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HKDSE CHEMISTRY – A Modern View

(Second Edition)

(Chemistry)
Coursebook 7
Suggested answers

Page
Chapter 61 Detecting the presence of chemical species
Number
 Class practice 1

 Think about 5

 Chapter exercise 6

Chapter 62 Separation and purification methods

 Class practice 11

 Think about 15

 Chapter exercise 15

Chapter 63 Quantitative methods of analysis

 Class practice 19

 Think about 23

 Chapter exercise 24

Chapter 64 Instrumental analytical methods

 Class practice 28

 Think about 33

 Chapter exercise 33
Chapter 65 Contribution of analytical chemistry to our society

 Class practice 40

 Think about 41

 Chapter exercise 42
 Part exercise 46
HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Chapter 61 Detecting the presence of chemical species

Class Practice
A61.1 (p.61-8)
(a) BaSO4 and CaCO3 are not likely to be X because they are insoluble in water.
(b) BaSO4 and CaCO3 are not likely to be X because they are insoluble in water.
CuSO4 and Fe(NO3)3 are not likely to be X because the aqueous solutions of
CuSO4 and Fe(NO3)3 are blue and yellow in colour respectively.
(c) NH4Cl and CaCO3 are not likely to be X because they decompose on heating.
(d) X is KCl.

A61.2 (p.61-13)
(a) Perform flame test. Sodium chloride solid gives a golden yellow flame while
potassium chloride solid gives a lilac flame in the test.
(b) Test with sodium hydroxide solution or aqueous ammonia. Magnesium chloride
solution gives a white precipitate while there is no observable change for
ammonium chloride solution.
(c) Add aqueous ammonia dropwise to each of the solution samples until in excess.
Both aluminium sulphate solution and zinc sulphate solution give a white
precipitate. However, only the precipitate in zinc sulphate solution dissolves in
excess aqueous ammonia to give a colourless solution.

A61.3 (p.61-16)
(a) (i) Lead(II) sulphate
(ii) Pb2+(aq) + SO42−(aq) → PbSO4(s)
(b) (i) Aluminium hydroxide
(ii) Al3+(aq) + 3OH−(aq) → Al(OH)3(s)
(c) Solution B contains Al3+ and Zn2+. Both Al3+ and Zn2+ give a white precipitate
when a small amount of aqueous ammonia is added to them. However, only the
white precipitate formed by Zn2+ (i.e. Zn(OH)2(s)) can dissolve in excess
aqueous ammonia to give a colourless solution.

A61.4 (p.61-22)
1. (a) Test with dilute hydrochloric acid. Zinc carbonate gives a colourless gas
which can turn limewater milky. There is no observable change for zinc
chloride.
(b) Test with blue litmus paper. The litmus paper turns white for sodium
hypochlorite (solution). There is no observable change for sodium sulphite

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(solution).
(c) Test with acidified silver nitrate solution. Sodium chloride reacts with
acidified silver nitrate solution to give a white precipitate while sodium
iodide reacts to give a yellow precipitate.

2. (a) (i) Magnesium carbonate


(ii) Mg2+(aq) + CO32−(aq) → MgCO3(s)
(b) (i) Silver chloride
(ii) Ag+(aq) + Cl−(aq) → AgCl(s)

A61.5 (p.61-28)
1. (a) Gas A is ammonia.
NH4+(aq) + OH−(aq) → NH3(g) + H2O(l)
Gas B is carbon dioxide.
CaCO3(s) → CaO(s) + CO2(g)
Gas C is sulphur dioxide.
SO32−(aq) + 2H+(aq) → SO2(g) + H2O(l)
Gas D is chlorine.
OCl−(aq) + Cl−(aq) + 2H+(aq) → Cl2(g) + H2O(l)
(b) Test for ammonia:
Test the gas with moist red litmus paper. The litmus paper turns blue in the
presence of ammonia. OR
Place concentrated hydrochloric acid near the gas. A dense white fume
forms when ammonia reacts with hydrogen chloride.
Test for carbon dioxide:
Test the gas by bubbling it through limewater. The limewater turns milky in
the presence of carbon dioxide.
Test for sulphur dioxide:
Test the gas with filter paper soaked with acidified potassium dichromate
solution. The filter paper changes from orange to green in the presence of
sulphur dioxide.
Test for chlorine:
Test the gas with moist blue litmus paper. The litmus paper turns red and
then white very quickly in the presence of chlorine.

2. This is because both of them react with limewater to give a white precipitate.
CO2(g) + Ca(OH)2(aq) → CaCO3(s) + H2O(l)
SO2(g) + Ca(OH)2(aq) → CaSO3(s) + H2O(l)

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A61.6 (p.61-29)
(a) Both the cation and anion are colourless. The compound may contain Group I
metal ions, Group II metal ions, aluminium or zinc ions.
(b) The cation may be ammonium ion.
(c) Ammonium ions do not give a characteristic flame colour in the flame test.
(d) The anion may be chloride ion.
(e) Ammonium chloride

A61.7 (p.61-32)
(a) Test with acidified potassium dichromate solution. Propan-1-ol changes the
colour of the acidified potassium dichromate solution from orange to green while
there is no observable change for propene.
[O] [O]
CH3CH2CH2OH → CH3CH2CHO → CH3CH2COOH
OR
Test with bromine (dissolved in an organic solvent). Propene changes the colour
of the bromine solution from red-orange to colourless rapidly while there is no
observable change for propan-1-ol.
CH3CH=CH2 + Br2 → CH3CHBrCH2Br
(b) Test with acidified potassium dichromate solution. Butan-1-ol changes the colour
of the acidified potassium dichromate solution from orange to green while there
is no observable change for methylpropan-2-ol.
[O] [O]
CH3CH2CH2CH2OH → CH3CH2CH2CHO → CH3CH2CH2COOH

A61.8 (p.61-36)
1. (a) X gives a negative result when tested with Tollens’ reagent. X should not be
an aldehyde. Hence, compound E is not likely to be X.
(b) X gives a negative result when tested with bromine (dissolved in an organic
solvent). X should not contain carbon-carbon double bond. Hence,
compound A is not likely to be X.
(c) X gives a negative result when tested with sodium hydrogencarbonate
solution. X should not be a carboxylic acid. Hence, compound D is not
likely to be X.
(d) X gives a positive result when tested with acidified potassium dichromate
solution. X should be a 1 alcohol, 2 alcohol or aldehyde. Compound C is
not likely to be X as it is a 3 alcohol. Thus, compound B should be X.

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2. (a) Test with sodium hydrogencarbonate solution/sodium carbonate solution.


Propanoic acid gives a colourless gas which turns limewater milky, while
there is no observable change for propan-1-ol. OR
Test with acidified potassium dichromate solution. Propan-1-ol changes the
colour of the acidified potassium dichromate solution from orange to green,
while there is no observable change for propanoic acid.
(b) Test with Tollens’ reagent. A silver mirror forms when methanal reacts with
Tollens’ reagent while there is no observable change for methanol. OR
Test with 2,4-dinitrophenylhydrazine. An orange precipitate forms when
methanal reacts with 2,4-dinitrophenylhydrazine while there is no
observable change for methanol.
(c) Test with Tollens’ reagent. A silver mirror forms when propanal reacts with
Tollens’ reagent while there is no observable change for propanone.

A61.9 (p.61-43)
Hazardous chemicals Hazardous
Safety precautions Reference
used or made nature
1. Concentrated Corrosive For 1 to 3, 1. Handbook on
hydrochloric acid (a) Wear a laboratory coat, Safety in Science
(used in flame test) safety spectacles and Laboratories
gloves 2. MSDS
2. Sodium hydroxide Corrosive (b) Perform the experiment
in fume cupboard
3. Silver nitrate Corrosive (c) Avoid contact with eyes
and skin; when
accidentally spilt into the
eyes or onto the skin,
wash the affected area
with running water for at
least 3 minutes and go
for medical check-up

4. Potassium Oxidizing (a) Make sure the container


permanganate is properly stoppered
(b) Keep away from heat and
naked flame
(c) Keep away from metals,
combustible materials

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and flammable chemicals


(d) Avoid contact with the
eyes or skin; when
accidentally spilt into the
eyes or onto the skin,
wash the affected area
with running water for at
least 3 minutes and go
for medical check-up

Harmful (a) Avoid breathing in its


vapour
(b) The laboratory should be
well-ventilated

5. Hex-1-ene Flammable (a) Make sure the container


is properly stoppered
(b) Keep away from heat and
naked flames
Disposal of residues: Disposal of hex-1-ene in waste bottle. Prepared by:
________________
Remarks: Date:
________________

Think about
Think about (p.61-2)
1. No, we cannot.
2. Yes, we can.
3. We can detect the presence of chemical species in distilled water and in
mineralized water using chemical tests such as test with sodium hydroxide
solution, test with aqueous ammonia, tests for halides, test for carbonate ions, etc.
Then, we can distinguish between distilled water and mineralized water.

Think about (p.61-3)


No, this is because different substances may have the same colour.

Think about (p.61-12)


Aqueous ammonia is a solution formed by dissolving ammonia in water. Ammonia

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ionizes only very slightly in water to give hydroxide ions.

NH3(aq) + H2O(l) ⇌ NH4+(aq) + OH−(aq)

Think about (p.61-24)


If no water is present, chlorine cannot react with water to produce hydrogen ions and
hypochlorite ions. The hydrogen ions are responsible for its acidic property while
hypochlorite ions are responsible for its bleaching property.

Think about (p.61-34)


It is improper to test carboxylic acid by reacting it with sodium metal. This is because
sodium metal reacts with both carboxylic acid and alcohol to give hydrogen gas. The
observations of these two reactions are similar.

