A2 Organic Mixed

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Name: ________________________

Mixed Organic Exam


questions
Class: ________________________

Date: ________________________

Time: 88 minutes

Marks: 69 marks

Comments:

Page 1 of 18
Q1.
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.

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(1)

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

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(6)
(Total 7 marks)

Q2.
This question is about intermediates in reaction mechanisms.

(a) Figure 1 shows an intermediate formed in the first step of a


nucleophilic addition–elimination mechanism.

Figure 1

Complete Figure 1 to show the structures of the two reactant species with curly
arrows and relevant lone pairs of electrons involved in the formation of the
intermediate.

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Draw curly arrows and relevant lone pairs of electrons on the intermediate to show
how the final products are formed.

(4)

(b) Figure 2 shows an intermediate formed in the first step of a reaction mechanism of
methylbenzene.

Figure 2

Complete Figure 2 to show the reactant species and any curly arrows involved in
the formation of the intermediate.

Draw a curly arrow on the intermediate to show how the product is formed.

Give the name of the reaction mechanism.

Name of mechanism ________________________________________________


(4)

(c) Figure 3 shows the reactant species involved in the first step of a mechanism.

Figure 3

Complete Figure 3 to show the structure of the intermediate formed with curly
arrows involved in its formation.

Give the name of the reaction mechanism.

Name of mechanism ________________________________________________


(4)
(Total 12 marks)

Q3.
Polystyrene can be made from benzene in the series of steps shown.

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(a) State the type of reaction in step 1.

Identify the reagent(s) and conditions needed for step 1.

Type of reaction _____________________________________________________

Reagent(s) _________________________________________________________

Conditions _________________________________________________________
(3)

(b) State the name of the mechanism for the reaction in step 2.

Identify the inorganic reagent needed for step 2.

Name the organic product of step 2.

Name of mechanism _________________________________________________

Inorganic reagent ____________________________________________________

Name of organic product ______________________________________________


(3)

(c) The organic product of step 2 is reacted with concentrated sulfuric acid in step 3.

Outline the mechanism for step 3.

(3)

(d) Draw the repeating unit of polystyrene.

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(1)
(Total 10 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

B 2-methylbutan-2-ol

C 3-methylbutan-2-ol

D pentan-3-ol
(Total 1 mark)

Q6.
(a) The infra-red spectrum of compound A, C3H6O2, is shown below.

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Identify the functional groups which cause the absorptions labelled X and Y.

Using this information draw the structures of the three possible structural isomers for
A.

Label as A the structure which represents a pair of optical isomers.

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(6)

(b) Draw the structures of the three branched-chain alkenes with molecular formula
C5H10

Draw the structures of the three dibromoalkanes, C 5H10Br2, formed when these three
alkenes react with bromine.

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One of these dibromoalkanes has only three peaks in its proton n.m.r. spectrum.
Deduce the integration ratio and the splitting patterns of these three peaks.

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(10)
(Total 16 marks)

Q7.
Prilocaine is used as an anaesthetic in dentistry.
Figure 1 shows the structure of prilocaine.

Figure 1

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(a) Draw a circle around any chiral centre(s) in Figure 1.
(1)

(b) Identify the functional group(s) in the prilocaine molecule.

Tick (✓) the box(es) corresponding to the functional group(s).

Amide Amine Ester Ketone

(1)

(c) Prilocaine is completely hydrolysed in the human body to give a mixture of products.

Draw the structures of the two organic products formed in the complete hydrolysis of
prilocaine in acidic conditions.

(3)

(d) Figure 2 shows optical isomers F and G.

Figure 2

Isomer F is the active compound in the medicine ibuprofen.

In the manufacture of ibuprofen both isomers F and G are formed. An enzyme is


then used to bind to isomer G and catalyse its hydrolysis.

After the products of hydrolysis of G are removed, a pure sample of isomer F is


collected.

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Explain how a structural feature of this enzyme enables it to catalyse the hydrolysis
of isomer G but not the hydrolysis of isomer F.

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(2)
(Total 7 marks)

Q8.
N-phenylethanamide is used as an inhibitor in hydrogen peroxide decomposition and also
in the production of dyes.

N-phenylethanamide can be produced in a laboratory by the reaction between


phenylammonium sulfate and an excess of ethanoic anhydride:

(a) A student carried out this preparation using 1.15 g of phenylammonium sulfate (Mr
= 284.1) and excess ethanoic anhydride.

(i) Calculate the maximum theoretical yield of N−phenylethanamide that could be


produced in the reaction. Record your answer to an appropriate precision.

Show your working.

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(3)

(ii) In the preparation, the student produced 0.89 g of N−phenylethanamide.

Calculate the percentage yield for the reaction.

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______________________________________________________________
(1)

(b) The student purified the crude solid product, N−phenylethanamide, by


recrystallisation.

(i) Outline the method that the student should use for this recrystallisation.

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(4)

(ii) Outline how you would carry out a simple laboratory process to show that the
recrystallised product is a pure sample of N−phenylethanamide.

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(3)

(iii) Assume that the reaction goes to completion.

