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Aldehydesandketones

The document consists of a chemistry examination focusing on aldehydes and ketones, including various questions about reactions, mechanisms, and properties of these compounds. It covers topics such as acyl chlorides, structural isomers, stereoisomerism, and the oxidation of alcohols. The exam is structured with multiple-choice questions, short answer sections, and requires detailed explanations and chemical equations.

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0% found this document useful (0 votes)

39 views83 pages

Aldehydesandketones

Uploaded by

hossinjaffari99

We take content rights seriously. If you suspect this is your content, claim it here.

Available Formats

Download as RTF, PDF, TXT or read online on Scribd

You are on page 1/ 83

_______________________

Name:
_
Aldehydes and ketones
_______________________
Class:
_

_______________________
Date:
_

Time: 331 minutes

Marks: 323 marks

Comments:

Page 1 of 83
Q1.
Acyl chlorides are useful reagents in synthesis. They react with aromatic compounds and
also with alcohols.

(a) CH3CH2COCl reacts with benzene in the presence of AlCl3 in an electrophilic

substitution reaction.

Give an equation for the reaction of CH3CH2COCl with AlCl3 to form the electrophile.
Outline a mechanism for the reaction of this electrophile with benzene.

Equation ___________________________________________________________

Mechanism

(4)

(b) The organic product in part (a) can be converted into the alcohol shown.

Give the IUPAC name of the alcohol.

Give the reagent needed for this reaction and name the mechanism.

IUPAC name _______________________________________________________

Reagent ___________________________________________________________

Name of mechanism _________________________________________________

(3)

Describe what would be observed when the alcohol reacts with ethanoyl chloride.
Name the mechanism for the reaction to form the ester.
Draw the structure of the ester.

Observation ________________________________________________________

___________________________________________________________________

Name of mechanism __________________________________________________

Page 2 of 83
Structure of ester

(3)
(Total 10 marks)

Q2.
How many structural isomers with the molecular formula C5H10O react with Tollens’
reagent?

A 3

B 4

C 5

D 6

(Total 1 mark)

Q3.
The aldehyde CH3CH2CH2CH2CHO reacts with KCN followed by dilute acid to form a
racemic mixture of the two stereoisomers of CH3CH2CH2CH2CH(OH)CN

(a) Give the IUPAC name of CH3CH2CH2CH2CH(OH)CN

___________________________________________________________________
(1)

(b) Describe how you would distinguish between separate samples of the two
stereoisomers of CH3CH2CH2CH2CH(OH)CN

___________________________________________________________________

___________________________________________________________________
(2)

(c) Explain why the reaction produces a racemic mixture.

___________________________________________________________________

Page 3 of 83
___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(d) An isomer of CH3CH2CH2CH2CHO reacts with KCN followed by dilute acid to form a
compound that does not show stereoisomerism.

Draw the structure of the compound formed and justify why it does not show
stereoisomerism.

Structure

Justification

___________________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)

Q4.
Which pair of compounds does not form a racemic mixture when the compounds react?

A +
HCl

B +
HCN

C +
HCl

D
+
HCN
(Total 1 mark)

Q5.
Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

A 2,2-dimethylpropan-1-ol

Page 4 of 83
B 2-methylbutan-2-ol

C 3-methylbutan-2-ol

D pentan-3-ol
(Total 1 mark)

Q6.
Which compound forms a racemic mixture when reacted with KCN followed by dilute
acid?

A HCHO

B CH3CHO

C CH3COCH3

D (CH3CH2)2CO
(Total 1 mark)

Q7.
Butanone is reduced in a two-step reaction using NaBH4 followed by dilute hydrochloric
acid.

(a) Write an overall equation for the reduction of butanone using [H] to represent the
reductant.

___________________________________________________________________
(1)

(b) By considering the mechanism of the reaction, explain why the product has no
effect on plane polarised light.

___________________________________________________________________

Page 5 of 83
(6)
(Total 7 marks)

Q8.
Ethanol can be oxidised by acidified potassium dichromate(VI) to ethanoic acid in a two-
step process.

ethanol ethanal ethanoic acid

(a) 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.

___________________________________________________________________

___________________________________________________________________
(3)

(b) Write a half-equation for the overall oxidation of ethanol into ethanoic acid.

___________________________________________________________________
(1)

Compound ethanol ethanal ethanoic acid

Boiling point / °C 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.

___________________________________________________________________

Page 6 of 83
___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(5)

(d) Use your knowledge of structure and bonding to explain why it is possible to
separate ethanal in this way.

___________________________________________________________________

___________________________________________________________________
(2)

(e) A student obtained a sample of a liquid using the apparatus in part (c).

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

___________________________________________________________________

___________________________________________________________________
(5)
(Total 16 marks)

Q9.
Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

A 2-methylbutan-1-ol

B 2-methylbutan-2-ol

Page 7 of 83
C 3-methylbutan-1-ol

D 3-methylbutan-2-ol
(Total 1 mark)

Q10.
Hemiacetals and acetals are compounds formed by the reaction of aldehydes with
alcohols, such as the reaction of ethanal with ethanol.

(a) (i) Use your knowledge of carbonyl mechanisms to suggest the name of the
mechanism of this reaction.

______________________________________________________________
(1)

(ii) Outline how an ethanol molecule reacts with an ethanal molecule in the first
step of this mechanism. Include two curly arrows to show the movement of
electron pairs.

(2)

(b) The reaction produces a racemic mixture of chiral molecules.

(i) Explain the meaning of the term racemic mixture.

______________________________________________________________

______________________________________________________________
(1)

(ii) State the relationship between two chiral molecules with the same structural
formula.

______________________________________________________________

______________________________________________________________
(1)

(c) In the presence of an acid catalyst such as dry hydrogen chloride, ethanal reacts
with an excess of ethanol to form an acetal.

Page 8 of 83
The overall reaction of ethanal with an excess of ethanol forms an equilibrium
mixture as shown. All reactants and products are liquids.

A mixture of 0.75 mol of ethanal and 5.00 mol of ethanol was left to reach
equilibrium in the presence of dry hydrogen chloride at a given temperature. The
equilibrium mixture contained 0.42 mol of the acetal.

(i) Calculate the amount, in moles, of ethanal and of ethanol in this equilibrium
mixture.

Amount of ethanal ______________________________________ mol

Amount of ethanol ______________________________________ mol

Space for working __________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) In a different experiment using the same reaction as in part (c), an equilibrium
mixture was established at a given temperature.
This mixture contained 0.58 mol of ethanal, 3.76 mol of ethanol, 0.37 mol of
the acetal and 0.65 mol of water in a total volume of 310 cm3.

Write an expression for the equilibrium constant Kc for this reaction.

Calculate a value for Kc at this temperature. Give units with your answer.

Kc ___________________________________________________________

______________________________________________________________

Calculation _____________________________________________________

______________________________________________________________

______________________________________________________________
(4)

Page 9 of 83
(d) Draw the structure of the acetal (C4H8O2) formed by the reaction of ethanal with
ethane-1,2-diol.

(1)
(Total 12 marks)

Q11.
The carbonyl compound CH3CH2CHO reacts very slowly with HCN

(a) Name and outline a mechanism for the reaction of CH3CH2CHO with HCN

Name of mechanism ________________________________________________

Mechanism

(5)

(b) The reaction in part (a) produces a pair of enantiomers.

(i) Draw the structure of each enantiomer to show how they are related to each
other.

(2)

(ii) State and explain how you could distinguish between the two enantiomers.

______________________________________________________________

______________________________________________________________
(2)

Page 10 of 83
(c) Give the IUPAC name of the product of the reaction in part (a).

___________________________________________________________________
(1)

(d) In practice, KCN rather than HCN is added to the carbonyl compound.

Given that Ka for HCN = 4.0 × 10–10 mol dm–3, suggest why the reaction with HCN is
very slow.

___________________________________________________________________

___________________________________________________________________
(2)

(e) Acrylic fibres are used as a substitute for wool. Acrylics are copolymers of
acrylonitrile with other compounds.

Acrylonitrile is the common name for the following compound.

H2C = CH − C ≡ N

(i) Acrylonitrile can be formed from propene.

Write an equation for the reaction of propene with ammonia and oxygen to
form acrylonitrile and one other product.

______________________________________________________________
(1)

(ii) The term copolymer is used to describe the product obtained when two or
more different monomers form a polymer.

Draw the repeating unit of the acrylic copolymer that contains 75% acrylonitrile
monomer and 25% chloroethene monomer.

(1)

(iii) Name the type of polymerisation involved in part (ii)

______________________________________________________________
(1)
(Total 15 marks)

Q12.

Page 11 of 83
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.