Chapter exercise (p.61-53)


1. sodium; potassium; calcium; copper(II)
2. Aluminium; lead(II); zinc
3. Copper(II); zinc
4. silver nitrate
5. carbon dioxide
6. hypochlorite
7. sulphite
8. bromine; acidified potassium permanganate
9. (a) acidified potassium dichromate
(b) carboxylic acid
10. (a) 2,4-dinitrophenylhydrazine
(b) Tollens’ reagent
11. (a) carbonate; hydrogencarbonate
(b) alcohol
12. (a) Potassium ion
(b) Ammonium ion
(c) Iron(II) ion
(d) Aluminium ion, zinc ion, lead(II) ion
(e) Calcium ion, magnesium ion

13. (a) It changes the colour of moist blue litmus paper to red and then white very
quickly.

Cl2(aq) + H2O(l) ⇌ HCl(aq) + HOCl(aq)

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(b) It changes the colour of the filter paper soaked with acidified potassium
dichromate solution from orange to green.
Cr2O72−(aq) + 3SO2(aq) + 2H+(aq) → 2Cr3+(aq) + 3SO42−(aq) + H2O(l)
(c) It changes the colour of moist red litmus paper to blue.

NH3(aq) + H2O(l) ⇌ NH4+(aq) + OH−(aq) OR

When concentrated hydrochloric acid is placed near it, a dense white fume
forms.
NH3(g) + HCl(g) → NH4Cl(s)
(d) It burns with a ‘pop’ sound when tested with a burning splint.
2H2(g) + O2(g) → 2H2O(l)
(e) It relights a glowing splint.

14. (a) Perform flame test. Calcium carbonate gives a brick-red flame while
sodium carbonate gives a golden yellow flame.
(b) Add sodium hydroxide solution or aqueous ammonia separately to each of
the two solutions until the alkaline solution is in excess. Both magnesium
chloride solution and zinc chloride solution form a white precipitate.
However, only the white precipitate formed from zinc chloride solution
dissolves in excess alkaline solution.
(c) Add dilute hydrochloric acid separately to each of the two solutions and test
any gas evolved with a piece of filter paper soaked with acidified potassium
dichromate solution. The gas evolved from potassium sulphite solution can
change the colour of filter paper from orange to green. There is no
observable change for the gas evolved from potassium carbonate solution.
(d) Test with bromine (dissolved in organic solvent). In the dark, pent-1-ene
decolorizes the bromine solution rapidly while there is no observable
change for pentane. OR
Test with acidified potassium permanganate solution. Pent-1-ene
decolorizes the acidified potassium permanganate solution while there is no
observable change for pentane.
(e) Heat with a carboxylic acid in the presence of concentrated sulphuric acid.
Methanol forms a substance which gives a characteristic fruity smell while
there is no observable change for methanal. OR
Test with Tollens’ reagent. Methanal forms a silver mirror while there is no
observable change for methanol. OR
Test with 2,4-dinitrophenylhydrazine. Methanal forms an orange precipitate
while there is no observable change for methanol.

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(f) Test with sodium hydrogencarbonate solution or sodium carbonate solution.


Propanoic acid gives out colourless gas bubbles while there is no observable
change for propan-1-ol. OR
Test with acidified potassium dichromate solution. Propan-1-ol changes the
colour of acidified potassium dichromate solution from orange to green
while there is no observable change for propanoic acid.

15. C
Potassium permanganate solution is purple in colour while nickel(II) sulphate
solution is green in colour.

16. A
Lead(II) oxide is yellow in colour at room temperature.

17. C

18. C
Sodium ions give a golden yellow flame in the flame test. Sulphur dioxide,
which has a choking smell of burning sulphur, is produced when dilute
hydrochloric acid is added to a solution containing sulphite ions:
SO32–(aq) + 2H+(aq) → SO2(g) + H2O(l).

19. C
The equation for the reaction involved is: NH3(g) + HCl(g) → NH4Cl(s)

20. D
Sulphur dioxide is a reducing agent. It can be oxidized to sulphate ions by
common oxidizing agents such as (1) acidified potassium dichromate solution
and (2) acidified potassium permanganate solution. There is reaction between
dilute hydrochloric acid and sulphite solution (3). However, it is not a redox
reaction.

21. A

22. (a) (i) Silver chloride


(ii) Ag+(aq) + Cl−(aq) → AgCl(s)
(b) (i) Aluminium hydroxide
(ii) Al3+(aq) + 3OH−(aq) → Al(OH)3(s)

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(c) Potassium ion and ammonium ion


(d) Perform flame test. If solution D gives a lilac flame, potassium ion is
present in solution D.
Warm solution D with sodium hydroxide solution and test any gas formed
with moist red litmus paper. If a gas formed which turns the red litmus
paper blue, ammonium ion is present in solution D.

23. (a) (i) Moisten a clean platinum wire with concentrated hydrochloric acid.
Then dip the platinum wire into crushed sample of compound P. After
that, heat the end of wire strongly in a non-luminous flame.
(ii) Compound P should contain calcium ion.
(b) (i) Carbon dioxide
(ii) CO32−(aq) + 2H+(aq) → CO2(g) + H2O(l)
(c) Calcium oxide
(d) CaO(s) + H2O(l) → Ca(OH)2(aq)
(e) Compound P should be calcium carbonate.

24. (a) (i) Gas P is sulphur dioxide.


(ii) 5SO2(aq) + 2MnO4−(aq) + 2H2O(l)
→ 5SO42−(aq) + 2Mn2+(aq) + 4H+(aq)
(b) Gas Q is chlorine.
(c) Test with a burning splint. If the gas burns with a ‘pop’ sound, it should be
hydrogen.

25.
A: B:

C: D:

As A forms a silver mirror with Tollens’ reagent, it should be an aldehyde.


A is reduced by lithium aluminium hydride and dilute acid to form B, which is a
primary alcohol.
A is oxidized by acidified potassium dichromate solution to form C, which is a
carboxylic acid.
B undergoes esterification to give D when heated with C under reflux in the
presence of concentrated sulphuric acid. As D has pleasant fruity smell, it should
be an ester.

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26. (a) Empirical formula: C11H16O; molecular formula: C22H32O2


(b) Carboxyl group and carbon-carbon double bond
(c) Test for carboxyl group:
It reacts with sodium hydrogencarbonate solution/sodium carbonate
solution to give a colourless gas which can turn limewater milky (i.e. carbon
dioxide). OR
By heating with an alcohol under reflux in the presence of concentrated
sulphuric acid, a pleasant fruity smell product (i.e. an ester) forms.
Test for carbon-carbon double bond:
It changes the colour of bromine (dissolved in an organic solvent) from
red-orange to colourless. OR
It changes the colour of acidified potassium permanganate solution from
purple to colourless.

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Chapter 62 Separation and purification methods

Class Practice
A62.1 (p.62-3)
(a) (2)
(b) (4)
(c) (3)
(d) (1)

A62.2 (p.62-9)
(a) Fractional distillation
(b) Simple distillation

A62.3 (p.62-11)
(a) (CH3)2C=CHCH2CH2COONa
(b)

separating funnel
compound B dissolved
aqueous solution of the
in diethyl ether
salt of compound A

(c) After the reaction mixture is shaken with excess sodium carbonate solution,
discard the aqueous layer (containing the salt of compound A). As compound B is
more soluble in diethyl ether than in water, it is extracted into the organic layer.
Diethyl ether can be removed from compound B by simple distillation.

A62.4 (p.62-19)
1. (a)

solvent front

red spot
blue spot

original ink spot

(b) The ink is a mixture because there are more than one spot in the

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chromatogram.
(c) Different dyes have different solubilities in water on paper fibres (stationary
phase) and in the developing solvent (mobile phase). The dye that is more
soluble in the developing solvent moves up the paper more quickly. As a
result, different dyes in the ink are separated out.

2. (a) Put the chromatographic plate into a jar saturated with iodine vapour. OR
Shine ultraviolet light on the plate that contains a fluorescent material.
(b) Component A is the most soluble in the developing solvent because it
moves up the plate fastest.
2.2 cm
(c) Rf value of spot B = = 0.55
4.0 cm
(d) Component A

A62.5 (p.62-23)
1. (a) The identity of a compound cannot be confirmed by melting point alone
because different compounds may have the same melting point.
(b) Spot the sample solution of solid X on the baseline of a chromatographic
plate.
Then spot the sample solution of urea next to the spot of solid X.
Put the plate vertically in a suitable developing solvent.
After that, put the chromatographic plate in a jar saturated with iodine
vapour.
Compare the distance travelled by the two spots. If the two spots travel with
the same distance, solid X is likely to be urea.

2. (a) To prevent the loss of volatile substances on prolonged heating.


(b) Distil the reaction mixture. Collect the distillate with a boiling point range
from 36.5C to 40.5C.
(c) By determining the boiling point of the crude product (bromoethane).
Check whether it agrees with that given in the data book.

A62.6 (p.62-26)
1. Add excess Na2SO4(aq) to the solution. SO42−(aq) forms insoluble white
precipitate CaSO4(s) with Ca2+(aq).
Filter the mixture. The residue is CaSO4(s). The filtrate contains Al3+(aq) and
Cu2+(aq).
Add HCl(aq) to dissolve the white precipitate (residue). The solution formed

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contains Ca2+(aq).
Add a little and then excess NaOH(aq) to the filtrate. Cu2+(aq) forms an insoluble
blue precipitate Cu(OH)2(s). Al3+(aq) forms an insoluble white precipitate
Al(OH)3(s) first and it dissolves in excess NaOH(aq) to give a colourless solution
[Al(OH)4]−(aq).
Filter the mixture. Add excess HCl(aq) to the filtrate and the resultant solution
contains Al3+(aq).
Add excess HCl(aq) to dissolve the blue precipitate (residue). The solution
formed contains Cu2+(aq).

