3.3.9.1 Carboxylic acids and esters (A-level only)

Name: ________________________
3.3.9.1 Carboxylic acids

and esters (A-level only)
Class: ________________________
Date: ________________________
Time: 271 min.
Marks: 261 marks
Comments:
Page 1 of 71
Q1.
Benzoic acid can be prepared from ethyl benzoate.
Ethyl benzoate is first hydrolysed in alkaline conditions as shown:
A student used the following method.
Add 5.0 cm3 of ethyl benzoate (density = 1.05 g cm−3, Mr = 150) to 30.0 cm3 of aqueous
2 mol dm−3 sodium hydroxide in a round-bottomed flask.
Add a few anti-bumping granules and attach a condenser to the flask. Heat the mixture
under reflux for half an hour. Allow the mixture to cool to room temperature.
Pour 50.0 cm3 of 2 mol dm−3 hydrochloric acid into the cooled mixture.
Filter off the precipitate of benzoic acid under reduced pressure.
(a) Suggest how the anti-bumping granules prevent bumping during reflux.
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(1)
(b) Show, by calculation, that an excess of sodium hydroxide is used in this reaction.
(2)
(c) Suggest why an excess of sodium hydroxide is used.
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(1)
(d) Suggest why an electric heater is used rather than a Bunsen burner in this
hydrolysis.
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(1)
(e) State why reflux is used in this hydrolysis.
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(1)
(f) Write an equation for the reaction between sodium benzoate and hydrochloric acid.
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(1)
(g) Suggest why sodium benzoate is soluble in cold water but benzoic acid is insoluble
in cold water.
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(2)
(h) After the solid benzoic acid has been filtered off, it can be purified.
Describe the method that the student should use to purify the benzoic acid.
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(6)
(i) In a similar experiment, another student used 0.040 mol of ethyl benzoate and
obtained 5.12 g of benzoic acid.
Calculate the percentage yield of benzoic acid.
Page 3 of 71
Suggest why the yield is not 100%.
Percentage yield ____________________ %
Suggestion _________________________________________________________
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(3)
(Total 18 marks)
Q2.
A four-step synthesis of compound T is shown.
(a) Give the reagent and conditions for Step 1.

State how you could obtain a sample of the alcohol from the reaction mixture
formed in Step 1.
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(3)
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(b) Draw the structure of compound S.
For each of Steps 3 and 4, give a reagent and one condition, other than heat.
(5)
(Total 8 marks)
Q3.
Esters are used as raw materials in the production of soaps and biodiesel.
(a) A student prepared an ester by two different methods.
Method 1 alcohol + acid anhydride
Method 2 alcohol + acyl chloride
(i) An ester was prepared using method 1, by reacting (CH3)2CHOH with

(CH3CO)2O
Write an equation for this reaction and give the IUPAC name of the ester
formed.
Equation
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IUPAC name of the ester __________________________________________

(2)
(ii) The same ester was prepared using method 2 by reacting (CH3)2CHOH with
CH3COCl
Outline a mechanism for this reaction.
(4)
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(b) The ester shown occurs in vegetable oils.
It can be hydrolysed to make soap and can also be used to produce biodiesel.
(i) Write an equation for the reaction of this ester with sodium hydroxide to form
soap.
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(2)
(ii) Give the formula of the biodiesel molecule with the highest Mr that can be
produced by reaction of this ester with methanol.
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(1)
(Total 9 marks)
Q4.
This question is about some isomers of C5H8O2
(a) Compound H is a cyclic ester that can be prepared as shown.
On the structure of H, two of the carbon atoms are labelled.
HOCH2CH2CH2CH2COCl + HCL
(i) Name and outline a mechanism for this reaction.
Use Table C on the Data Sheet to give the 13C n.m.r. δ value for the carbon
atom labelled a and the δ value for the carbon atom labelled b.
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(7)
(ii) HOCH2CH2CH2CH2COCl can also react to form a polyester in a mechanism

similar to that in part (i).
Draw the repeating unit of the polyester and name the type of polymerisation
involved.
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(2)
(b) State how you could distinguish between compounds J and K by a simple test-tube
reaction.
State how you could distinguish between J and K by giving the number of peaks in
the 1H n.m.r. spectrum of each compound.
J K
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(5)
(c) Draw the structure of each of the following isomers of C 5H8O2

Label each structure you draw with the correct letter L, M, N, P or Q.
L is methyl 2-methylpropenoate.
M is an ester that shows E-Z stereoisomerism.
N is a carboxylic acid with a branched carbon chain and does not show
stereoisomerism.
P is an optically active carboxylic acid.
Q is a cyclic compound that contains a ketone group and has only two peaks in its
1
H n.m.r. spectrum.
(5)
(Total 19 marks)
Q5.
Esters are produced by the reaction of alcohols with other esters and by the reaction of
alcohols with carboxylic acids.
(a) The esters which make up biodiesel are produced industrially from the esters in
vegetable oils.
(i) Complete the equation for this formation of biodiesel.
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(2)
(ii) Write an equation for the complete combustion of C17H35COOCH3.
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(2)
(b) The ester commonly known as diethyl malonate (DEM) occurs in strawberries and
grapes. It can be prepared from acid A according to the following equilibrium.
(i) A mixture of 2.50 mol of A and 10.0 mol of ethanol was left to reach
equilibrium in an inert solvent in the presence of a small amount of
concentrated sulfuric acid.
The equilibrium mixture formed contained 1.80 mol of DEM in a total volume,
V dm3, of solution.
Calculate the amount (in moles) of A, of ethanol and of water in this

equilibrium mixture.
Moles of A ____________________________________________________
Moles of ethanol _______________________________________________
Moles of water _________________________________________________

(3)
(ii) The total volume of the mixture in part (b)(i) was doubled by the addition of
more of the inert solvent.
State and explain the effect of this addition on the equilibrium yield of DEM.
Effect _________________________________________________________
Explanation ____________________________________________________
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(2)
(iii) Using A to represent the acid and DEM to represent the ester, write an
expression for the equilibrium constant Kc for the reaction.
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(1)
(iv) In a second experiment, the equilibrium mixture was found to contain 0.85 mol
of A, 7.2 mol of ethanol, 2.1 mol of DEM and 3.4 mol of water.
Calculate a value of Kc for the reaction and deduce its units.
Page 9 of 71
Calculation ____________________________________________________
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(3)
(Total 13 marks)
Q6.
Salicylic acid, C6H4(OH)COOH, reacts with magnesium to produce magnesium salicylate
and hydrogen.
(a) Complete the equation for this reaction.
C6H4(OH)COOH
(1)
(b) In an alternative method for determining percentage purity, a student reacted a

solution of salicylic acid with an excess of magnesium and collected the hydrogen
gas that was released.
Complete the diagram below to show an apparatus that could be used to collect and
measure the volume of hydrogen gas produced.
(1)
(Total 2 marks)
Q7.
The slowing down of chemical processes is important in food storage. Over time, fats may
become rancid. This involves the formation of compounds that have unpleasant odours
and flavours within the food.
Hydrolysis of fats is one way in which rancid flavours are formed. Fats break down to
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long-chain carboxylic (fatty) acids and glycerol.
(a) Complete the right-hand side of the equation below to show how hydrolysis affects
the molecule of fat shown.
+ 3H2O → 3 ........................ + ........................

(2)
(b) Other than by cooling, suggest one method that would decrease the rate of
hydrolysis of fats.
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(1)
(c) Food can also acquire unpleasant flavours when the fatty acids, produced by
hydrolysis of fats, are oxidised by air. This oxidation occurs by a free-radical
mechanism.
Chemicals called anti-oxidants can be added to food to slow down the oxidation.
Suggest why anti-oxidants are not regarded as catalysts.
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(2)
(d) A student investigated the extent of hydrolysis in an old sample of the fat in part (a).
The carboxylic acid extracted from a 2.78 g sample of this fat (Mr = 806.0) reacted
with 24.5 cm3 of a 0.150 mol dm–3 solution of NaOH.
Calculate the percentage of the fat that had hydrolysed.
Show your working.
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(4)
(Total 9 marks)
Q8.
The reactions of molecules containing the chlorine atom are often affected by other
functional groups in the molecule.
Consider the reaction of CH3CH2COCl and of CH3CH2CH2Cl with ammonia.
(a) For the reaction of CH3CH2COCl with ammonia, name and outline the mechanism
and name the organic product.
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(6)
(b) For the reaction of CH3CH2CH2Cl with an excess of ammonia, name and outline the
mechanism and name the organic product.
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(6)
(c) Suggest one reason why chlorobenzene (C6H5Cl) does not react with ammonia
under normal conditions.
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(1)
(Total 13 marks)
Q9.
(a) Propanoic acid can be made from propan-1-ol by oxidation using acidified
potassium dichromate(VI). Propanal is formed as an intermediate during this
oxidation.
(i) State the colour of the chromium species after the potassium dichromate(VI)
has reacted.
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(1)
(ii) Describe the experimental conditions and the practical method used to ensure
that the acid is obtained in a high yield. Draw a diagram of the assembled
apparatus you would use.
Conditions _____________________________________________________
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Apparatus
(4)
(iii) Describe the different experimental conditions necessary to produce propanal

in high yield rather than propanoic acid.
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(2)
(b) Propan-1-ol is a volatile, flammable liquid.

