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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Gravimetric Analysis

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Outcome(1(
(

On(completion(of(this(unit(the(student(
should(be(able(to(evaluate(the(suitability(of(
techniques(and(instruments(used(in(
chemical(analyses.(
(

Key(Knowledge(
!Gravimetric(analysis(
!the(application(of(chemical(equations(to(
(volumetric(and)(gravimetric(analyses(
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Gravimetric(analysis(
This(form(of(quantitative(analysis(involves(
@ind(the(mass(of(a(part(of(the(sample(and(
relating(it(back(to(the(sample,(often(as(a(
percentage(by(mass(
The(part(of(the(sample(we(are(interested(
in(may(be(the(water(in(the(product,(or(
perhaps(we(might(be(focussing(on(a(
particular(ion(that(is(present.(
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Measuring(water(content(
Many(solids(have(a(high(proportion(of(water.(
Dehydration(removes(the(water(and(
decreases(the(mass(
This(may(be(heating(at(just(above(100(C(
Mass(loss(=(mass(of(water(originally(present(

%(water(content(=(m(water)((100(((((((((((((((((((((((((((
(((((((((((((((((((((((((((((((((((((((m(sample)(
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Weigh&the&
sample&

Heat&the&sample&
in&an&oven&just&
above&100&C&

Allow&the&
sample&to&cool&
in&a&desiccator&

This cycle is
repeated until
the sample
assumes a
constant mass

Reweigh&the&
sample&
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Finding(the(composition(of(a(
mixture(
1. Dissolve(the(mixture(in(water(
2. Add(an(ionic(solution(which(will(
form(a(precipitate(with(the(ion(
that(is(required((eg(SO42P).(
3. This(new(solid(is(then(@iltered(out,(
dried(and(weighed.

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The(most(common(precipitates&
Element'you'wish' Substance'that'is' Formula'of'
to'analyse'
added'to'create' precipitate'
precipitate'
Chlorine&&

Silver&nitrate&

AgCl&

Bromine&

Silver&nitrate&

AgBr&

Sulfur&

Barium&chloride&

BaSO4&

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Application(of(gravimetric(analysis(

! Gravimetric(analysis(is(used(in(the(
food(industry(to(determine(the(
amount(of(salt(in(products.(
! When(an(AgNO3(solution(is(added(((
((((to(the(dissolved(food,(chloride(ions(((
(((((present(as(NaCl)(are(precipitated(out((((
as(AgCl.(
(&
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Calculations(
m(AgCl)
Find(n(AgCl)(using:(n(AgCl)(=(( M(AgCl)

Then:&

n(AgCl)&=&n(Cl.)&=&n(NaCl)(
!Convert(n(NaCl)(to(m(NaCl)(using((
((((((m(NaCl)(=(n(NaCl)((M(NaCl)(
(
!%(NaCl)(=(m(NaCl)((100(
( ((((((((m(food)(((((1(
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Experiment((
(Analysis(of(Lawn(food(

Lawn(food(contains(many(nutrients(
required(by(plants(such(as(sulfate(ions,(
SO42P,(nitrate(ions,(NO3P(and(phosphate(
ions,(PO43B.&
&
Using&gravimetric&analysis&to&;ind&the&
amount&of&sulfate&ions&in&a&sample&of&
lawn&food&
1. Dissolve(lawn(food(in(water(
2. Add(barium(chloride(solution(
3. Sulfate(ions(precipitate(out(as(barium(
sulfate(

((((((((((BaCl2(aq)(+(SO42P((aq)((BaSO4(s)(+(2ClP(aq)(
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10

4. Filter,(wash(and(dry(the(BaSO4(to(obtain(a(pure(
sample(of(precipitate.(
(
5. During(washing(stages(@iltrate(is(tested(for(
presence(of(left(over(chloride(ions(by(adding(silver(
nitrate.(
(AgNO3(aq)+(ClP((AgCl(s)(+(NO3P(aq)(
(
(If(ions(are(in(the(@iltrate,(then(they(have(
probably(also(stuck(to(the(solid(and(its(mass(will(
be(too(high.(
((
(

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6. Barium(sulfate(is(dried,(then(weighed.(
(
7. Using(M(BaSO4),(n(BaSO4)((is(calculated(so(
n(SO42P)(can(be(deduced.((
(n(SO42P)(=(n(BaSO4)(
8. m(SO42P)(=(n(SO42P)((M(SO42P)((
9. m(S)(=(n(SO42P)((M(S)((

m(S)
100

10.%(S(=((
m(sample) 1

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Sample(exam(question(
An(8.64g((sample(of(rock(was(thought(to(be(made(up(of(
CaCO3(which(reacted(with(HCl(according(to:(
2HCl(aq)(+(CaCO3(s)((CaCl2(aq)((+((H2O(l)(+(CO2(g)(
and(1.55g(of(insoluble(SiO2.(
(a)Calculate(the(expected(percentage(of(CaCO3(in(the(
rock(sample(
(b)The(dissolved(calcium(ions(were(precipitated(out(as(
CaC2O4.H2O(which(was(collected,(washed(and(dried.(It(
was(converted(to(CaO((M(=(56.1gmolP1)(and(3.87g(was(
obtained.(Calculate(the(%(CaCO3(in(the(rock(sample.(
(signi@icant(@igures)(
(VCAA(June(2007(Q3)(
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Answers(

(a)m(CaCO3)(=(8.64((1.55(=(7.09g(
(
7.09 100
(((((%(CaCO3)(=(

= 82.1%
8.64 1
((
3.87
= 0.06898
b) n(CaO)(=(( ( (((mol(
56.1
((((((n(Ca2+)(=(0.06898(mol(=(n(CaCO3)((
m(CaCO3)(=(0.06898((100.1(=(6.905g(
(
6.905 100
%(CaCO3)(=(( ( ( ( (( = 79.9%
8.64
1
( ( ( ( ((((((((((((3(sig(@igs)(
(

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QUESTION 1
Xylose is a compound that has five carbon atoms in each molecule and
contains 40% carbon by mass. What is the molar mass of xylose?
A. 30
B. 67
C. 150
D. It cannot be determined without further information.
(VCAA Q3 June 2008)

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QUESTION 1 (ANSWER)
Xylose is a compound that has five carbon atoms in each molecule and
contains 40% carbon by mass. What is the molar mass of xylose?
A. 30
B. 67
C. 150
D. It cannot be determined without further information.
Alternative C is the correct answer
M(C) = 12.0 gmol-1
1 mol xylose molecules contains 5 mol C atoms (5 C atoms per molecule, so 5 mol of C
atoms per 1 mol of molecules)
m(5 mol C atoms) = 60.0 g
40% of xylose is carbon, so 40% of M(xylose) = 60.0
This can also be written as 0.40 M(xylose) = 60.0
60.0

M(xylose) =
0.40
= 150.0 gmol-1
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(VCAA Q3 June 2008)

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QUESTION 2
The amount of calcium carbonate (:molar mass = 100.1 g ) in the ore dolomite can be
determined by gravimetric analysis. The dolomite sample is dissolved in acid and the
calcium ions () present are precipitated as calcium oxalate ( :molar mass = 128.1 g ).
The calcium oxalate is foltered, dried and strongly heated to form calcium oxide
(CaO); molar mass = 56.1 g ).
In one analysis the mass of dolomite used was 3.72 g. The mass of calcium oxide
formed was found to be 1.24 g.
The percentage of calcium carbonate in the dolomite sample is closest to
A. 26.9
B. 33.3
C. 56.0
D. 59.5
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(VCAA Q8 June 2005)


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QUESTION 2 (ANSWER)
The amount of calcium carbonate (:molar mass = 100.1 g ) in the ore dolomite can be
determined by gravimetric analysis. The dolomite sample is dissolved in acid and the
calcium ions () present are precipitated as calcium oxalate ( :molar mass = 128.1 g ).
The calcium oxalate is foltered, dried and strongly heated to form calcium oxide
(CaO); molar mass = 56.1 g ).
In one analysis the mass of dolomite used was 3.72 g. The mass of calcium oxide
formed was found to be 1.24 g.
The percentage of calcium carbonate in the dolomite sample is closest to
A. 26.9
B. 33.3
C. 56.0
D. 59.5

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Alternative D is the correct answer


2.21 100
= 59.5%
n(CaO) =
3.72 1

n(Ca2+) = n(CaO) = n(CaCO3) = 0.0221


m(CaCO3) in dolomite = 0.0221 100.1 = 2.21g
%(CaCO3) = 2.21 100
= 59.5%
3.72 1
(VCAA Q8 June 2005)

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19

QUESTION 3
When 2.54 g of solid iodine reacts with excess chlorine and the unreacted chlorine is
evaporated, 4.67 g of a yellow product remains.
The empirical formula of the product is

A. ICl2
B. ICl3
C. ICl4
D. ICl5
(VCAA Q4 June 2007)

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QUESTION 3 (ANSWER)
When 2.54 g of solid iodine reacts with excess chlorine and the unreacted chlorine is
evaporated, 4.67 g of a yellow product remains.
The empirical formula of the product is