Al3+(aq), Cu2+(aq), Ca2+(aq)

1. Add excess Na2SO4(aq)


2. Filtration

CaSO4(s) Al3+(aq), Cu2+(aq)


white precipitate (in the filtrate)

Add excess HCl(aq) 1. Add excess NaOH(aq)


2. Filtration

Ca2+(aq)
Cu(OH)2(s) [Al(OH)4]−(aq)
blue precipitate (in the filtrate)

Add excess HCl(aq) Add excess HCl(aq)

Cu2+(aq) Al3+(aq)

2. Add excess BaCl2(aq) to the solution. SO42−(aq) forms insoluble white


precipitate BaSO4(s) with Ba2+(aq).
Filter the mixture. The residue is BaSO4(s). The filtrate contains NO3−(aq) and
I−(aq).
Add excess AgNO3(aq) to the filtrate. I−(aq) forms insoluble yellow precipitate
AgI(s) with Ag+(aq).
Filter the mixture. The residue is AgI(s). The filtrate contains NO3−(aq) as the
only anion.

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NO3−(aq), SO42−(aq), I−(aq)

1. Add excess BaCl2(aq)


2. Filtration

BaSO4(s) NO3−(aq), I−(aq)


white precipitate (in the filtrate)

1. Add excess AgNO3(aq)


2. Filtration

AgNO3(aq) AgI(s)
(in the filtrate) yellow precipitate

A62.7 (p.62-28)
1. (a) Add water to the solid mixture with stirring until no more solids can
dissolve. Filter the mixture and the residue is calcium carbonate.
(b) Distil the liquid mixture. Collect the distillate (butanal) with a boiling point
range from 72.8C to 76.8C.
(c) Add excess sodium hydrogencarbonate solution to the mixture in a
separating funnel and shake the mixture, until no more colourless gas
evolves. Methanoic acid reacts with sodium hydrogencarbonate solution
and dissolves in the solution (aqueous layer). Heptane has no reaction and
forms the organic layer.
Allow the aqueous layer and organic layer to separate. Discard the aqueous
layer.
Add anhydrous calcium chloride to the organic layer. Filter the organic
layer and carry out distillation of the filtrate.
Collect the distillate (heptane) with a boiling point range from 96C to
100C.

2. (a) As ethanol and pentane are miscible, the mixture cannot be separated by
using a separating funnel. The mixture should be separated using simple
distillation.
(b) As both sodium chloride and ammonium chloride are soluble in water, the
mixture cannot be separated by dissolution and filtration. The mixture can

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be separated by heating as only ammonium chloride sublimes on heating.


3. (a) This is to extract all hexanoic acid from hexanal (hexanoic acid is
temporarily converted into sodium hexanoate).
(b) Separating funnel
(c) To regenerate the hexanoic acid from the aqueous layer.
(d) By carrying out distillation/fractional distillation

Think about
Think about (p.62-2)
1. Chemical methods will change the chemical nature of the components in ginseng
but physical methods will not.
2. Separation methods such as liquid-liquid extraction, chromatographic methods
are used to separate the components in ginseng.
3. They can test the purity of solid components by measuring their melting points
and test the purity of liquid components by measuring their boiling points.

Think about (p.62-5)


Crystals may form on the cool inner wall of the stem. This will block the stem of the
funnel.

Think about (p.62-12)


The pen ink is composed of different dyes. If the baseline were drawn with a pen, the
ink might interfere with the experimental results.

Think about (p.62-22)


A flammable liquid catches fire easily when it is heated directly with a naked flame.
Therefore, a water bath is required.

Chapter exercise (p.62-33)


1. Crystallization
2. Recrystallization
3. solvent
4. miscible; fractionating column
5. separating funnel
6. Chromatography; paper chromatography; thin-layer chromatography; column
chromatography
7. melting; boiling
8. B

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9. B
Crystallization is the most suitable for separating a dissolved substance from a
solution.

10. B
Sodium chloride solution and cyclohexane are immiscible.

11. C
Benzene and methylbenzene are miscible. The difference in their boiling points
is (111°C – 80.1°C) = 30.9°C.

12. D

13. A
Iron(III) oxide is insoluble in water while potassium chloride is soluble in water.

14. D
(CH3)3CBr is miscible with (CH3)3COH. They cannot be separated by the use of
a separating funnel. Besides, the (CH3)3CBr separated out using column
chromatography can be further used.

15. B
(CH3)3CBr is a liquid under room conditions.

16. (a) Three types of colourings are present in drink X because there are three
spots in the chromatogram of drink X.
(b) Drinks X and Y are not identical as their chromatograms are different.
(c) Diagram B:

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17. (a) Draw a baseline with a pencil across the bottom (about 1 cm from the edge)
of a plastic plate.
Add a small amount of water to extract the brown colouring in the sweet. At
the same time, prepare a sample solution of E104.
Spot the sample solution of E104 onto the baseline. Then spot the solution
of brown colouring next to the E104 spot.
Put the plate vertically in a suitable developing solvent.
Finally, compare the Rf value of the E104 with that of the components of
brown colouring. If there is a component with the same Rf value as that of
E104, it is likely that the brown colouring contains E104.
(b) Yes, this is because one of the components has the same Rf value as that of
E104.
(c) (i) Column chromatography
(ii) Alumina is the stationary phase in the set-up.
(iii) Band A

4.2 cm 2.4 cm
18. (a) (i) Rf value of X = = 0.84; Rf value of Y = = 0.48;
5.0 cm 5.0 cm
2.2 cm
Rf value of Z = = 0.44
5.0 cm
(ii) No, as the Rf values of Y and Z are very close.
(b) (i)

(ii) The components in the mixture may have different Rf values when
different developing solvents are used.
The components in the mixture have different solubilities in different
developing solvents. Components that are more soluble in a particular
developing solvent will move up the plate/paper more quickly.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

19. (a) CH3(CH2)8COOH(in diethyl ether) + NaHCO3(aq)


→ CH3(CH2)8COONa(aq) + H2O(l) + CO2(g)
(b) Separating funnel
(c) Filter the aqueous layer. The residue obtained is the white precipitate.
(d) If the crude product (decanoic acid) melts over a temperature range from
31.4°C to 32.4°C, it should be pure.

20. (a) By using a separating funnel


(b) By using fractional distillation
(c) By using crystallization
(d) By using paper chromatography/thin-layer chromatography/column
chromatography
(e) By fractional distillation

21. Add excess sodium hydrogencarbonate solution to the mixture in a separating


funnel and shake the mixture, until no more colourless gas evolves. Benzoic acid
reacts with sodium hydrogencarbonate solution and dissolves in the solution
(aqueous layer). Pentane and butanone have no reactions and form the organic
layer.
Allow the aqueous layer and organic layer to separate. Collect the two layers
separately.
Add a small amount of dilute hydrochloric acid to the aqueous layer to
regenerate the benzoic acid.
Filter the aqueous layer. The residue is benzoic acid. (Benzoic acid can be
purified by carrying out recrystallization.)
Pentane and butanone can be separated by carrying out simple distillation.

22. (a) Methanol


(b) Water
(c) Add anhydrous calcium chloride to distillate X. Filter distillate X. Carry out
simple distillation again. Collect the distillate with a boiling point range
from 62.6C to 66.6C.
(d) The crude benzoic acid can be purified by recrystallization.
(e) Determine the melting point of the product (benzoic acid) and compare
whether it agrees with that given in the data book.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Chapter 63 Quantitative methods of analysis

Class Practice
A63.1 (p.63-7)
25.0
(a) Number of moles of NaOH used = 0.100 × mol = 2.5 × 10−3 mol
1000
H2SO4(aq) + 2NaOH(aq) → Na2SO4(aq) + 2H2O(l)
From the equation, mole ratio of NaOH to H2SO4 = 2 : 1.
∴number of moles of 0.050 M H2SO4 required
2.5  10−3
= mol = 1.25 × 10−3 mol
2
Volume of 0.050 M H2SO4 required
1.25  10 −3
= dm3 = 0.025 dm3 (25 cm3)
0.050
100.0
(b) Number of moles of Na2CO3 used = 0.100 × mol = 0.01 mol
1000
H2SO4(aq) + Na2CO3(aq) → Na2SO4(aq) + CO2(g) + H2O(l)
From the equation, mole ratio of Na2CO3 to H2SO4 = 1 : 1.
∴number of moles of 0.050 M H2SO4 required = 0.01 mol
0.01
Volume of 0.050 M H2SO4 required = dm3 = 0.2 dm3 (200 cm3)
0.050

A63.2 (p.63-11)
(a) Chromate indicator
26.70
(b) Number of moles of AgNO3 required = 0.100 × mol = 2.67 × 10–3 mol
1000
Ag+(aq) + Cl–(aq) → AgCl(s)
From the equation, mole ratio of Ag+ to Cl– = 1 : 1.
∴number of moles of Cl– present in the water sample = 2.67 × 10–3 mol
Concentration of Cl–(aq) in the water sample
1000
= 2.67 × 10–3 × mol dm–3
25.0
= 0.107 mol dm–3

A63.3 (p.63-15)
(a) From red to orange
(b) Inappropriate practice: in step (3), the burette should not be rinsed with distilled
water only.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Correct practice: the burette should be rinsed with distilled water, and then with
the standard sodium hydroxide solution prepared in step (1).
Inappropriate practice: in step (4), the calculation of concentration of
hydrochloric acid should not be based on only one titration result.
Correct practice: the student should repeat the titration several times in order to
get the reasonable average for the volume of the standard sodium hydroxide
solution used. Then he should use this average value to calculate the
concentration of hydrochloric acid.
25.50
(c) Number of moles of NaOH required = 0.010 × mol = 2.55 × 10–4 mol
1000
NaOH(aq) + HCl(aq) → NaCl(aq) + H2O(l)
From the equation, mole ratio of NaOH to HCl = 1 : 1.
∴number of moles of HCl that reacted with NaOH = 2.55 × 10–4 mol
1000
Concentration of HCl(aq) = 2.55 × 10–4 × mol dm–3 = 0.0102 mol dm–3
25.0

