H C =CH
2
CH CH OH
3
Identify a suitable catalyst for Reaction 3.

Identify the type of reaction.
Give two conditions, in addition to the presence of a catalyst, necessary for
Reaction 3 to produce a high yield of ethanol.
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(4)
(Total 15 marks)
Q12.The reaction of butane-1,4-diol with butanedioic acid produces the polymer PBS used in
biodegradable packaging and disposable cutlery.
Butanedioic acid is produced by two different processes.
Process 1
Aqueous sodium hydroxide reacts with 1,4-dibromobutane to make butane-1,4-diol.
Butane-1,4-diol is oxidised to butanedioic acid.
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Process 2
Glucose reacts with carbon dioxide in the presence of microorganisms to produce

butanedioic acid directly.
The carbon dioxide used in this process is obtained from a local factory that
produces bioethanol.
(a)
Deduce one safety reason and one environmental reason why Process 2 is
preferred to Process 1.
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(2)
(b)
(i)
Name and outline a mechanism for the following reaction that occurs in
Process 1.
BrCH CH CH CH + NaOH
Br
2
BrCH CH CH CH + NaBr
OH
2
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(3)
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(ii)
The infrared spectra shown are those of three compounds.

Compound A 1,4-dibromobutaneCompound B butane-1,4-diol
Compound C butanedioic acid
Identify the compound responsible for each spectrum by writing the correct
letter, A, B or C, in the box next to each spectrum.
You may find it helpful to refer to Table 1 on the Data Sheet.
(3)
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(c)
In the production of bioethanol, glucose (C H O ) is converted into a dilute aqueous

solution of ethanol and carbon dioxide.
6
12
Give the name of this process and state three essential conditions necessary to
produce a good yield of ethanol.
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(4)
(d)
State the class of alcohols to which the diol butane-1,4-diol belongs.

Identify a suitable reagent or combination of reagents for the conversion of butane1,4-diol into butanedioic acid (HOOCCH CH COOH).
2
Write an equation for this oxidation reaction using [O] to represent the oxidising
agent.
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(Total 15 marks)
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M1.(a)
Percentage of oxygen by mass = 100 40.9 4.5 = 54.6

1
= 3.41
= 4.5
= 3.41
%
Divide by Ar
Divide by smallest =
Nearest whole number ratio = 1 3
1.32 3
13
= 3 : 3.96 : 3
Nearest integer ratio =
3
1
Empirical formula C3H4O3

Empirical formula mass = 88 = molecular formula mass
Therefore, molecular formula is same as the empirical formula - C3H4O3
1
(b)
C6H12O6
2C2H5OH + 2CO2
1
(c)
Advantage ethanol is produced at a faster rate

1
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Disadvantage more energy is used / required in the reaction

1
(d)
Air gets in / oxidation occurs

1
(e)
Alcohol OH absorption in different place (32303550 cm1) from acid OH

absorption (25003000 cm1)
1
The C=O in acids has an absorption at 16801750 cm1

1
[10]
M2.(a)
3-methylbutan-2-ol
1
(b)
Allow (CH3)2CHCOCH3
1
(c)
Elimination
1
(d)
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Allow (CH3)2C=CHCH3
1
Allow (CH3)2CHCH=CH2
1
(e)
Position
1
(f)
CBA
1
(g)
Allow (CH3)2C(OH)CH2CH3
1
(h)
Allow (CH3)3CCH2OH
1
[9]
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M3.(a)
A mixture of liquids is heated to boiling point for a prolonged time

1
Vapour is formed which escapes from the liquid mixture, is changed back into
liquid and returned to the liquid mixture
1
Any ethanal and ethanol that initially evaporates can then be oxidised
1
(b)
CH3CH2OH + H2O
CH3COOH + 4H+ + 4e
1
(c)
Mixture heated in a suitable flask / container

A labelled sketch illustrating these points scores the marks
1
With still head containing a thermometer

1
Water cooled condenser connected to the still head and suitable cooled
collecting vessel
1
Collect sample at the boiling point of ethanal

1
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Cooled collection vessel necessary to reduce evaporation of ethanal