Give one safety precaution that should be used during the reaction to minimise this
hazard.
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(1)
(c) A student followed the progress of the oxidation of propan-1-ol to propanoic acid by
extracting the organic compounds from one sample of reaction mixture.
(i) Give a chemical reagent which would enable the student to confirm the
presence of propanal in the extracted compounds.
State what you would observe when propanal reacts with this reagent.
Reagent _______________________________________________________
Observation ____________________________________________________
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(2)
(ii) Give a chemical reagent that would enable the student to confirm the presence
of propanoic acid in the extracted compounds.
State what you would observe when propanoic acid reacts with this reagent.
Reagent _______________________________________________________
Observation ____________________________________________________
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(2)
(d) Predict which one of the compounds, propan-1-ol, propanal and propanoic acid will
have the highest boiling point. Explain your answer.
Prediction __________________________________________________________
Explanation _________________________________________________________
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(3)
(Total 15 marks)
Q10.
Synthesis gas is a mixture of carbon monoxide and hydrogen. Methanol can be
manufactured from synthesis gas in a reversible reaction as shown by the following
equation.
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CO(g) + 2H2(g) CH3OH(g) ΔHο = –91 kJ mol–1
(a) A sample of synthesis gas containing 0.240 mol of carbon monoxide and 0.380 mol
of hydrogen was sealed together with a catalyst in a container of volume 1.50 dm 3.
When equilibrium was established at temperature T1 the equilibrium mixture
contained 0.170 mol of carbon monoxide.
Calculate the amount, in moles, of methanol and the amount, in moles, of hydrogen
in the equilibrium mixture.
Methanol __________________________________________________________
Hydrogen __________________________________________________________
(2)
(b) A different sample of synthesis gas was allowed to reach equilibrium in a similar
container of volume 1.50 dm3 at temperature T1
At equilibrium, the mixture contained 0.210 mol of carbon monoxide, 0.275 mol of
hydrogen and 0.0820 mol of methanol.
(i) Write an expression for the equilibrium constant Kc for this reaction.
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(1)
(ii) Calculate a value for Kc for the reaction at temperature T1 and state its units.
Calculation _____________________________________________________
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(4)
(iii) State the effect, if any, on the value of Kc of adding more hydrogen to the
equilibrium mixture.
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(1)
(c) The temperature of the mixture in part (b) was changed to T2 and the mixture was
left to reach a new equilibrium position. At this new temperature the equilibrium
concentration of methanol had increased.
Deduce which of T1 or T2 is the higher temperature and explain your answer.
Page 15 of 71
Higher temperature ___________________________________________________
Explanation _________________________________________________________
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(3)
(d) The following reaction has been suggested as an alternative method for the
production of methanol.
CO2(g) + 3H2(g) CH3OH(g) + H2O(g)
The hydrogen used in this method is obtained from the electrolysis of water.
Suggest one possible environmental disadvantage of the production of hydrogen by

electrolysis.
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(1)
(e) One industrial use of methanol is in the production of biodiesel from vegetable oils
such as
Give the formula of one compound in biodiesel that is formed by the reaction of
methanol with the vegetable oil shown above.
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(1)
(Total 13 marks)
Q11.
Esters have many important commercial uses such as solvents and artificial flavourings in
foods.
Esters can be prepared in several ways including the reactions of alcohols with carboxylic
acids, acid anhydrides, acyl chlorides and other esters.
(a) Ethyl butanoate is used as a pineapple flavouring in sweets and cakes.
Write an equation for the preparation of ethyl butanoate from an acid and an alcohol.
Give a catalyst used for the reaction.
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(4)
(b) Butyl ethanoate is used as a solvent in the pharmaceutical industry.
Write an equation for the preparation of butyl ethanoate from an acid anhydride and
an alcohol.
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(3)
(c) Name and outline a mechanism for the reaction of CH3COCl with CH3OH to form an
ester.
(5)
(d) The ester shown below occurs in vegetable oils. Write an equation to show the
formation of biodiesel from this ester.
CH2OOCC17H31
│
CHOOCC17H33
│
CH23OOCC17H29
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(3)
(e) Draw the repeating unit of the polyester Terylene that is made from
benzene-1,4-dicarboxylic acid and ethane-1,2-diol.
Although Terylene is biodegradeable, it is preferable to recycle objects made from

Terylene.
Give one advantage and one disadvantage of recycling objects made from
Terylene.
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(4)
(Total 19 marks)
Q12.
The triester, T, shown below is found in palm oil. When T is heated with an excess of
sodium hydroxide solution, the alcohol glycerol is formed together with a mixture of three
other products as shown in the following equation.
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(a) (i) Give the IUPAC name for glycerol.
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(1)
(ii) Give a use for the mixture of sodium salts formed in this reaction.
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(1)
(b) When T is heated with an excess of methanol, glycerol is formed together with a
mixture of methyl esters.
(i) Give a use for this mixture of methyl esters.
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(1)
(ii) One of the methyl esters in the mixture has the IUPAC name
methyl (Z)-octadec-9-enoate. Draw two hydrogen atoms on the diagram below
to illustrate the meaning of the letter Z in the name of this ester.
(1)
(iii) One of the other methyl esters in the mixture has the formula
CH3(CH2)12COOCH3
Write an equation for the complete combustion of one molecule of this ester.
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(1)
(Total 5 marks)
Q13.
(a) Write an equation for the formation of methyl propanoate, CH 3CH2COOCH3, from
methanol and propanoic acid.
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(1)
(b) Name and outline a mechanism for the reaction between methanol and propanoyl
chloride to form methyl propanoate.
Name of mechanism _________________________________________________
Mechanism
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(5)
(c) Propanoic anhydride could be used instead of propanoyl chloride in the preparation
of methyl propanoate from methanol. Draw the structure of propanoic anhydride.
(1)
(d) (i) Give one advantage of the use of propanoyl chloride instead of propanoic
acid in the laboratory preparation of methyl propanoate from methanol.
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(ii) Give one advantage of the use of propanoic anhydride instead of propanoyl
chloride in the industrial manufacture of methyl propanoate from methanol.
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(2)
(e) An ester contains a benzene ring. The mass spectrum of this ester shows a
molecular ion peak at m/z = 136.
(i) Deduce the molecular formula of this ester.
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(ii) Draw two possible structures for this ester.
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(3)
(Total 12 marks)
Q14.
Consider the sequence of reactions below.
(a) Name and outline a mechanism for Reaction 1.
Name of mechanism _________________________________________________
Mechanism
(5)
(b) (i) Name compound Q
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(ii) The molecular formula of Q is C4H7NO. Draw the structure of the isomer of Q
which shows geometrical isomerism and is formed by the reaction of ammonia
with an acyl chloride.
(3)
(c) Draw the structure of the main organic product formed in each case when R reacts
separately with the following substances:
(i) methanol in the presence of a few drops of concentrated sulphuric acid;
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(ii) acidified potassium dichromate(VI);
(iii) concentrated sulphuric acid in an elimination reaction.
(3)
(Total 11 marks)
Q15.
(a) Compound A, HCOOCH2CH2CH3, is an ester. Name this ester and write an
equation for its reaction with aqueous sodium hydroxide.
Name _____________________________________________________________
Equation ___________________________________________________________
(2)
(b) The initial rate of reaction between ester A and aqueous sodium hydroxide was
measured in a series of experiments at a constant temperature. The data obtained
are shown below.
Experiment Initial Initial

Initial rate
concentration of concentration of A
/ mol dm–3 s–1
NaOH / mol dm–3 / mol dm–3
1 0.040 0.030 4.0 × 10–4
2 0.040 0.045 6.0 × 10–4
3 0.060 0.045 9.0 × 10–4
4 0.120 0.060 to be calculated
Use the data in the table to deduce the order of reaction with respect to A and the
order of reaction with respect to NaOH. Hence calculate the initial rate of reaction in
Experiment 4.
Order with respect to A ________________________________________________
Order with respect to NaOH ____________________________________________
Initial rate in Experiment 4 _____________________________________________
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(3)
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(c) In a further experiment at a different temperature, the initial rate of reaction was
found to be 9.0 × 10–3 mol dm–3 s–1 when the initial concentration of A was 0.020 mol
dm–3 and the initial concentration of NaOH was 2.00 mol dm –3.
Under these new conditions with the much higher concentration of sodium
hydroxide, the reaction is first order with respect to A and appears to be zero order
with respect to sodium hydroxide.
(i) Write a rate equation for the reaction under these new conditions.
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(ii) Calculate a value for the rate constant under these new conditions and state
its units.
Calculation _____________________________________________________
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(iii) Suggest why the order of reaction with respect to sodium hydroxide appears
to be zero under these new conditions.
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(6)
(d) A naturally-occurring triester, shown below, was heated under reflux with an excess
of aqueous sodium hydroxide and the mixture produced was then distilled. One of
the products distilled off and the other was left in the distillation flask.
(i) Draw the structure of the product distilled off and give its name.
Structure
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Name _________________________________________________________
(ii) Give the formula of the product left in the distillation flask and give a use for it.
Formula _______________________________________________________
Use __________________________________________________________
(4)
(Total 15 marks)
Q16.
Which one of the following is not a correct statement about vitamin C, shown below?
A It is a cyclic ester.
B It can form a carboxylic acid on oxidation.
C It decolourises a solution of bromine in water.
D It is a planar molecule.
(Total 1 mark)
Q17.
(a) Describe how propanal, CH3CH2CHO, and propanone, CH3COCH3, can be
distinguished using
(i) a chemical test and
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(3)
(ii) the number of peaks in their proton n.m.r. spectra.
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(2)
(b) Compound Z can be produced by the reaction of compound X with compound Y as

shown in the synthesis outlined below.
Identify compounds X and Y.