A63.4 (p.63-19)
(a) For Brand A bleach,
number of moles of S2O32– reacted with I2
22.50
= 0.100 × mol = 2.25 × 10–3 mol
1000
I2(aq) + 2S2O32–(aq) → 2I–(aq) + S4O62–(aq)
From the equation, mole ratio of S2O32– to I2 = 2 : 1.
∴number of moles of I2 liberated from the reaction between OCl–(aq) and I–(aq).
1
= × 2.25 × 10–3 mol = 1.125 × 10–3 mol
2
OCl–(aq) + 2I–(aq) + 2H+(aq) → I2(aq) + Cl–(aq) + H2O(l)
From the equation, mole ratio of I2 to OCl– = 1 : 1.
∴number of moles of OCl– in 25.0 cm3 diluted bleach solution
= 1.125 × 10–3 mol
Number of moles of OCl– in 250.0 cm3 diluted bleach solution
250.0
= 1.125 × 10–3 × mol = 0.01125 mol
25.0
Number of moles of OCl– in 1000 cm3 Brand A bleach solution
1000
= 0.01125 × mol = 0.450 mol
25.0
15.8
The cost per mole of NaOCl for Brand A bleach =$ = $35.1
0.450

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For Brand B bleach,


number of moles of S2O32– reacted with I2
28.00
= 0.100 × mol = 2.8 × 10–3 mol
1000
I2(aq) + 2S2O32–(aq) → 2I–(aq) + S4O62–(aq)
From the equation, mole ratio of S2O32– to I2 = 2 : 1.
∴number of moles of I2 liberated from the reaction between OCl–(aq) and I–(aq).
1
= × 2.8 × 10–3 mol = 1.4 × 10–3 mol
2
OCl–(aq) + 2I–(aq) + 2H+(aq) → I2(aq) + Cl–(aq) + H2O(l)
From the equation, mole ratio of I2 to OCl– = 1 : 1.
∴number of moles of OCl– in 25.0 cm3 diluted bleach solution
= 1.4 × 10–3 mol
Number of moles of OCl– in 250.0 cm3 diluted bleach solution
250.0
= 1.4 × 10–3 × mol = 0.014 mol
25.0
Number of moles of OCl– in 2000 cm3 Brand B bleach solution
2000
= 0.014 × mol = 1.12 mol
25.0
26.2
The cost per mole of NaOCl for Brand B bleach =$ = $23.4
1.12
(b) Brand B chlorine bleach is more economical to buy.

A63.5 (p.63-21)
(a) For Brand A iron tablet,
MnO4–(aq) + 8H+(aq) + 5Fe2+(aq) → Mn2+(aq) + 5Fe3+(aq) + 4H2O(l)
0.0500 M ?M
3
15.70 cm 25.0 cm3
Number of moles of MnO4– used for titration
15.70
= 0.0500 × mol = 7.85 × 10–4 mol
1000
From the equation, mole ratio of MnO4– to Fe2+ = 1 : 5.
∴number of moles of Fe2+ in 25.0 cm3 iron tablet solution
= 7.85 × 10–4 × 5 mol = 3.93 × 10–3 mol
Number of moles of Fe2+ in 250.0 cm3 iron tablet solution
250.0
= 3.93 × 10–3 × mol = 0.0393 mol
25.0
Mass of Fe in the Fe tablet = 0.0393 × 55.8 g = 2.19 g

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2.19 g
Percentage composition of Fe in Brand A iron tablet = ×100% = 43.8%
5.00 g
For Brand B iron tablet,
MnO4–(aq) + 8H+(aq) + 5Fe2+(aq) → Mn2+(aq) + 5Fe3+(aq) + 4H2O(l)
0.0500 M ?M
3
14.80 cm 25.0 cm3
Number of moles of MnO4– used for titration
14.80
= 0.0500 × mol = 7.4 × 10–4 mol
1000
From the equation, mole ratio of MnO4– to Fe2+ = 1 : 5.
∴number of moles of Fe2+ in 25.0 cm3 iron tablet solution
= 7.4 × 10–4 × 5 mol = 3.7 × 10–3 mol
Number of moles of Fe2+ in 250.0 cm3 iron tablet solution
250.0
= 3.7 × 10–3 × mol = 0.037 mol
25.0
Mass of Fe in the iron tablet = 0.037 × 55.8 g = 2.06 g
2.06 g
Percentage composition of Fe in Brand B iron tablet = ×100% = 41.2%
5.00 g
320.5
(b) The cost per gram of iron for Brand A iron tablet = $ = $146.3
2.19
280.6
The cost per gram of iron for Brand B iron tablet = $ = $136.2
2.06
(c) Brand B iron tablet is more economical to buy.

A63.6 (p.63-25)
(a) Reasonable average volume of KMnO4(aq) used
1.55 + 1.50 + 1.50 3
= cm = 1.52 cm3
3
(b) There are altogether three equations for the reactions in the analysis.
MnO4–(aq) + reducing species → Mn2+(aq) + oxidizing species…………………….(1)
2MnO4–(aq) + 5C2O42–(aq) + 16H+(aq) → 2Mn2+(aq) + 10CO2(g) + 8H2O(l)……….(2)
excess from 0.010 M
Equation (1) 10.0 cm3
2MnO4–(aq) + 5C2O42–(aq) + 16H+(aq) → 2Mn2+(aq) + 10CO2(g) + 8H2O(l)……….(3)
0.005 M excess from
3
1.52 cm Equation (2)
(results obtained from titration)
From Equation (3), the number of moles of MnO4– that reacted with excess

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

C2O42–
1.52
= 0.005 × mol = 7.6 × 10–6 mol
1000
∵mole ratio of MnO4– to C2O42– = 2 : 5.
∴number of moles of excess C2O42– from Equation (2)
5
= 7.6 × 10–6 mol × = 1.9 × 10–5 mol
2
From Equation (2), the number of moles of C2O42– that reacted with excess
MnO4–.
10.0
= (0.010 × – 1.9 × 10–5) mol = 8.1 × 10–5 mol
1000
∵mole ratio of MnO4– to C2O42– = 2 : 5.
∴number of moles of excess MnO4– from Equation (1)
2
= 8.1 × 10–5 × mol = 3.24 × 10–5 mol
5
From Equation (1), number of moles of MnO4– that reacted with the reducing
species in 1000 cm3 water sample
10.0
= (0.005 × – 3.24 × 10–5) mol = 1.76 × 10–5 mol
1000
Mass of KMnO4 used = (39.1 + 54.9 + 16.0 × 4) × 1.76 × 10–5 g = 2.78 × 10–3 g
1000 3
Permanganate index = 2.78 × 10–3 g  dm = 2.78 × 10–3 g dm–3
1000
∴permanganate index of the water sample is 2.78 mg dm–3.
The water is safe for public consumption since the permanganate index does not
exceed 4 mg dm–3.

Think about
Think about (p.63-2)
1. Chemists use quantitative method of analysis (e.g. volumetric analysis) to
determine, for example, the amount of oxidizable matters per litre of Dongjiang
water sample, so as to monitor the quality of Dongjiang water.
2. Refer to p.3 to 4 of this chapter.
3. Refer to Example 63.5 on p.13 to 15 of this chapter.

Think about (p.63-7)


The end point is the stage at which the indicator changes colour sharply. The
equivalence point is the stage at which the acid and the alkali have just reacted
completely during titration.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Think about (p.63-16)


OCl–(aq) is the oxidizing agent and I–(aq) is the reducing agent.

Think about (p.63-20)


The light purple colour comes from the MnO4–(aq) ions. Its appearance indicates that
all iron(II) ions have been oxidized to iron(III) ions which are yellow. This sharp
colour change from yellow to light purple is obvious enough for us to detect the end
point of the titration.

Chapter exercise (p.63-29)


1. Volumetric
2. titrimetric; indicator
3. Acid-alkali; Precipitation; Redox
4. conductivity; indicator
5. potassium chromate
6. hypochlorite
7. potassium permanganate
8. permanganate index; potassium permanganate
9. A
Refer to p.12 of chapter 63 for details.