1
(d)
Hydrogen bonding in ethanol and ethanoic acid or no hydrogen bonding in

ethanal
1
Intermolecular forces / dipole-dipole are weaker than hydrogen bonding

1
(e)
Reagent to confirm the presence of ethanal:

Add Tollens reagent / ammoniacal silver nitrate / aqueous silver nitrate
followed by 1 drop of aqueous sodium hydroxide, then enough aqueous
ammonia to dissolve the precipitate formed
OR
Add Fehlings solution
1
Warm
M2 and M3 can only be awarded if M1 is given correctly
1
Result with Tollens reagent:

Silver mirror / black precipitate
OR
Result with Fehlings solution:
Red precipitate / orange-red precipitate
1
Reagent to confirm the absence of ethanoic acid

Add sodium hydrogencarbonate or sodium carbonate
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1
Result; no effervescence observed; hence no acid present

1
M5 can only be awarded if M4 is given correctly

OR
Reagent; add ethanol and concentrated sulfuric acid and warm
Result; no sweet smell / no oily drops on the surface of the liquid,
hence no acid present
[16]
M4.(a)
M1 C6H12O6
2CH3CH2OH
(2C2H5OH)
+ 2CO2
Penalise C2H6O for ethanol in M1.

M2 and M3
Mark M2 and M3 independently.
Any two conditions in any order for M2 and M3 from
(enzymes from) yeast or zymase
25 C T 42 C
anaerobic / no oxygen / no air OR neutral pH

A lack of oxygen can mean either without oxygen or not
having enough oxygen and does not ensure no oxygen,
therefore only credit lack of oxygen if it is qualified.
Penalise bacteria, phosphoric acid, high pressure using
the list principle.
OR
298 K T 315 K
M4 (fractional) distillation or GLC

Ignore reference to aqueous or water (ie not part of the list
principle).
M5 Carbon-neutral in this context means
There is no net / overall (annual) carbon dioxide / CO2 emission to the
atmosphere
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OR
There is no change in the total amount / level of carbon dioxide / CO2 present
in the atmosphere
For M5 must be about CO2 and the atmosphere.
The idea that the carbon dioxide / CO2 given out equals the
carbon dioxide / CO2 that was taken in from the atmosphere.
5
(b)
M1 q = m c T (this mark for correct mathematical formula)

Full marks for M1, M2 and M3 for the correct answer.
In M1, do not penalise incorrect cases in the formula.
M2 = (75 4.18 5.5)
1724 (J) OR 1.724 (kJ) OR 1.72 (kJ) OR 1.7 (kJ)
(also scores M1)
Ignore incorrect units in M2.
M3 Using 0.0024 mol
therefore H = 718 (kJ mol1)
(Accept a range from 708 to 719 but do not penalise more than 3 significant
figures)
Penalise M3 ONLY if correct numerical answer but sign is
incorrect. Therefore +718 gains two marks.
If units are quoted in M3 they must be correct.
If T = 278.5, CE for the calculation and penalise M2 and
M3.
M4 and M5 in any order
Any two from
incomplete combustion
heat loss
heat capacity of Cu not included
some ethanol lost by evaporation
not all of the (2.40 103 mol) ethanol is burned / reaction is incomplete
If c = 4.81 (leads to 1984) penalise M2 ONLY and mark on
for M3 = 827
5
(c)
Page 33
(i)
M1 enthalpy / heat / energy change (at constant pressure) or enthalpy /
heat / energy needed in breaking / dissociating (a) covalent bond(s)

Ignore bond making.
M2 averaged for that type of bond over different / a range of molecules /
compounds
Ignore reference to moles.
2
(ii)
M1
B(reactants) B(products) = H
OR
Sum of bonds broken Sum of bonds formed = H
OR
B(C-C) + B(C-O) + B(O-H) + 5B(C-H) + 3B(O=O)
4B(C=O) 6B(OH) = H = 1279
Correct answer gains full marks.
Credit 1 mark for 496 (kJ mol1)
For other incorrect or incomplete answers, proceed as
follows
check for an arithmetic error (AE), which is either a

transposition error or an incorrect multiplication; this
would score 2 marks (M1 and M2).
If no AE, check for a correct method; this requires either a
correct cycle with 2CO2 and 3H2O OR a clear statement of
M1 which could be in words and scores only M1.
M2 (also scores M1)
348+360+463+5(412)+ 3B(O=O)
(3231)
(or 2768 if OH cancelled)
4(805) 6(463) = H = 1279
(5998)
(or 5535 if OH cancelled)
3B(O=O) = 1488 (kJ mol1)