A. ICl2
B. ICl3
C. ICl4
D. ICl5

The empirical formula is ICl3 so the correct answer is B


The yellow product is only made up of chlorine and iodine
In 4.67g of the yellow product, 2.54g is iodine and (4.67-2.54) 2.13g is chlorine
Empirical formula:
I : Cl
2.54g : 2.13g

2.54 2.13
:
126.9 35.5
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(VCAA Q4 June 2007)

0.0200 : 0.0600
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1 : 3
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21

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Simple titrations

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22

Key(Knowledge(
volumetric(analysis(including(determination(of(
excess(and(limiting(reagents((and(titration(
curves):(simple((and(back)(titrations,(acidPbase(
(and(redox(titrations)(
calculations(including(amount(of(solids,(liquids(
and(gases;(concentration;(volume,(pressure(and(
temperature(of(gases(
the(application(of(chemical(equations(to(
volumetric((and(gravimetric)(analyses(

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23

Key(skills((a(reminder)(
These(skills(include(the(ability(to:(
! conduct(investigations(that(include(collecting,(
processing,(recording(and(analysing(qualitative(
and(quantitative(data;(draw(conclusions(
consistent(with(the(question(under(investigation(
and(the(information(collected;(evaluate(
procedures(and(reliability(of(data(
! construct(questions((and(hypotheses);(plan(and/
or(design,(and(conduct(investigations;(identify(
and(address(possible(sources(of(uncertainty(

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24

Volumetric(analysis(
A(technique(in(which(two(solutions(are(
reacted(together.(
Typically(we(will(be(conducting(an(acidPbase(
reaction,(or(a(redox(reaction.(
Concentration(of(one(solution(must(be(
accurately(known((the(known)(
We(use(a(Primary(standard(to(make(up(a(
standard(solution(in(a(volumetric(or(
standard(@lask.(
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25

What(is(a(Primary(standard?(

Solid(at(room(temp(
Readily(obtainable(in(pure(form(
Known(formula((Does(not(react(with(
atmosphere)(
High(molar(mass((small(amount(has(a(
reasonable(mass(
Cheap(
eg(anhydrous(sodium(carbonate((Na2CO3)(
potassium(hydrogen(phthalate(KH(C8H4O4)(
NOT(NaOH(and(HCl(
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26

Standard(solution(
Made(up(in(standard((volumetric)(@lask(
So(volume(is(known(accurately((
Known(mass(of(solute(is(measured(and(
transferred(into(the(@lask(
Solution(will(have(an(accurately(known(
concentration(with(very(small(error(

amount
Remember:(concentration(=(
volume
Volume(must(be(in(litres!((
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27

Making(a(standard(solution(

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28

Volumetric(Pipette(
Used(to(very(accurately(dispense(a(known(
volume((aliquot)(of(the(standard(solution(
(accurately(known(concentration)(into(a(
conical(@lask.(
Uncertainty(is(usually(0.05mL,(although(
does(change(with(size(of(pipette(

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29

Correct(use(of(pipette

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30

BureDe&
Dispenses(a(volume((titre)(of(the(unknown(
solution((concentration(unknown)(into(the(
aliquot(that(is(already(in(the(conical(@lask.(
Burette(is(graduated,(so(volume(is(
determined(by(difference(between(initial(
reading(and(@inal(reading(
Uncertainty(is(usually(0.02(mL(per(reading,(
so(will(be(0.04(mL(for(one(volume(
delivered.(
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31

Correct(use(of(burette

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32

Titration(
The(addition(of(a(solution(from(the(burette(
into(a(conical(@lask(containing(an(aliquot(is(
called(a(titration.(
If(an(acidPbase(reaction(is(being(
performed,(an(acidPbase(indicator(is(used(
to(determine(the(end(of(the(titration.(

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33

The(end(of(a(titration((
The(equivalence(point(of(a(titration(is(the(
point(at(which(the(exact((stoichiometric)(
amount(of(acid(has(been(added(to(react(
with(the(base(in(the(conical(@lask.(
In(a(titration,(we(aim(to(stop(adding(the(
acid(from(the(burette(at(the(equivalence(
point.(This(is(called(the(end(point(and(is(
determined(by(the(indicator(changing(
colour.(
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34

Indicators(
An(indicator(is(usually(a(weak(acid(which(is(
a(different(colour(in(its(acidic(form(and(its(
basic(form.(
It(can(be(represented(as(HIn((acid(form)(
HIn(aq)((H+(aq)(+(InP(aq)(
((((((((((Colour(1(((((((((((((((colour(2(

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35

Considering(the(reaction:(
Na2CO3(aq)((+(2HCl(aq)((2NaCl(aq)(+((H2O(l)(+(CO2(aq)(
aliquot ((((titre(

The(methyl(orange(indicator(is(yellow(in(the(
sodium(carbonate(solution(because(it(was(in(its(
basic(form((InP)(

InP(aq)((+((H+(aq)(((HIn(aq)(
methyl(orange:yellow (

(pink(

The(HCl(reacted(with(the(sodium(carbonate(until(
none(was(left,(then(it(reacted(with(the(indicator(
which(gained(an(H+(and(turned(into(HIn(
(
This(colour(change(is(the(endpoint(
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36

Accuracy(
The(accuracy(of(volumetric(analysis(is(
obtained(by(repeating(the(titration(until(we(
obtain(3(concordant(results.((
Concordant(results(fall(within(a(range(of(
0.10mL(ie(The(smallest(titre(is(no(more(than(
0.10mL(less(than(the(largest(titre.(

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Non-concordant values

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37

Acid(base(equations(which(MUST(be(
known(
! Acid&+&base&&salt&+&water&

((((((((((((((((((((eg(HCl(aq)(+(NaOH(aq)((NaCl(aq)((+(H2O(l)(
Ionic(equation:((H+((aq)(+(OHP((aq)(((H2O(l)(
(

! Acid&+&carbonate&&&&
& & &&&&&&&&salt&+&water&+&carbon&dioxide&
(((((((((((((((((eg((2HCl(aq)(+(Na2CO3(aq)((2NaCl(aq)(+(CO2(g)(+(H2O(l)(
Ionic(equation:(2H+((aq)(+(CO32P((aq)(((CO2(g)(+(H2O(l)(
(

! Acid&+&hydrogencarbonate&&
&& &&&&&&&&&&&&&&&&&salt&+&water&+&carbon&dioxide&
(((((((((((((((((((eg((HCl(aq)(+(NaHCO3(aq)((NaCl(aq)(+(CO2(g)(+(H2O(l)(
Ionic(equation:(H+((aq)(+(HCO3P((aq)((CO2(g)(+(H2O(l)(
(
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38

Using(titration(results(to(@ind(
concentration(of(unknown.(
1. Average(the(concordant(titres.(This(gives(
you(the(volume(of(solution(that(reacted(
with(the(aliquot.(
2. Use(the(known(concentration(of(the(
standard(solution(and(the(volume(of(the(
pipette((the(aliquot)(to(@ind(the(amount(of(
primary(standard(in(an(aliquot:(n(=(cV(

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3. Use(the(molar(ratio(from(the(equation(for(the(
reaction(to(@ind(the(amount(in(mol(of(acid(that(
reacted(with(the(aliquot(of(standard(solution.(
4. Find(concentration(of(acid(by(dividing(amount(
that(reacted(by(average(volume(of(titre:((
(

(c(=((

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n
V

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40

Sample(exam(question(based(on(a(simple(
titration(
Titration(between(standard(solution(of(HCl(and(NaHCO3.(
100.0(mL(of(1.00M(HCl(solution(was(to(be(diluted(to(0.100M(
in(1.00L(volumetric(@lask,(but(900(mL(of(0.0222M(NaOH(was(
added(instead(of(water.(
(a) Write(the(equation(for(the(reaction(that(occurs(in(the(
volumetric(@lask.(
(b)Calculate(the(concentration(of(the(HCl(in(the(volumetric(
@lask.(Correct(sig(@igs.(
(c) If(contaminated(HCl(is(used(in(the(titration,(will(the(
calculated(concentration(of(HCO3(be(greater(or(smaller(
than(the(true(value.(Justify(your(answer(
(VCAA(June(2009(Question(3)(
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(a)(In(the(volumetric(@lask:(
(((((((((HCl(aq)((+((NaOH(aq)(( NaCl(aq) + H2O(l)
(b) Calculate n(HCl) = cV = 1.00 0.100 = 0.100 mol
n(NaOH)added = cV = 0.0222((0.900 = 0.01998 mol
n(HCl)remaining after reaction = 0.100 0.01998 = 0.08002 mol
n
Concentration =
= 0.08002 M

(c) The(concentration(of(HCl(is(lower(than(we(are(
expecting,(((so(a(greater(volume(of(HCl(will(be(required(to(
react(with(the(NaHCO3.(This(will(make(it(seem(as(though(
the(NaHCO3(is(more(concentrated(than(it(actually(is,(so(the(
calculated(concentration(of(HCO3(will(be(greater(than(it(
actually(is.(
(
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42