For each of the three steps in the synthesis, name the type of reaction involved and
give reagents and conditions. Equations are not required.
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(10)
(Total 15 marks)
Q18.
Propanoic acid reacts with methanol in the presence of a small amount of concentrated
sulphuric acid. The empirical formula of the ester formed is
A CH2O
B C2H6O2
C C2H4O2
D C2H4O
(Total 1 mark)
Q19.
Butenedioic acid, HOOCCH=CHCOOH, occurs as two stereoisomers. One of the isomers
readily forms the acid anhydride C4H2O3 when warmed.
(a) Draw the structures of the two isomers of butenedioic acid and name the type of
isomerism shown.
Use the structures of the two isomeric acids to suggest why only one of them readily
forms an acid anhydride when warmed. Draw the structure of the acid anhydride
formed.
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(6)
(b) Identify one electrophile which will react with butenedioic acid and outline a
mechanism for this reaction.
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(4)
(c) Write an equation for a reaction which occurs when butenedioic acid is treated with
an excess of aqueous sodium hydroxide.
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(2)
(d) Describe and explain the appearance of the proton n.m.r. spectrum of butenedioic
acid.
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(3)
(Total 15 marks)
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Q20.
(a) The gaseous reactants W and X were sealed in a flask and the mixture left until the
following equilibrium had been established.
2W(g) + X(g) 3Y(g) + 2Z(g) ΔH = –200 kJ mol–1
Write an expression for the equilibrium constant, Kp, for this reaction.
State one change in the conditions which would both increase the rate of reaction
and decrease the value of Kp. Explain your answers.
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(7)
(b) Ethyl ethanoate can be prepared by the reactions shown below.
Reaction 1
CH3COOH(l) + C2H5OH(l) CH3COOC2H5(l) + H2O(l) ∆H = –2.0 kJ mol–1
Reaction 2
CH3COCl(l) + C2H5OH(l) → CH3COOC2H5(l) + HCl(g) ∆H = –21.6 kJ mol–1
(i) Give one advantage and one disadvantage of preparing ethyl ethanoate by
Reaction 1 rather than by Reaction 2.
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(2)
(ii) Use the information given above and the data below to calculate values for the
standard entropy change, ∆S , and the standard free-energy change, ∆G ,
for Reaction 2 at 298 K.
CH3COCl(l) C2H5OH(l) CH3COOC2H5(l) HCl(g)
S /JK1mol1 201 161 259 187
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(6)
(Total 15 marks)
Q21.
Which one of the following is not a correct general formula for the non-cyclic compounds
listed?
A alcohols CnH2n+2O
B aldehydes CnH2n+1O
C esters CnH2nO2
D primary amines CnH2n+3N

(Total 1 mark)
Q22.
For this question refer to the reaction scheme below.
Page 29 of 71
Which one of the following statements is not correct?
A Reaction of W with sodium cyanide followed by hydrolysis of the resulting product

gives propanoic acid.
B Mild oxidation of Z produces a compound that reacts with Tollens’ reagent, forming
a silver mirror.
C Z reacts with ethanoic acid to produce the ester propyl ethanoate.
D W undergoes addition polymerisation to form poly(propene).

(Total 1 mark)
Q23.
(a) Consider the following pair of isomers.
(i) Name compound C.
______________________________________________________________
(ii) Identify a reagent which could be used in a test-tube reaction to distinguish

between C and D. In each case, state what you would observe.
Reagent ______________________________________________________
Observation with C ______________________________________________
Observation with D______________________________________________

(4)
(b) Consider the following pair of isomers.
Page 30 of 71
(i) Name compound E.
______________________________________________________________
(ii) Identify a reagent which could be used in a test-tube reaction to distinguish

between E and F. In each case, state what you would observe.
Reagent ______________________________________________________
Observation with E ______________________________________________
Observation with F______________________________________________

(4)
(c) Draw the structure of the chain isomer of F which shows optical isomerism.
(1)
(Total 9 marks)
Q24.
Ibuprofen is a drug used as an alternative to aspirin for the relief of pain, fever and
inflammation. The structure of ibuprofen is shown below.
Which one of the following statements is not correct?
A It has optical isomers.
B It liberates carbon dioxide with sodium carbonate solution.
C It undergoes esterification with ethanol.
D It undergoes oxidation with acidified potassium dichromate(VI).

(Total 1 mark)
Page 31 of 71
Q25.
Butan-1-ol was converted into butyl propanoate by reaction with an excess of propanoic
acid. In the reaction, 6.0 g of the alcohol gave 7.4 g of the ester. The percentage yield of
ester was
A 57
B 70
C 75
D 81
(Total 1 mark)
Q26.
Which compound is formed by the reaction of ethane-1,2-diol with an acid?
D CH3CH2 — O — CH2CH2OH
(Total 1 mark)
Q27.
Three sections of the proton n.m.r. spectrum of CH 3CHClCOOH are shown below.
Page 32 of 71
(a) Name the compound CH3CHClCOOH
___________________________________________________________________
(1)
(b) Explain the splitting patterns in the peaks at δ 1.72 and δ 4.44
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
(2)
(c) Predict the splitting pattern that would be seen in the proton n.m.r. spectrum of the
isomeric compound ClCH2CH2COOH
___________________________________________________________________
___________________________________________________________________
(1)
(d) The amino acid alanine is formed by the reaction of CH3CHClCOOH with an excess
of ammonia. The mechanism is nucleophilic substitution. Outline this mechanism,
showing clearly the structure of alanine.
Page 33 of 71
(5)
(e) The amino acid lysine has the structure
Draw structures to show the product formed in each case when lysine reacts with
(i) an excess of aqueous HCl,
(ii) an excess of aqueous NaOH,
(iii) another molecule of lysine.
(3)
(Total 12 marks)
Q28.
Page 34 of 71
An excess of methanol was mixed with 12 g of ethanoic acid and an acid catalyst. At
equilibrium the mixture contained 8 g of methyl ethanoate. The percentage yield of ester
present was
A 11
B 20
C 54
D 67
(Total 1 mark)
Q29.
Acid hydrolysis of produces
A CH3CH(OH)CH2CH2COOH
B CH2(OH)CH2CH2CH2COOH
C CH3CH(OH)CH2CH2OCHO
D CH2(OH)CH2CH2CH2OCHO
(Total 1 mark)
Q30.
The structural formula of ethyl 2-methylpropanoate is
D
(Total 1 mark)
Page 35 of 71
Q31.
Hydrolysis of the ester, CH3COOCH2CH2CH3, produces ethanoic acid. In an experiment,
2.04 g of the ester was used and 0.90 g of ethanoic acid was produced. The percentage
yield of ethanoic acid was:
A 44
B 59
C 75
D 90
(Total 1 mark)
Q32.
How many structural isomers, which are esters, have the molecular formula C 4H8O2?
A 2
B 3
C 4
D 5
(Total 1 mark)
Q33.
Summarised directions for recording responses to multiple completion

questions
A B C D
(i), (ii) and (iii) (i) and (iii) only (ii) and (iv) only (iv) alone
only
Isomers of the ester HCOOCH2CH2CH3, include
(i) ethyl ethanoate
(ii) methyl propanoate
(iii) butanoic acid
(iv) butyl methanoate

(Total 1 mark)
Q34.
Summarised directions for recording responses to multiple completion

questions
Page 36 of 71
A B C D
(i), (ii) and (iii) (i) and (iii) only (ii) and (iv) only (iv) alone
only
Products from the acid hydrolysis of the ester CH3CH2COOCH2CH3 include
(i) CH3CH2COOH
(ii) CH3COOH
(iii) CH3CH2OH
(v) CH3CH2CH2OH
(Total 1 mark)
Page 37 of 71
Mark schemes
Q1.
(a) allows smaller bubbles to form / prevents the formation of (very) large bubbles
ALLOW provides large surface area for bubbles to form on
IGNORE ‘air’
NOT no bubbles form / prevents bubbles forming
1
(b) (Mass of ester = 1.05 × 5.0 = 5.25g)

amount of ester = 5.25 / 150.0 = 0.0350 mol
1
amount of NaOH = 30 × 2 / 1000 = 0.06 mol

1
OR
(Mass of ester = 1.05 × 5.0 = 5.25g)

amount of ester = 5.25 / 150.0 = 0.0350 mol
1
Vol of 0.035 mol of NaOH = (0.035/2) × 1000 = 17.5 cm 3

