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Deduce the empirical and molecular formulas of the carboxylic acid formed.
(b)
(c)
(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?
Page 1
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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)
(b)
Draw the structure of the organic product, B, formed when A is oxidised in the
reaction with acidified potassium dichromate(VI).
(1)
(c)
Page 2
Two isomeric alkenes, C and D, are formed when A is dehydrated in the reaction
with concentrated sulfuric acid.
(d)
Isomer D
(2)
(e)
(f)
(g)
Draw the structure of the isomer of A that is not oxidised by acidified potassium
dichromate(VI).
(1)
Page 3
(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)
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)
Page 4
(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)
(e)
Page 5
Page 6
(b)
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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(Extra space)...................................................................................................
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(5)
Page 7
(c)
(ii)
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
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(3)
(Total 15 marks)
Page 8
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.
Page 9
(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.
Page 10
(a)
(i)
(ii)
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)
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Page 11
Condition 1 ......................................................................................................
Condition 2 ......................................................................................................
(3)
(c)
(i)
CH COOH(I) + H O(I)
3
(1)
(ii)
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(1)
(iii)
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(1)
(iv)
Page 12
(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)
(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)
Page 13
(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)
(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 .......................................................
Page 14
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Observation for tertiary alcohol .............................................................
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(3)
(ii)
(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)
(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.
Page 15
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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)
H (g)
CH OH(g)
H O(g)
394
201
242
H /kJ mol
f
(i)
CO (g)
2
CH OH(g)
3
H O(g)
2
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(Extra space) ........................................................................................
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(3)
(ii)
State why the standard enthalpy of formation for hydrogen gas is zero.
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Page 16
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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
(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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Page 17
(d)
(ii)
...............................................................................................................
(1)
(iii)
CO (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)
Page 18
(e)
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(3)
(Total 16 marks)
Page 19
(a)
(b)
Page 20
CH CH Br
3
CH CH OH
3
Suggest one reason, other than safety, why this method is not used in industry to
make ethanol.
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(6)
(c)
Page 21
H C =CH
2
CH CH OH
3
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
Page 22
Process 2
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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(Extra space) .................................................................................................
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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)
Page 23
(ii)
(3)
Page 24
(c)
12
Give the name of this process and state three essential conditions necessary to
produce a good yield of ethanol.
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(Extra space) .................................................................................................
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(4)
(d)
Write an equation for this oxidation reaction using [O] to represent the oxidising
agent.
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(3)
Page 25
Page 26
M1.(a)
= 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
(b)
C6H12O6
2C2H5OH + 2CO2
1
(c)
Page 27
(d)
(e)
[10]
M2.(a)
3-methylbutan-2-ol
1
(b)
Allow (CH3)2CHCOCH3
1
(c)
Elimination
1
(d)
Page 28
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]
Page 29
M3.(a)
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)
Water cooled condenser connected to the still head and suitable cooled
collecting vessel
1
Page 30
(d)
(e)
Warm
M2 and M3 can only be awarded if M1 is given correctly
1
Page 31
M4.(a)
M1 C6H12O6
2CH3CH2OH
(2C2H5OH)
+ 2CO2
25 C T 42 C
OR
298 K T 315 K
Page 32
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)
incomplete combustion
heat loss
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)
(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
[15]
Page 34
[4]
Page 35
or
Obs with 2-methylpropan-2-ol orange
Obs with butan-2-ol
green
[3]
M7.(a)
3 2
(b)
(c)
(d)
Page 36
[4]
M8.(a)
(i)
CH O
2
12
(ii)
(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)
(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)
Ignore state symbols
Negative charge on electron not essential
Accept multiples
Accept electrons subtracted from LHS
2
(iv)
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)
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)
(iii)
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
M9.(a)
HOOCCHOHCHOHCOOH
Any suitable structural formula.
Displayed formula not required but bond sequences must be
correct if shown.
1
(b)
(c)
(d)
(i)
Page 40
(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)
(g)
[11]
M10.
Page 41
(a)
(i)
must have
all Hsymbols and the or SUM)
M1
H = H (products) - H (reactants)
OR
M2
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
(ii)
It is an element / elemental
Ignore reference to standard state
OR
By definition
1
(b)
Page 42
(c)
(d)
(i)
Page 43
(ii)
CH OH + 1 O
Ignore state symbols
Accept multiples
3
CO
2H O
2
(iii)
3H
+ 1 O
Ignore state symbols
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
M2
= 4389 (J) OR 4.389 (kJ) OR 4.39 (kJ) OR 4.4 (kJ)(also scores M1)
M3
[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
(b)
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
(c)
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)
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
(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
M3
(d)
M1
primary OR 1 (alcohol)
Mark independently
M2
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
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