______________________________________________________________

______________________________________________________________
(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

Page 12 of 83
involved.

______________________________________________________________

______________________________________________________________
(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

___________________________________________________________________

___________________________________________________________________
(5)

(c) Draw the structure of each of the following isomers of C5H8O2

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.

Page 13 of 83
(5)
(Total 19 marks)

Q13.
Lactic acid, CH3CH(OH)COOH, is formed in the human body during metabolism and
exercise. This acid is also formed by the fermentation of carbohydrates such as sucrose,
C12H22O11.

(a) (i) Give the IUPAC name for lactic acid.

______________________________________________________________
(1)

(ii) Write an equation for the formation of lactic acid from sucrose and water.

______________________________________________________________
(1)

(b) A molecule of lactic acid contains an asymmetric carbon atom.

The lactic acid in the body occurs as a single enantiomer.
A racemic mixture (racemate) of lactic acid can be formed in the following two-stage
synthesis.

(i) Name and outline a mechanism for Stage 1.

Name of mechanism _____________________________________________

Mechanism

(5)

(ii) Give the meaning of the term racemic mixture (racemate).

______________________________________________________________

Page 14 of 83
______________________________________________________________

______________________________________________________________
(1)

(iii) Explain how you could distinguish between a racemic mixture (racemate) of
lactic acid and one of the enantiomers of lactic acid.

______________________________________________________________

______________________________________________________________
(2)

(c) A mixture of lactic acid and its salt sodium lactate is used as an acidity regulator in
some foods. An acidity regulator makes sure that there is little variation in the pH of
food.

(i) Write an equation for the reaction of lactic acid with sodium hydroxide.

______________________________________________________________
(1)

(ii) The acid dissociation constant Ka for lactic acid has the value
1.38 × 10−4 mol dm−3 at 298 K.

Calculate the pH of an equimolar solution of lactic acid and sodium lactate.

______________________________________________________________

______________________________________________________________
(2)

(iii) Suggest an alternative name for the term acidity regulator.

Explain how a mixture of lactic acid and sodium lactate can act as a regulator
when natural processes increase the acidity in some foods.

Name ________________________________________________________

Explanation ____________________________________________________

______________________________________________________________

______________________________________________________________
(3)

(d)

Page 15 of 83
The cup shown is made from PLA, poly(lactic acid).
PLA is the condensation polymer formed from lactic acid.

The polymer is described as 100% biodegradable and 100% compostable.

Compostable material breaks down slowly in contact with the moist air in a garden
bin. This produces compost that can be used to improve soil.

The manufacturers stress that PLA cups differ from traditional plastic cups that are
neither biodegradable nor compostable.

(i) Draw a section of PLA that shows two repeating units.

(2)

(ii) Name the type of condensation polymer in PLA.

______________________________________________________________
(1)

(iii) An intermediate in the production of PLA is a cyclic compound (C6H8O4) that is

formed from two PLA molecules.

Draw the structure of this cyclic compound.

Page 16 of 83
(1)

(iv) Traditional non-biodegradable plastic cups can be made from

poly(phenylethene), commonly known as polystyrene.

Draw the repeating unit of poly(phenylethene).

(1)

(v) The manufacturers of PLA claim that the material will break down to compost
in just 12 weeks.

Suggest one reason why PLA in landfill may take longer than 12 weeks to
break down.

______________________________________________________________

______________________________________________________________
(1)
(Total 22 marks)

Q14.
Suggest one reason why Tollens’ reagent is used as the oxidising agent in the specific
test for aldehydes rather than the less expensive acidified potassium dichromate(VI).

_______________________________________________________________________

_______________________________________________________________________
(Total 1 mark)

Q15.
The triiodomethane reaction is often used as a test for aldehydes and ketones that contain
the CH3CO group shown.

The aldehyde or ketone is reacted with an alkaline solution of iodine. Triiodomethane

(CHl3) is formed as a precipitate. Compounds that contain a group that can be oxidised to
the CH3CO group will also give a positive result in this test.

(a) State, with a reason, whether or not ethanol will give a positive result in the

Page 17 of 83
triiodomethane reaction.

___________________________________________________________________

___________________________________________________________________
(1)

(b) The equation for the reaction of ethanal with an alkaline solution of iodine is

CH3CHO + 3l2 + 4NaOH CHl3 + HCOONa + 3Nal + 3H2O

In an experiment using this reaction, the yield of triiodomethane (CHl3) obtained by a

student was 83.2%.

Calculate the minimum mass of iodine that this student would have used to form
10.0 g of triiodomethane.
Give your answer to the appropriate precision.
Show your working.

___________________________________________________________________

___________________________________________________________________
(5)

(c) Triiodomethane can be separated from the reaction mixture by filtration.

State one reason why the solid residue is then washed with water after the filtration.

___________________________________________________________________

___________________________________________________________________
(1)

(d) State one reason, other than cost or availability, why water is suitable for washing
this solid residue after the filtration.

___________________________________________________________________

___________________________________________________________________
(1)

Page 18 of 83
(Total 8 marks)

Q16.
Each of the following conversions involves reduction of the starting material.

(a) Consider the following conversion.

Identify a reducing agent for this conversion.

Write a balanced equation for the reaction using molecular formulae for the nitrogen-
containing compounds and [H] for the reducing agent.

Draw the repeating unit of the polymer formed by the product of this reaction with
benzene-1,4-dicarboxylic acid.

___________________________________________________________________

___________________________________________________________________
(5)

(b) Consider the following conversion.

Identify a reducing agent for this conversion.

State the empirical formula of the product.

State the bond angle between the carbon atoms in the starting material and the
bond angle between the carbon atoms in the product.

___________________________________________________________________

Page 19 of 83
___________________________________________________________________
(4)

(c) The reducing agent in the following conversion is NaBH4

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

Name of mechanism _____________________________________________

Mechanism

(5)

(ii) By considering the mechanism of this reaction, explain why the product formed
is optically inactive.

______________________________________________________________

______________________________________________________________
(3)
(Total 17 marks)

Q17.
Chemists have to design synthetic routes to convert one organic compound into another.

Propanone can be converted into 2-bromopropane by a three-step synthesis.

Step 1: propanone is reduced to compound L.

Step 2: compound L is converted into compound M.
Step 3: compound M reacts to form 2-bromopropane.

Page 20 of 83
Deduce the structure of compounds L and M.

For each of the three steps, suggest a reagent that could be used and name the
mechanism.

Equations and curly arrow mechanisms are not required.

_______________________________________________________________________

_______________________________________________________________________
(Total 8 marks)

Q18.
(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.

______________________________________________________________
(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 _____________________________________________________

______________________________________________________________

Apparatus
(4)

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

Page 21 of 83
in high yield rather than propanoic acid.

______________________________________________________________

______________________________________________________________
(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.

___________________________________________________________________
(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 ____________________________________________________

______________________________________________________________
(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 ____________________________________________________

______________________________________________________________
(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 _________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)
(Total 15 marks)

Page 22 of 83
Q19.
Many synthetic routes need chemists to increase the number of carbon atoms in a
molecule by forming new carbon–carbon bonds. This can be achieved in several ways
including

• reaction of an aromatic compound with an acyl chloride

• reaction of an aldehyde with hydrogen cyanide.

(a) Consider the reaction of benzene with CH3CH2COCl

(i) Write an equation for this reaction and name the organic product.
Identify the catalyst required in this reaction.
Write equations to show how the catalyst is used to form a reactive
intermediate and how the catalyst is reformed at the end of the reaction.

______________________________________________________________

______________________________________________________________
(5)

(ii) Name and outline a mechanism for the reaction of benzene with this reactive
intermediate.

______________________________________________________________

______________________________________________________________
(4)

(b) Consider the reaction of propanal with HCN

(i) Write an equation for the reaction of propanal with HCN and name the
product.

Page 23 of 83
______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) Name and outline a mechanism for the reaction of propanal with HCN

______________________________________________________________

______________________________________________________________
(5)

(iii) The rate-determining step in the mechanism in part (b) (ii) involves attack by
the nucleophile.
Suggest how the rate of reaction of propanone with HCN would compare with
the rate of reaction of propanal with HCN
Explain your answer.

______________________________________________________________

______________________________________________________________
(2)
(Total 18 marks)

Q20.
Two isomeric ketones are shown below.

Page 24 of 83
(a) Name and outline a mechanism for the reaction of compound Q with HCN and
name the product formed.

Name of mechanism ________________________________________________

Mechanism

Name of product ___________________________________________________

(6)

(b) Some students were asked to suggest methods to distinguish between isomers Q
and R.

One student suggested testing the optical activity of the products formed when Q
and R were reacted separately with HCN.

By considering the optical activity of these products formed from Q and R, explain
why this method would not distinguish between Q and R.