(so 30 cm3 used is an excess)
1
OR
amount of NaOH = 30 × 2 / 1000 = 0.06 mol

1
0.06 mol of ester = 9 g = 8.57 cm3

(only 5 cm3 used so NaOH in excess)
1
Mark independently
Max 2
(c) To ensure that the ester is completely hydrolysed / to ensure all the ester
reacts
ALLOW to ensure the other reagent has completely reacted
1
(d) Many organic compounds / the ester / ethanol are flammable

ALLOW prevent ignition of any flammable vapours formed
1
(e) Reflux allows reactant vapours (of volatile organic compounds) to be returned
to the reaction mixture / does not allow any reactant vapour to escape
IGNORE reference to products
1
(f) C6H5COONa + HCl → C6H5COOH + NaCl

Allow ionic equation.
ALLOW molecular formulae (C7H5O2Na and C7H6O2 )
ALLOW skeletal benzene ring
Page 38 of 71
1
(g) Sodium benzoate soluble because it is ionic

IGNORE polar
1
Benzoic acid insoluble because: despite the polarity of the COOH group /
ability of COOH to form H-bonds, the benzene ring is non-polar.
ALLOW ‘part of molecule’ or ‘one end’ for COOH
1
(h) Dissolve crude product in hot solvent/water

ALLOW ethanol
If no M1 max = 4
1
of minimum volume
ALLOW reference to saturated soln as alternative to ‘min vol’
1
Filter (hot to remove insoluble impurities)

IGNORE use of Buchner funnel here
1
Cool to recrystallise
apply list principle for each additional process in an incorrect
method but IGNORE additional m.pt determination
1
Filter under reduced pressure / with Buchner/Hirsch apparatus

1
wash (with cold solvent) and dry

1
(i) 5.12 / 122 (= 0.042 mol)

method mark
1
(0.042/0.04) × 100 = 105 %

ecf for M1/0.04
or calculation that 0.04 mol of benzoic = 4.88 g (M1) so
% yield = (5.12/4.88) × 100 = 105%
1
Product not dried / impurities present in product

Only allow M3 if M2>100%
1
[18]
Q2.
(a) M1 NaOH
Only score M2 if M1 gained, but mark on from hydroxide.
Mention of acid loses M1 & M2
1
Page 39 of 71
M2 Aqueous/(warm)
Ignore alcoholic / conc / dil.
1
M3 (Fractional) distillation or described

Not just evaporation; not reflux
Allow chromatography
1
(b) M1 S is CH3CH(CN)CH2CH3
Allow without brackets
1
Step 3
M2 KCN (mark on from CN-)

Not HCN, not KCN with acid
1
M3 Alcoholic / (aqueous)
Allow ethanolic
Can only score M3 if M2 gained
1
Step 4
M4 H2
LiAlH4
Na
Can only score M5 if M4 gained
1
M5 Ni or Pt or Pd
Ethoxyethane or ether
LiAlH4 with acid loses both M4 and M5
Ignore ‘followed by acid’
Na
Ethanol
NOT NaBH4 OR Sn/HCl
Penalise other extras as list
Ignore pressure or temperature
1
[8]
Q3.
(a) (i) (CH3)2CHOH + (CH3CO)2O → CH3COOCH(CH3)2 + CH3COOH
Allow CH3CO2CH(CH3)2 and CH3CO2H
Ignore (CH3)2 −C in equation
Page 40 of 71
1
(1)-methylethyl ethanoate OR
Propan-2-yl ethanoate
Ignore extra or missing spaces, commas or hyphens
1
(ii)
M4 for 3 arrows and lp
NO Mark for name of mechanism

M1 for lone pair on O and arrow to C or to mid-point of space
between O and C
M2 for arrow from C=O bond to O
• M2 not allowed independent of M1, but
allow M1 for correct attack on C+
• + rather than δ+ on C=O loses M2
• If Cl lost with C=O breaking, max1 for M1
M3 for correct structure with charges (penalise wrong alcohol
here) but lone pair on O is part of M4
Penalise (CH3)2 −C in M3
M4 for lone pair on O and three arrows
• Only allow M4 after correct / very close M3
• M4 can be gained over more than one structure
• Ignore Cl− removing H+
4
(b) (i)
Penalise covalent Na e.g. -O-Na

LHS 1
RHS 1
(ii) C17H33COOCH3
Allow C19H36O2
1
[9]
Page 41 of 71
Q4.
(a) (i) (nucleophilic) addition-elimination
Not electrophilic addition-elimination
Ignore esterification
1
M3 for structure
• If wrong nucleophile used or O–H broken in first step,
can only score M2.
• M2 not allowed independent of M1, but allow M1 for
correct attack on C+
• + rather than δ+ on C=O loses M2.
• If Cl lost with C=O breaking lose M2.
• M3 for correct structure with charges but lone pair on O
is part of M4.
• Only allow M4 after correct / very close M3.
• Ignore HCl shown as a product.
4
a 20-50 (ppm) or single value or range entirely within this range

If values not specified as a or b then assume first is a.
1
b 50-90 (ppm) or single value or range entirely within this range

1
(ii)
Must have trailing bonds, but ignore n.

1
OR –OCH2CH2CH2CH2CO– OR –CH2CH2CH2CH2COO–
Allow
but not - C4H8−
one unit only
Condensation
1
(b)
Page 42 of 71
Tollens’ Fehling’s / Benedicts Acidified potassium
dichromate
Penalise wrong formula for Tollens or missing acid with

potassium dichromate but mark on.
1
J No reaction / no No reaction / no No reaction / no

(visible) change (visible) change (visible) change /
/ / stays
no silver mirror stays blue / no r orange / does not turn
ed green
ppt
Ignore ‘clear’, ‘nothing’.

Penalise wrong starting colour for dichromate.
1
K Silver mirror / Red ppt (orange) turns

grey ppt green
(allow brick red
or
red-orange)
1
J Two (peaks)
Allow trough, peak, spike.
1
K Four (peaks)
Ignore details of splitting.
If values not specified as J or K then assume first is J.
1
(c) If all the structures are unlabelled, assume that the first drawn ester is L, the
second ester is M; the first drawn acid is N, the second P. The cyclic
compound should be obvious.
L
ester
OR H2C=C(CH3)COOCH3
All C5H8O2 L to P must have C=C.
Allow CH3−.
Allow -CO2CH3 etc.
Allow CH2C(CH3)COOCH3.
1
Page 43 of 71
M
ester
CH3CH=CHCOOCH3 CH3CH=CHOOCCH3 CH3CH=C(CH3)OOCH
CH3CH=CHCH2OOCH CH3CH2CH=CHOOCH
Allow either E–Z isomer.

Allow CH3− or C2H5− but not CH2CH3−.
Allow CH3CHCHCOOCH3 etc.
1
N
acid
(CH3)2C=CHCOOH H2C=C(CH3)CH2COOH H2C=C(COOH)CH2

CH3
Allow CH3− or C2H5− but not CH2CH3−.
Allow −CO2H.
Not cyclic isomers.
Not the optically active isomer.
Allow (CH3)2CCHCOOH etc.

1
P
acid
Allow −CO2H.
CH3CH(COOH)CH=CH2
Allow CH3CH(CO2H)CHCH2 or
CH3CH(CO2H)C2H3.
1
Page 44 of 71
Not cyclic esters.
1
[19]
Q5.
(a) (i) 3CH3OH
Not molecular formula
1
HOCH2CH(OH)CH2OH
1
(ii) → 19CO2 + 19H2O

Or doubled
1
C17H35COOCH3 + 27½ or 55/2 O2

Consequential on correct right-hand side
1
(b) (i) A0.7

1
Ethanol6.4
1
Water3.6
1
(ii) No effect
If wrong, CE = 0
1
Equal moles on each side of equation OR V cancels

Ignore moles of gas
1
(iii) M1
Must have all brackets but allow ( )

1
(iv) M2
Page 45 of 71
If Kc wrong can only score M4 for units consequential to their
Kc working in (b)(iv)
1
M3 0.55 (min 2dp)

1
M4 No units
1
[13]
Q6.
(a) Mg + 2C6H4(OH)COOH → (C6H4(OH)COO)2Mg + H2
Accept multiples, including fractions.
1
(b) Gas syringe / inverted burette over water / measuring cylinder over water
Collection apparatus must show graduations or be clearly
labelled (eg syringe, burette, measuring cylinder).
1
[2]
Q7.
(a) CH3(CH2)14COOH
Allow molecular formulae.
1
CH2OHCHOHCH2OH
Allow one mark only if formulae are swapped in position.
1
(b) Keeping the foodstuff dry

Allow an answer which refers to removal of water from the
environment.
Do not allow dehydration / removal of water from the fat.
1
(c) They (antioxidants) react with free radicals

1
And they are used up in the reaction / do not remain behind after reaction
Lose one mark for any reference to ‘catalysts can’t slow
down a reaction’.
1
(d) Mol of fat = (2.78 / 806 =) 3.45 × 10 –3