Credit a maximum of one mark if the only scoring point is
bonds formed adds up to 5998 (or 5535) OR bonds broken
includes the calculated value of 3231 (or 2768).
M3
B(O=O) = 496 (kJ mol1)
Award 1 mark for 496
Students may use a cycle and gain full marks
3
[15]
Page 34
M5.Identification of acid by suitable method eg named indicator, named carbonate, specified

reactive metal
Ignore any reference to the smell of the ester.
1
with expected results

Do not allow the use of any instrumental method eg i.r. or
n.m.r.; must be a chemical test.
1
Identification of alcohol by suitable method eg oxidation by acidified potassium

dichromate(VI)
1
with expected results

1
[4]
M6.Acidified potassium dichromate

Accept words or formulae.
Accept acidified potassium permanganate.
Accept Lucas reagent (conc HCl, ZnCl2) (cloudy in 5 mins for
2, instantly for 3).
Mark on for incomplete reagent.
Incorrect reagent CE = 0 / 3
Inclusion of Tollens etc with acidified potassium dichromate
is incorrect reagent.
Not no reaction.
Either
Obs with 2-methylpropan-2-ol
No visible change
1
Page 35
Obs with butan-2-ol

Orange to green (both colours needed)
1
or
Obs with 2-methylpropan-2-ol orange
Obs with butan-2-ol
green
[3]
M7.(a)
Structure for 3-methylbut-1-ene

H C=CHCH(CH )
Any correct structural representation.
Credit sticks and require the double bond.
2
3 2
(b)
Structure for 2-methylpropan-2-ol

(CH ) COH
3 3

Credit sticks.
1
(c)
Structure for propene

H C=CHCH
2

Credit sticks and require the double bond.
1
(d)
Structure for 2-aminobutane

CH CH CH(NH )CH
3
Page 36

Credit sticks.
1
[4]
M8.(a)
(i)
CH O
2
Atoms in any order

Accept a clear indication that C H O yields CH O as the
answer
6
12
(ii)
No peak / no absorption / no C=O in the range 1680 to 1750 (cm )

(suggesting no evidence of C=O)
Allow the words dip, spike, low transmittance and
trough as alternatives for absorption
Ignore references to other wavenumbers
1
(b)
M1 C H O
6
12
2CH CH OH + 2CO
Penalise (C H O)
Allow multiples of the equation in M1
3
Either order
M2 (enzymes from) yeast or zymase
M3 25 C T 42 C OR 298 K T 315 K
For M2 and M3
Ignore aqueous
Ignore anaerobic / absence of oxygen
Ignore controlled pH
Ignore warm
3
(c)
Page 37
(i)
Displayed formula for CH COOH

3
All bonds must be drawn out, but ignore bond angles

1
(ii)
O + 4H + 4e
2H O
Ignore state symbols
Negative charge on electron not essential
Accept multiples
Accept electrons subtracted from RHS
+
(iii)
CH CH OH + H O
3
CH COOH + 4H + 4e
(C H O or C H OH)
Negative charge on electron not essential
Accept multiples
Accept electrons subtracted from LHS
2
(iv)
M1 Acidified potassium or sodium dichromate

For M1, it must be a whole reagent and / or correct formulae
OR H SO / K Cr O OR H / K Cr O etc.
Do not penalise incorrect attempt at formula if name is
correct or vice versa
2
OR correct combination of formula and name

If oxidation state given in name, it must be correct, but mark
on from an incorrect attempt at a correct reagent.
M2 (requires an attempt at M1)
orange to green
Credit acidified potassium chromate(VI) / H SO +
K CrO
2
Possible alternative
M1 (acidified) potassium manganate(VII) OR KMnO / H SO
M2 purple to colourless
Other alternatives will be accepted but M2 is dependent on
M1 in every case
M2 requires an attempt at a correct reagent for M1
Ignore reference to states
4
Page 38
(d)
(i)
An activity which has no net / overall (annual) carbon emissions to the

atmosphere / air
The idea that the carbon / CO given out equals the carbon /
CO that was taken in from the atmosphere / air
2
OR
An activity which has no net / overall (annual) greenhouse gas
emissions to the atmosphere / air.
Answer must refer to the atmosphere or air
OR
There is no change in the total amount of carbon dioxide / carbon
/greenhouse gas present in the atmosphere / air
1
(ii)
Renewable / sustainable ONLY