___________________________________________________________________

___________________________________________________________________
(3)
(Total 9 marks)

Q21.
A possible synthesis of phenylethene (styrene) is outlined below.

Page 25 of 83
(a) In Reaction 1, ethanoyl chloride and aluminium chloride are used to form a reactive
species which then reacts with benzene.
Write an equation to show the formation of the reactive species.
Name and outline the mechanism by which this reactive species reacts with
benzene.

___________________________________________________________________

___________________________________________________________________
(6)

(b) NaBH4 is a possible reagent for Reaction 2.

Name and outline the mechanism for the reaction with NaBH4 in Reaction 2.
Name the product of Reaction 2.

___________________________________________________________________

Page 26 of 83
(6)

___________________________________________________________________

___________________________________________________________________
(2)
(Total 14 marks)

Q22.
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

______________________________________________________________

(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)

Page 27 of 83
separately with the following substances:

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

(ii) acidified potassium dichromate(VI);

(iii) concentrated sulphuric acid in an elimination reaction.

(3)
(Total 11 marks)

Q23.
Consider the reaction sequence shown below.

(a) Name and outline a mechanism for the reaction in Step 1.

Name of mechanism _________________________________________________

Mechanism

Page 28 of 83
(5)

(b) (i) Name compound Q formed in Step 2.

______________________________________________________________

(ii) Two stereoisomers are formed by the dehydration of Q. Give the structures of
these two isomers and name the type of stereoisomerism shown.

Structures of isomers

Type of stereoisomerism _______________________________________________

(4)

(i) Draw the repeating unit of the polymer PHB.

(ii) Suggest a reason why the polymer is biodegradeable.

Page 29 of 83
______________________________________________________________

______________________________________________________________
(2)

(d) The amino acid R is shown below.

(i) Draw the structure of the zwitterion formed by R.

(ii) Draw the structure of the major organic product formed when an excess of R is
reacted with bromomethane.

(iii) Name the mechanism of the reaction which results in the formation of the
product given in part (ii).

______________________________________________________________
(3)
(Total 14 marks)

Q24.
Which one of the following reactions will produce an organic compound that has optical
isomers?

A dehydration of butan-2-ol by heating with concentrated sulphuric acid

B reduction of pentan-3-one by warming with NaBH4

C addition of Br2 to 3-bromopropene

D reduction of 2,3-dimethylpent-2-ene with H2 in the presence of a nickel catalyst

Page 30 of 83
(Total 1 mark)

Q25.
(a) Describe how propanal, CH3CH2CHO, and propanone, CH3COCH3, can be
distinguished using

(i) a chemical test and

______________________________________________________________

______________________________________________________________
(3)

(ii) the number of peaks in their proton n.m.r. spectra.

______________________________________________________________

______________________________________________________________
(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.

Page 31 of 83
For each of the three steps in the synthesis, name the type of reaction involved and
give reagents and conditions. Equations are not required.

___________________________________________________________________

___________________________________________________________________
(10)
(Total 15 marks)

Q26.
(a) Addition reactions to both alkenes and carbonyl compounds can result in the
formation of isomeric compounds.

(i) Choose an alkene with molecular formula C4H8 which reacts with HBr to form
two structural isomers. Give the structures of these two isomers and name the
type of structural isomerism shown.

Outline a mechanism for the formation of the major product.

______________________________________________________________

Page 32 of 83
______________________________________________________________

______________________________________________________________

______________________________________________________________
(7)

(ii) Using HCN and a suitable carbonyl compound with molecular formula C3H6O,
outline a mechanism for an addition reaction in which two isomers are
produced.
Give the structures of the two isomers formed and state the type of isomerism
shown.

______________________________________________________________

Page 33 of 83
______________________________________________________________
(7)

(b) Explain why ethanoyl chloride reacts readily with nucleophiles.

Write an equation for one nucleophilic addition–elimination reaction of ethanoyl
chloride.
(A mechanism is not required.)

___________________________________________________________________

___________________________________________________________________
(4)
(Total 18 marks)

Q27.
In which one of the following mixtures does a redox reaction occur?

A ethanal and Tollens’ reagent

B ethanoyl chloride and ethanol

C ethanal and hydrogen cyanide

D ethanoic acid and sodium hydroxide

(Total 1 mark)

Q28.
Propanone can be reduced to form an alcohol. A functional group isomer of the alcohol
formed is

A CH3CH2CH2OH

B CH3CH2CHO

C CH3OCH2CH3

D CH3COCH3
(Total 1 mark)

Q29.
(a) (i) Give a suitable reagent and state the necessary conditions for the conversion
of propan-2-ol into propanone. Name the type of reaction.

Page 34 of 83
Reagent _______________________________________________________

Conditions _____________________________________________________

Type of reaction _________________________________________________

(ii) Propanone can be converted back into propan-2-ol. Give a suitable reagent
and write an equation for this reaction.
(Use [H] to represent the reagent in your equation.)

Reagent ______________________________________________________

Equation

______________________________________________________________
(5)

(b) Propanal is an isomer of propanone.

(i) Draw the structure of propanal.

(ii) A chemical test can be used to distinguish between separate samples of

propanone and propanal. Give a suitable reagent for the test and describe
what you would observe with propanone and with propanal.

Test reagent ___________________________________________________

Observation with propanone _______________________________________

(4)
(Total 9 marks)

Q30.
Compounds C and D, shown below, are isomers of C5H10O

Page 35 of 83
C D

(a) Name compound C.

___________________________________________________________________
(1)

(b) Use Table 2 on the Data Sheet to help you to answer this question.

(i) Suggest the wavenumber of an absorption which is present in the infra-red

spectrum of C but not in that of D.

______________________________________________________________

(ii) Suggest the wavenumber of an absorption which is present in the infra-red

spectrum of D but not in that of C.

______________________________________________________________
(2)

(c) Deduce the number of peaks in the proton n.m.r. spectrum of C.

___________________________________________________________________
(1)

(d) Identify a reagent that you could use to distinguish between C and D. For each of C
and D, state what you would observe when the compound is treated with this
reagent.

Reagent ___________________________________________________________

Observation with C ___________________________________________________

Observation with D ___________________________________________________

(3)

(e) Compound E, CH3CH2CH2CH2CHO, is also an isomer of C5H10O

Identify a reagent which will react with E but not with C or D. State what you would
observe when E is treated with this reagent.

Reagent ___________________________________________________________

Observation with E ___________________________________________________

(2)
(Total 9 marks)

Page 36 of 83
Q31.
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)

Q32.
(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.

(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 ______________________________________________

Page 37 of 83
Observation with F______________________________________________
(4)

(1)
(Total 9 marks)

Q33.
The three compounds CH3CH2CH2CH2OH, (CH3)3COH and CH3CH2CH2CHO can be
distinguished by use of the following three reagents

1. potassium dichromate(VI) acidified with dilute sulphuric acid

2. Tollens’ reagent
3. ethanoic acid, together with a small amount of concentrated sulphuric acid.

(a) Identify which of these three organic compounds would reduce acidified potassium
dichromate(VI). Give the structures of the organic products formed. Write a half-
equation for the reduction of dichromate(VI) ions in acidic solution.

___________________________________________________________________

___________________________________________________________________
(6)

(b) Identify which one of these three organic compounds would reduce Tollens’ reagent.
Give the structure of the organic product formed. Write a half-equation for the
reduction of Tollens’ reagent.

___________________________________________________________________

Page 38 of 83
___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Identify which of these three organic compounds would react with ethanoic acid in
the presence of concentrated sulphuric acid. In each case, give the structure of the
organic product formed.

___________________________________________________________________

___________________________________________________________________
(4)

(d) State the number of peaks in the proton n.m.r. spectra of CH3CH2CH2CH2OH and of
(CH3)3COH. (Analysis of peak splitting is not required.)

___________________________________________________________________

___________________________________________________________________
(2)
(Total 15 marks)

Q34.
(a) Outline a mechanism for the reaction of CH3CH2CH2CHO with HCN and name the
product.

Mechanism

Page 39 of 83
Name of product ____________________________________________________
(5)

(b) Outline a mechanism for the reaction of CH3OH with CH3CH2COCl and name the
organic product.

Mechanism

Name of organic product _______________________________________________

(5)

(c) An equation for the formation of phenylethanone is shown below. In this reaction a
reactive intermediate is formed from ethanoyl chloride. This intermediate then reacts
with benzene.

(i) Give the formula of the reactive intermediate.

______________________________________________________________

(ii) Outline a mechanism for the reaction of this intermediate with benzene to form
phenylethanone.

(4)
(Total 14 marks)

Q35.
Which one of the following would not reduce an acidified aqueous solution of potassium

Page 40 of 83
dichromate(VI)?