Mol of NaOH = 3.68 × 10–3 = mol of fatty acid
1
Mol of NaOH = 3.68 × 10–3

Mol of fat hydrolysed = 1.23 × 10 –3
1
Mol of fat hydrolysed = (3.68 × 10–3 / 3 =) 1.23 × 10–3
Page 46 of 71
Mass of fat hydrolysed = 0.987 g
1
Percentage hydrolysed = 35.5 – 35.7

Percentage hydrolysed = 35.5 – 35.7
Do not penalise precision at any point.
Since there are a variety of approaches to this calculation,
award four marks for a correct answer but it must be clear
that there is some relevant working.
The answer alone gets M4 only.
Any incorrect use of the 3:1 ratio is CE – lose M3 and M4.
1
[9]
Q8.
(a) (Nucleophilic) addition-elimination
• Minus sign on NH3 loses M1(but not M4 also)
• M2 not allowed independent of M1, but
1
• allow M1 for correct attack on C+

• If Cl lost with C=O breaking, max1 for M1
• M3 for correct structure with charges but lp on O is part of
M4
• only allow M4 after correct/very close M3
• For M4, ignore NH3 removing H+ but lose M4 for Cl–
removing
H+ in mechanism,
• but ignore HCl shown as a product
4
propanamide (Ignore -1- )

penalise other numbers
penalise propaneamide and N-propanamide
1
(b) Nucleophilic substitution

• Minus sign on NH3 loses M1 (not M4 also)
1
Page 47 of 71
• ALLOW SN1 so allow M2 for loss of Cl– before attack of
NH3 on C+ for M1
• only allow M4 after correct/very close M3
• For M4, ignore NH3 removing H+ but lose M4 for Cl–
removing H+ in mechanism,
Propylamine (ignore number 1)

• but ignore HCl shown as a product
4
or propan-1-amine or 1-aminopropane (number 1 needed)

penalise other numbers
allow 1-propanamine
1
(c) electron rich ring or benzene or pi cloud repels nucleophile/ammonia

Allow
• C–Cl bond is short/stronger than in haloalkane
• C–Cl is less polar than in haloalkane
• resonance stabilisation between ring and Cl
1
[13]
Q9.
(a) (i) Green
Ignore shades of green.
1
(ii) Excess acidified potassium dichromate(VI)

1
Reflux (for some time)

1
In the diagram credit should be given for

• a vertical condenser
Lose M3 and M4 for a distillation apparatus.
1
• an apparatus which would clearly work

Do not allow this mark for a flask drawn on its own.
Penalise diagrams where the apparatus is sealed.
1
(iii) Distillation
1
Page 48 of 71
Immediately (the reagents are mixed)
1
(b) Keep away from naked flames

Allow heat with water-bath or heating mantle.
If a list is given ignore eye protection, otherwise lose this
mark.
1
(c) (i) Tollens’ or Fehling’s reagents

Incorrect reagent(s) loses both marks.
Accept mis-spellings if meaning is clear.
1
Silver mirror / red ppt. formed

Accept ‘blue to red’ but not ‘red’ alone.
1
(ii) Sodium carbonate (solution) / Group II metal

Allow indicator solutions with appropriate colours.
Accept any named carbonate or hydrogen carbonate.
1
Effervescence / evolves a gas

Accept ‘fizzes’.
1
(d) Propanoic acid

If this mark is lost allow one mark if there is reference to
stronger intermolecular forces in the named compound.
Lose M1 and M3.
1
Contains hydrogen bonding

1
Some comparison with other compounds explaining that the intermolecular

forces are stronger in propanoic acid
1
[15]
Q10.
(a) mol CH3OH = 0.07(0)
1
mol H2 = 0.24(0)
1
(b) (i)
or
allow ( ) but expression using formulae must have brackets
alternative expression using numbers must include volumes
1
Page 49 of 71
(ii) M1 divides by vol
Mark independently from (b)(i)
any AE is –1
if volume missed, can score only M3 and M4
1
M2
mark is for correct insertion of correct numbers in correct Kc
expression in b(ii)
If Kc expression wrong, can only score M1 & M4
If numbers rounded, allow M2 but check range for M3
1
M3 11.6 or 11.7
mark for answer
above 11.7 up to 12.2 scores 2 for M1 and M2
if vol missed, can score M3 for 5.16 (allow range 4.88 to
5.21)
1
M4 mol–2 dm6
Units conseq to their Kc in (b)(ii)
1
(iii) no effect or no change or none

1
(c) M1 T1
if wrong - no further marks
1
M2 (forward) reaction is exothermic OR gives out heat
backward reaction is endothermic

only award M3 if M2 is correct
1
M3 shifts to RHS to replace lost heat
OR to increase the temperature
OR to oppose fall in temp
backward reaction takes in heat
OR to lower the temperature

not just to oppose the change
1
(d) fossil fuels used

OR
CO2 H2O produced/given off/formed which are greenhouse gases
OR
SO2 produced/given off/formed which causes acid rain
OR
Page 50 of 71
Carbon produced/given off/formed causes global dimming
not allow electricity is expensive
ignore just global warming
ignore energy or hazard discussion
1
(e) C17H35COOCH3 or C17H31COOCH3 or C17H29COOCH3
OR
CH3OOCC17H35 or CH3OOCC17H31 or CH3OOCC17H29

1
[13]
Q11.
(a) M1 CH3CH2CH2COOH
not C3H7COOH
1
M2 CH3CH2OH or C2H5OH
1
M3 CH3CH2CH2COOCH2CH3 + H2O
allow C3H7COOC2H5
penalise M3 for wrong products and unbalanced equation
1
M4 H2SO4 or HCl or H3PO4 conc or dil or neither

not HNO3
1
(b) M1 CH3CH2CH2CH2OH
1
not C4H9OH
M2 (CH3CO) 2O
1
M3 → CH3COOCH2CH2CH2CH3 + CH3COOH
allow CH3COOC4H9
penalise M3 for wrong products and unbalanced equation
1
(c) (nucleophilic) addition-elimination
not acylation alone

M2 not allowed indep of M1 but allow M1 for correct attack
Page 51 of 71
on C+
+C=O loses M2
only allow M4 after correct or v close M3
ignore Cl– removing H+
5
(d)
(1) (1) (1)

ignore errors in initial triester
First mark for 3CH3OH
Third mark for all three esters
3
(e)
First mark for correct ester link second mark for the rest
including trailing bonds
If ester link wrong, lose second mark also
2
Adv reduces landfill

saves raw materials
lower cost for recycling than making from scratch
reduces CO2 emissions by not being incinerated
not allow cost without qualification
ignore energy uses
1
Disad difficulty/cost of collecting/sorting/processing

product not suitable for original purpose, easily contaminated
not allow cost without qualification
ignore energy uses
1
[19]
Q12.
(a) (i) propan(e)-1,2,3-triol or 1,2,3- propan(e)triol
not propyl
ignore hyphen, commas
1
(ii) soaps
allow anionic surfactant
Page 52 of 71
not cationic surfactant
not detergents, not shampoos
1
(b) (i) (bio)diesel

Allow fuel for diesel engines
not biofuel, not oils
1
(ii)
ignore anything else attached except any more H atoms.

1
(iii) CH3(CH2)12COOCH3 + 21½O2 → 15CO2 + 15 H2O
OR
C15H30O2 or 43/2
not allow equation doubled
1
[5]
Q13.
(a) CH3OH + CH3CH2COOH → CH3CH2COOCH3 + H2O
1
(b) (nucleophilic) addition–elimination NOT acylation

1
ignore use of Cl– to remove H+

M3 for structure
M4 for 3 arrows and lone pair
4
(c)
allow C2H5 and –CO2–

allow CH3CH2COOCOCH2CH3
or (CH3CH2CO)2O
1
Page 53 of 71
(d) (i) faster/not reversible/bigger yield/purer product/no(acid) (catalyst)
required
1
(ii) anhydride less easily hydrolysed or reaction less violent/exothermic

no (corrosive) (HCl) fumes formed or safer or less toxic/dangerous
expense of acid chloride or anhydride cheaper
any one
1
(e) (i) C8H8O2

1
(ii) any two from
Allow –CO2– allow C6H5

2
[12]
Q14.
(a) nucleophilic addition
1
(b) (i) 2-hydroxybutanenitrile

1
(ii)
(allow 1 for amide even if not C4H7NO, i.e. RCONH2)
Page 54 of 71
(if not amide, allow one for any isomer of C4H7NO which shows
geometric isomerism)
2
(c) (i)
(ii)
(iii) CH3CH=CHCOOH
1
[11]
Q15.
(a) propyl methanoate;
HCOOC3H7 + OH– → HCOO– + C3H7OH

1
OR
HCOOC3H7 + NaOH → HCOONa + C3H7OH;

1
(b) order wrt A = 1;

1
order wrt NaOH = 1;

1
Initial rate in Exp 4 = 2.4 × 10 –3;

1
(c) (i) r(ate) = k[A]
OR
r(ate) = k[A][NaOH]0;
(penalise missing [ ] but mark on)
(penalise missing [ ] once per paper)
(if wrong order, allow only units mark conseq on their rate
eqs)
(penalise ka or kw etc)
1
Page 55 of 71
(ii) ;
1
= 0.45;
1
s–1;
l
(iii) (large) excess of OH– or [OH–] is large/high;