Ignore references to global warming or greenhouse gases
1
(iii)
Any one statement about this process from

Subject to weather / climate
Ignore batch
OR
Depletes food supply OR the land use for (specified) food
OR
Requires use of / uses more fossil fuels
OR
Not carbon-neutral OR CO produced during a named process (eg
harvest, transport etc.)
2
OR
Slow process / slow rate of reaction / takes a long time (to grow crops)
OR
This route leads to the production of a mixture of water and ethanol /
impure ethanol that requires separation / further processing
1
Page 39

[13]
M9.(a)
HOOCCHOHCHOHCOOH
Any suitable structural formula.
Displayed formula not required but bond sequences must be
correct if shown.
1
(b)
C4H6O6 + NaHCO3 C4H5O6Na + CO2 + H2O

OR
C4H6O6 + 2NaHCO3 C4H4O6Na2 + 2CO2 + 2H2O
Allow equations based on the structural formula.
Allow multiples including fractions.
Allow any structure for C4H6O or C4H5O6Na
1
(c)
Suitable named indicator (eg litmus, methyl orange, Universal Indicator) /

identified reactive metal (Mg, Zn or Fe)
Do not allow phenolphthalein without explanation of how a
colour change would be seen.
Incorrect reagent, chemical error = 0 / 2
1
Appropriate colour in acid (eg red) / gas evolved

1
(d)
(i)
Reagent: Acidified potassium dichromate (solution)

If incomplete (correct) reagent, lose M1 but mark on.
Incorrect reagent, chemical error = 0 / 3
Allow acidified potassium manganate(VII)
1
Page 40
Obs: orange to green

Purple to colourless (solution).
1
Obs: no (visible) change

Allow no visible reaction, but do not allow no reaction
without qualification.
1
(ii)
Both would give the same result / both oxidised by reagent / both react
with the reagent or similar
Allow consequential answer from (i).
Chemical error if reagent in (i) is incorrect, 0 / 1
1
(e)
The water would allow the tartaric acid and sodium hydrogencarbonate to
react (before use)
Ignore any reference to water reacting with the ingredients.
Ignore references to prevention of caking or clumping.
Ignore references to shelf life without qualification.
1
(f)
Acid reacts (with NaHCO3 / Na2CO3) to form CO2

Allow neutralises (NaHCO3 / Na2CO3) to form CO2.
1
(g)
It is only used in very small quantities

Allow decomposes in the reaction.
Do not allow reacts without qualification.
Ignore reference to formation of salts.
1
[11]
M10.
Page 41
(a)
(i)
M1 (could be scored by a correct mathematical expression which
must have
all Hsymbols and the or SUM)
M1
H = H (products) - H (reactants)
OR
a correct cycle of balanced equations with 1C, 3H and 1O
M2
H = 201 + ( 242) ( 394)

H = 201 242 + 394
H = 443 + 394
(This also scores M1)
r
r
M3 = 49 (kJ mol )
(Award 1 mark ONLY for + 49)
Correct answer gains full marks
Credit 1 mark ONLY for + 49 (kJ mol )
For other incorrect or incomplete answers, proceed as
follows
check for an arithmetic error (AE), which is either

a transposition error or an incorrect multiplication;
this would score 2 marks (M1 and M2)
If no AE, check for a correct method; this requires

either
correct cycle of balanced equations with 1C, 3H and
1O
OR a clear statement of M1 which could be in words
and
scores only M1
1
(ii)
It is an element / elemental
Ignore reference to standard state
OR
By definition
1
(b)
M1 (The yield) increases / goes up / gets more