Watch this lesson online:


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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Titration Curves

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43

Key(Knowledge(
volumetric(analysis(including(
(determination(of(excess(and(limiting(
reagents(and)(titration(curves:(simple((and(
back)(titrations,(acidPbase((and(redox)(
titrations(

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44

TitraFon&curves&
As(an(acid(is(added(to(a(basic(solution,((or(a(
base(added(to(an(acidic(solution)(the(pH(of(
the(solution(changes.(
As(we(near(the((
(((equivalence(point,((
(((the(pH(changes((
(((more(rapidly.(

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45

A(titration(curve(tells(us((
whether(the(starting(solution(was(an(
acid(or(a(base(AND(whether(it(was(
strong(or(weak((
The(volume(of(the(second(solution(
added(when(neutralisation(occurred(
The(pH(at(the(equivalence(point(

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46

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47

Choice(of(indicator(
Each(different(indicator(has(a(particular(
pH(range(in(which(it(changes(colour.(
Methyl(orange(changes(colour(from((
((((pH(=(3.2(to(4.4.(
This(means(that(it(will(change(colour(
(have(an(endpoint)(near(the(equivalence(
point(of(the(reaction(between(HCl(and(
Na2CO3((a(strong(acid(and(a(weak(base.(

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48

Phenolphthalein(changes(colour(in(the(pH(
range(8.2(P(10.0(making(it(suitable(for(the(
titration(of(a(weak(acid(with(a(strong(base.(
See&data&booklet&table&11&

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49

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50

When(a(strong(acid(is(titrated(with(a(strong(
base,(the(equivalence(point(is(at(pH(=(7.(
Phenolphthalein(can(be(used,(or(even(
methyl(orange,(but(it(might(be(better(to(use(
another(indicator,(such(as(bromothymol(
blue(which(changes(colour(between(6.0(and(
7.6(((

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51

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52

Neutralising&strong&and&weak&acids&
Students(commonly(assume(that(a(strong(
acid(will(require(more(base(to(neutralise(it(
than(a(weak(acid,(but(this(is(NOT(true.(
Consider(the(equations(for(the(reactions:(
HCl(aq)((+((NaOH(aq)( NaCl(aq) + H2O(l)
Strong acid
CH3COOH(aq)((+((NaOH(aq)(
weak acid
CH3COONa(aq) + H2O(l)

Both(demonstrate(a(1:1(ratio(with(NaOH(
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53

Sample(exam(questions((pH(curves(
The(following(titration(curve(was(obtained(by(measuring(the(
pH(in(a(reaction(@lask(during(an(acidPbase(titration(
The(graph(represents(the(change(
in(pH(in(the(reaction(@lask(when(
(
(
(
A. A(weak(acid(is(added(to(a(strong(base(
B. A(weak(base(is(added(to(a(strong(acid(
C. A(strong(acid(is(added(t(a(weak(base(
D. A(strong(base(is(added(to(a(weak(acid.((
VCAA(June(2010(Q1(
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54

Which(one(of(the(following(is(a(suitable(indicator(for(
use(in(this(titration?(
A. Phenol(red(
B. Thymol(blue(
C. Phenolphthalein(
D. Bromophenol(blue((

(
(
(
VCAA(June(2010(Q2(
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55

Sample&exam&quesFon&&FtraFng&strong&and&weak&acids&
Two(titrations(were(performed(as(shown(below(
(
(
(
(
Which(one(of(the(following(statements(is(true?(
A. The(weak(acid(will(require(a(greater(volume(of(NaOH(solution(
than(the(strong(acid(to(reach(the(equivalence(point(
B. The(weak(acid(will(require(a(smaller(volume(of(NaOH(solution(
than(the(strong(acid(to(reach(the(equivalence(point(
C. The(weak(acid(will(require(the(same(amount(of(NaOH(solution(as(
the(strong(acid(to(reach(the(equivalence(point(
D. The(equivalence(point(in(a(titration(of(a(weak(monoprotic(acid(
with(NaOH(solution(cannot(be(determined.(
VCAA(June(2011(Q11(
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56

Watch this lesson online:


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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Back Titrations
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57

Key(Knowledge(
volumetric(analysis(including(
determination(of(excess(and(limiting(
reagents((and(titration(curves):((simple(
and)(back(titrations,(acidPbase(and(redox(
titrations(
calculations(including(amount(of(solids,(
liquids(and(gases;(concentration;((volume,(
pressure(and(temperature(of(gases)(
the(application(of(chemical(equations(to(
volumetric((and(gravimetric)(analyses(
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58

Back(titrations(
The(reaction(between(a(weak(acid(and(a(
weak(base(does(not(give(a(sharp(change(in(
pH(at(the(end(point,(so(there(is(not(a(distinct(
colour(change.(
This(makes(it(impossible(to(perform(a(direct(
titration.(
Instead(a(back(titration(is(used.(
In(a(back(titration(two(reactions(occur,(one(
after(the(other.(
Both(reactions(are(likely(to(be(acidPbase(
reactions.(
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59

1. A(measured(excess(of(a(strong(base(is(added(to(
the(weak(acid(to(make(sure(that(it(all(reacts.(
(Weak&acid&+&strong&base& salt + water
&
2. After(reaction,(the(remaining(strong(base(is(
titrated(with(a(strong(acid.(In(this(way(the(
amount(of(remaining(strong(base(can(be(
accurately(determined.(
(Strong&acid&+&strong&base& salt + water
&
3. Knowledge(of(how(much(strong(base(was(
originally(added(allows(the(calculation:(
(
n(reacting)&=&n(added&initially)&&n(remaining)&
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60

The(distribution(of(added(strong(base(in(a(back(titration(
Amount&of&strong&base&that&
did&not&react&with&the&weak&
acid,&but&was&titrated&later&
with&the&strong&acid&

Amount&of&strong&base&
that&reacted&with&the&
weak&acid&

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Total&
amount&
of&
strong&
base&
added&
initially&

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61

Calculations(associated(with(back(
titrations(
(1)(Total(amount(of(strong(base(added(
initially(=(volume((concentration(
(2)(Amount(of(strong(base(that(did&
not&react(with(the(weak(acid(is(found(
in(the(titration.(
! n(strong(acid)(=(cV(titre)(
! n(strong(base)(=(n(strong(acid)((for(
a(monoprotic(acid((most(common)(
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&

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62

Amount(of(strong(base(that(did&react&with(
the(weak(acid(is(found(by(subtraction:(
n(reacting)&=&n(added&initially)&&n(remaining)&
Amount(of(weak(acid(in(the(original(sample(is(then(
found(from(the(equation(for(the(reaction(between(
the(reacting(strong(base(and(the(original(weak(
acid.(
&

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63

Sample(exam(question((back(
titration(

0.415(g(of(a(pure(acid,(H2X(s)(is(added(to(exactly(100(mL(
of(0.105(M(NaOH(aq).(A(reaction(occurs(according(to:(
H2X(s)((+((2NaOH(aq)(( Na2X(aq) + 2H2O(l)
The NaOH is in excess. This excess NaOH requires 25.21
mL of 0.197M HCl(aq) for neutralisation.
(a) Calculate the amount, in mol, of NaOH that is added to
the acid H2X initially.
(b) Calculate the amount, in mol, of NaOH that reacts with
the acid H2X.
(c) Calculate the molar mass, in gmol-1, of the acid H2X.
VCAA June 2008 Q8(
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64

Answer(
(a) n(NaOH)(=(cV(=(0.105((0.100(=(0.0105&mol&
&
b) NaOH(+(HCl((NaCl(+(H2O(
((((((((EXCESS(NaOH(was(titrated(with(HCl,(so(
n(NaOH)excess(=(n(HCl)(=(0.197((0.02521(=(0.004966(mol(
n(NaOH)reacting(with(H2X(=(0.0105(P(0.004966(=(0.00553&mol&
&
c) (H2X(s)((+((2NaOH(aq)(( Na2X(aq) + 2H2O(l)
((((((so(n(H2X)(=((n(NaOH)(=(0.002767(mol(
((((((0.002767(mol(H2X(has(a(mass(of(0.415g(
((((((so(1(mol(of(H2X(has(a(mass(of( ( 0.415
((((=(150(g(molP1(
0.002767
(
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65

QUESTION 1
1. The graph below shows the change in pH of a reaction solution during a titration of
0.10M NaOH with 0.10M CH3COOH

A suitable indicator for the titration and the colour change observed is

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Indicator

Colour change

A. Methyl red

Yellow to red

B. Methyl red

Red to yellow

C. Phenolphthalein

Colourless to red

D. Phenolphthalein

Red to colourless

(VCAA
Q4 June
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66

QUESTION 1 (ANSWER)
1. The graph below shows the change in pH of a reaction solution during a titration of
0.10M NaOH with 0.10M CH3COOH