1
[OH–] is (effectively) constant
OR
[A] is the limiting factor (Q of L mark)

1
(d) (i)
propan(e)-1,2,3-triol
OR
1,2,3-propan(e)triol
OR
Glycerol;
1
(ii) CH3(CH2)16COONa or C17H35COONa or C18H35O2Na;

(ignore 3 in front of formula but not if indicating trimer)
1
(not just anion and penalise Na shown as covalently bonded) soap -

allow with detergent but not detergent alone;
1
[15]
Q16.
D
[1]
Q17.
(a) (i)
Reagent Tollens Fehlings or K2Cr2O7/H+ KMnO4/H+ I2/NaOH
Page 56 of 71
Benedicts
or acidified
Propanal silver red ppt or goes red goes green goes No

(mirror) (not red solution) colourless reaction
Propanone no no reaction no reaction no reaction Yellow

reaction (ppt)
(penalise incomplete reagent e.g. K 2Cr2O7 or Cr2O72–/H+ then mark on)

3
(ii) propanal 3 peaks

ignore splitting even if wrong
1
propanone 1 peak
1
(b) X is CH3CH2COOH or propanoic acid if both name and formula given,

both must be correct, but
Y is CH3CH(OH)CH3 or propan-2-ol allow propanol with correct formula

1
Mark the type of reaction and reagent/condition independently.

The reagent must be correct or close to score condition
Step 1 Oxidation
K2Cr2O7/H+ or other oxidation methods as above

allow Cr2O72–H+ if penalised above (ecf)
reflux (not Tollens/Fehlings) or heat or warm
1
Step 2 reduction or nucleophilic reduction or reduction or

1
addition nucleophilic addition hydrogenation
NaBH4 LiAlH4 H2 1
in (m)ethanol or water or ether or dry Ni / Pt etc

ether 1
or dry
Step 3 esterification or (nucleophilic) addition-elimination or condensation

1
(conc) H2SO4 or HCl

1
warm (allow without acid reagent if X and Y given as reagents)

1
or reflux or heat
1
[15]
Page 57 of 71
Q18.
D
[1]
Q19.
(a)
1
NB The bonds shown in the structure must be correct
Isomerism: E-Z isomerism

If written answer is correct, ignore incorrect labelling of
structures.
If no written answer, allow correctly labelled structures.
1
Both COOH groups must be on the same side/ close together/ cis
1
No rotation about C=C axis

1
Structure
(b) Br2 / HBr / H2SO4 / H+ / Br+ / NO2+ (Mark M1)
Page 58 of 71
NB If electrophile H+ / Br+ / NO2+ allow M1, M2 and M4
If the acid is incorrect, M2 and M3 can still be scored
Allow M4 consequentially if repeat error from part (a)
4
(c) e.g. 2NaOH + HO2CCHCHCO2H → NaO2CCHCHCO2Na + 2H2O
Both H replaced
1
Balanced for atoms and charges

1
NB Allow ionic equations and
2NaOH + C4H4O4 → C4H2O4Na2+ 2H2O
Allow one if structure incorrect but molecular formula
correct
Allow one for a correct equation showing one H replaced
(d) M1 Two peaks

1
M2 No splitting or singlets
1
M3 (Two) non-equivalent protons or two proton environments

1
M4 No adjacent protons
1
M5 Same area under the two peaks or same relative intensity

1
NB Doublet could score M1 and M3 or M5 (Max 2)
More than two peaks CE = 0
Apply the “list principle” to incorrect answers if more
than 3 given
Max 3
[15]
Q20.
(a) M1 Kp = (PY)3. (PZ)2/ (PW)2.( PX) NB [ ] wrong
1
M2 temperature
1
Page 59 of 71
M3 increase
1
M4 particles have more energy or greater velocity/speed

1
M5 more collisions with E > Ea or more successful collisions

1
M6 Reaction exothermic or converse

1
M7 Equilibrium moves in the left

1
Marks for other answers

Increase in pressure or concentration allow M1, M5, M6 Max 3
Addition of a catalyst; allow M1, M5, M6 Max 3
Decrease in temperature; allow M1, M2, M6 Max 3
Two or more changes made; allow M1, M6 Max 2
(b) (i) Advantage; reaction goes to completion, not reversible

or faster
1
Disadvantage; reaction vigorous/dangerous

(exothermic must be qualified)
or HCl(g) evolved/toxic
or CH3COCl expensive
NB Allow converse answers
Do not allow reactions with other reagents e.g. water
or ease of separation
1
(ii) ΔS = ΣS products – ΣS reactants

1
ΔS = (259 + 187) – (201 + 161)

1
ΔS = 84 (JK–1 mol–1) (Ignore units)

Allow – 84 to score (1) mark
1
ΔG = ΔH – TΔS
1
= – 21.6 – 298 × 84/1000

= – 46.6 kJ mol–1 or – 46 600 J mol–1
1
Allow (2) for – 46.6 without units
(Mark ΔG consequentially to incorrect ΔS)
(e.g. ΔS = –84 gives ΔG = +3.4 kJ mol–1)
1
[15]
Page 60 of 71
Q21.
B
[1]
Q22.
A
[1]
Q23.
(a) (i) propyl methanoate (1)
not propanyl
• A wrong reagent or no reagent scores zero
• An incomplete reagent such as silver nitrate for Tollens,
or potassium dichromate loses the reagent mark, but can
get both observation marks
• penalise observations which just say colour change
occurs or only state starting colour
(ii) Reagent: NaHCO3 (1)

Observation with C: no reaction (1)
Observation with D: effervescence (1)
for C and D NOT Tollens
Test an identified acidified acidified correct UI or stated PCl5

(hydrogen) K2Cr2O7 KMnO4 metal indicator
carbonate
Observatio no reaction goes green goes no no change no

n with C colourless reaction reaction
observatio bubbles or no change no change bubbles or red or (misty)

n with D CO2 H2 correct fumes
colour
pH 3 – 6.9
(b) (i) Reagent: pentan-2-one (1)

or 2-pentanone
but not pent-2-one or pentyl
(ii) Reagent: Tollen’s or Fehling’s (1)
Observation with E: no reaction (1)
Observation with F: silver mirror or red ppt (1)
for E and F
Test Tollens Fehlings or iodoform or acidified Schiff’s

Benedicts I2/NaOH K2Cr2O7
Page 61 of 71
observation no reaction no reaction yellow (ppt) no change no reaction
with E
observation silver or red or ppt no reaction goes green goes pink

with F mirror or grey not red
or ppt solution
(c) (1)
must be aldehyde. Allow C2H5 for CH3CH2 otherwise this is
the only answer
1
[9]
Q24.
D
[1]
Q25.
B
[1]
Q26.
B
[1]
Q27.
(a) 2-chloropropanoic acid (1)
1
(b) δ 1.72 Doublet next to CH (1)
δ 4.44 Quartet next to CH3 (1)

2
(c) Two triplets (1)

