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Summer 2002 C4

1. (a) An alcohol with the molecular formula C4H9OH is chiral.

(i) Explain what is meant by the term chiral.

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(ii) Draw two diagrams to clearly represent the optical isomers that result from the
chirality of this alcohol.

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(iii) Explain how you could distinguish between these two isomers experimentally.

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(b) Alcohols react with carboxylic acids to form esters.

(i) Write an equation for a typical esterification reaction.

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(ii) Suggest how this type of reaction could be used to form polyesters.
Experimental details are not required.

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Summer 2002 C4

(iii) Suggest, with reasoning, whether a laboratory coat made from a polyester might be
damaged by a spillage on it of hot concentrated aqueous sodium hydroxide solution.

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(iv) Give another type of reagent that could be used to make an ester from an alcohol.

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(Total 13 marks)

2. (a) Write an equation which represents the change when the second electron affinity of
oxygen is measured.

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(b) Construct a Born-Haber cycle and use it and the data below to calculate the second
electron affinity of oxygen.

∆H / kJ mol–1
Enthalpy of atomisation of magnesium +150
Bond energy of O == O in oxygen +496
1st ionisation energy of magnesium +736
2nd ionisation energy of magnesium +1450
Ist electron affinity of oxygen –142
Lattice enthalpy of magnesium oxide –3889
Enthalpy of formation of magnesium oxide –602

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(c) (i) MgO(s) has the same crystal structure as NaCl(s). The lattice enthalpy of NaCl(s) is
–771 kJ mol–1 whilst that of MgO(s) is –3889 kJ mol–1.

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Summer 2002 C4

Explain the difference in lattice enthalpies.

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(ii) Despite its high lattice enthalpy sodium chloride is soluble in water.

What other factor is important in enabling compounds such as sodium chloride to


be soluble in polar solvents such as water?

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(iii) Explain why magnesium oxide is insoluble in water.

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(Total 13 marks)

3. Consider the following reaction scheme starting from propanone.

CH 3
I2 HCN
H+J NaOH
C O NaCN K
CH 3
Reagent 1
propanone

CH 3 Cl CH 3 OH
Reagent 2
C C
CH 3 C O CH 3 COOH

Cl
Reagent 3

CH 3 Cl
C
Br2
CH 3 C O M
NaOH
NH 2
(a) Give the structural formula of:

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Summer 2002 C4

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(b) Identify:

Reagent 1: ..................................................................................................................

Reagent 2: ..................................................................................................................

Reagent 3: ..................................................................................................................
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(c) Compounds produced when glucose C6H12O6, is metabolised include:

CH2(OH)CH(OH)CHO CH3COCOOH CH3CH(OH)COOH


2,3-dihydroxypropanal 2-oxopropanoic acid 2-hydroxypropanoic acid

(i) Draw the full structural formula for 2,3-dihydroxypropanal.

(1)

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Summer 2002 C4

(ii) Suggest two of these compounds which would give a positive test with 2,4-
dinitrophenylhydrazine solution. State what you would see for a positive test result.

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(iii) Describe a test which would enable you to distinguish between the two compounds
identified in part (ii).

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(Total 13 marks)

4. (a) (i) Write an equation for the reaction between magnesium oxide and dilute sulphuric
acid, including the state symbols.

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(ii) Describe what you would see during this reaction.

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(b) (i) Write an equation for the reaction between phosphorus(V) oxide and aqueous
sodium hydroxide solution.

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(ii) With the aid of two equations show how aluminium hydroxide exhibits amphoteric
character.

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Summer 2002 C4

(c) With reference to the reactions in (a) and (b) describe the variation in the metallic
character of the elements across Period 3 of the Periodic Table (sodium to argon).

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(d) Suggest, with reasoning, the acid-base character of Indium(III) oxide, In2O3.
Indium is the fourth element down Group 3 of the Periodic Table.

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(Total 13 marks)

5. (a) Methane reacts with steam in a reversible reaction. In industry this reaction, carried out at
a pressure of 30 atm, is used to produce hydrogen for the manufacture of ammonia

CH4(g) + H2O(g) CO(g) + 3H2(g) ∆H = +210 kJ mol–1

(i) Define the term partial pressure as applied to a gas mixture.

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(ii) Write an expression for the equilibrium constant, Kp, for this reaction.

(1)

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Summer 2002 C4

(iii) State and explain the effect of increasing the total pressure on the position of this
equilibrium;

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(b) State the effect on the value of Kp for this equilibrium of the following.

(i) Increasing the total pressure.

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(ii) Increasing the temperature.

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(iii) Adding a catalyst.

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(c) There is a theory that methane, CH4, constantly leaks from the earth’s crust. This is not
noticeable on land but at the bottom of a cold sea, such as off the Canadian coast, the
methane is trapped in a solid cage of water molecules.

CH4(g) + 6H2O(s) [CH4(H2O)6](s)


methane hydrate

At –29 °C the equilibrium pressure of the methane is 101.3 kPa.

(i) Write an expression for Kp for this equilibrium.

(1)

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Summer 2002 C4

(ii) Deduce the value of Kp at –29 °C, stating its units.

(1)

(iii) At 0 °C the equilibrium pressure of methane rises to 2600 kPa. What does this tell
you about the effect of temperature change on the position of equilibrium and about
the enthalpy change for this reaction?

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(iv) Some people have suggested collecting the methane hydrate from the bottom of the
sea and allowing it to warm up to 0 °C on board a ship. Comment on whether this
would be a useful method for collecting methane.

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(Total 12 marks)

6. Ethanoic acid, CH3COOH, is a weak acid which can be used, with its salts, to make buffer
solutions.

(a) Explain what is meant by the term weak acid.

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(b) Explain what is meant by the term buffer solution.

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Summer 2002 C4

(c) An aqueous solution of ethanoic acid of concentration 1.00 mol dm–3 has a pH of 2.8.
Sketch, with care, how the pH changes during the titration of 25.0 cm3 1.00 mol dm–3
aqueous ethanoic acid with aqueous sodium hydroxide of the same concentration.

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pH
12

10

0
0 10 20 30 40 50
Volume of alkali added/cm 3
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(d) Indicate on your sketch the portion of the curve where the mixture is behaving as a buffer.
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(e) (i) Write an expression for the dissociation constant, Ka, for ethanoic acid.

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(ii) Explain how the pKa of ethanoic could be found from the graph.

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(Total 11 marks)