A suitable indicator for the titration and the colour change observed is

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Indicator

Colour change

A. Methyl red

Yellow to red

B. Methyl red

Red to yellow

C. Phenolphthalein

Colourless to red

D. Phenolphthalein

Red to colourless

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67

Phenolphthalein suits this titration best because the equivalence point is at approximately pH
= 9. Phenolphthalein changes colour (according to the data book) between pH = 8.3 and
10.0, so would suit this equivalence point. The titration starts at a high pH, when
phenolphthalein is red and then it would become colourless.
(VCAA Q4 June 2008)

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68

QUESTION 2
2. 20.0 mL of 0.10 M hydrochloric acid (HCl) reacts with 20.0 mL of 0.30 M
potassium hydroxide (KOH) solution.
The concentration of potassium ions in the resultant solution, in mole per litre, is

A. 0.10
B. 0.15
C. 0.20
D. 0.30

(VCAA June 2005 Q 13)


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69

QUESTION 2 (ANSWER)
2. 20.0 mL of 0.10 M hydrochloric acid (HCl) reacts with 20.0 mL of 0.30 M
potassium hydroxide (KOH) solution.
The concentration of potassium ions in the resultant solution, in mole per litre, is

A. 0.10
B. 0.15
C. 0.20
D. 0.30

(VCAA June 2005 Q 13)


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70

n(KOH) = 0.30 0.0200 = 0.0060 mol


total volume of solution = 40.0 mL = 0.0400 L
c(K+) ions =

0.0060
= 0.15 molL-1
0.04

Note that the fact that the HCl reacts with the KOH has nothing to do with the final
concentration of K+ ions.

(VCAA June 2005 Q 13)

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71

QUESTION 3
3. Sulfuric acid (H2SO4) and nitric acid (HNO3) are both strong acids. Ethanoic acid
(CH3COOH) is a weak acid.
20.00 mL solutions of 0.10 M concentration of each of these three acids were
separately titrated with a 0.10 M solution of sodium hydroxide (NaOH).
In order to react completely

A. All three acids would require the same amount of NaOH


B. HNO3 would require more NaOH than CH3COOH but less than H2SO4.
C. H2SO4 and HNO3 would require the same amount of NaOH but CH3COOH would
require less.
D. CH3COOH and HNO3 would require the same amount of NaOH but H2SO4 would
require more.
(VCAA June 2006 Section A Q5)
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72

QUESTION 3 (ANSWER)
3. Sulfuric acid (H2SO4) and nitric acid (HNO3) are both strong acids. Ethanoic acid
(CH3COOH) is a weak acid.
20.00 mL solutions of 0.10 M concentration of each of these three acids were
separately titrated with a 0.10 M solution of sodium hydroxide (NaOH).
In order to react completely

A. All three acids would require the same amount of NaOH


B. HNO3 would require more NaOH than CH3COOH but less than H2SO4.
C. H2SO4 and HNO3 would require the same amount of NaOH but CH3COOH would
require less.
D. CH3COOH and HNO3 would require the same amount of NaOH but H2SO4 would
require more.

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73

H2SO4 is a diprotic acid, so it is not the strength of the acid, but its proticity that matters
here. For every one mol of H2SO4 reacting, two mol of NaOH would be required, while for
every one mol of CH3COOH or HNO3 reacting, only one mol of NaOH would be required.
Note that the fact that CH3COOH is a weak acid does not have any bearing on the acid.
Equal mol of strong or weak acids react with equal mol of NaOH.

(VCAA June 2006 Section A Q5)

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74

QUESTION 4(a)
4.(a) The hydrogen carbonate ion, (HCO3-) can act both as an acid and as a
base.
i. Write a chemical equation that shows HCO3- acting as an acid when it reacts with water.
ii. Write a chemical equation that shows HCO3- acting as an base when
water.

it reacts with
(2 marks)

Please write down your answer on a piece of paper. We will show you the answer
in the next section.

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(VCAA June 2006 Q5 Parts [a] and [c][i])

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75

QUESTION 4(a) (ANSWER)


4.(a) The hydrogen carbonate ion, (HCO3-) can act both as an acid and as a
base.
i. Write a chemical equation that shows HCO3- acting as an acid when it reacts with water.
HCO3-(aq) + H2O(l)
CO32-(aq) + H3O+(aq)
Note that when HCO3- is acting as an acid, it will donate an H+ to the water.
ii. Write a chemical equation that shows HCO3- acting as an base when
water.
HCO3-(aq) + H2O(l)
H2CO3(aq) + OH-(aq)

it reacts with

Note that when HCO3- is acting as an base, it will accept an H+ from the water.
(2 marks)

(VCAA June 2006 Q5 Parts [a] and [c][i])


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76

QUESTION 4(b)
4(b). The hydrogen ion concentration of a solution is described by the term pH. The
hydroxide ion concentration is described in the same way by the term pOH.
A solution has a pOH of 3 at 25C.

i. Calculate the hydroxide ion concentration of the solution in mol L-1

(VCAA June 2006 Q5 Parts [a] and [c][i])


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77

QUESTION 4(b) (ANSWER)


4(b). The hydrogen ion concentration of a solution is described by the term pH. The
hydroxide ion concentration is described in the same way by the term pOH.
A solution has a pOH of 3 at 25C.

i. Calculate the hydroxide ion concentration of the solution in mol L-1


Answer : 0.001 M
If pOH is described in the same way as pH (pH = -log[H3O+]), then pOH = -log[OH-]
So [OH-] = 10-pOH
= 10-3 = 0.001 M

(VCAA June 2006 Q5 Parts [a] and [c][i])


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78

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/chemical-analysis-vol-analysis-oxidation-numbers/key-knowledge/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Oxidation Numbers and Partial Ionic Equations

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79

79

Key(Knowledge(
volumetric(analysis(including(determination(of(
excess(and(limiting(reagents((and(titration(
curves):((simple(and(back(titrations,(acidPbase)(
and(redox(titrations(
calculations(including(amount(of(solids,(liquids(
and(gases;(concentration;((
the(writing(of(balanced(chemical(equations,(
including(the(use(of(oxidation(numbers(to(write(
redox(equations,(and(the(application(of(chemical(
equations(to(volumetric((and(gravimetric(
analyses)(
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80

80

Redox(reactions(
A(redox(reaction(involves(the(transfer(of(
electrons(from(a(reductant(to(an(oxidant.(
Reductants(are(usually(metals(eg(Mg,(Zn(or(nonP
metal(anions(eg(ClP,(BrP(
Oxidants(are(usually(nonPmetals(eg(Cl2,(O2(or(
metal(cations(eg(Cu2+,(Ag+(
A(redox(reaction(usually(results(in(the(formation(
of(an(ionic(compound.(

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81

81

Oxidation(is(the(loss(of(electrons(
An(oxidation(half(equation(has(electrons(on(
the(right(
Reductants(undergo(oxidation(
Mg((Mg2+(+(2eP(
(
Reduction(is(the(gain(of(electrons(
A(reduction(half(equation(has(electrons(on(
the(left(
Oxidants(undergo(reduction(
O2(+((4eP(((2O2P(
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82

82

Overall(equations(
An(oxidation(reaction(cannot(occur(without(
a(reduction(reaction(
When(two(half(equations(are(combined(the(
electrons(must(be(balanced(on(both(sides(of(
the(equation((no(left(over(electrons.(

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83

83

Oxidation(numbers(
Oxidation(numbers(are(used(to(judge(
whether(a(substance(is(undergoing(
reduction(or(oxidation.(
Follow(the(rules(to(assign(oxidation(
numbers((
While(oxidation(numbers(are(manPmade(
they(represent(the(charge(that(would(
appear(if(the(element(were(to(completely(
lose((or(gain)(electrons,(rather(than(just(
sharing(in(a(covalent(bond.(
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84

84

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85

85

! An(increase(in(oxidation(number(during(a(
chemical(reaction(indicates(that(the(substance(
has(been(oxidized.(
! A(decrease(in(oxidation(number(indicates(that(
the(substance(has(been(reduced.(
! eg((Fe(s)((+((Cu2+(aq)(((Fe2+(aq)((+((Cu(s)(
ONs(((0((((((((((((+2(((((((((((((((((((+2((((((((((((((((0(
(
Fe(has(increased(from(0(to(+2((has(been(
oxidised)(
Cu(has(decreased(from(+2(to(0((has(been(
reduced)(
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86

86

Sample(exam(question((oxidation(
numbers(
The(equation(for(a(reaction(that(occurs(during(the(
extraction(of(iron(from(iron(ore(is(
Fe2O3(s)((+((3CO(g)((((2Fe(l)((+((3CO2(g)(
(
During(this(reaction(the(oxidation(number(of(iron(changes(
from(
A. +(3(to(0,(and(CO(is(the(reductant(
B. +6(to(0,(and(CO(is(the(reductant(
C. +3(to(0(and(CO(is(the(oxidant(
D. +6(to(0(and(CO(is(the(oxidant(
VCAA(June(2006(Q14(
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87