Suggest two practical reasons why the percentage yield for this reaction may
not be 100%.

1. ____________________________________________________________

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2. ____________________________________________________________

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______________________________________________________________
(2)

(c) The reaction to form N−phenylethanamide would happen much more quickly if the
student used ethanoyl chloride instead of ethanoic anhydride.

Explain why the student might prefer to use ethanoic anhydride, even though it has
a slower rate of reaction.

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(2)
(Total 15 marks)

Page 11 of 18
Mark schemes

Q1.
(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.

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]

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Q2.
(a)

M1 Structures of reactant species

M2 Arrow from lp on O to C

M3 Arrow from C=O bond to O

M4 3 curly arrows and lp on intermediate

Allow full marks for candidates who draw a second


intermediate formed after formation of C=O and loss of Cl -
then loss of H+

Ignore any attempt to show the final products


4

(b)

M1 Structures of reactant species including + on N of +NO2

M2 Arrow from ring (inside hexagon) to N or + on N

M3 Arrow from C-H bond into hexagon

M4 Electrophilic substitution
Apply list principle
4

(c)

M1 Arrow from lp on hydride to C

Page 13 of 18
M2 Arrow from C=O to O

M3 Intermediate structure / Allow displayed or abbreviated


structures
Ignore any attempt to show further steps if correct Penalise
further incorrect steps

M4 Nucleophilic addition
Apply list principle
4
[12]

Q3.
(a) M1 Acylation
Allow electrophilic substitution
Allow ethanoic anhydride for M2
1

M2 CH3COCl OR Ethanoyl chloride


M3 dependent on M2
1

M3 AlCl3 OR Aluminium chloride (mark could be awarded in space for M2)


Allow Dry/anhydrous for M3
Apply list principle to extra incorrect conditions
1

(b) M1 Nucleophilic addition


1

M2 NaBH4
Allow LiAlH4 for M2
1

M3 1-phenyl ethan(-1-)ol
If H2/Ni stated allow M2 and M3 but to score a matching M1 it
would have to be Catalytic addition
1

(c)

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Penalise M1 for mistakes on structure of H2SO4
Allow H+ attacked in M1
Allow M3 as two steps
Allow displayed formulae
3

(d)

Must show trailing bonds


Ignore brackets and any use of n
Allow C6H5 for phenyl group
1
[10]

Q4.
D
[1]

Q5.

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B
[1]

Q6.
(a) X (O–H) (alcohols)
penalise acid or missing “alcohol”
1

Y C=O
allow carbonyl
1

NOT acid
4

(b)

Allow conseq dibromocompounds following incorrect


unbranched alkenes
NOT allow dibromocompound consequent on a
duplicate alkene
NOT allow monobromocompounds if HBr added
3

6:3:1 either next to correct structure or to none


1

Allow a mark for identifying correct dibromocompound with three peaks


even if integration ratio is wrong
1

if 6:3:1 missing or wrong, no marks for splitting

Only award a mark for splitting if it is clear which integration number it


refers to

6 singlet or drawn
1

3 doublet or drawn
1

1 quartet/quadruplet or drawn

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1
(max 10 marks)
[16]

Q7.
(a) One circled C atom only – The C attached to CH3/C=O/ H and NH
1

(b) Two ticks only for amine and amide


1

(c)

M1 for choosing the correct bond to hydrolyse


M2 and M3 for the correct structures of the products
Allow protonated amino acid for M2

Allow C6H5NH3+ or + outside a square bracket


3

(d) M1 Enzyme has an active site


1

M2
The G-Enantiomer / Enzyme has the correct stereo chemistry / stereospecific
Or
The G-Enantiomer / Enzyme has the complementary shape
For M2 allow opposite argument for F-Enantiomer
1
[7]

Q8.
(a) (i) Mr N−phenylethanamide = 135.0
1

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Theoretical yield = 135.0 × 2 (1.15 / 284.1) = 1.09 g
1

Answer recorded to 3 significant figures.


1

(ii) × 100

= 81.4 %
Mark consequentially to (a)
Allow 81 to 82
1

(b) (i) Dissolve the product in the minimum volume of water / solvent (in a
boiling tube / beaker)
If dissolving is not mentioned, CE = 0 / 4
1

Hot water / solvent


Steps must be in a logical order to score all 4 marks
1

Allow the solution to cool and allow crystals to form.


1

Filter off the pure product under reduced pressure / using a Buchner
funnel and side arm flask
Ignore source of vacuum for filtration (electric pump, water
pump, etc.)
1

(ii) Measure the melting point


1

Use of melting point apparatus or oil bath


1

Sharp melting point / melting point matches data source value


1

(iii) Any two from:


Product left in the beaker or glassware
Sample was still wet
Sample lost during recrystallisation.
Do not allow “sample lost” without clarification.
2 Max

(c) An identified hazard of ethanoyl chloride


E.g. “Violent reaction”, “harmful”, “reacts violently with water”
Do not allow “toxic”, “irritant” (unless linked with HCl gas).
1

HCl gas / fumes released / HCl not released when ethanoic anhydride used
1
[15]

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