10. B
Refer to p.10 of chapter 63 for details.

11. B
15.10
Number of moles of AgNO3 used = 0.100 × mol = 1.51 × 10–3 mol
1000
Ag+(aq) + Cl–(aq) → AgCl(s)
From the equation, mole ratio of Ag+ to Cl– = 1 : 1.
∴number of moles of Cl– in the 25.0 cm3 water sample = 1.51 × 10–3 mol
Concentration of Cl–(aq) in the water sample
1000
= 1.51 × 10–3 × mol dm–3 = 0.0604 mol dm–3 (i.e. 0.06 mol dm–3)
25.0

12. C
Refer to p.20 of chapter 63 for details.

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13. D
15.50
Number of moles of KMnO4 used = 0.100 × mol = 1.55 × 10–3 mol
1000
MnO4–(aq) + 8H+(aq) + 5Fe2+(aq) → Mn2+(aq) + 5Fe3+(aq) + 4H2O(l)
From the equation, mole ratio of MnO4– to Fe2+ = 1 : 5.
∴number of moles of Fe2+ present = 1.55 × 10–3 × 5 mol = 7.75 × 10–3 mol
1000
Concentration of FeSO4(aq) = 7.75 × 10–3 × mol dm–3 = 0.310 mol dm–3
25.0

14. A
Volume of titrant used = (28.80 – 28.20) cm3 = 0.60 cm3

15. B
25.0
Number of moles of Na2C2O4 used = 0.20 × mol = 5.0 × 10–3 mol
1000
2MnO4–(aq) + 5C2O42–(aq) + 16H+(aq) → 2Mn2+(aq) + 10CO2(g) + 8H2O(l)
From the equation, mole ratio of C2O42– to MnO4– = 5 : 2.
2
∴number of moles of KMnO4 = 5.0 × 10–3 mol × = 2.0 × 10–3 mol
5
1000
Molarity of KMnO4(aq) = 2.0 × 10–3 × mol dm–3 = 0.10 mol dm–3
20.00

16. (a) Conductivity is high at the beginning due to the presence of a large number
of mobile Pb2+(aq) ions and NO3– (aq) ions in lead(II) nitrate solution.
After adding some hydrochloric acid, conductivity decreases due to the
removal of Pb2+(aq) ions (to form PbCl2(s)).
Conductivity is the lowest at the equivalence point as all the Pb2+(aq) ions
are precipitated out.
Conductivity increases after the equivalence point due to the addition of
excess mobile H+(aq) and Cl–(aq) ions from hydrochloric acid.
(b) 21.5 cm3
25.0
(c) Number of moles of Pb(NO3)2 reacted = 0.200 × mol = 5 × 10–3 mol
1000
Pb(NO3)2(aq) + 2HCl(aq) → PbCl2(s) + 2HNO3(aq)
From the equation, mole ratio of Pb(NO3)2 to HCl = 1 : 2.
∴number of moles of HCl reacted = 5 × 10–3 × 2 mol = 0.01 mol
1000
Molarity of HCl(aq) = 0.01 × mol dm–3 = 0.465 mol dm–3
21.5

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

17. (a) Pipette (25.0 cm3 type)


(b) Burette
24.20
(c) Number of moles of NaOH used = 0.120 × mol = 2.90 × 10–3 mol
1000
2NaOH(aq) + H2SO4(aq) → Na2SO4(aq) + 2H2O(l)
From the equation, mole ratio of NaOH to H2SO4 = 2 : 1.
∴number of moles of H2SO4 in 25.0 cm3 diluted acid
1
= 2.90 × 10–3 × mol = 1.45 × 10–3 mol
2
Concentration of H2SO4(aq) in the car battery
1000
= 1.45 × 10–3 × × 100 mol dm–3 = 5.80 mol dm–3
25.0

18. (a) Chromate indicator


(b) Mohr’s method should be carried out in a pH range of 6.5–9. If the pH is
too low, the chromate ions will change to hydrogen chromate ions or
dichromate ions.
35.95
(c) Number of moles of AgNO3 used = 0.200 × mol = 7.19 × 10–3 mol
1000
Ag+(aq) + Cl–(aq) → AgCl(s)
From the equation, mole ratio of Ag+ to Cl– = 1 : 1.
∴number of moles of Cl– present = 7.19 × 10–3 mol
Mass of NaCl in 25.0 cm3 soup = 7.19 × 10–3 × (23.0 + 35.5) g = 0.421 g

19. (a) If the titration is carried out in an alkaline medium, the silver ions may react
with the hydroxide ions, forming silver oxide precipitate.
(b) From pale yellow to red
(c) There are altogether two equations for the reactions in the analysis.
Ag+(aq) + Cl–(aq) → AgCl(s) ..............................(1)
3
0.100 M (in 25.0 cm
50.0 cm3 sample)
+
Ag (aq) + SCN–(aq) → AgSCN(s).........................(2)
excess from 0.150 M
Equation (1) 18.35 cm3
From equation (2), the number of moles of SCN– that reacted with excess
Ag+
18.35
= 0.150 × mol = 2.75 × 10–3 mol
1000

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From equation (2), mole ratio of Ag+ to SCN– = 1 : 1.


∴number of moles of excess Ag+ = 2.75 × 10–3 mol
Number of moles of Ag+ in 50.0 cm3 of 0.100 M AgNO3 solution
50.0
= 0.100 × mol = 5 × 10–3 mol
1000
From equation (2), the number of moles of Ag+ that reacted with Cl–
= (5 × 10–3 – 2.75 × 10–3) mol = 2.25 × 10–3 mol
From equation (1), mole ratio of Ag+ to Cl– = 1 : 1.
∴number of moles of Cl– in the 25.0 cm3 sea water sample
= 2.25 × 10–3 mol
Concentration of Cl–(aq) in the sea water sample
1000
= 2.25 × 10–3 × mol dm–3 = 0.09 mol dm–3
25.0

20. (a) C6H8O6(aq) → C6H6O6(aq) + 2H+(aq) + 2e–


(b) Reducing agent
(c) Pipette (25.0 cm3 type) and volumetric flask (250.0 cm3 type)
(d) C6H8O6(aq) + I3–(aq) → C6H6O6(aq) + 2H+(aq) + 3I–(aq)
Number of moles of I3– that reacted with C6H8O6
6.45
= 0.005 × mol = 3.23 × 10–5 mol
1000
From the equation, mole ratio of I3– to C6H8O6 = 1 : 1.
∴number of moles of C6H8O6 in the 25.0 cm3 diluted solution
= 3.23 × 10–5 mol
Concentration of C6H8O6 in the 25.0 cm3 diluted solution
1000
= 3.23 × 10–5 × mol dm–3 = 1.29 × 10–3 mol dm–3
25.0
Concentration of vitamin C in the original fruit juice sample
250.0
= 1.29 × 10–3 mol dm–3 × = 0.0129 mol dm–3
25.0

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Chapter 64 Instrumental analytical methods

Class Practice
A64.1 (p.64-9)
(a) Absorbance

Concentration of erioglaucine (10–5 M)

(b) (i) From the calibration curve, the concentration of the solution prepared was
0.7 × 10−5 M.
(ii) Number of moles of erioglaucine
250.0
= 0.7 × 10−5 × mol = 1.75 × 10−6 mol
1000
0.0014
Molar mass of erioglaucine = −6
g mol−1 = 800 g mol−1
1.75  10
∴relative molecular mass of erioglaucine is 800.

A64.2 (p.64-15)
(a) Characteristic wavenumber range 3230−3670 cm−1 for O−H bond in alcohol;
1680−1800 cm−1 for C=O bond.
(b) Characteristic wavenumber range 2500−3300 cm−1 for O−H bond in carboxylic
acid; 3230–3670 cm–1 for O−H bond in alcohol.
(c) Characteristic wavenumber range 3350−3500 cm−1 for N−H bond; 1680−1800
cm−1 for C=O bond.

A64.3 (p.64-19)
(a) Major absorption peaks are interpreted as follows:
Wavenumber (cm−1) Interpretation
2940
C−H bond
2860

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(b) Major absorption peaks are interpreted as follows:


Wavenumber (cm−1) Interpretation
3080
2960 C−H bond
2860
1640 C=C bond
(c) Major absorption peaks are interpreted as follows:
Wavenumber (cm−1) Interpretation
2980
C−H bond
2880
2250 C N bond
(d) Major absorption peaks are interpreted as follows:
Wavenumber (cm−1) Interpretation
3340 O−H bond
2980
2920 C−H bond
2880
(e) Major absorption peaks are interpreted as follows:
Wavenumber (cm−1) Interpretation
3370 N−H bond
2950
C−H bond
2880
(f) Major absorption peaks are interpreted as follows:
Wavenumber (cm−1) Interpretation
3100 O−H bond
2980
C−H bond
2880
1720 C=O bond

A64.4 (p.64-23)
1. The absorption peak at 1720 cm−1 corresponds to the C=O bond. Compound Y
should contain the C=O group.
The broad absorption peak at 3100 cm−1 corresponds to the O−H bond in
carboxylic acid. Compound Y should contain the −COOH group.
Possible structures of compound Y:

CH3CH2CH2COOH OR
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2. (a) Mass of carbon in the carbon dioxide produced after combustion


12.0
= 17.6 × g = 4.80 g
12.0 + 16.0  2
Mass of hydrogen in water produced after combustion
1.0  2
= 10.8 × g = 1.20 g
1.0  2 + 16.0
Since all carbon and hydrogen come from compound X, mass of carbon and
hydrogen in compound X are 4.80 g and 1.20 g respectively. As compound
X contains only carbon, hydrogen and oxygen, mass of oxygen in
compound X is (9.20 − 4.80 − 1.20) g = 3.20 g
Carbon Hydrogen Oxygen
Mass (g) 4.80 1.20 3.20
Number of 4.80 1.20 3.20
= 0.40 = 1.20 = 0.20
moles (mol) 12.0 1.0 16.0
0.40 1.20 0.20
Mole ratio =2 =6 =1
0.20 0.20 0.20
∴empirical formula of compound X is C2H6O.
1200 cm3
(b) Number of moles of 2.30 g of compound X = = 0.05 mol
24 000 cm3 mol −1
2.30 g
Molar mass of compound X = = 46.0 g mol−1
0.05 mol
∴molecular mass of compound X is 46.0.
(c) Let the molecular formula of compound X be (C2H6O)n.
n × (12.0 × 2 + 1.0 × 6 + 16.0) = 46.0
n=1
∴molecular formula of compound X is C2H6O.
(d) A strong and broad absorption peak is observed at 3320 cm−1 which
corresponds to the O−H bond of alcohol. Compound X should contain
hydroxyl group.
Possible structure of compound X: CH3CH2OH

A64.5 (p.64-28)
(a) The peaks at m/e = 15, m/e = 94 and m/e = 96 are due to the ion CH3+, CH379Br+
and CH381Br+ respectively.
(b) (i) 1 : 1
(ii) It indicates that the relative abundance of the two isotopes of bromine (79Br
and 81Br) is in the ratio of 1 : 1.
(c) Relative molecular mass of CH3Br = 94 × 50% + 96 × 50% = 95

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

A64.6 (p.64-31)
Interpretation of prominent peaks in the mass spectrum P:
m/e ratio Ion
58 CH3CH2CHO+
57 CH3CH2CO+
29 CH3CH2+ OR CHO+
The absence of peak at m/e = 43 indicates that no CH3CO+ ion forms during
fragmentation. Hence, mass spectrum P belongs to propanal.
Interpretation of prominent peaks in the mass spectrum Q:
m/e ratio Ion
58 CH3COCH3+
43 CH3CO+
The presence of peak at m/e = 43 corresponds to the CH3CO+ ion. Hence, mass
spectrum Q belongs to propanone.