A CH3COOH

B Zn

C CH3CHO

D Fe2+(aq)
(Total 1 mark)

Page 41 of 83
Mark schemes

Q1.

(a)
Allow + on C or O in equation –
But must be on C in mechanism
M1

M2 Arrow from inside hexagon to C or + on C

1
M3 Structure of intermediate
• horseshoe centred on C1 and must not extend beyond C2
and
C6, but can be smaller
• + in intermediate not too close to C1 (allow on or “below” a
line
from C2 to C6)
1
M4 Arrow from bond into hexagon (Unless Kekule)
• Can allow M4 arrow independent of wrong M3 structure
• + on H in intermediate loses M3 not M4
• Ignore Cl– and AlCl4–
- used in M4
1

(b) Either...

1-phenylpropan-1-ol
1
NaBH4 / LiAlH4
1
Nucleophilic addition
1

Or...

1-phenylpropan-1-ol
1
H2 with Ni/Pd/Pt

Page 42 of 83
1
Addition/hydrogenation
1
Both numbers needed for names
Ignore solvents

(c) Misty fumes / steamy fumes

Allow sweet/fruity smell / white fumes
Not smoke
1

(Nucleophilic) addition-elimination
1

1
[10]

Q2.
B
[1]

Q3.
(a) 2-hydroxyhexanenitrile
1

(b) (Plane) polarised light

Enantiomers would rotate light in opposite directions

not different alone
1

(c) planar carbonyl group or

planar
Not planar molecule,
not planar bond, not planar C=O
1

Attack from either side

With equal probability

OR produces equal amounts (of the two isomers/enantiomers)

Page 43 of 83
(d)

Does not contain a chiral centre

OR does not contain C attached to 4 different groups

OR contains two identical/ethyl groups

OR symmetrical (product)
Allow C2H5 or skeletal

M2 dependent on correct M1 (No structure = 0)

If pentan-3-one drawn then allow symmetrical ketone for M2
[8]

Q4.
D
[1]

Q5.
B
[1]

Q6.
B
[1]

Q7.
(a) CH3CH2COCH3 + 2[H] CH3CH2CH(OH)CH3
1

(b) This question is marked using levels of response. Refer to the Mark Scheme
Instructions for Examiners for guidance on how to mark this question.

All stages are covered and the explanation of each stage is generally correct
and virtually complete.

Page 44 of 83
Answer is communicated coherently and shows a logical progression from
stage 1 to stage 2 then stage 3.
Level 3
5 – 6 marks

All stages are covered but the explanation of each stage may be incomplete or
may contain inaccuracies OR two stages are covered and the explanations
are generally correct and virtually complete.

Answer is mainly coherent and shows progression from stage 1 to stage 3.

Level 2
3 – 4 marks

Two stages are covered but the explanation of each stage may be incomplete
or may contain inaccuracies, OR only one stage is covered but the
explanation is generally correct and virtually complete.

Answer includes isolated statements but these are not presented in a logical
order or show confused reasoning.
Level 1
1 – 2 marks

Insufficient correct chemistry to gain a mark.

Level 0
0 marks

Indicative Chemistry content

Stage 1: Formation of product

• Nucleophilic attack
• Planar carbonyl group
• H – attacks from either side (stated or drawn)

Stage 2: Nature of product

• Product of step 1 shown
• This exists in two chiral forms (stated or drawn)
• Equal amounts of each enantiomer / racemic mixture formed

Stage 3: Optical activity

• Optical isomers / enantiomers rotate the plane of polarised light equally
in
• With a racemic / equal mixture the effects cancel
6
[7]

Q8.
(a) A mixture of liquids is heated to boiling point for a prolonged time
1

Vapour is formed which escapes from the liquid mixture, is changed back into
liquid and returned to the liquid mixture
1

Any ethanal and ethanol that initially evaporates can then be oxidised
1

(b) CH3CH2OH + H2O CH3COOH + 4H+ + 4e–

Page 45 of 83
1

(c) Mixture heated in a suitable flask / container

A labelled sketch illustrating these points scores the marks
1

With still head containing a thermometer

Water cooled condenser connected to the still head and suitable cooled
collecting vessel
1

Collect sample at the boiling point of ethanal

Cooled collection vessel necessary to reduce evaporation of ethanal

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

ethanal
1

Intermolecular forces / dipole-dipole are weaker than hydrogen bonding

(e) Reagent to confirm the presence of ethanal:

Add Tollens’ reagent / ammoniacal silver nitrate / aqueous silver nitrate

followed by 1 drop of aqueous sodium hydroxide, then enough aqueous
ammonia to dissolve the precipitate formed

Add Fehling’s solution

Warm
M2 and M3 can only be awarded if M1 is given correctly
1

Result with Tollen’s reagent:

Silver mirror / black precipitate

Result with Fehling’s solution:

Red precipitate / orange-red precipitate

Reagent to confirm the absence of ethanoic acid

Add sodium hydrogencarbonate or sodium carbonate

Result; no effervescence observed; hence no acid present

1
M5 can only be awarded if M4 is given correctly

Page 46 of 83
OR

Reagent; add ethanol and concentrated sulfuric acid and warm

Result; no sweet smell / no oily drops on the surface of the liquid,

hence no acid present

[16]

Q9.
B
[1]

Q10.
(a) (i) Nucleophilic addition
Any extra loses the mark
Allow minor spelling errors e.g. nucleophyllic
1

(ii)
M1 for arrow from lone pair on oxygen in ethanol to C of
C=O (or to space half way between O and C)
M2 for arrow from C=O bond to oxygen in ethanal
Do not allow M2 as first step without nucleophilic attack, but
can allow M1 for attack on C+ produced
+ rather than δ+ on C=O loses M2
Ignore any further steps
Mark independently
1
1

(b) (i) Equal mixture of enantiomers/optical isomers OWTTE

(ii) (Non-superimposable) mirror images

Ignore rotates light in opposite directions
Ignore stereoisomers
1

(c) (i) Ethanal 0.33

Ethanol 4.16
Allow 4.2 for ethanol
1

Page 47 of 83
(ii)
Ignore slips in acetal structure or formula C6H14O2
If Kc wrong, allow M4 only for units conseq to their Kc
If volume omitted (gives 2.93 × 10-2) may only score M1 and
M4
If volume used = 310 cm3 allow M2 then award M3 for 9.08 –
9.23 only and M4 for mol–1 cm3 only
Treat error in converting 310 cm3 to dm3 as AE
M1
M2

9.1 × 10-3

Allow range 9.08 × 10-3 – 9.23 × 10-3

mol-1dm3

Not moles-1dm3
M4

(d)
1
[12]

Q11.
(a) Nucleophilic addition
1

M4 for lp, arrow and H+

Allow C2H5− for CH3CH2−

• M1 and M4 include lone pair and curly arrow.
• Allow: CN− but arrow must start at lone pair on C.
• M2 not allowed independent of M1, but allow M1 for
correct attack on C+.
• + rather than δ+ on C=O loses M2.

Page 48 of 83
• Penalise incorrect partial charges.
• M3 is for correct structure including minus sign but lone
pair
is part of M4.
• Penalise extra curly arrows in M4.
4

(b) (i) M1

M1 for correct structure of product of part (a).

Allow C2H5− for CH3CH2−.
Penalise wrongly bonded, OH or CN or CH2CH3 once only in
clip.
1

M2 cannot be gained by simply swapping two or more

groups with no attempt to show a mirror image., e.g. do not
allow M2 for

because these do not show the enantiomers as mirror

images.

Students must show an attempt at mirror images, eg allow

ie vertical groups same and horizontal swapped as if there was a mirror

between them

No mirror need be shown

Do not penalize wedge bond when wedge comes into contact with both
C&N
However these two could score M2 if placed as below as if
with a “mirror” horizontally between them.

Page 49 of 83
1

(ii) M1 (Plane) polarized light

M2 only scores following correct M1
1

M2 Rotated in opposite directions (equally) (only allow if M1 correct

or close)
Not just in different directions but allow one rotates light to
the left and one to the right.
Not molecules rotate.
1

(d) Weak acid / (acid) only slightly / partially dissociated / ionised

Ignore rate of dissociation.
1

[CN−] very low

Allow (very) few cyanide ions.
Mark independently.
1

(e) (i) H2C=CH−CH3 + NH3 + O2 H2C=CH−CN + 3H2O

H2C=CH−CH3 + NH3 + 3O2 H2C=CH−CN + 3H2O2

OR doubled.
Allow C3H6 and CH2CHCN or C3H3N on this occasion only.
1

(ii)

Ignore n.
Must show trailing bonds.
Do not penalise C–NC bond here on this occasion.