87

Balancing(partial(ionic(equations(
Some(half(equations(are(not(as(simple(as(
((((Fe2+((+((2eP((((Fe(
They(may(involve(oxygen(atoms,(such(as(
when(H2SO4(is(reduced(to(form(H2S(
In(this(case(a(special(method(is(used(to(
balance(the(equation(

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88

88

Step&

Example&
ReducFon&of&Cr2O72B&to&Cr3+(

Balance&all&atoms&except&O&
and&H(

Cr2O72B&&&&&&&&&&Cr3+&
(

Balance&O&atoms&using&&
H2O(

Cr2O72B&&&&&&&&&&Cr3+&
(

Balance&H&atoms&using&&
H+(

Cr2O72B&&&&&&&&&&&&&&&&Cr3+&
(

Balance&charge&using&
electrons(

Cr2O72B&&&&&&&&&&&&&&&&&&&&&&&Cr3+&
(

Add&state&symbols(

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89

89

Sample(exam(question((balancing(
partial(ionic(equations&
When(this(half(equation(is(balanced(
correctly,((

VO2+(aq)(+(xH2O(l)((VO3P(aq)(+(yH+(aq)(+(zeP(

the(coef@icients,(x,(y(and(z(are(equal(to(
A. 1,(2,(4(
B. 2,(4,(1(
C. 2,(4,(2(
D. 3,(6,(2(
&

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90

VO2+(aq)(+(_H2O(l)((VO3P(aq)(+(_H+(aq)(+(_eP(
(

Balance(oxygen(using(H2O(
Balance(hydrogen(using(H+(
Balance(charge(using(eP(
The(answer(is(B(

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91

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/chemical-analysis-vol-analysis-redox-titrations/how-does-a-redoxtitration-differ/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Redox Titrations

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92

How(does(a(redox(titration(differ(to(an(
acidPbase(titration?(
Often(an(indicator(is(not(required(because(
the(reactant(and(product(have(different(
colours(
eg(Cr2O72P(is(orange(while(Cr3+(is(green(
In(other(redox(titrations(an( indicator (
such(as(starch(solution(is(added(near(the(
end(point.(It(will(react(with(the(excess(
titrant.(
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93

What(sort(of(reactants(can(be(analysed(
using(a(redox(titration?(
Sulfur(dioxide(P(a(preservative(used(in(wine:(
titrate(with(iodine(solution(
Ethanol((major(component(of(wine:(titrate(
with(thiosulfate(solution(after(reaction(with(
excess(dichromate(
Vitamin(C((in(fruit(juices:(titrate(with(iodine(
solution(

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94

Sample(exam(question((redox(titrations(
The(amount(of(iron(in(an(aluminium(alloy(is(to(be(
determined.(80.50(g(of(alloy(is(dissolved(in(HCl(and(iron(
atoms(convert(to(Fe2+((aq)(ions.(This(solution(is(transferred(
to(a(250.0(mL(volumetric(@lask(and(made(up(to(mark.(20.00(
mL(aliquots(of(this(solution(are(titrated(against(0.0400(M(
KMnO4(solution.(
5Fe2+(aq)(+(MnO4P(aq)(+(8H+(aq)((5Fe3+(aq)(+(Mn2+(aq)(+(4H2O(l)(

Four(titrations(were(carried(out:(
(
Titra:on'number'
1'
(
Vol&of&KMnO4&(mL)&
22.03&

2'

3'

4'

20.25&

21.97&

21.99&

VCAA((June(2010(Q1(
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95

(a)(Write(a(balanced(halfPequation,(including(states,(for(the(
conversion(of(MnO4P(in(an(acidic(solution(to(Mn2+(ions.(
Answer:((MnO4P((((((((((((((((((((((((((((((((((((((Mn2+(
(
(b)(Calculate(the(average(volume,(in(mL,(of(the(concordant(
titres(of(the(KMnO4(solution(
Answer:(20.25(mL(is(not(concordent,(so(do(not(include(in(
average(
Average(=((22.03(+(21.97(+(21.99)/3(=(22.00(mL(
(c)((Use(your(answer(to(part((b)(to(calculate(the(amount,(in(
mol,(of(MnO4P((aq)(ions(used(in(this(titration.(
Answer:(n(=(cV(=(0.0400((0.02200(=(8.80((10P4(mol(
(
(
(
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(

96

(d)((Calculate(the(amount,(in(mol,(of(Fe2+(ions(present(in(
the(250.0(mL(volumetric(@lask(
Answer:(n(Fe2+)(in(20.00(mL(=(5((n(MnO4P)(=(5((8.80((
10P4(=(4.40(10P3(mol(
250.0
n(Fe2+)(in(250.00(mL(=(4.40(10P3(( (=(0.0550(mol(
20.00
(
(e)((Calculate(the(percentage(by(mass,(of(iron(in(the(80.50(g(
sample(of(alloy.(Express(your(answer(to(the(correct(
number(of(signi@icant(@igures.(
Answer:(m(Fe)(=(n(Fe2+)((55.8(=(0.0550((55.8(=(3.069g(
100
%Fe(=(3.069((((((((((=(3.81%(

80.50 1
(
(Note(that(the(current(data(book(gives(Ar(Fe)(to(be(55.8,(
whereas(in(2010(it(was(given(as(55.9)(
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97

QUESTION 1&
Which one of the following is least likely to be a product of a redox reaction
between sulphuric acid and zinc metal?
A. H2
B. H2S
C. SO2
D. SO3

(VCAA Q9 June 2007)

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98

QUESTION 1&
Which one of the following is least likely to be a product of a redox reaction
between sulphuric acid and zinc metal?
A. H2
B. H2S
C. SO2
D. SO3

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99

The correct answer is D


Before you do anything, consider the oxidation number of S in sulfuric acid and of Zn:
S in H2SO4 oxidation number is +6 this is the highest oxidation number that S can have (is
equivalent to the S atom losing all 6 electrons in its valence shell). Since the oxidation number
must change in a redox reaction, this means that the oxidation number of S must be less than
+6 in the products. (reduction)
Oxidation number of Zn is 0. Its oxidation number must increase in the reaction (oxidation).
Also a standard reaction that should be known is acid + reactive metal
gas

salt + hydrogen

We are looking for the least likely answer:


A. is quite likely (see standard reaction above)
B. oxidation number of S is -2. This is possible (S has been reduced)
C. oxidation number of S is + 4. This is also possible
D. oxidation number of S is +6. The S has not been reduced, therefore this cannot be the
result of a redox reaction.

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100

QUESTION 2&
When solid sodium hydride, NaH, is added to water, the hydride ion reacts
according to the following equation.
H-(aq) + H2O(l)
OH-(aq) + H2(g)
This reaction can be classified as
A. Acid-base only
B. Oxidation-reduction only
C. Both acid-base and oxidation-reduction
D. Neither acid-base nor oxidation-reduction

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101

QUESTION 2 (ANSWER)&
When solid sodium hydride, NaH, is added to water, the hydride ion reacts
according to the following equation.
H-(aq) + H2O(l)
OH-(aq) + H2(g)
This reaction can be classified as
A. Acid-base only
B. Oxidation-reduction only
C. Both acid-base and oxidation-reduction
D. Neither acid-base nor oxidation-reduction

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102

The correct answer is C.


With any question of this sort, the first thing you do is check oxidation numbers. If they change,
then you have a redox reaction. After that you can look for transfer of H+ ions.
Oxidation numbers: -1
+1 -2
-2 +1
H-(aq) + H2O(l)
OH-(aq) + H2(g)

The oxidation number of O has not changed, but that of H has changed from -1 to 0 (oxidation)
and from +1 to 0 (reduction), so this is a redox reaction.
Also, an H+ ion has been transferred from H2O to H- forming the OH- (conjugate base of H2O)
and H2 (conjugate acid of H-), so this is also an acid-base reaction.

(VCAA Q7 June 2009)

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103

QUESTION 3&
In the following four substances, H2S2O7, N2O5, HIO3, Cl2O7, the atom with the
highest oxidation number is

A. I
B. S
C. N
D. Cl

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104

QUESTION 3 (ANSWER)&
In the following four substances, H2S2O7, N2O5, HIO3, Cl2O7, the atom with the
highest oxidation number is
A. I
B. S
C. N
D. Cl

The correct answer is D


Calculate the oxidation number of each of the four atoms in the four molecules
H2S2O7 oxidation number of S: (2 +1) + 2x + (7-2) = 0, 2x = +12, x = +6
N2O5 oxidaton number of N: 2x + (5-2) = 0, 2x = +10, x = +5
HIO3

oxidation number of I: +1 + x + (3 -2) = 0, x = +5

Cl2O7 oxidation number of Cl: 2x + (7 -2) = 0, x = +7


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105

QUESTION 4(a)
For quality control, a chemist analyses the vitamin C (molecular formula C6H8O6)
content of a new brand of fruit juice. The reaction used is an oxidation-reduction
reaction in which I3- is the oxidant and vitamin C is the reductant.
The reaction is C6H8O6(aq) + I3-(aq)
C6H6O6(aq) + 2H+(aq) + 3I-(aq)
The half equation for the reduction of I3- to I- is I3-(aq) + 2e3I-(aq)

(a) Give the half reaction for the oxidation of vitamin C.