A64.7 (p.64-32)
Interpretation of the peaks at m/e = 120 and m/e = 91 in the mass spectrum:
m/e ratio Ion
120 C6H5CH2CHO+
91 C6H5CH2+
The peak at m/e = 120 corresponds to the molecular ion C6H5CH2CHO+.
The peak at m/e = 91 is observed because of the cleavage of the C−C bond in the
molecular ion C6H5CH2−CHO+. This results in forming fragment ion of C6H5CH2+.

A64.8 (p.64-34)
(a) Compound B should contain carbonyl group.
(b) The peaks at m/e = 57 and 91 correspond to the ion of CH3CH2CO+ and
C6H5CH2+ respectively.
(c) Oxidation of compound A gives compound B. Compound B gives a positive
result when tested with 2,4-dinitrophenylhydrazine. Hence, compound B should
be an aldehyde or ketone. Compound B has 10 carbon atoms and it produces
fragment ions of CH3CH2CO+ and C6H5CH2+ during fragmentation. Therefore,
compound B is a ketone. Its possible structure is:

A64.9 (p.64-37)
1. (a) Let the mass of compound X be 100 g. Therefore,

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

the mass of carbon in the compound = 72.0 g


the mass of hydrogen in the compound = 12.0 g
the mass of oxygen in the compound = 16.0 g
Carbon Hydrogen Oxygen
Mass (g) 72.0 12.0 16.0
Number of 72.0 12.0 16.0
=6 = 12 =1
moles (mol) 12.0 1.0 16.0
Mole ratio 6 12 1
∴the empirical formula of compound X is C6H12O.
(b) From the mass spectrum, the peak at m/e = 100 corresponds to the
molecular ion of compound X. Hence, the relative molecular mass of
compound X is 100.
(c) Let the molecular formula of compound X be (C6H12O)n.
n × (12.0 × 6 + 1.0 × 12 + 16.0) = 100
n=1
∴molecular formula of compound X is C6H12O.
From the IR spectrum, there is a strong absorption peak at 1750 cm−1. This
indicates the presence of the C=O bond. The compound may be hexanal,
hexan-2-one or hexan-3-one.
Interpretation of prominent peaks in the mass spectrum:
m/e ratio Ion
100 CH3CH2CH2COCH2CH3+
71 CH3CH2CH2CO+
57 CH3CH2CO+
∴compound X is hexan-3-one.

2. (a) (i) From the result of test (1), the compound should contain hydroxyl
group or aldehyde group.
(ii) From the result of test (2), the compound should contain aldehyde
group.
(b) From the IR spectrum, there is a strong absorption peak at 1720 cm−1 which
corresponds to the C=O bond. Compound Z should contain carbonyl group.
(c) m/e = 134 is due to the molecular ion C6H5CH2CH2CHO+.
m/e = 105 is due to the fragment ion C6H5CH2CH2+.
(d)

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Think about
Think about (p.64-2)
1. Compared with volumetric analysis, instrumental analytical method is more
rapid, more accurate, more sensitive, usually non-destructive, and causes less
human error.
2. The presence of functional group(s) in a carbon compound can be identified by
using infrared spectroscopy.
The relative atomic mass of an element, the relative molecular mass of a
compound and the structure of an unknown compound can be determined by
using mass spectrometry.

Think about (p.64-23)


Tom is wrong. Since the atoms in optical isomers are linked together in the same order,
their infrared spectra should look the same.

Chapter exercise (p.64-44)


1. concentration
2. Colorimetry
3. calibration curve
4. infrared spectroscopy
5. wavenumber
6. functional groups
7. relative atomic mass; relative molecular mass; structural formula
8. vaporization; ionization; acceleration; deflection; detection
9. mass-to-charge
10. molecular ion
11. fragmentation pattern
12. (a) Pentan-1-ol
The peak at 3350 cm–1 corresponds to the O–H bond of alcohol and the
peaks at 2850 cm–1 and 2950 cm–1 correspond to the C–H bond.
(b) Pentanenitrile
The peaks at 2880 cm–1 and 2950 cm–1 correspond to the C–H bond and the
peak at 2250 cm–1 corresponds to the C N bond of nitrile.
(c) Pent-1-ene
The peaks at 2850 cm–1, 2950 cm–1 and 3080 cm–1 correspond to the C–H
bond and the peak at 1650 cm–1 corresponds to the C=C bond.
(d) Pentanal
The peaks at 2850 cm–1 and 2950 cm–1 correspond to the C–H bond and the

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

peak at 1720 cm–1 correspond to the C=O bond.


(e) Pentane
The peaks at 2850 cm–1 and 2950 cm–1 correspond to the C–H bond.

13. B
Refer to p.4 of chapter 64 for details.

14. C
If a sample under test is colourless or has a pale colour, a reagent can be added to
give an intense colour for measurement.

15. C

16. B
Refer to p.19 of chapter 64 for details.

17. D
The absorption peak at 1700 cm–1 corresponds to the C=O bond.

18. A
An absorption peak at 1750 cm–1 is observed. The compound should contain
C=O bond.
There is no absorption peak in the range of 1610–1680 cm–1. The compound
should not contain C=C bond.
There is no broad absorption peak in the range of 3230–3670 cm–1. The
compound should not contain O–H bond of alcohol.

19. D
The broad absorption peak at 3230–3670 cm–1 corresponds to the O–H bond of
alcohol.

20. D
(2): we may deduce the structure of a molecule by looking at the fragmentation
pattern.

21. C
Ions with a lower mass-to-charge ratio are deflected more.

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Mass-to-charge ratio (m/e)


(A) 35
=35
1
(B) 37
=37
1
(C) 35
=17.5
2
(D) 37
=18.5
2

22. C
The peaks at m/e = 50 and m/e = 52 are due to the molecular ions CH335Cl+ and
CH337Cl+ respectively.

23. A

24. D
The peak at m/e = 91 is due to the fragment ion C6H5CH2+.

25. (a) Br2(aq) is the only species that has colour in the reaction mixture. As
reaction proceeds, the colour intensity of the reaction mixture drops because
of the consumption of the Br2(aq).
(b) Measure the absorbance of bromine solution at different known
concentrations using a colorimeter.
Construct a calibration curve of the bromine solution using the data
obtained.
Measure the absorbance of the reaction mixture using the colorimeter.
Determine the concentration of bromine in the reaction mixture by
comparing the absorbance of the reaction mixture to the calibration curve of
the bromine solution.
(c) (i) By finding the slope of the tangent drawn on the curve at every minute,
the rate of reaction at different times can be obtained.
(ii) Initial rate of reaction = slope of the tangent drawn at time t = 0
0.05 − 0.09
=– M min–1
0.08 − 0
= 0.5 M min–1

26. (a) To obtain an absorbance comparable to that of standard solutions.

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(b)

Absorbance

Concentration (mg cm–3)

When the absorbance was equal to 0.170, the concentration of haemoglobin


in the diluted blood sample was 4.3 mg cm−3. Therefore, the concentration
of haemoglobin in the blood of the patient was 4.3 × 30 mg cm−3 = 129 mg
cm−3.
(c) Since the level of haemoglobin in the patient’s blood is higher than 120 mg
cm−3, the patient does not suffer from the mentioned diseases.

27. (a) The infrared spectrum on the right belongs to compound A.


The absorption peak at 1720 cm−1 corresponds to the C=O bond. Compound
B does not contain C=O bond.
(b) (i)

(ii) and
(iii) No, this is because the atoms in enantiomers are linked together in the
same order. Their infrared spectra should look the same.
(c) (i) Use concentrated sulphuric acid as catalyst; heat the reaction mixture
under reflux
(ii)

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28. (a)

(b) The absorption peak at 1680 cm−1 corresponds to the C=O bond. And the
broad absorption peak at around 3100 cm−1 corresponds to the O−H bond of
carboxylic acid. The absorption peak at 1640 cm−1 corresponds to the C=C
bond.
Compound E should be a carboxylic acid with carbon-carbon double bond.
It has the structure of:

.
(c) (i) For compound E, there is an absorption peak corresponding to O–H
bond at 3100 cm–1. For compound D, there is no absorption peak
corresponding to O–H bond.
(ii) Test with sodium hydrogencarbonate solution/sodium carbonate
solution. Effervescence occurs for compound E but there is no
observable change for compound D.

29. (a) Major absorption peaks are interpreted as follows:


Wavenumber (cm−1) Interpretation
1720 C=O bond
2500−3300 O−H bond of carboxylic acid
3230−3670 O−H bond of alcohol

(b) (i) The peak at m/e = 31 is due to the ion.


(ii) The molecular ion of compound J is very unstable and it breaks down
to smaller fragment ions.

(c) (i)
(ii) (1) Test with sodium hydrogencarbonate solution/sodium carbonate
solution. Effervescence occurs for compound J while there is no
observable change for propane-1,2-diol.
(2) For compound J, there is an absorption peak corresponding to
C=O bond at 1720 cm−1. For propane-1,2-diol, there is no

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absorption peak corresponding to the C=O bond.