Must contain, in any order,

Page 50 of 83
3 of

Allow

and one of

Allow –CH2CH(CN)CH2CHCl− etc.

(iii) Addition (polymerization)

Allow self-addition.
Do not allow additional.
1
[15]

Q12.
(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.

Page 51 of 83
1

b 50-90 (ppm) or single value or range entirely within this range

(ii)

Must have trailing bonds, but ignore n.

OR –OCH2CH2CH2CH2CO– OR –CH2CH2CH2CH2COO–
Allow

but not - C4H8−

one unit only

Condensation
1

(b)

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)

Page 52 of 83
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

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)CH2C

H3
Allow CH3− or C2H5− but not CH2CH3−.
Allow −CO2H.
Not cyclic isomers.
Not the optically active isomer.

Page 53 of 83
Allow (CH3)2CCHCOOH etc.
1

P
acid

Allow −CO2H.

CH3CH(COOH)CH=CH2
Allow CH3CH(CO2H)CHCH2 or
CH3CH(CO2H)C2H3.
1

Not cyclic esters.

1
[19]

Q13.
(a) (i) 2-hydroxypropanoic acid
OR
2-hydroxypropan(-1-)oic acid
Do not penalise different or missing punctuation or extra
spaces.
Spelling must be exact and order of letters and numbers as
here.
Can ignore −1− before –oic, but penalise any other numbers
here.
1

(ii) C12H22O + H2O

11 4CH3CH(OH)COOH
Allow 4C3H6O3

C12H22O11 + H O
2 2CH3CH(OH)COOH + C6H12O6
Allow 2C3H6O3
1

(b) (i) Nucleophilic addition

Page 54 of 83
M4 for lp, arrow and H+

• M1 lp and minus must be on C

• M1 and M4 include lone pair and curly arrow.
• M2 not allowed independent of M1, but allow following
some attempt at attack on carbonyl C
• allow M1 for correct attack on C+
• + rather than δ+ on C=O loses M2
• M3 is for correct structure including minus sign but lone
pair is part of M4
• Allow arrow in M4 to H of H-CN with arrow forming cyanide
ion.
5

(ii) Equal mixture of enantiomers / (optical) isomers

(iii) (Plane) polarized light

If missing no further mark.
1

(Polarised light) rotated by single enantiomer but unaffected by

racemate
Both needed; not allow bend, twist etc.
1

(c) (i) CH3CH(OH)COOH + NaOH → CH3CH(OH)COONa + H2O

OR CH3CH(OH)COOH + OH− → CH3CH(OH)COO− + H2O
Not ambiguous mol formulae for product - must show
COONa or CO2Na or COO− or CO2−
1

(ii) [H+] = Ka OR pH = pKa

pH = 3.86
Allow more than 2 decimal places but not fewer.
1

(iii) M1 buffer
Ignore acidic but penalise alkaline or basic.
1

Any two out of the three marks M2 , M3 & M4

M2 Large lactate concentration in buffer

OR sodium lactate completely ionised

Page 55 of 83
M3 added acid reacts with / is removed by lactate ion or A− or sodium
lactate or salt
OR equation H+ + A− → HA
Ignore reaction of H+ with OH−
Ignore reference to equilibrium unless it is shown.

M4 ratio [HA] / [A−] stays almost constant

Ignore H+ or pH remains constant.
Max 2

(d) (i)

No marks if ester link missing

Correct ester link

allow –COO–
NB Correct answer scores 2
Ignore n here (compare with (d)(iv).
Ignore brackets
1

All rest correct with trailing bonds

If OH or COOH on either or both ends, lose one, ie dimer
scores 1
If more than two repeating units, lose 1
1

(ii) (Poly)ester ie allow ester

Not terylene.
Ignore spaces and brackets in answer.
1

(iii)

Allow any cyclic C6H8O4

Page 56 of 83
(iv)

Penalise n here (compare with (d)(i)

Ignore brackets.
Not allow Ph for phenyl.
1

(v) In landfill, no air or UV, to assist decay

OR not enough water or moisture (to hydrolyse polyester)
Allow landfill has / contains:
no or few bacteria / micro-organisms / enzymes compared
with compost heap
OR less oxygen
OR lower temperature.
1
[22]

Q14.
Dichromate(VI) will also oxidise / give a positive test with alcohols
Allow ‘dichromate’.
Allow ‘dichromate(VI) will oxidise other organic molecules /
functional groups’.
[1]

Q15.
(a) Yes, because it is oxidised to ethanal / CH3CHO
OR it is oxidised to a compound that contains CH3CO group
Ignore ‘primary alcohols are oxidised to aldehydes’.
Need ‘yes’ and an explanation to be awarded the mark.
1

(b) Mr CHI3 = 393.7 (M1)

Allow if clearly shown in a calculation.
Allow 394
1

Moles CHI3 = 10 / 393.7 = 2.54 × 10−2 (M2)

Allow a consequential answer on an incorrect Mr.
2.54 × 10−2 scores M1 and M2.
1

Moles I2 = 7.62 × 10−2 (M3)

Allow 3 × M2.
1

Mass I2 = 7.62 × 10−2 × 253.8 = 19.34g (M4)

Page 57 of 83
Allow M3 × 253.8 or M3 × 254
1

Scaling 19.34 / 0.832 = 23.2g (M5)

Allow M4 / 0.832
Lose this mark if the answer is not given to 3 significant
figures.
Answer without working scores M5 only.
Allow any chemically correct alternative method.
Calculations which combine several steps in one expression
can score the marks for all of these individual steps.
1

(c) Remove soluble impurities

Allow ‘remove excess sodium hydroxide / iodine’.
Allow ‘remove excess sodium methanoate / sodium iodide’.
Allow ‘remove excess reagents’.
1

(d) Will not dissolve solid / solid is insoluble in water

Allow ‘will not react with solid’.
1
[8]

Q16.
(a) Sn / HCl OR Fe / HCl not conc H2SO4 nor any HNO3

Ignore subsequent use of NaOH

Ignore reference to Sn as a catalyst with the acid
Allow H2 (Ni / Pt) but penalise wrong metal
But NOT NaBH4 LiAlH4 Na / C2H5OH
1

Equation must use molecular formulae

C6H4N2O4 + 12 [H]
12[H] and 4H2O without correct molecular formula scores 1
out of 2
1

→C6H8N2 + 4H2O
Allow .... + 6H2 if H2 / Ni used
Allow −CONH− or −COHN− or −C6H4−
1

Mark two halves separately: lose 1 each for

• error in diamine part

Page 58 of 83
• error in diacid part
• error in peptide link
• missing trailing bonds at one or both ends
• either or both of H or OH on ends
Ignore n
2

(b) H2 (Ni / Pt) but penalise wrong metal

NOT Sn / HCl, NaBH4 etc.
1

CH2
1

In benzene 120°
1

In cyclohexane 109° 28’ or 109½°

Allow 108° - 110°

If only one angle stated without correct qualification, no mark awarded

(c) (i) Nucleophilic addition

• M2 not allowed independent of M1, but allow M1 for

correct attack on C+
• + rather than δ+ on C=O loses M2
• M3 is for correct structure including minus sign but lone
pair is part of M4
• Allow C2H5
• M1 and M4 include lp and curly arrow
• Allow M4 arrow to H in H2O (ignore further arrows)
4

(ii) M1 Planar C=O (bond / group)

Not just planar molecule
1

M2 Attack (equally likely) from either side

Not just planar bond without reference to carbonyl
1

M3 (about product): Racemic mixture formed OR 50:50 mixture or

each enantiomer equally likely

Page 59 of 83
1
[17]

Q17.
L

Allow (CH3)2CHOH or CH3CH(OH)CH3

Allow name propan–2–ol
Penalise contradiction of name and structure
1

Allow CH3CH=CH2
Allow name propene
ignore -1- but penalise other numbers
Penalise contradiction of name and structure
1

Step 1 NaBH4 or LiAlH4

Zn/HCl or Sn/HCl

or H2/Ni or H2/Pt
Ignore name if formula is correct
ignore solvent
ignore acid (for 2nd step) but penalise acidified NaBH4
Apply list principle for extra reagents and catalysts.

M1
1

(nucleophilic) addition

Addition (not nucleophilic)

Penalise electrophilic
Ignore reduction

M2
1

Step 2 conc H2SO4 or conc H3PO4 or Al2O3

Apply list principle for extra reagents and catalysts.

M3
1

Page 60 of 83
elimination
Independent from M3
penalise nucleophilic or electrophilic
ignore dehydration

M4
1

Step 3 HBr
Apply list principle for extra reagents and catalysts.