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106

QUESTION 4(a)
For quality control, a chemist analyses the vitamin C (molecular formula C6H8O6)
content of a new brand of fruit juice. The reaction used is an oxidation-reduction
reaction in which I3- is the oxidant and vitamin C is the reductant.
The reaction is C6H8O6(aq) + I3-(aq)
C6H6O6(aq) + 2H+(aq) + 3I-(aq)
The half equation for the reduction of I3- to I- is I3-(aq) + 2e3I-(aq)

(a) Give the half reaction for the oxidation of vitamin C.

(1 mark)

We have two equations to work with


The overall equation: C6H8O6(aq) + I3-(aq)
C6H6O6(aq) + 2H+(aq) + 3I-(aq)
The reduction equation: I3-(aq) + 2e3I-(aq)
The oxidation equation is found by subtraction of the reduction equation from the overall
equation: C6H8O6(aq)
C6H6O6(aq) + 2H+(aq) + 2eQuick check this is an oxidation equation because the electrons are on the RHS (lost)

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107

QUESTION 4(b)i
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(i) Calculate the amount of I3- present in the average titre, in mole.

(1 mark)

Note: Please follow this specific format while entering your answer:
For example, if your answer is 10.5 x 10-10, enter it as 10.50*10^(-10)
Please do not leave any spaces.
Enter ^ by holding [shift] and pressing the 6 at the top of your keyboard.
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108

QUESTION 4(b)i (ANSWER)


A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(i) Calculate the amount of I3- present in the average titre, in mole.

(1 mark)

n(I3-) = cV (concentration of solution volume of average titre)


= 2.00 10-4 0.01565
= 3.13 10-6 mol in the average titre

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109

QUESTION 4(b)ii
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(ii) Calculate the amount, in mole, of vitamin C present in each 25.00 mL


aliquot.

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110

QUESTION 4(b)ii (ANSWER)


A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(ii) Calculate the amount, in mole, of vitamin C present in each 25.00 mL


aliquot.

(1 mark)

25.00 mL aliquots were titrated, so n(vitamin C) in 25.00 mL aliquot can be calculated


using the equation for the reaction and the amount of I3- in the average titre.
Molar ratio C6H8O6(aq) : I3-(aq)
1
: 1
n(C6H8O6)in 25.00 mL = n(I3-) = 3.13 10-6 mol

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111

QUESTION 4(b)iii
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(iii) Calculate the concentration of vitamin C in the original (undiluted)


sample of fruit juice in mole per litre.
(2 marks)

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112

QUESTION 4(b)iii (ANSWER)


A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.

(iii) Calculate the concentration of vitamin C in the original (undiluted)


sample of fruit juice in mole per litre.
(2 marks)

n(C6H8O6)in 250.0 mL = 3.13 10-6 = 3.13 10-5


This is the same amount of vitamin C in the original 20.00 mL of orange juice,
So, c(vitamin C) = in the original sample of fruit juice.

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113

QUESTION 4(c)
During the analysis the chemist rinsed, but did not dry, each item of glassware.
She had available for use: pure water, the original fruit juice, the diluted fruit
juice and the standard I3- solution. For each item listed below, name the liquid
that should be used to rinse it by placing a tick in the appropriate box.
(4 marks)

Pure Water

Original Fruit
Juice

Diluted Fruit
Juice

Standard I3Solution

20.00 mL
pipette
250.00mL
Volumetric
Flask
25.00mL
pipette
Conical Flask
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114

QUESTION 4(c) (ANSWER)


During the analysis the chemist rinsed, but did not dry, each item of glassware.
She had available for use: pure water, the original fruit juice, the diluted fruit
juice and the standard I3- solution. For each item listed below, name the liquid
that should be used to rinse it by placing a tick in the appropriate box.
(4 marks)

Pure Water
20.00 mL
pipette
250.00mL
Volumetric
Flask

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Diluted Fruit
Juice

Standard I3Solution

25.00mL
pipette
Conical Flask

Original Fruit
Juice

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115

QUESTION 5 (i)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(i)

Calculate the oxidation number of iodine in the IO4-(aq) ion.

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116

QUESTION 5 (i) (ANSWER)


One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(i)

Calculate the oxidation number of iodine in the IO4-(aq) ion.

(1 mark)

Oxidation number of I in IO4-(aq): x + (4 -2) = -1, x = +7

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117

QUESTION 5 (ii)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(ii) Give a half equation for the conversion of IO4-(aq) into IO3-(aq) in acid solution.
(1 mark)
Note: please follow this specific format while entering your answer:
Please do not leave any spaces.
If your answer is AAB+(I) + CCD-(aq) + 3-> EEF+(I) + GGH-(aq)
Please enter AAB(+)(I)+CCD(-)(aq)+3->EEF(+)(I)+GGH(-)(aq)
To make the arrow enter a hyphen (next to 0, at the top of the keyboard)
and then a greater than sign ([shift]+the second key right from M)
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118

QUESTION 5 (ii) (ANSWER)


One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(ii) Give a half equation for the conversion of IO4-(aq) into IO3-(aq) in acid solution.
(1 mark)
IO4-(aq) + 2H+(aq) + 2e- IO3-(aq) + H2O(l)
Balance Oxygens on LHS with water on RHS,
Balance Hydrogens on RHS with H+ on LHS,
Balance charge (+1 on LHS and -1 on RHS) with electrons

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119

QUESTION 5 (iii)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(iii) Is the IO4-(aq) ion acting as an oxidant or reductant? Explain your choice.
(1 mark)

Note: please only enter oxidant or reductant.


We recommend you write your explanation down on some paper or in a document
before you check your answer.
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120

QUESTION 5 (iii) (ANSWER)


One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).

(iii) Is the IO4-(aq) ion acting as an oxidant or reductant? Explain your choice.
(1 mark)
IO4- is reduced in the above half equation (it gains electrons), so it is the oxidant. This is
because it causes the other reactant to be oxidised and the IO4- is reduced.

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121

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Chromatography
General Features and TLC

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122

Key(Knowledge:(
Principles(and(applications(of(chromatographic(
techniques((excluding(features(of(instrumentation(
and(operation),(and(interpretation(of(qualitative(and(
quantitative(data(from:(
(thin(layer(chromatography((TLC),(including(
calculation(of(Rf(
high(performance(liquid(chromatography((HPLC)(
gas(chromatography((GC)(including(Rt(and(the(use(
of(a(calibration(graph(to(determine(amount(of(
analyte.(
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123

General(features(of(chromatography(
A(technique(which(is(used(to(separate(parts(
of(a(mixture.(
There(are(always(two(phases((the(
stationary(phase(and(the(mobile(phase.(
Stationary(phase(does(not(move.((is(usually(
a(solid,(but(may(be(a(viscous(liquid(coated(
on(beads.((
Mobile(phase(is(a(liquid(or(gas(which(moves(
over(the(stationary(phase(
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124

Why(does(separation(occur?(
Components(have(different(structures,(so(
are(capable(of(different(degrees(of(
intermolecular(bonding(
Separation(occurs(due(to(the(difference(
in(solubility(in(the(mobile(phase(and(
difference(of(adsorption(to(stationary(
phase(of(the(components(of(the(mixture(

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125

How(does(it(work?(
Sample(is(placed(at(the(origin(
(on(the(stationary(phase)(
(
The(mobile(phase(is(added(
and(the(sample(starts(to(
move(along(the(stationary(
phase(as(the(mobile(phase(
moves((
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126

The(different(components(separate(as(
they(adsorb(onto(the(stationary(phase(
and(desorb(back(into(the(mobile(phase.(

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127

Thin(layer(chromatography((TLC)(
Stationary(phase((glass(or(plastic(
plate(with(thin(layer(of(aluminium(
oxide(powder(on(the(plate(
Mobile(phase((a(solvent(that(will(
dissolve(the(sample.((
eg(water,(NaCl(aq)(or(a(mixture(of(two(or(
more(liquids(eg(methylated(spirits(and(
acetone.(
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128

Interpreting(chromatograms(
A(chromatogram(is(the(pattern(of(bands(or(
spots(formed(on(the(plate.(
Each(component(of(the(mixture(travels(a(
different(distance(along(the(plate(or(paper.(
When(the(chromatogram(is(dried/
developed(a(spot(or(line(is(present(to(
represent(the(component.((

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129

Rf(values((Rf(=(retention(factor)(
Two(distances(are(measured(from(the(
origin:(
The(distance(that(the(solvent(has(travelled(
The(distance(that(the(component(has(
travelled(