30. (a) The broad absorption peak at 3350 cm−1 corresponds to the O−H bond of
alcohol. Compound H belongs to the alcohol series.
(b) Test with carboxylic acid. In the presence of conc. sulphuric acid,
compounds containing hydroxyl group (except tertiary alcohol) produce a
substance which gives a pleasant fruity smell.
(c) (i) The peaks at m/e = 57 and m/e = 43 are due to the CH3CH2CO+ ion
and CH3CO+ ion respectively.
(ii) Oxidation of compound H gives compound G with only one oxygen
atom. Compound G should be an aldehyde or a ketone. There are only
four carbon atoms in compound G. Thus, compound G may be butanal
or butanone.
If compound G is butanal, a peak at m/e = 71 due to CH3CH2CH2CO+
ion should appear in the mass spectrum. The absence of such peak
indicates that compound G is not a butanal but a butanone.
Possible structure of G is:

31. (a) The negative result of test (1) shows that carbonyl group is not found in
compound F.
(b) (i) This is used to test for the presence of carboxyl group in compound F.
(ii) The negative result of test (2) shows that carboxyl group is not found
in compound F.
(c) The presence of absorption peak at 1720 cm−1 indicates that compound F
contains C=O bond. However, compound F is not an aldehyde, ketone or
carboxylic acid. Hence, it may be an ester. Ester group may be present in
compound F.
(d) Since all carbon and hydrogen come from compound F,
12.0
mass of carbon in the compound = 15.9 × g = 4.34 g
12.0 + 16.0  2
1.0  2
mass of hydrogen in the compound = 6.6 × g = 0.73 g
1.0  2 + 16.0
The rest of the mass of compound F comes from the mass of oxygen
= (7.00 − 4.34 − 0.73) g = 1.93 g
Carbon Hydrogen Oxygen
Mass (g) 4.34 0.73 1.93

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Number of 4.34 0.73 1.93


= 0.362 = 0.73 = 0.121
moles (mol) 12.0 1 .0 16.0
0.362 0.73 0.121
Mole ratio =3 =6 =1
0.121 0.121 0.121
∴empirical formula of compound F is C3H6O.
(e) (i) From the mass spectrum, the peak at m/e = 116 is due to the molecular
ion of compound F. Hence, the relative molecular mass of compound
F is 116.
Let the molecular formula of F be (C3H6O)n.
n × (12.0 × 3 + 1.0 × 6 + 16.0) = 116
n=2
∴molecular formula of compound F is C6H12O2.
(ii) The peak at m/e = 71 is due to CH3CH2CH2CO+ or
CH3CH2CH2CH2CH2+ ion.
(f) The peak at m/e = 116 is due to molecular ion CH3CH2CH2COOCH2CH3+ or
HCOOCH2CH2CH2CH2CH3+.
The peak at m/e = 43 is due to CH3CH2CH2+ ion.
Some possible structures of F:

OR

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Chapter 65 Contribution of analytical chemistry to our


society

Class Practice
A65.1 (p.65-8)
(a) (i)

(ii) Trichloromethane has a low boiling point. It can be easily removed by


evaporation.
Benzoic acid dissolves well in trichloromethane.
(b) Reasonable average for the volume of NaOH(aq) required
16.20 + 16.30 + 16.35 3
= cm = 16.28 cm3
3
(c) NaOH + C6H5COOH → C6H5COONa + H2O
16.28
Number of moles of NaOH required = 0.01 × mol = 1.63 × 10−4 mol
1000
From the equation, mole ratio of NaOH to C6H5COOH = 1 : 1.
∴number of moles of C6H5COOH in the beverage sample = 1.63 × 10−4 mol
Molar mass of benzoic acid
= (12.0 × 7 + 1.0 × 6 + 16.0 × 2) g mol−1 = 122.0 g mol−1
Concentration of benzoic acid in 25.0 cm3 beverage sample in mg dm−3
1.63  10 −4 mol  122.0 g mol −1
=
25.0
dm 3
1000
= 0.795 g dm−3 = 795 mg dm–3

A65.2 (p.65-10)
(a) Hydroxyl group, carbon-carbon double bond and carbonyl group
1.6 cm
(b) Rf value of compound A = = 0.42
3.8 cm
(c) Yes, this is because a spot corresponding to compound A is found in the
chromatogram of the suspected fake drug.

A65.3 (p.65-14)
(a) Complete combustion of petrol produces carbon dioxide and water.
(b) The absorption peak at around 3000 cm−1 is observed because of the C−H bond

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

in unburnt hydrocarbons from the petrol.


The absorption peak at around 2100 cm−1 is observed because of the C O bond
in carbon monoxide formed in the incomplete combustion of petrol.
(c) From the IR spectrum of exhaust from a hybrid car, there is absence of
absorption peaks at around 3000 cm−1 and 2100 cm−1. This indicates that unburnt
hydrocarbons and carbon monoxide are absent in the exhaust. Thus, hybrid car
causes less pollution to the environment.

A65.4 (p.65-20)
(a) From orange to green
(b) The degree of the colour change in the breathalyser is directly related to the
ethanol content in the breath.
(c) 2Cr2O72−(aq) + 3CH3CH2OH(aq) + 16H+(aq)
→ 4Cr3+(aq) + 3CH3COOH(aq) + 11H2O(l)
(d) (i) Blood or urine
(ii) The alcohol content in the driver’s body can be analysed more accurately.

A65.5 (p.65-24)
(a) The higher the concentration of albumin in urine, the higher is the absorbance.
(b) From the calibration curve, the concentration of albumin in Cindy’s urine = 57.5
g dm−3.
(c) Since the concentration of albumin in Cindy’s urine is above the normal range,
she should consult a doctor to have further checking.

Think about
Think about (p.65-2)
1. Chemists carry out analysis to find out any excessive and non-permitted
contaminants in foods so that the public can avoid taking in harmful foods.
2. Chemists use modern analytical methods like thin-layer chromatography, gas
chromatography-mass spectrometry to spot unsatisfactory food samples.
3. Chemists use mass spectrometer, infrared spectrophotometer, equipments for
chromatographic methods, colorimeter, etc. in performing the chemical tests.

Think about (p.65-12)


Carbon monoxide in the atmosphere mainly comes from the burning of fossil fuels in
car engines and power stations.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Think about (p.65-20)


The ‘brown’ fingerprint becomes dark blue when starch is sprayed onto it.

Chapter exercise (p.65-31)


1. thin-layer chromatography
2. volumetric analysis
3. gas chromatography-mass spectrometry
4. infrared spectroscopy; colorimetry
5. gas chromatography-mass spectrometry
6. infrared spectroscopy; colorimetry
7. poisons; drugs
8. mass spectrometry; infrared spectroscopy
9. thin-layer chromatography
10. gas chromatography-mass spectrometry
11. iodine sublimation
12. Thin-layer chromatography
13. chromatography; mass spectrometry

14. C

15. B
Refer to p.12 of chapter 65 for details.

16. A
(3): gas chromatography-mass spectrometry can be used to determine the
extremely low level of dioxin in air.

17. B
The alcohol is separated out from a sample of body fluid by gas chromatography.
It is then identified by mass spectrometry.

18. C
(1): no new substance form when iodine crystals change to iodine vapour. Hence,
the sublimation of iodine crystals is a physical change.
(2): the fingerprint appears brown after exposed to iodine vapour.

19. D

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20. C

21. D
Gas chromatography-mass spectrometry should be used to analyse the ketamine
in fake drugs.

22. (a) To change all the salt of salicylic acid back to salicylic acid.
(b) Diethyl ether has a low boiling point. It can be removed easily by
evaporation.
(c) To make sure that all salicylic acid has reacted with FeCl3.
(d) From the calibration curve, the concentration of salicylic acid in the sample
solution was 51 mg dm−3.

23. (a) No, this is because more than one spot are found in the chromatogram.
(b) Hydroxyl group, amide group and phenyl group (Any TWO)
(c) Yes, she obtained paracetamol from the experiment.
Absorption peaks corresponding to C=O bond and N−H bond in amide can
be identified in the IR spectrum.
From the mass spectrum, the prominent peaks can be explained as follows:
m/e ratio Ion

151

108

(d) The procedure is as follows:


Spot the test sample on the baseline of the chromatographic plate.
Then spot the drug sample of paracetamol next to the test sample spot.
Put the plate upright in a suitable developing solvent.
Compare the distance travelled by the two spots.

24. (a) This is because they contain the same functional groups.
(b) (i) Ice-cream A contains vanillin. This is because ice-cream A produces a
1.5 cm
spot (the first spot) that has a Rf = = 0.3 in the chromatogram.
5.0 cm
(ii) Ice-cream B contains ethylvanillin. This is because ice-cream B

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2.7 cm
produces a spot (the second spot) that has the Rf value = = 0.54
5.0 cm
in the chromatogram.
(c) Gas chromatography-mass spectrometry

25. (a) Furniture made of wood with urea-formaldehyde as an adhesive or coating


material.
(b) Colorimetry or infrared spectroscopy
(c) This is because the formaldehyde level in the indoor air environment is
usually very low.

26. (a) The broad absorption peak at 3400 cm–1 corresponds to the O–H bond of
alcohol.
(b) The breath of the driver contains water vapour. The O–H bond in water also
gives a strong and broad absorption peak at around 3400 cm–1.
(c) The dichromate crystals inside the breathalyser change from orange to green
if the breathed air contains ethanol. So, dichromate breathalyser can be used
to detect ethanol in the breath.
(d) The alcohol content measured using infrared spectroscopy is more accurate.