M5
1

electrophilic addition
Independent from M5

M6
1
[8]

Q18.
(a) (i) Green
Ignore shades of green.
1

(ii) Excess acidified potassium dichromate(VI)

Reflux (for some time)

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

Immediately (the reagents are mixed)

(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.

Page 61 of 83
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

Some comparison with other compounds explaining that the intermolecular

forces are stronger in propanoic acid
1
[15]

Q19.
(a) (i) C6H6 + CH3CH2COCl → C6H5COCH2CH3 + HCl
OR
C6H6 + CH3CH2CO+ → C6H5COCH2CH3 + H+
allow C2H5
penalise C6H5–CH3CH2CO
allow + on C or O in equation
1

Phenylpropanone

OR ethylphenylketone OR phenylethylketone
Ignore 1 in formula, but penalise other numbers
1

AlCl3
can score in equation
1

CH3CH2COCl + AlCl3 → CH3CH2CO+ + AlCl4–

allow C2H5
allow + on C or O in equation
1

AlCl4– + H+ → AlCl3 + HCl

Page 62 of 83
(ii) electrophilic substitution
can allow in (a)(i) if no contradiction
1

M1 arrow from circle or within it to C or to + on C

horseshoe must not extend beyond C2 to C6 but can be
smaller
+ not too close to C1
M2 penalise C6H5–CH3CH2CO (even if already penalized in
(a)(i))
M3 arrow into hexagon unless Kekule
allow M3 arrow independent of M2 structure
ignore base removing H in M3
3

(b) (i) CH3CH2CHO + HCN → CH3CH2CH(OH)CN OR

C2H5CH(OH)CN
aldehyde must be –CHO brackets optional
1

2-hydroxybutanenitrile OR 2-hydroxybutanonitrile
no others
1

(ii) nucleophilic addition

Page 63 of 83
M1 includes lp and arrow to Carbonyl C and minus charge
(on either C or N)
Not allow M2 before M1, but allow M1 to C+ after non-scoring
carbonyl arrow
Ignore δ+, δ– on carbonyl group, but if wrong way round or
full + charge on C lose M2
M3 for correct structure including minus sign. Allow C2H5
M4 for lp and curly arrow to H+
4

(iii) (propanone) slower OR propanal faster

inductive effects of alkyl groups

OR
C of C=O less δ+ in propanone
OR
alkyl groups in ketone hinder attack
OR
easier to attack at end of chain
if wrong, no further marks
1
[18]

Q20.
(a) nucleophilic addition
1

Attack by HCN loses M1 and M2

M2 not allowed independent of M1, but
allow M1 for correct attack on C+
+C=O loses M2
M2 only allowed if correct carbon attacked
allow minus charge on N i.e. :CN–
4

M3 for completely correct structure not including lp

Page 64 of 83
allow C3H7 in M3

M4 for lp and arrow

allow without –
1

2-hydroxy-2-methylpentan(e)nitrile
allow 2-hydroxy-2-methylpentanonitrile

(b) Product from Q is a racemic mixture/equal amounts of enantiomers

if no reference to products then no marks;
1

racemic mixture is inactive or inactive explained

not Q is optically active or has a chiral centre etc
1

Product from R is inactive (molecule) or has no chiral centre

1
[9]

Q21.

(a) CH3COCl + AlCl3 → CH3 O + AlCl

(1) equation (1)
2

penalise wrong alkyl group once at first error

position of + on electrophile can be on O or C or outside [ ]
penalise wrong curly arrow in the equation or lone pair on AlCl3 else ignore

Electrophilic substitution
NOT F/C acylation
1

horseshoe must not extend beyond C2 to C6 but can be

smaller
+ not too close to C1
M3 arrow into hexagon unless Kekule
allow M3 arrow independent of M2 structure

M1 arrow from within hexagon to C or to + on C

+ must be on C of
3

(b) Nucleophilic addition

Page 65 of 83
NOT reduction
1

M2 not allowed independent, but can allow M1 for attack of

H– on C+ formed
4

1–phenylethan(–1–)ol or (1–hydroxyethyl)benzene
l

(c) dehydration or elimination

(conc) H2SO4 or (conc) H3PO4

allow dilute and Al2O3
Do not allow iron oxides
1
[14]

Q22.
(a) nucleophilic addition
1

(b) (i) 2-hydroxybutanenitrile

(ii)

Page 66 of 83
(allow 1 for amide even if not C4H7NO, i.e. RCONH2)

(if not amide, allow one for any isomer of C4H7NO which shows
geometric isomerism)
2

(ii)

(iii) CH3CH=CHCOOH
1
[11]

Q23.
(a) necleophilic addition;

M3 structure;
(be lenient on position of charge on CN– )
(M2 not allowed independent of M1,
but allow M1 for correct attack on C+
if M2 show as independent first.)
(+on C of C=O loses M2 but ignore δ+ if correct)
(M4 for arrow and lone pair (only allow for correct M3 or
close))
4

(b) (i) 2-hydroxybutanoic acid

(ii)

Page 67 of 83
1

geometric(al) or cis-trans
1

(one unit only) (ignore brackets or n) (trailing bonds are

needed)
1

(ii) can be hydrolysed

can be reacted with/attacked by acid/base/nucleophiles/H2O/OH–;

(d) (i)

(allow –NH )
3
+

(ii)

(or zwitterions product)

(iii) nucleophilic substitution;

1
[14]

Q24.
D
[1]

Page 68 of 83
Q25.
(a) (i)

Reagent Tollens Fehlings or K2Cr2O7/H+ KMnO4/H+ I2/NaOH

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. K2Cr2O7 or Cr2O72–/H+ then mark on)

(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
1

Y is CH3CH(OH)CH3 or propan-2-ol allow propanol with correct formula

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

(conc) H2SO4 or HCl

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

Page 69 of 83
or reflux or heat
1
[15]

Q26.
(a) (i) An appropriate alkene; CH3CH2CHCH2 or (CH3)2CCH2
1

Isomer 1
1

Isomer 2
1

Position isomerism
1

Mechanism

electrophilic attack and electron shift to Br (Unless H+ used)

carbocation
1

reaction with carbocation

[Allow mechanism marks for the alkene CH CHCHCH ]
3 3

[Allow one mark if mechanism for minor product given]

(ii) An appropriate carbonyl; CH3CH2CHO

Mechanism nucleophilic attack and electron shift to O

anion intermediate
1

reaction with anion

[Allow mechanism marks for the carbonyl (CH ) CO]3 2

Isomer 1
1

Isomer 2
1

Optical isomerism
NB Isomer structures must be tetrahedral
NB Penalise “stick” structures once in part (a)
1

(b) QoL
Large charge on carbonyl carbon atom due to bonding
to O and Cl
1

Page 70 of 83
Nucleophiles have electron pairs which can be donated
1

Equation Species
1

Balanced
1
[18]

Q27.
A
[1]

Q28.
C
[1]

Q29.
(a) (i) Potassium (OR sodium) dichromate(VI) OR correct formula
OR potassium manganate(VII)
(Oxidation state not needed, but must be correct if included)
(Penalise errors in the formula or oxidation state, but mark
conditions)
1

Acidified OR H2SO4 / HCl (NOT with KMnO4) / H3PO4 / HNO3

(Ignore heat or reflux)
(Credit “acidified” as part of reagent)
1

Oxidation or redox
1

(ii) NaBH4 OR LiAlH4 OR H2/Ni

CH3COCH3 + 2[H] → CH3CH(OH)CH3

(Credit H2 in the equation if H2 has been chosen as reagent)
1

(b) (i)
(Structure must show aldehyde structure)
(Credit C2H5 as alternative to CH3CH2)

(ii)

M1 Tollens’ OR Fehling’s OR acidified

reagent OR solution potassium
ammoniacal silver dichromate
nitrate

Page 71 of 83
OR AgNO3 + NH3 1

M2 stays colourless stays blue stays orange

1
(Provided reagent is correct, credit “no reaction”, “no
change”, “nothing”, “no observation” for M2)

M3 silver mirror / red / brown / orange goes green

deposit precipitate / solid
OR black / grey 1
precipitate
(Credit other correct reagents and observation)

(For M1, penalise AgNO3 alone, penalise Ag(NH3) , penalise

“potassium dichromate”, etc., but, in each case, mark on and
credit correct M2 and M3)
(If totally wrong reagent or no reagent, CE = no marks for
M1,M2 or M3)
1
[9]

Q30.
(a) Pentan-2-one
1

(b) (i) 1680 – 1750 (cm–1)

(ii) 3230 – 3550 or 1000 – 1300 (cm–1)

(iii) 4
1

(c)

Reagent K2Cr2O7/H+ KMnO4 /H+ Na CH3COOH/ 1

H2SO4
with C no reaction no reaction no reaction no reaction 1
with D goes green goes effervescenc smell 1
colourless e
(penalise incomplete reagent e.g. K2Cr2O7 or Cr2O7 2–/H+ then
mark on)

(d)
Reagent Tollens Fehlings or Benedicts 1
with E silver red ppt or goes red 1
(mirror) (not red solution)

[9]

Q31.