If M1 is given as decreases / no effect / no change then
CE= 0 for clip, but mark on only M2 and M3 from a blank M1
M2 There are more moles / molecules (of gas) on the left / of reactants
OR fewer moles / molecules (of gas) on the right
/ products
OR there are 4 moles /molecules (of gas) on the left and 2 moles / molecules on the
right.
OR (equilibrium) shifts / moves to the side with less moles / molecules
Ignore volumes, particles atoms and species for M2
Page 42
M3: Can only score M3 if M2 is correct

The (position of) equilibrium shifts / moves (from left to right) to oppose the increase
in pressure
For M3, not simply to oppose the change
For M3 credit the equilibrium shifts / moves (to right) to lower
/ decrease the pressure
(There must be a specific reference to the change that is
opposed)
3
(c)
M1 Yield increases goes up

M2 The (forward) reaction / to the right is endothermic OR takes in/ absorbs
heat
OR
The reverse reaction / to the left is exothermic OR gives out / releases heat
If M1 is given as decrease / no effect / no change then
CE= 0 for clip, but mark on only M2 and M3 from a blank M1
Can only score M3 if M2 is correct
M3 The (position of) equilibrium shifts / moves (from left to right) to oppose the
increase
in temperature (QoL)
For M3, not simply to oppose the change
For M3, credit the (position of) equilibrium shifts / moves
(QoL)
to absorb the heat OR
to cool the reaction OR
to lower the temperature
(There must be a specific reference to the change that is
opposed)
3
(d)
(i)
An activity which has no net / overall (annual) carbon emissions to the

atmosphere
OR
An activity which has no net / overall (annual) greenhouse gas emissions
to the atmosphere.
OR
There is no change in the total amount / level of carbon dioxide /CO carbon
/greenhouse gas present in the atmosphere.
The idea that the carbon /CO given out equals the carbon
/CO that was taken in from the atmosphere
2
Page 43
(ii)
CH OH + 1 O
Accept multiples
3
CO
2H O
2
(iii)
3H
+ 1 O
3H O
OR
Accept multiples
2H
+ O
2H O
Extra species must be crossed through
2
(e)
M1
q = m c T
Award full marks for correct answer
Ignore the case for each letter
OR
q = 140 4.18 7.5
M2
= 4389 (J) OR 4.389 (kJ) OR 4.39 (kJ) OR 4.4 (kJ)(also scores M1)
M3
Using 0.0110 mol

therefore H = 399 (kJmol )
OR 400
Penalise M3 ONLY if correct numerical answer but sign is
incorrect; +399 gains 2 marks
Penalise M2 for arithmetic error and mark on
In M1, do not penalise incorrect cases in the formula
If T = 280.5; score q = m c T only
If c = 4.81 (leads to 5050.5) penalise M2 ONLY and mark on
for M3 = 459
1
+399 or +400 gains 2 marks

Ignore incorrect units
3
[16]
Page 44
M11.(a)
M1 C H O
6
12
2CH CH OH + 2CO
(2C H OH)
Mark independently
For M1 and M3 ignore state symbols and credit multiples
For M1 and M3 penalise C H O once only
M2 fermentation
M3 CH CH OH + 3O
(C H OH)
3
2CO + 3H O
M4 A specified process e.g. planting / harvesting / transport / extracting sugar /

distilling ethanol solution / fertiliser production etc.
M5 The specified process uses / burns (fossil) fuel that releases CO
For M5, releases / increases carbon emissions is
insufficient as an alternative to releases CO
(b)
M1 sodium or potassium hydroxide / NaOH / KOH

Mark on to M2 from hydroxide ion
M2 depends on correct M1
Ignore OH if KOH/ OH
warm / heat / reflux and aqueous or (aq) or water

For M2 ignore dilute
For M2 penalise T > 100 C
M3 nucleophilic substitution
Acidified KOH/NaOH or H SO with KOH/NaOH loses M1
and M2
2
For M3, both words required

NB The arrows here are double-headed
M4 must show an arrow from the lone pair of electrons on the oxygen atom of
the
negatively charged hydroxide ion to the C atom.
Penalise M4 if covalent NaOH / KOH is used
Penalise one mark from M4 or M5 if half-headed arrows are
used
M5 must show the movement of a pair of electrons from the
C Br bond to the Br atom. Mark M5 independently provided it is from their original
Page 45
molecule.
Penalise M5 for formal charge on C of the CBr or incorrect
partial charges on CBr
Penalise once only for a line and two dots to show a bond.
For M4 and M5, award full marks for an S 1 mechanism
For M4 and M5, maximum 1 of 2 marks if wrong reactant is
used.
Penalise M5 if an extra arrow is drawn from the Br of the C
Br bond to, for example, K span>
Do not penalise the use of sticks
N
M6 One statement from