27. (a) By interpreting the infrared spectrum, the absorption peaks at 2850 cm −1
and 2950 cm−1 are observed because of the presence of C−H bonds. There
are no other prominent absorption peaks, so no other functional groups are
present.
From the mass spectrum, the highest m/e ratio occurs at 86. Therefore, the
molecular mass of the flammable liquid is 86. Prominent peaks are also
found at m/e = 71, 57, 43 and 29. The same difference (i.e. 14) is found
between these peaks. It is likely to be a fragment of CH2.
Interpretation of prominent peaks in the mass spectrum:
m/e Ion
86 CH3CH2CH2CH2CH2CH3+
71 CH3CH2CH2CH2CH2+
57 CH3CH2CH2CH2+
43 CH3CH2CH2+
29 CH3CH2+

Therefore, the flammable liquid should be hexane.


(b) Iodine sublimation

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(c) Check the sample using mass spectrometry. If the sample contains Fe2+, a
peak corresponding to Fe2+ should appear in the mass spectrum.
(d) Compare whether the pattern of shoeprints matches with the suspect’s
shoes.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

Part XV Analytical Chemistry


Part exercise (p.65-37)
1. B
(2): the concentration of OH−(aq) ions is too low in aqueous ammonia that the
Ca2+(aq) ions will not precipitate out as Ca(OH)2(s).

2. A
Chlorine has pungent smell of bleaching solution while sulphur dioxide has a
choking smell of burning sulphur.

3. B
(2): NH3(g) + HCl(aq) → NH4Cl(aq)
(3): SO2(g) + H2O(l) → H2SO3(aq)
SO32−(aq) + 2H+(aq) → SO2(g) + H2O(l)
SO2(g) + 2NaOH(aq) → Na2SO3(aq) + H2O(l)

4. B
Tollens’ reagent has no reaction with ketones and carboxylic acids.

5. C

6. C

7. A
Number of moles of Na2SO3•7H2O required
300  10−3
= mol = 1.19 × 10−3 mol
23.0  2 + 32.1 + 16.0  3 + 7  (1.0  2 + 16.0)
Since 1 mole of Na2SO3•7H2O contains 1 mole of SO32−, number of moles of
SO32− = 1.19 × 10−3 mol
5SO32−(aq) + 2MnO4−(aq) + 6H+(aq) → 5SO42−(aq) + 2Mn2+(aq) + 3H2O(l)
From the equation, mole ratio of SO32− to MnO4− = 5 : 2.
2
∴number of moles of MnO4− reacted = 1.19 × 10−3 mol × = 4.76 × 10−4 mol
5
1000
Molarity of KMnO4(aq) = 4.76 × 10−4 × M = 0.0190 M
25.00

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

8. A
Number of moles of Na2CO3 in 250.0 cm3 solution
2.65
= mol = 0.025 mol
23.0  2 + 12.0 + 16.0  3
Number of moles of Na2CO3 in 25.0 cm3 solution
25.0
= 0.025 × mol = 0.0025 mol
250.0
Na2CO3(aq) + 2HCl(aq) → 2NaCl(aq) + H2O(l) + CO2(g)
From the equation, mole ratio of Na2CO3 to HCl = 1 : 2.
∴number of moles of HCl reacted = 0.0025 × 2 mol = 0.005 mol
1000
Molarity of HCl(aq) = 0.005 × M = 0.25 M
20.00

9. C
If the conical flask was rinsed with the acid, some acid would remain in the flask.
More alkali than actually needed is used to reach the titration end point.

10. A
The absorption peaks at 1730 cm−1 and 3480 cm−1 correspond to the C=O bond
and N−H bond respectively.

11. C
The peak at m/e = 77 is due to the cation C6H5+ formed from the molecular ion
C6H5CHO+ by stripping off a −CHO group.

12. D
The paints cannot be analysed by infrared spectroscopy as they do not contain
only one compound.

13. (a) Antacid relieves stomach trouble by neutralizing the excess acid in stomach.
(b) Calcium ion is present in the tablet as a brick-red flame is produced in the
flame test.
(c) Carbonate ion is present in the tablet as carbon dioxide is given out when
HCl(aq) is added to the tablet. Carbon dioxide can turn limewater milky.
(d) Calcium carbonate
(e) Number of moles of NaOH that required to react with the excess HCl
20.60
= 0.60 × mol = 0.0124 mol
1000

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NaOH(aq) + HCl(aq) → NaCl(aq) + H2O(l)


From the equation, mole ratio of NaOH to HCl = 1 : 1.
∴number of moles of excess HCl = 0.0124 mol
Number of moles of HCl that reacted with the CaCO3 in the antacid tablet
25.0
= (1.00 × − 0.0124) mol = 0.0126 mol
1000
2HCl(aq) + CaCO3(s) → CaCl2(aq) + CO2(g) + H2O(l)
From the equation, mole ratio of HCl to CaCO3 = 2 : 1.
∴number of moles of CaCO3 in the antacid tablet
0.0126
= mol = 6.3 × 10−3 mol
2
Mass of CaCO3 in the antacid tablet
= 6.3 × 10−3 × (40.1 + 12.0 + 16.0 × 3) g = 0.63 g
Percentage by mass of CaCO3 in the antacid tablet
0.63 g
= ×100% = 42%
1.50 g
(f) Carbon dioxide forms when calcium carbonate reacts with the acid in the
stomach. Pressure will build up in the stomach, making the patient feel
uncomfortable. No gas forms when magnesium hydroxide reacts with the
acid in the stomach.

14. (a) Hydrogen bromide


(b) 2-bromobutane
(c) Compound A is the only species that contains the C=C bond. When no
absorption peak at 1610−1680 cm−1 is observed in the infrared spectrum of
the reaction mixture any more, this indicates that all compound A has been
consumed. In other words, the reaction has gone to completion.

(d) and
(e) The atoms in enantiomers are linked together in the same order. Hence, the
infrared spectra of the two enantiomers should look the same.
(f) Polarimeter

15. (a) Place the chromatographic plate in a jar saturated with iodine vapour. OR
Shine ultraviolet light on the plate that contains a fluorescent material.
(b) No, this is because the chromatogram contains more than one spot.

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HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

(c) He should use column chromatography to separate X and Y. X and Y have


different solubilities in eluting solvent. They come out from the column at
different times.
(d) Aldehyde series
(e) (i) From the mass spectrum, the peak at m/e = 72 corresponds to the
molecular ion. Hence, the relative molecular mass of Y is 72.
(ii) The peak at m/e = 43 corresponds to the CH3CO+ ion.
The peak at m/e = 57 corresponds to the CH3CH2CO+ ion.
(iii) Compound Y should be butanone.

16. (a) P belongs to the aldehyde series.


(b) Let the mass of compound P be 100 g. Therefore,
the mass of carbon in the compound = 80.6 g
the mass of hydrogen in the compound = 7.5 g
the mass of oxygen in the compound = 11.9 g
Carbon Hydrogen Oxygen
Mass (g) 80.6 7.5 11.9
Number of 80.6 7.5 11.9
= 6.72 = 7.5 = 0.74
moles (mol) 12.0 1.0 16.0
6.72 7.5 0.74
Mole ratio ≈9 ≈ 10 =1
0.74 0.74 0.74
∴the empirical formula of compound P is C9H10O.
(c) (i) From the mass spectrum, the peak at m/e = 134 corresponds to the
molecular ion. Hence, the relative molecular mass of P is 134.
Let the molecular formula of P is (C9H10O)n.
n × (12.0 × 9 + 1.0 × 10 + 16.0) = 134
n=1
∴the molecular formula of compound P is C9H10O.
(ii) The peak at m/e = 91 corresponds to the C6H5CH2+ ion.
The peak at m/e = 105 corresponds to the C6H5CH2CH2+ ion.
(d) The difference between the peaks at m/e = 134 and m/e = 105 is 29. Since P
is an aldehyde, the C6H5CH2CH2+ ion is probably produced from the
molecular ion by stripping off a −CHO group (formula mass = 29). Hence,
the possible structure of P is:

17. (a) Hydroxyl group, carbon-carbon double bond, carbonyl group

© Aristo Educational Press Ltd. 2015 49


HKDSE CHEMISTRY ⎯ A Modern View (Second Edition) Coursebook 7

(b) Major absorption peaks are interpreted as follows:


Wavenumber (cm−1) Interpretation
3400 O−H bond
1650 C=C bond
1700 C=O bond
(c) (i) For nandrolone, there is a strong absorption peak corresponding to
C=O bond at around 1700 cm−1. For oestradiol, there is no absorption
peak corresponding to C=O bond.
(ii) Orange-yellow precipitate forms when 2,4-dinitrophenylhydrazine
reacts with nandrolone while there is no reaction for oestradiol.
(d) (i) No, this is because no spot corresponding to the nandrolone sample is
found in the chromatogram.
(ii) Gas chromatography-mass spectrometry

18. (a) Alloy is a mixture of metals. The flames produced by different metals will
interfere the experimental results.
(b) (i) To dissolve the metals in the alloy.
(ii) Chromatographic method
(c) Place the hammer in a closed container with iodine crystals.
Heat the crystals gently, causing them to sublime.
The iodine vapour then dissolves in the grease of fingerprint, making it
‘brown’.

19. (1) Suspected tablets identified as morphine: likely


Reason: The sample produces a spot that has the same position (same Rf
value) as morphine in the chromatogram.
(2)
Wavenumber (cm−1) Interpretation
3000−3600 O−H bond
1610 C=C bond
Suspected tablets identified as aspirin: unlikely
Reason: An absorption peak corresponding to O−H bond is observed.
However, there is no absorption peak due to C=O bond. Thus, the
compound is not likely to be aspirin.
Suspected tablets identified as morphine: likely
(3) Molecular ion peak at m/e = 285
Suspected tablets identified as morphine: likely
(4) Conclusion: The suspected tablets are morphine

© Aristo Educational Press Ltd. 2015 50

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