Page 72 of 83
B
[1]

Q32.
(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

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

Page 73 of 83
4

Q33.
(a) K2Cr2O7/H2SO4 reuced by

CH3CH2CH2CH2OH (1)

oxidised to CH3(CH2)2CHO (1)

and CH3(CH2)2COOH (1)

CH3CH2CH2CHO (1)

oxidised to CH3(CH2)2COOH (1)

Equation: Cr2O72– + 14H+ + 6e– → 2Cr3+ + 7H2O (1)

Note: Deduct one if all three compounds given as reducing
agents.
6

(b) Tollens’ reduced by

CH3CH2CH2CHO (1)

oxidised to CH3(CH2)2COOH (1)

Equation [Ag(NH3)2]+ + e– → Ag + 2NH3 (1)

(c) CH3CH2CH2CH2OH (1)

Product CH3CH2CH2CH2OOCCH3 (1)

(CH3)3COH

Product (CH3)3COOCCH3 (1)

(d) CH3CH2CH2OH has five peaks (1)

(CH3)3COH has two peaks (1)

2
[15]

Q34.
(a) Mechanism

Page 74 of 83
Allow C3H7 if structure shown elsewhere
penalise HCN splitting if wrong

Name of product: 2-hydroxypenta(neo)nitrile (1)

or 1-cyanobutan-1-ol
5

(b) Mechanism

Name of organic product: methylpropanoate (1)

(c) (i) ([) CH3CO (])+ (1)

(ii)

Notes

(abc) extra curly arrows are penalised

(a) be lenient on position of negative sign on : CN– but arrow must come from lp

(a)/(b) alone loses M2 but can score M1 for attack on C+, similarly

(a) allow 2-hydroxypentanonitrile or 2-hydroxypenta(ne)nitrile ... pentylnitrile

(b) in M4, allow extra: Cl– attack on H, showing loss of H+

Page 75 of 83
(c) (i) allow formula in an “equation”(balanced or not)
be lenient on the position of the + on the formula

(ii) for M1 the arrow must go to the C or the + on the C

don’t be too harsh about the horseshoe, but + must not be close to the
saturated C
M3 must be final step not earlier; allow M3 even if structure (M2) is wrong
[14]

Organic points

(1) Curly arrows: must show movement of a pair of electrons,

i.e. from bond to atom or from lp to atom / space
e.g.

(2) Structures

penalise sticks (i.e. ) once per paper

Penalise once per paper

allow CH3– or –CH3 or or CH3

or H3C–

Q35.
A
[1]

Page 76 of 83
Examiner reports

Q1.
(a) This was a straightforward question on a familiar topic and many good students
(46.5%) scored full marks. However, some drew structures, such as the horseshoe
in the mechanism, with insufficient care and consequently failed to gain marks.
Others omitted charges on the ions in the equation (especially on AlCl4–), or in the
mechanism did not draw the + on the carbonyl carbon in the electrophile.

(b) In this question, although some students struggled with the name, a number failed
to gain the mark due to a failure to label 1-phenyl in an otherwise correct name.
Most identified a correct reagent but “electrophilic addition” and “reduction” were
frequent wrong answers for the name of the mechanism.

(c) This question was generally answered well, especially the name of the mechanism
and the structure of the ester. A common error was to give the name of the product,
i.e. ‘HCl gas’, rather than an observation as required, or alternatively to describe this
as a ‘white precipitate’.

Q2.
A was the commonest incorrect response to this question which had a 47% success rate.
This suggests there were many students who recognised that the answer is an aldehyde,
but who then missed a possible isomer. Drawing out possible structures in a logical
sequence is the key here. Students are advised to start with a 5C chain, then 4C and find
possible positions for the fifth C (carbon 2 or carbon 3), and finally a 3C chain and find
positions for the remaining two carbons (both on carbon 2).

Q3.
(a) As usual, naming nitriles proved difficult for some, but 56% of students gave the
correct answer.

(b) Although this question was answered well by most, an appreciable number of
students were careless with language and appeared to say that the enantiomers
themselves rotate, or that the plane polarised light is ‘refracted’ or ‘bent’ rather than
‘rotated in opposite directions’.

(c) The first mark was less commonly scored than expected as many students wrote
about a planar molecule or a planar bond rather than planar carbonyl group; the
other two marks were frequently awarded.

(d) A significant number were not able to deduce the correct product and many
incorrect products were seen. These included the cyanohydrin formed from
pentanal. This showed a lack of care in reading the question.

Q10.
Both parts of question (a) were answered very well and it was good to see the correct use
of curly arrows. Part (b)(i) was well done but in (b)(ii) many students simply stated what
stereoisomers do to plane polarised light and so failed to answer the question. Part (c)(i)
was answered extremely well and the Kc expression in part (c)(ii) was also answered well.
The calculation was well done but a frequent error was to use amounts, in moles, rather
than concentrations by not using the volume. Better students answered part (d) correctly

Page 77 of 83
while others showed only one hydroxyl group from the diol reacting and so produced an
answer for the acetal which did not match the given molecular formula.

Q11.
In part (a), the nucleophilic addition mechanism was very well done; common errors
included missing the charge on the nucleophile or on the intermediate structure and
showing a bond between the carbonyl carbon and the N of CN in the intermediate. In part
(b)(i), students were not used to drawing 3D structures, and credit was given where
attempts showed a pair of mirror images. Again there were some problems with wrongly
bonded OH, CN and CH2CH3 groups in these structures. The method needed to
distinguish between two enantiomers was well known, although to gain M2 polarised light
had to be ‘rotated’ not turned or reflected, and rotated in ‘opposite’ directions not just
different directions. A few students suggested wrongly that the molecules polarised the
light or that the molecules themselves were rotated. The name in part (c) was well
answered but part (d) was answered poorly. There was confusion of Ka, the acid
dissociation constant, with a rate constant, and many students missed the link to low
concentrations of cyanide ions from the weak acid HCN and focused mainly on the rate of
the dissociation of the acid. Parts (e)(i) and (e)(iii) were answered well but responses to
part (e)(ii) sometimes included the C=C bond or the CN group as part of the polymer
chain.

Q12.
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 NaHCO3 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
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.

Q13.
Parts (a), (b)(i) and (b)(ii) were answered well. In part (b)(iii), students often correctly
identified that polarised light could be used but then failed to gain the marks because they
did not mention the effect of a racemic mixture on the light. Another concern was that
answers appeared to suggest that the light caused the molecules themselves to rotate.

Parts (c)(i) and (c)(ii) were answered well but very few students scored full marks for part

Page 78 of 83
(c)(iii) where explanations were often muddled or referred to unspecified equilibria.

Part (d) was generally well attempted, with the main errors being in part (d)(i), where
many gave three or more repeating units or failed to show an ester linkage, in part (d)(iv),
where many gave the formula of the polymer or missed this part out completely, and in
part (d)(v), where hydrogen bonding was often offered as an explanation.

Part (d)(iii) contained an unfortunate typographical error, which was identified after the
examination had taken place. The end of the first sentence should have read “...from two
lactic acid molecules” rather than “.....from two PLA molecules”. AQA apologises for this
error. The expected answer was given by about a quarter of the students. To ensure that
students were not disadvantaged, a mark was also awarded to those students who drew
any correct cyclic compound with molecular formula C6H8O4. The number of students
who did not attempt this question was low and in line with other question parts on this
paper. The most common errors involved attempts to draw a cyclic compound but with
one or more carbons having fewer than four bonds or oxygens with fewer than two bonds.

Q14.
In this Question, many students stated that Tollens’ Reagent is specific to aldehydes and
were allowed the mark. This answer did little more than reword the question. A specific
reference to potassium dichromate(VI) was needed to earn the mark.

Q15.
In this part (a), many students gave the answer ’primary alcohols are oxidised to
aldehydes’. Since ethanol is the only primary alcohol which will give a positive
triiodomethane test this answer missed the point, and teachers were told to ignore that
answer in the Marking Guidelines. However, sometimes teachers wrongly allowed a mark
for this answer. This was another question where answers that included a disqualifier,
such as ’ethanol is oxidised to ethanal, CH3CO’, were often incorrectly allowed a mark
despite the absence of ’Yes’ and use of an incorrect formula for ethanal.

