A2 Organic Mixed
A2 Organic Mixed
A2 Organic Mixed
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.
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.
Page 2 of 18
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.
(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.
Q3.
Polystyrene can be made from benzene in the series of steps shown.
Page 3 of 18
(a) State the type of reaction in step 1.
Reagent(s) _________________________________________________________
Conditions _________________________________________________________
(3)
(b) State the name of the mechanism for the reaction in step 2.
(c) The organic product of step 2 is reacted with concentrated sulfuric acid in step 3.
(3)
Page 4 of 18
(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.
Page 5 of 18
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.
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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.
Page 6 of 18
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
Page 7 of 18
(a) Draw a circle around any chiral centre(s) in Figure 1.
(1)
(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)
Figure 2
Page 8 of 18
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.
(a) A student carried out this preparation using 1.15 g of phenylammonium sulfate (Mr
= 284.1) and excess ethanoic anhydride.
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(3)
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Page 9 of 18
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(1)
(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)
Suggest two practical reasons why the percentage yield for this reaction may
not be 100%.
1. ____________________________________________________________
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2. ____________________________________________________________
Page 10 of 18
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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.
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.
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
Page 12 of 18
Q2.
(a)
M2 Arrow from lp on O to C
(b)
M4 Electrophilic substitution
Apply list principle
4
(c)
Page 13 of 18
M2 Arrow from C=O to O
M4 Nucleophilic addition
Apply list principle
4
[12]
Q3.
(a) M1 Acylation
Allow electrophilic substitution
Allow ethanoic anhydride for M2
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)
Page 14 of 18
Penalise M1 for mistakes on structure of H2SO4
Allow H+ attacked in M1
Allow M3 as two steps
Allow displayed formulae
3
(d)
Q4.
D
[1]
Q5.
Page 15 of 18
B
[1]
Q6.
(a) X (O–H) (alcohols)
penalise acid or missing “alcohol”
1
Y C=O
allow carbonyl
1
NOT acid
4
(b)
6 singlet or drawn
1
3 doublet or drawn
1
1 quartet/quadruplet or drawn
Page 16 of 18
1
(max 10 marks)
[16]
Q7.
(a) One circled C atom only – The C attached to CH3/C=O/ H and NH
1
(c)
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
Page 17 of 18
Theoretical yield = 135.0 × 2 (1.15 / 284.1) = 1.09 g
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
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
HCl gas / fumes released / HCl not released when ethanoic anhydride used
1
[15]
Page 18 of 18