The yield is (very) low / not a high yield OR elimination occurs / ethene
formed
The rate of reaction slow
Bromoethane has to be manufactured / made first
Bromoethane is expensive
For M6 ignore references to other costs and expenses
6
(c)
M1 concentrated phosphoric acid / conc. H PO OR concentrated sulfuric acid /conc.

H SO
Answers in any order
Ignore reference to support medium in M1
3
M2 hydration or (electrophilic) addition

For M3 and M4 any two from
Do not apply the list principle to these three chosen criteria
in M3 and M4
Excess ethene
OR Excess steam / water / H O
2
OR remove the ethanol as it forms

OR recycle the ethene
Specified Pressure
50 atm P 100 atm
OR 5000 kPa P 10000 kPa
OR 5 MPa P 10 MPa
HighTemperature unless they give a value that is not in the ranges given here;
Page 46
OR 300 C T 600 C
OR 570 K T 870 K
Accept a reference to low temperature if they specify a
correct temperature range or a correct temperature in the
range
4
[15]
M12.
(a)
M1 Safety (in Process 1)
Sodium hydroxide / alkali is corrosive / harmful / caustic or sodium hydroxide is

alkali(ne)
Ignore references to chromium compounds
OR
Bromine compounds are toxic / poisonous
Carbon-neutral alone is insufficient for M2
M2 Environmental
Ignore references to greenhouse gases
Process 2 could be used as a carbon sink / for carbon capture
OR
uses waste / recycled CO / CO from the factory / CO from the bioethanol (or
biofuel) production
2
OR
reduces or limits the amount of CO released / given out (into the atmosphere)
2
OR
Process 2 uses renewable glucose / renewable resource(s)
2
(b)
Page 47
(i)
M1 nucleophilic substitution
For M1, both words required
M2 must show an arrow from the lone pair of electrons on the oxygen atom of
the negatively charged hydroxide ion to the C atom.
Penalise M2 if covalent NaOH / KOH is used
Penalise one mark from M2 or M3 if half-headed arrows are
used
M3 must show the movement of a pair of electrons from the CBr bond to the
Br atom. Mark M3 independently provided it is from the original molecule
Penalise M3 for formal charge on C of the CBr or incorrect
partial charges on CBr
Penalise once only for a line and two dots to show a bond.
For M2 and M3 award full marks for an S 1 mechanism
For M2 and M3, maximum 1 of 2 marks for the mechanism if
wrong reactant is used.
Penalise M3 if an extra arrow is drawn from the Br of the C
Br bond to, for example, K
Accept the correct use of sticks
N
NB The arrows here are double-headed

3
(ii)
M1 B
M2 C
M3 A
3
(c)
M1 fermentation
Mark M2 to M4 independently
Three conditions in any order for M2 to M4
Penalise bacteria and phosphoric acid using the list
principle
Page 48
M2
(enzymes from) yeast or zymase
M3
25C T 42C OR 298 K T 315 K

Ignore reference to aqueous or water, closed container,
pressure, lack of oxygen,
concentration of ethanol and batch process (i.e. not part
of the list principle)

M4
anaerobic / no oxygen / no air OR neutral pH

4
(d)
M1
primary OR 1 (alcohol)
Mark independently
M2
acidified potassium or sodium dichromate

For M2, it must be a whole reagent and/or correct formulae
OR
H SO / K Cr O OR H / K Cr O
Do not penalise incorrect attempt at formula if name is
correct or vice versa
Accept phonetic spelling
If oxidation state given in name, it must be correct.
For M2 accept acidified potassium manganate(VII)
OR
correct combination of formula and name
M3
HOCH CH CH CH OH + 4[O]
HOOCCH CH COOH + 2H O
For M3 structures must be correct and not molecular formula
2
[15]
Page 49

Q1.Glucose Can Decompose in The Presence of Microorganisms To Form A Range of Products

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