The calculation in this part (b) was answered well. Many teachers did not penalise
students who did not give their final answer to 3 significant figures. Some did not always
give credit for alternative methods, such as employing the scaling to 100% yield at the
start of the calculation. The omission of the word ’soluble’ in this part (c) often went
unpunished while part (d) was answered well.

Q16.
In part (a), many students thought NaBH4 or LiAlH4 could be used as the reducing agent.
Most did not give the molecular formulae in the equation but could balance it correctly; the
repeating unit of the polymer was very well done.

Similarly, in part (b), NaBH4 was often suggested as the reducing agent and the empirical
formula was frequently wrong. Students found the bond angles difficult, with many failing
to deduce that there is a tetrahedral arrangement around a C atom in cyclohexane and
appearing simply to guess any angle. Only the most able scored both marks for the bond
angles.

There was a good spread of marks in the mechanism with over 40% gaining full marks.
In part (c)(ii), most realised that the product was a racemic mixture and that it was
produced as a result of attack on the ketone from both sides, but often this was thought to
be by an electrophile or an H ion. Some thought that a carbocation intermediate was
+

attacked.

Page 79 of 83
Q17.
This three–step synthesis was slightly easier than the three–step synthesis in last year’s
paper. The question discriminated very well; there were many excellent answers and
some very poor ones, too. Many students were able to see their way through this
synthetic route and had clearly learned reagents and types of mechanism very thoroughly.
Others struggled to get started. Common errors included giving L as propan–1–ol, naming
M as prop–2–ene, omitting the concentrated condition from sulfuric acid and calling the
mechanism in step 2 dehydration rather than elimination.

Q18.
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
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.

Q19.
As is usual, mechanism questions such as this discriminate well. In part (a)(i), 13% of the
candidates gained all five marks whereas a similar number scored only one mark. Many
candidates omitted the name of the product in an otherwise perfect answer. In part (a)(ii),
two fifths of the candidates gained full marks.

In part (b)(i), a number of candidates lost a mark because they gave the formula of the
aldehyde propanal as CH3CH2COH rather than as CH3CH2CHO. For clarification of
acceptable formulae styles, candidates and teachers are advised to consult the document
“General principles applied to marking CHEM4 papers by CMI+ January 2011” which is
available with the Mark Scheme for this paper.

The mechanism in part (b)(ii) was well known and two fifths of candidates gained full
marks.

Part (b)(iii) was a How Science Works question where candidates were not required to
know the answer, but were expected to apply understanding gained from other areas of
the specification. The inductive effect of alkyl groups is part of the explanation of the
relative stability of carbocations. A similar effect using two alkyl groups will reduce the δ+
nature of the carbonyl carbon in propanone more than the single alkyl group does for the
carbonyl carbon in propanal. Hence it can be predicted that the nucleophile will attack
propanal more easily than propanone. About a third of the candidates gained both marks;
most of these gave an answer based on inductive effects as above, but others correctly
discussed steric effects and this answer was also accepted.

Page 80 of 83
Q20.
In part (a), large numbers of candidates were able to write a correct mechanism for the
nucleophilic addition of HCN to ketone Q. By contrast, most found it difficult to name the
product correctly and so only 15% scored full marks overall. In part (b) many answers
discussed the optical activity of the original ketones Q and R rather than that of the
products of their reactions with HCN. Many also thought that both ketones produced
racemic mixtures.

Q21.
Part (a) was well answered and many candidates scored highly. The mechanism in part
(b) proved more difficult and some candidates tried to use BH instead of H as expected.
4
– –

The name of the product proved very difficult for most candidates and many made no
attempt to answer the question. In part (c), many confused Reaction 3, which is a
dehydration or an elimination of water, with the removal of hydrogen from ethylbenzene
using iron oxides.

Q22.
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.

Q23.
The name of the mechanism was well answered in part (a) but the actual mechanism itself
was much more discriminating. Too many candidates are still careless in their drawing of
curly arrows and fail to start every arrow either at a bond or a lone pair. Attack by the
cyanide ion must show a lone pair on the carbon atom as the source of the curly arrow.
The carbonyl group carbon has a δ+ charge not a full positive charge as suggested by
several. Part (b) was less well done. Although many answered part (b)(i) correctly, several
omitted the number 2 in the name or failed to count the number of carbons carefully. Part
(b)(ii) was misread by many, who simply drew the two optical isomers of Q rather than the
two geometrical isomers of the dehydration product of Q. The repeating unit was usually
correct in part (c) although some gave an extra oxygen in their structure and others gave
more than the single repeating unit requested. The zwitterion in part (d)(i) was generally
well known, but many drew incorrectly a quaternary ammonium salt in part (d)(ii).

Q25.
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 81 of 83
wrong or missing conditions in the reactions.

Q26.
Part (a)(i) was well answered. Many candidates chose a correct alkene, gave two
structural isomers formed in the reaction with HBr and named the type of structural
isomerism. Candidates who chose an incorrect alkene were able to score three marks for
a correct mechanism. In (a)(ii) choosing a carbonyl compound with the molecular formula
C H O which forms two isomers when HCN is added proved more difficult and many
3 6

candidates gave the incorrect carbonyl (CH ) CO. Marks were again allowed for a correct
3 2

mechanism even when the carbonyl was incorrect. Candidates were only allowed to score
a mark for stating that the isomers formed were optically active if the isomers given had
an asymmetric carbon. As square planar molecules are not optically active, structure
marks were only awarded when isomers were shown as tetrahedral arrangements. Almost
all candidates were able to write an equation for a nucleophilic addition-elimination
reaction of ethanoyl chloride but equations involving NH were only given full marks if
3

NH CI rather than HCl was given as a product. Many candidates omitted to state the
4

polarising effects of both the oxygen and the chlorine atoms when explaining why the
reactions occur readily. Most also failed to state that nucleophiles are able to react
because they have a lone electron pair which they can donate.

Q29.
This was a relatively high scoring question. In part (a), many correct answers were seen,
although answers to part (a)(ii) often included unbalanced equations or an incorrect
formula for propanone. The intended answer in (a)(ii) was NaBH4, but due credit was
given to those candidates who chose to use Ni/H2 and ignored the requirement to use [H]
in the equation. The structure of propanal was generally well known and the choice of a
suitable reagent for the test to distinguish propanone from propanal caused few problems;
Tollens’ reagent being the most common choice. Many candidates received full credit for
part (b)(ii), but some credit was withheld when an incomplete reagent was used e.g. [Ag
(NH3)2]+ or the results were recorded the wrong way around.

Q30.
Compound C was named correctly by the more able, but the requirement for the number 2
was not appreciated by the weaker candidates. Part (b) was answered well by most,
although some did not distinguish between the O-H absorption in alcohols such as
compound D and the O-H absorption in carboxylic acids. A surprising number of
candidates gave the answer 5 in part (c) rather than the expected 4. Answers to part (d)
were disappointing even from otherwise good candidates. It seemed that as soon as the
ketone C was seen, then tests using Fehlings or Tollens’ solutions were suggested,
without the candidates noticing that D was an alcohol and not an aldehyde. Those who
chose a correct test usually scored well. Answers to part (e) were better.

Q32.
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.

Page 82 of 83
Q33.
Although many candidates were able to identify which of the three organic compounds
would reduce acidified potassium dichromate(VI), as required in part (a), only a relatively
small number gave a correct half-equation for the reduction of dichromate(VI) ions. In part
(b), many candidates correctly identified the aldehyde as the compound which reduces
Tollens’ reagent. Some also gave the correct silver complex present in Tollens’ reagent but
few gave a correct half-equation for the reduction of this species to silver metal. The
formation of two esters by the reactions of the two alcohols with ethanoic acid was quite
well known and many correct equations for their formation were given in answers to part
(c). Part (d) proved, as expected, to be more challenging and only the best candidates
were able to deduce correctly the number of peaks in the proton n.m.r. spectra of the two
compounds given.

Q34.
In organic mechanisms, a curly arrow must start at a lone pair or at a bond. This idea was
still forgotten by some candidates. In part(a), several used a lone pair on the nitrogen
atom rather than one on the carbon of the cyanide ion. A few confused the nucleophilic
addition in part (a) with the addition-elimination in part (b) and tried in part (a) to reform a
carbon to oxygen double bond. An appreciable number thought that the name of the
product was a propanenitrile instead of 2-hydroxypentanenitrile. In both parts (a) and (b)
the C=O bond should not be shown breaking before the nucleophile attacks. The ester
was often correctly named as methyl propanoate but many other suggestions were also
seen. Part (c) discriminated well. Only the better candidates were able to identify the
correct electrophile, join it correctly to the benzene ring, draw the correct intermediate and
show the loss of H+ correctly.

Page 83 of 83

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