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130

Qualitative(use(of(Rf(values(
The(Rf(value(is(used(
to(identify(a(
component(by(
comparing(it(to(Rf((
(((values(of(known((
(((substances(under((
((the(same(conditions.(

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131

TLC(Sample(exam(question(
1. Consider(the(following(TLC(plate(of(compounds,(X,(
Y(and(Z(developed(using(a(suitable(mobile(phase(on(
a(polar(stationary(phase(

(((((((The(Rf(value(of(the(most(polar(component(in(this((((
(((((((TLC(separation(is(
A.(0.29 (B.(0.62( (C.(0.78( (D.(0.80(
(VCAA(June(2010(Q6)(
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132

Answer(
A.((
The(most(polar(component(will(have(the(strongest(
attraction(to(the(stationary(phase,(so(will(have(the(
smallest(Rf(value.((
Spot(X(has(travelled(the(smallest(distance(and(its(
Rf(value(is(0.80/2.75(=(0.29(

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133

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Chromatography
HPLC and GLC

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134

Column(chromatography(
(The(basis(for(HPLC(and(GLC)(
In(the(simplest(form,(column((
(chromatography(is(carried((
(out(in(the(laboratory(
(in(a(glass(column(packed((
(with(a(solid(such(as((
(alumina,(Al2O3.(

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135

HPLC(
Separation(occurss(
in(a(short(column(
Stationary(phase:(
(very(@ine(solid((
(particles(tightly(
packed(eg(silica((
Mobile(phase:(liquid(under(high(pressure(to(
force(its(way(through(the(solid(
&

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136

The&Chromatogram&
Rt - retention time - determines sample identity
Rt

Rt
mAU

Area or height is
proportional to the
quantity of analyte.

Injection
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time
137

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137

HPLC(Applications((
HPLC(is(very(sensitive!(

Bioscience

Chemical

proteins
peptides
nucleotides

polystyrenes
dyes
phthalates

Pharmaceuticals

tetracyclines
corticosteroids
antidepressants
barbiturates

Consumer Products
lipids
antioxidants
sugars

Environmental
Clinical

polyaromatic hydrocarbons
Inorganic ions
herbicides
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amino acids
vitamins
homocysteine

138

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138

HPLC(Sample(exam(question(
HPLC(uses(a(nonPpolar(stationary(phase(together(
with(a(polar(mobile(phase.(Which(of(the(following(
molecules(will(have(the(greatest(retention(time(on(
such(a(column?(

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((VCAA(June(2009(Q(5)(
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139

Answer((
The(answer(is(A(
Molecules(B,(C(and(D(are(all(polar.(To(see(this(
observe(the(OH(and(NH(groups(on(the(
hydrocarbon(chain(of(the(molecules.(
A(nonPpolar(molecule(will(have(the(greatest(
attraction(to(the(stationary(phase,(so(will(take(the(
longest(time(to(move(along(the(column(=(greatest(
retention(time.(

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140

GC(
Sample(and(the(solvent(it(is(dissolved(in(
must(be(volatile(as(they(are(heated(in(an(
oven(
Mobile(phase:(
(((Inert(gas(
Stationary(phase:(
((((porous(beads((
((((coated(with((
((((high(bpt(liquid(
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141

Most(sensitive(of(all(chromatography(
techniques(
Used(for(testing(urine(samples(for(drugs(
Compounds(must(be(able(to(be(vaporised(
without(decomposing((usually(low(
molecular(mass(<500(g(molP1(samples)(

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142

SeparaFon&of&mixture&
Sample(passes(along(column(with(mobile(
phase(
Passes(in(and(out(of(solution(in(stationary(
phase(
Component(which(is(least(soluble(in(
stationary(phase(will(be(eluted(@irst((moves(
quickest(along(column)(
As(components(are(eluted(they(are(detected(
by(@lame(ionisation(detector.(
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143

Chromatogram(
A(graph(with(peaks(which(correspond(to(
components(of(mixture(
Retention(time(=(time(taken(for(component(
to(pass(through(column(

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144

Quantitative(use(of(GC(
Run(a(series(of(standards(of(known(
concentration(under(the(same(
conditions(as(the(sample.(
The(area(under(the(peak(is(proportional(
to(the(amount(of(the(substance(present.(
Draw(a(calibration(graph(to(link(area(
under(peak(to(concentration(
Find(sample(concentration(using(graph.(
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145

145

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146

146

GC(Sample(exam(questions(&
1.Analysis(of(the(components(of(a(mixture(using(gasP
liquid(chromatography(normally(involves(measuring(
the(
(((((A.((Rf(values(of(components(using(a(gas(as(the(mobile((
phase(
(((((B.(Rf(values(of(components(using(a(liquid(as(the(mobile(
phase(
(((((C.((Retention(times(of(components,(using(a(gas(as(the(
mobile(phase.(
(((((D.(Retention(times(of(components,(using(a(liquid(as(the(
mobile(phase.(
( ( ( ((VCAA(June(2007(Q71)(
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us!
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147

2. This(diagram(shows(the(gas(chromatogram(of(a(sample(
containing(4(straight(chain(alkanes.(Which(of(the(
statements(that(follow(are(true?(

I.

The(boiling(points(of(the(compounds(arranged(from(
highest(to(lowest(are(Z>Y>X>W(
II. The(retention(times(will(stay(the(same(if(the(temperature(
at(which(the(chromatogram(is(recorded(is(increased(and(
all(other(conditions(remain(constant.(
III. Hydrogen(gas(could(have(been(used(as(a(carrier(gas(to(
obtain(this(chromatogram.(((((((((((((((((VCAA(June(2009(Q6)(
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148

148

Answers(
1. C(is(the(answer(
Rf(values(are(used(for(TLC(and(paper(
chromatography,(while(retention(times(are(used(for(
columnPbased(chromatography.(In(GC,(the(mobile(
phase(is(a(gas.(
2. Statements(I(and(III(are(correct(
Changing(the(temperature(will(change(the(retention(
time(of(all(of(the(alkanes(

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149

149

QUESTION 1
A student used paper chromatography to separate two components, I and II, in a
solution. A spot of the solution was initially placed at the origin. When the spot
corresponding to component I (Rf = 0.50) had advanced 4.0 cm, the spot
corresponding to component II was 1.0 cm behind. The Rf value of component II is
closest to
A. 0.68
B. 0.38
C. 0.25
D. 0.13
(VCAA Q6 June 2006)

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150

QUESTION 1 (ANSWER)
A student used paper chromatography to separate two components, I and II, in a
solution. A spot of the solution was initially placed at the origin. When the spot
corresponding to component I (Rf = 0.50) had advanced 4.0 cm, the spot
corresponding to component II was 1.0 cm behind. The Rf value of component II is
closest to A. 0.68
B. 0.38
C. 0.25
D. 0.13
The answer is alternative B
First we need to calculate the distance that the solvent had travelled.
Since Rf
We can calculate that the distance travelled by the solvent
So now we can find the Rf of component II which travelled only 3.0 cm =
(1.0 cm behind component I)
Rf =

3.0 = 0.375=0.38 (to 2 sig figs)


8.0

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4.0
= 8.0cm
0.50
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151

QUESTION 2
Chromatogram 1 was obtained by analysis of a sample of a mixture of two sugars,
A and B, using high performance liquid chromatography (HPLC). Chromatogram 2
was obtained by analysing another sample of the same mixture by HPLC under
different conditions.
Consider the following changes, which could be made to the operating conditions
for HPLC.
I
decreasing the pressure of the mobile phase
II
decreasing the temperature
III
using a less tightly packed column
Which of the changes would be most likely to produce chromatogram 2?
A. I only
B. II only
C. III only
D. I and II only

(VCAA Q5 June 2007)


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152

QUESTION 2 (ANSWER)
Chromatogram 1 was obtained by analysis of a sample of a mixture of two sugars,
A and B, using high performance liquid chromatography (HPLC). Chromatogram 2
was obtained by analysing another sample of the same mixture by HPLC under
different conditions.
Consider the following changes, which could be made to the operating conditions
for HPLC.
I
decreasing the pressure of the mobile phase
II
decreasing the temperature
III
using a less tightly packed column
Which of the changes would be most likely to produce chromatogram 2?

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153

A. I only
B. II only
C. III only
D. I and II only

The answer is alternative C (III only).