1
(d)
Allow SN1
Page 62 of 71
5
(e) (i)
(ii)
(iii)
Or anhydride
3
[12]
Q28.
C
[1]
Q29.
A
[1]
Q30.
B
[1]
Q31.
C
[1]
Q32.
C
[1]
Q33.
A
[1]
Page 63 of 71
Q34.
B
[1]
Page 64 of 71
Examiner reports
Q1.
(a) This part, and others in this question, illustrate the importance of students paying
attention to why certain techniques and processes are used during practicals. The
role of anti-bumping granules was not as well understood as expected, with only
30% of students gaining this mark. Incorrect suggestions included that they slow the
reaction down by preventing the reactant particles from bumping into each other.
(b) This proved to be an easy question for most, although there were issues with the
layout of the calculation; it was not always clear which calculation related to which
reactant.
(c) Nearly 60% of students gained this mark but a lack of specific clarity cost many
dearly. Many students apparently did not retain an awareness of the context of a
question as they worked through the stages. They did not appear to recall, from the
stem of the question, that the reaction was between NaOH and ethyl benzoate. This
recall should have enabled students to make the specific statement that the excess
of sodium hydroxide was to ensure that all the ethyl benzoate would react.
(d) Answers here often incorrectly referred to the ‘control’ of the temperature rather than
recognising the risk of flammability of organic reagents. Clarity is again key,
because any suggestion that NaOH is flammable is incorrect.
(e) As was also evident in part (f), some students thought that reflux is a separation
method. A specific answer was again the key here, with a need to mention the fact
that reactant/organic vapours are returned to the reaction mixture. Suggestions that
reflux prevents vapour forming were incorrect.
(f) This was answered best by students who used structural or partial skeletal formulas.
Many students, who attempted to use molecular formulas, often miscounted the
number of hydrogens or carbons. Care was needed to avoid any suggestion that
there is an O−Na bond in sodium benzoate.
(g) As mentioned previously, this proved to be the trickiest question on the paper, with
only 1% of students earning both marks. Most could state that sodium benzoate is
ionic – although there were also many incorrect references to it being ‘polar’ or ‘a
molecule’. However, a proper description of why benzoic acid is insoluble was
beyond most students. Many stated that it is non-polar, while others suggested that
its ability to hydrogen-bond with itself is what prevents it dissolving. Very few were
able to clearly explain that, despite the polarity (and hence the ability to form
hydrogen bonds with water), the large non-polar benzene ring prevented dissolving.
(h) About a third of students earned 4 or more marks here, but about the same number
failed to score. Despite a statement in the stem that benzoic acid is a solid, many
answers referred incorrectly to methods based on distillation and/or solvent
extraction. Some answers implied that a solid would be expected to run through the
tap of a separating funnel! For those students who correctly recognised that
recrystallization was the correct method, there was often confusion in the order of
the steps, which prevented potentially good answers gaining full marks. An example
seen quite often was the suggestion that the solid obtained after
cooling/crystallisation should be washed before filtering. The steps most often
missing were the need for hot filtration after dissolving the impure solid in hot
solvent, and the final wash and dry after Buchner filtration.
Page 65 of 71
(i) This was another tricky question, with only 10% of students earning full marks. It
seemed that many were thrown by the realisation that the answer was over 100%,
with many students responding by doing the percentage calculation the wrong way
round, because they seemed to feel that the answer must be less than 100%.
Relative molecular masses were often calculated incorrectly despite that for ethyl
benzoate being given in the stem. The Mr of ethyl benzoate was sometimes used in
place of the Mr of benzoic acid.
Q2.
Most students knew that that the reagent was sodium hydroxide, but many did not know
the correct conditions for its use in question (a). Incorrect answers included ‘concentrated’
or ‘dilute’ and the occasional ‘acidified’. The separation part of this question was answered
well. In (b) the structure of compound S was frequently correct. The reagent and
conditions in Step 3 were often confused and acidified KCN was a popular incorrect
combination as was alcoholic HCN. In Step 4 most students correctly used hydrogen and
a nickel catalyst, while others gained the marks for LiAlH 4 in ethoxyethane. Sadly some
students who used LiAlH4 included acidic conditions with the hydride and hence lost the
marks. However, clearly stated use of acid after the reduction stage with LiAlH 4 was
accepted.
Q3.
The equation in part (a)(i) was fairly well written. By comparison, few students could name
the ester correctly. The more common errors in the equation were to give a straight chain
alkyl group in the ester, or to give the second product as water or to leave it out
altogether. In part (a)(ii), the nucleophilic addition-elimination mechanism was well done
with over half of the students scoring full marks.
In part (b)(i), the mark for 3NaOH was frequently scored, whereas the mark for the right
hand side of the equation was often lost mainly due to mistakes in the salts, such as an
incorrect number of hydrogen atoms, a covalent bond from O to Na, or covalent bonds
between the three salts. Almost half of the students gained the mark in part (b)(ii). Those
who lost it gave the carboxylic acid instead of the methyl ester or misread the question
and calculated the Mr of the molecule rather than giving its formula.
Q4.
The nucleophilic addition-elimination mechanism in part (a)(i) presented a real challenge
to many students, who were confused by the cyclic nature of the product, failed to identify
the correct nucleophile and suggested either separate nucleophiles such as H2O, CH3OH
and OH– or alternatively loss of the proton from the OH group before nucleophilic attack.
Most students gave the correct range for the carbon atom labelled b, but often the range
for the carbon atom labelled a was given as 160–185 as for a carbonyl carbon. In part
(a)(ii), the repeating unit for the polyester was answered well although some students
gave twice the repeating unit.
The distinguishing test in part (b) was well done, although a significant number of students
thought that substance K was an acid and wrongly suggested NaHCO 3 or Na2CO3 to
distinguish between the compounds. It was common for students to fail to see the
symmetry of J and so to predict, incorrectly, three peaks in its proton n.m.r. spectrum.
Five peaks was a common incorrect answer for K, suggesting that students had misread
the question and given the 13C n.m.r. result.
Part (c) of this question proved to be very challenging and fewer than 10% of students
scored full marks. Isomer Q was found particularly difficult where many students omitted
one of the O atoms from their suggested structure. Other common errors included missing
Page 66 of 71
the double bond in L, giving the structure of P as the structure of N (which suggests a
failure to recognise that optical isomerism is a form of stereoisomerism) or writing an
unbranched carbon chain for the acid N. Answers to part (c) were often very badly
presented, with a great deal of crossing out, duplication of answers and poor labelling of
structures.
Q5.
Full marks were scored by 50% of students in part (a)(i); the most common errors were
omitting the 3 on the left-hand side and including an extra H on C2 of propane-1,2,3-triol.
In part (a)(ii) several didn’t note the two O atoms in the ester so gave 28.5 instead of 27.5
for the moles of oxygen.
Part (b)(ii) proved to be quite difficult with 27% of students scoring 0. By contrast, parts
(b)(iii) and (iv) were found to be relatively straightforward and over 80% gained full marks.
Q6.
(a) The equation in this part proved demanding, with a surprising number of students
representing hydrogen as 2H.
(b) The diagram in this part was well drawn by the majority of students.
Q7.
(a) This part was well known
(b) This part often elicited answers requiring dehydration of the fat - this is a chemical
process which was not acceptable.
(c) In this part many students obtained a mark for the fact that the antioxidant was used
up but failed to mention which of the two reactions involved they were referring to.
There was a mistaken reliance on the ideas that catalysts can only speed up
reactions and on antioxidants raising the activation energy of the (unspecified)
reaction.
(d) In this part saw many full marks but a considerable number lost credit because they
did not compare like with like in their final percentage calculation. Nearly all students
were able to gain the first two marks.
Q8.
These mechanisms were well done and clearly presented with about a third of students
scoring full marks. However, many struggled to name both compounds correctly.
Propanamide proved especially difficult, with incorrect names based on aminoketone
appearing very frequently. There were some good answers to part (c), but many others
involved comments about ammonia not being attracted to the benzene ring rather than
actively being repelled by it. ‘Ammonia is a nucleophile’ was another frequent wrong
answer.
Q9.
The colour change in part (a)(i) was well known but most candidates failed to score both
marks for the conditions for the reaction in part (a)(ii). Many markers treated the word
‘excess’ as an optional extra and awarded a mark to candidates who just repeated
Page 67 of 71
information in the stem of the question. Most candidates were able to draw an acceptable
diagram for reflux. The usual mistake was to seal the condenser and many markers failed
to punish this serious error.
Part (a)(iii) was poorly answered, even by the better candidates. Distillation was often
appreciated but the concept of removal of the aldehyde immediately when it is formed was
rarely seen. Some centres were very generous indeed when marking this question.
The tests in part (c) were well known and better candidates scored all four marks. Some
candidates lost a mark by giving an incorrect formula for a reagent. Centres are reminded
that if the candidate chooses an incorrect test reagent the mark for the observation cannot
be awarded.
Most candidates could make some progress in part (d), and the presence of hydrogen
bonding in the acid and alcohol were known to the better candidates. Some centres were
very generous when marking this question. The final mark was often given for references
to stronger van der Waals forces in the carboxylic acid.
Q10.
In part (a), just over half the entry was able to use the mole ratio in the equation correctly
and calculate the number of moles of methanol and of hydrogen. The expression for Kc
was answered well in part (b) and half the candidates gained three or four marks in the
calculation. The most common error was to confuse the number of moles of each gas with
its concentration and forget to divide by the volume. Also, a considerable proportion
ended up with the wrong answer due to incorrect use of their calculator. Only half of the
candidates knew that Kc was unaffected by adding more hydrogen. In part (c), most
candidates correctly deduced that T1 was the higher temperature – although it was
sometimes difficult to decipher whether the number written was 1 or 2. Many lost a mark
in the explanation for giving a generic explanation such as “the equilibrium shifts to
oppose the change” rather than explaining specifically that if the temperature is lowered,
the equilibrium moves in the exothermic direction to oppose the lowering of the
temperature or to increase the temperature. In part (d), most candidates were able
correctly to link the process to produce hydrogen with an environmental problem but in
part (e) fewer than a third of the candidates could write the correct formula for a methyl
ester of one of the long chain carboxylic acids.
Q11.
A few candidates were unsure of the names of the esters involved and confused butyl
ethanoate with ethyl butanoate. In parts (a) and (b) a common error was the failure to
balance the equations due to the omission of water or ethanoic acid respectively. Weaker
candidates were also unsure of the structure of ethanoic anhydride.
The mechanism in part (c) was well answered although several omitted to give its name.
The reaction in part (d) proved unfamiliar to many candidates; some attempted to answer
the question in terms of alkaline hydrolysis of the ester to form soap rather than the
reaction with methanol to form the mixture of methyl esters which make up biodiesel. The
repeating unit was well answered in part (e).
Q12.
The IUPAC name of glycerol was given correctly by about two thirds. Whereas many
knew the use of the sodium salts produced in part (a)(ii) as soaps, only half as many
recognised that the methyl esters made in part (b)(i) are used as biodiesel. In part (b)(ii)
the position of hydrogen atoms in a Z-isomer was very well known but disappointingly,
only two-fifths of the candidates could write a correct equation for the combustion of the
Page 68 of 71
ester given.
Q13.
Good candidates were able to score high marks in this question.
The equation in part (a) was well answered; leaving out H 2O was the most common error.
The mechanism in part (b) was well done by many, although several weaker candidates
persist in writing a negative charge as well as a lone pair on nucleophiles such as
methanol used here. Incorrect structures for propanoic anhydride were common in part
(c); many contained only three carbon atoms in total. By contrast, most candidates were
able to answer part (d) correctly. In part (e)(i) many did not understand the meaning of the
term “molecular formula” and wrote semi-structural formulae instead. However many
correct structures were written in part (e)(ii).
Q14.
As usual, better candidates find organic mechanisms straightforward and many good
answers were seen to part (a). In part (b)(i) the name 2–hydroxybutanenitrile, was usually
given correctly. The abbreviation 2–hydroxybutanitrile was not allowed.
The structure of the isomer of C4H7NO was found difficult. It was possible to score one
mark for a structure with the correct molecular formula which showed geometric
isomerism. Sadly many candidates did not recognise that an acyl chloride reacts with
ammonia form an amide.
In part (c), there were many pentavalent carbons shown in the structures drawn,
especially in part (ii). The elimination of water in part (iii) to form an alkene was the least
well-known reaction.
Q15.
The first three parts of this question were well answered. In part (a), most candidates were
able to name the ester propyl methanoate correctly although the equation for its reaction
with sodium hydroxide was less well answered. The orders and the initial rate in part (b)
were correctly deduced by most candidates and many were able to deduce the correct
rate equation in part (c) and to use it correctly to calculate the rate constant. Those who
gave an incorrect rate equation were awarded a mark for units which were consistent with
their rate equation. By comparison, few were able to answer part (c)(iii) correctly by
stating that the large excess of sodium hydroxide meant that its concentration was
effectively constant. Part (b) distinguished fairly well between those who recognised the
alcohol formed by hydrolysis of the ester drawn and were able to deduce that it would
distil easily. Either the systematic name, propane-1,2,3-triol, or its common name glycerol,
were accepted. The formula of the sodium salt of the acid was accepted in several forms
and its use as soap was well known by most, even those who gained no other marks in
part (c).
Q17.
Part (a) was answered well. Most candidates were able to describe a correct chemical test
to distinguish between the aldehyde, propanal, and the ketone, propanone. However,
many thought that propanone had two peaks in its proton n.m.r. spectrum.
In part (b), better candidates had no difficulty in identifying propanoic acid as X and
propan-2-ol as Y and in giving correct descriptions of oxidation in Step 1, reduction in Step
2 and esterification in Step 3. Weaker candidates lost marks for incorrect reagents or for
Page 69 of 71
wrong or missing conditions in the reactions.
Q19.
Relatively few candidates scored high marks in part (a). Most candidates knew the type of
isomerism shown by butenedioic acid and were able to draw correct structures of the two
isomers. Only the best candidates then went on to deduce which isomer would readily
form an anhydride and drew its structure correctly.
Many candidates identified a correct electrophile in part (b) and outlined an accurate
mechanism but lost marks when their structures were inaccurately drawn. Sadly, a
significant number of weaker candidates scored no marks in part (b) as their answers
incorrectly referred to an attack by a nucleophile.
Although the structure of butenedioic acid was given in the question, a number candidates
lost marks when they gave an incorrect structure in their answer to part (c). Others failed
to recognise the acid-base nature of the reaction and gave equations for addition or
substitution reactions. One mark was lost by candidates who reacted the acid with one,
rather than two, moles of NaOH.
Part (d) was generally well done and many candidates deduced correctly that there were
just two different proton environments. Many, however, lost one mark when they stated
incorrectly that the two peaks would be doublets.
Q20.
Many candidates gave a correct expression for the equilibrium constant, Kp, for the
reaction given in part (a). Some, who gave correct indices, lost a mark as they included
square brackets, which are specific used to indicate concentration, in their expression.
Identifying the one change which would increase the rate of reaction and decrease the
value of Kp proved challenging but part marks were awarded for answers which addressed
either of the two required changes. Candidates who gave more than one change of
condition were able to score one mark for a correct Kp expression. There were many
vague answers to part (b)(i), some of which assumed there were other reactants present
with the most common example being water in Reaction 2. By contrast, (b)(ii) was very
well answered with many candidates scoring full marks. Most candidates now remember
to use either kJ mol–1 or J mol–1 throughout these calculations but a small number still
failed to do this. Consequential marks were awarded in each part of the calculation.
Q23.
This question discriminated well and better candidates were able to score full marks.
Weaker candidates were unable to recognise the ester C and acid D in part (a) and hence
could not distinguish correctly between them. As expected, methyl propanoate was a
common wrong answer in part (a)(i) and only the better candidates named E correctly as
pentan-2-one. Reagents distinguishing between the ketone E and the aldehyde F were
better known, but the term “chain isomer” was missed by many who failed to draw a
correct structure for 2‑methylbutanal, the only possible answer.
Q27.
In part (a), the name 2-chloropropanoic acid was deduced correctly by most, but
responses in part (b) were often unclear. Candidates were expected to state, for instance,
that the peak at δ 1.72 was due to the methyl group but was split into a doublet because of
the single proton on the next carbon. Many answers implied that the peak at δ 1.72 was
itself due to the single proton. Part (c) was usually well answered. The mechanism in part
Page 70 of 71
(d) was well answered by the better candidates while others gained the first two and the
last marks despite difficulties with the structure of the substituted ammonium ion and its
loss of a proton to yield the amino acid.
The effects of acid and of alkali on an amino acid were quite well answered although
many did not realise that both amine groups in lysine would be protonated in acidic
conditions. The structure of the dipeptide was answered much better than the similar
question in the January CHM4 paper. A few anhydride structures were again seen and
allowed in place of the dipeptide.
Page 71 of 71

