AQA Chemistry A-Level - Optical Isomerism QP PhysicsAndMathsTutor.

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Q1.
This question is about isomers with the molecular formula C5H10O

(a) Draw the skeletal formula of a branched chain aldehyde with molecular
formula C5H10O that is optically active.

(1)

(b) Describe how you distinguish between separate samples of the two
enantiomers of the branched chain aldehyde C5H10O

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(2)

(c) Draw the E and Z forms of a structural isomer of C5H10O that shows both
optical and geometric isomerism.

E isomer Z isomer

(2)

(d) Isomer J is cyclic and has an ether functional group (C–O–C)

Isomer J has only three peaks in its 13C NMR spectrum.

Isomer J

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Draw two other cyclic isomers of C5H10O that have an ether functional
group and only three peaks in their 13C NMR spectra.

(2)
(Total 7 marks)

Q2.
Prilocaine is used as an anaesthetic in dentistry.
Figure 1 shows the structure of prilocaine.

Figure 1

(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)

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(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.

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)

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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

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(1)

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

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(2)

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

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(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.

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Structure

Justification

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(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 compound does not show stereoisomerism?

A 1,2-dichloropropene

B 1,2-dichloropropane

C 1,3-dichloropropene

D 1,3-dichloropropane
(Total 1 mark)

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AQA Chemistry A-Level - Optical Isomerism QP PhysicsAndMathsTutor.com

Q6.
This question is about isomerism.

(a) How many isomers are represented by the formula C5H12?

Tick (✔) one box.

(b) Name the type of structural isomerism shown by the isomers of C5H12

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(1)

(c) 2-Hydroxypropanenitrile displays optical isomerism.

Draw three-dimensional representations of the two enantiomers of

2-hydroxypropanenitrile, showing how the two structures are related to
each other.

(2)

(d) Describe how separate samples of each of these enantiomers could be

distinguished.

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(2)

(e) Butan-2-ol reacts with concentrated sulfuric acid to produce three isomeric
alkenes.

Name and outline a mechanism to show how any one of the alkenes is
formed.

Explain how this reaction can lead to the formation of each of these three
alkenes.

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Name of mechanism
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Mechanism

Explanation
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(8)
(Total 13 marks)

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AQA Chemistry A-Level - Optical Isomerism QP PhysicsAndMathsTutor.com

Q7.
Which compound forms optically active compounds on reduction?

A CH3CH2C(CH3)=CHCH3

B CH3CH2C(CH3)=CH2

C CH3COCH3

D CH3CH2COCH3
(Total 1 mark)

Q8.
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.

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(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.

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(1)

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

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(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.

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 ________________________________________

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(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.

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Kc ____________________________________________________

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Calculation
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(4)

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

(1)
(Total 12 marks)

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