3.3.9.1 Carboxylic acids and esters (A-level only)

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3.3.9.1 Carboxylic acids and esters (A-level only)

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Name: ________________________

3.3.9.1 Carboxylic acids

Time: 271 min.

Marks: 261 marks

Ethyl benzoate is first hydrolysed in alkaline conditions as shown:

A student used the following method.

Filter off the precipitate of benzoic acid under reduced pressure.

(c) Suggest why an excess of sodium hydroxide is used.

(e) State why reflux is used in this hydrolysis.

Calculate the percentage yield of benzoic acid.

Percentage yield ____________________ %

(a) Give the reagent and conditions for Step 1.

(a) A student prepared an ester by two different methods.

Method 1 alcohol + acid anhydride

Method 2 alcohol + acyl chloride

(i) An ester was prepared using method 1, by reacting (CH3)2CHOH with

IUPAC name of the ester __________________________________________

Outline a mechanism for this reaction.

(a) Compound H is a cyclic ester that can be prepared as shown.

On the structure of H, two of the carbon atoms are labelled.

(i) Name and outline a mechanism for this reaction.

(ii) HOCH2CH2CH2CH2COCl can also react to form a polyester in a mechanism

(c) Draw the structure of each of the following isomers of C 5H8O2

M is an ester that shows E-Z stereoisomerism.

P is an optically active carboxylic acid.

(i) Complete the equation for this formation of biodiesel.

(ii) Write an equation for the complete combustion of C17H35COOCH3.

Calculate the amount (in moles) of A, of ethanol and of water in this

Moles of ethanol _______________________________________________

Moles of water _________________________________________________

Calculate a value of Kc for the reaction and deduce its units.

(a) Complete the equation for this reaction.

(b) In an alternative method for determining percentage purity, a student reacted a

+ 3H2O → 3 ........................ + ........................

Consider the reaction of CH3CH2COCl and of CH3CH2CH2Cl with ammonia.

(iii) Describe the different experimental conditions necessary to produce propanal

(b) Propan-1-ol is a volatile, flammable liquid.

Deduce which of T1 or T2 is the higher temperature and explain your answer.

CO2(g) + 3H2(g) CH3OH(g) + H2O(g)

Suggest one possible environmental disadvantage of the production of hydrogen by

(a) Ethyl butanoate is used as a pineapple flavouring in sweets and cakes.

Give a catalyst used for the reaction.

(b) Butyl ethanoate is used as a solvent in the pharmaceutical industry.

Although Terylene is biodegradeable, it is preferable to recycle objects made from

(i) Give a use for this mixture of methyl esters.

Name of mechanism _________________________________________________

(i) Deduce the molecular formula of this ester.

(ii) Draw two possible structures for this ester.

(a) Name and outline a mechanism for Reaction 1.

Name of mechanism _________________________________________________

(b) (i) Name compound Q

(i) methanol in the presence of a few drops of concentrated sulphuric acid;

(iii) concentrated sulphuric acid in an elimination reaction.

Experiment Initial Initial

1 0.040 0.030 4.0 × 10–4

2 0.040 0.045 6.0 × 10–4

3 0.060 0.045 9.0 × 10–4

4 0.120 0.060 to be calculated

Order with respect to A ________________________________________________

Order with respect to NaOH ____________________________________________