The retention times in chromatogram 1 are greater than those in chromatogram 2, so
changes which slow the progress of the mixture will result in chromatogram 1 and those
that speed it up will result in chromatogram 2.
Decreasing the pressure of the mobile phase will slow down the progress of the
components through the column, so this will match chromatogram 1, not 2
Decreasing the temperature of the column will also slow down the progress of the
components (chromatogram 1)
Using a less tightly packed column will allow the components to move more quickly
through the column so this will result in chromatogram 2.
(VCAA Q5 June 2007)
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154

QUESTION 3
Consider the following TLC plate of compounds X, Y and Z developed using a
suitable mobile phase on a polar stationary phase.
The Rf value of the most polar component in this TLC separation is:

A. 0.29
B. 0.62
C. 0.78
D. 0.80

(VCAA Q6 June 2010)

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155

QUESTION 3 (ANSWER)
Consider the following TLC plate of compounds X, Y and Z developed using a
suitable mobile phase on a polar stationary phase.
The Rf value of the most polar component in this TLC separation is:
A. 0.29
B. 0.62
C. 0.78
D. 0.80
The answer is alternative A
The question states that the stationary phase is polar, so the most polar component will
have the greatest attraction to the stationary phase and will take the longest to move
along the TLC plate. It will have the smallest Rf value.
It is component X that travels only 0.80 cm (BUT this is not its Rf)
Rf
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156

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Atomic Absorption Spectroscopy

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157

Key(Knowledge(
Principles(and(applications(of(spectroscopic(
techniques((excluding(features(of(instrumentation(
and(operation),(and(interpretation(of(qualitative(
and(quantitative(data(from:(
! atomic(absorption(spectroscopy((AAS)(including(
electron(transitions(and(use(of(calibration(graph(
to(determine(amount(of(analyte(
! visible(and(ultraviolet(spectroscopy((visiblePUV)(
including(electron(transitions(and(use(of(
calibration(graph(to(determine(amount(of(analyte(
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158

The&electromagnetic&spectrum(

Radiation(in(the(electromagnetic(spectrum(
has(a(range(of(differing(energies.(
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159

Wavelength&and&energy&
!Wavelength(is(the((
distance(between((
adjacent(crests(of(the((
electromagnetic(wave(
!The(shorter(the(wavelength,(the(greater(its(
energy(
hc
!Wavelength(is(related(to(energy(by((E =
((((Where(c(is(the(speed(of(light,(h(is(Plancks(constant(
and((is(the(wavelength.(
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160

Depending(on(its(energy,(radiation(
may(have(varying(effects(on(a(
substance(
Ultraviolet(and(visible(radiation(is(
absorbed(by(a(compound(and(excites(
the(electrons(of(a(molecule.((
The(absorption(of(infrared(radiation(
causes(a(molecule(to(vibrate.(

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161

Atomic&emission&spectra&
!Heat,(ligh(t(or(electricity(can(excite(the(
electrons(of(an(atom(to(higher(energy(
levels(
!An(emission(spectrum(is(formed(when(the(
excited(electrons(fall(back(from(higher(
energy(levels(to(the(2nd(electron(shell.(
!Each(line(corresponds(to(radiation(of(a(
speci@ic(energy((and(wavelength).(
!The(combination(and(energy(of(lines(is(
speci@ic(to(an(element,(like(a(@ingerprint(
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162

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163

Atomic(absorption(spectroscopy(
The(light(source((hollow(cathode(lamp)(is(
created(by(using(the(light(emitted(by(
excited(atoms(of(an(element,(making(it(
speci@ic(to(the(element.(
The(strongest(line(in(the(emission(
spectrum(is(chosen(for(analysis.(

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164

! Sample(solution(of(very(low(concentration(
is(aspirated(into(high(temperature(@lame(
where(it(meets(the(light(from(the(emission(
lamp.(
! Sample(absorbs(light(
! The(greater(the(concentration(of(the(
element(that(is(present,(the(more(light(is(
absorbed.(
! Light(that(passes(through(sample(is(
detected(and(compared(to(incident(light(
! Percentage(absorbance(is(recorded.(
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165

ApplicaFons&
!Analysis(of(metals(in(very(low(
concentrations.(
!Low(concentrations(are(measured(in(parts(
per(million((ppm)(=(mg(per(L(of(solution((
(or(parts(per(billion((ppb)(=(g(per(L(of(
solution(
!Eg(concentration(of(heavy(metal(such(as(
mercury(or(lead(in(water,(or(in(@ish,(or(
concentration(of(sodium(in(sports(drink(
!Is(a(speci@ic(form(of(analysis((you(have(to(
know(what(you(are(looking(for.((
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166

Obtaining(Quantitative(results(
Standard(solutions(with(known(
concentrations(of(the(element(are(measured(
and(results(used(for(calibration(graph.(

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167

AAS(sample(exam(question(
This(is(a(calibration(curve(for(Ba2+(ions(in(an(
Atomic(Absorption(Spectrometer(
(a) If(the(absorbance(of(a(
solution(is(0.11,(@ind(the(
concentration(of(Ba2+(
ions(in(the(solution(
(b)Calculate(the(mass(of(
Ba2+(ions(in(10(mL(of(
this(solution(
(VCAA(June(2009(Q10)(

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168

Answer(
a) Using(the(graph,(an(absorbance(of(0.11(
corresponds(to(a(concentration(of(19(
mgLP1(
mass
b) Concentration(=((
volume
((((((mass(=(concentration((volume(

(((((((((((((((((((((((((=(19((0.010(
((((((((((((((((((((((((((=((0.19(mg(
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169

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
UV-Visible Spectroscopy

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170

UVBVisible&Spectroscopy&
Radiation(in(the(UV(and(visible(parts(of(
the(spectrum(has(quite(high(energy(
It(is(able(to(be(absorbed(by(atoms,(ions(or(
molecules(and(excites(the(electrons(in(the(
compounds(from(low(energy(levels(to(
higher(energy(levels.(

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171

!Different(substances(have(many(different(
energy(levels,(so(the(energy(and(
wavelength(of(the(light(required(to(
promote(the(electrons(vary.(&
!If(a(substance(absorbs(visible(light,(it(will(
appear(coloured.(
!The(colour(of(light(that(is(absorbed(is(the(
complementary(colour(to(that(shown(by(
the(compound(eg(red(is(the(
complementary(colour(of(blue,(so(blue(
solutions(will(absorb(red(light.(
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172

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173

How(does(it(work?((
Light(of(a(selected(wavelength(is(shone(
through(a(sample.(
The(amount(of(light(that(is(transmitted(
(goes(through(the(sample)(is(measured:(%(
transmittance.(

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174

Quantitative(use(of(UVPVis(Spec(
!The(relative(absorbances(of(wavelengths(
from(200nm(to(800nm(is(measured(for(the(
compound.(
!Wavelength(of(light(that(is(strongly(
absorbed(by(compound(is(selected(for(
quantitative(use.(
&

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175

CalibraFon&graph&
As(for(AAS,(a(calibration(graph(is(created(by(
measuring(the(%(transmittance(of(a(series(
of(samples(of(known(concentration(and(
plotting(the(two(quantities(against(each(
other.(
A(straight(line(is(obtained.(
The(%(transmittance(of(the(sample(is(
measured(and(its(concentration(is(found(
from(the(calibration(graph.(
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176

ApplicaFons&of&UVBVis&
!Clinical(analysis(eg(determining(the(
haemoglobin(content(and(sugar(levels(in(blood(
!Identifying(the(presence(of(elements(by(
converting(them(into(coloured(compounds(if(
they(are(not(already(coloured(
!Determining(the(levels(of(nutrients,(additives(
and(contaminants(in(water(and(foods(
!Quantitative(analysis(of(DNA(and(proteins(
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177

UVPVis((sample(exam(question(
The(UVPvisible(absorption(spectrum(of(a(solution(of(
paracetamol(is(shown(below.(The(concentration(of(
paracetamol(in(the(solution(is15.1(g(mLP1(
(
(

(
(
(
(
The(absorbance(of(another(solution(of(paracetamol(is(
measured(under(the(same(conditions,(and(at(245(nm,(the(
absorbance(is(0.96.(What(is(the(concentration,(in(g(mLP1(
of(the(paracetamol(in(this(other(solution?(
(VCAA(June(2008(Q3)(
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178

Answer(
The(UVPvisible(spectrum(shows(an(
absorbance(of(1.6(for(the(concentration(of(
15.1g(mLP1(
Therefore,(if(the(absorbance(is(0.96,(we(can(
@ind(the(concentration( 15.1
x
=
(using(the(ratio(of((
1.6 0.96
concentration(to((
15.1
x = 0.96
absorbance(
1.6
(
= 9.1 gmL-1
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179

QUESTION 1
Which one of the following analyses is best performed using atomic absorption
spectroscopy?

A. Measuring the amount of potassium in salt


B. Determining the amount of caffeine in coffee
C. Measuring the carbonate content of mineral water
D. Detecting the presence of ethanoic acid in a sample of wine.

(VCAA Q2 June 2007)

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180

QUESTION 1
Which one of the following analyses is best performed using atomic absorption
spectroscopy?

A. Measuring the amount of potassium in salt


B. Determining the amount of caffeine in coffee
C. Measuring the carbonate content of mineral water
D. Detecting the presence of ethanoic acid in a sample of wine.

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181

Atomic absorption spectroscopy (AAS) is always used to determine concentration of metals in


solution. Each of the four alternatives should be considered with this in mind.
In B and D the substances that are being analysed are organic (Carbon-based). There is no metal
present in them, so AAS cannot be used. In alternative C, while the carbonate ion (CO32-) must have
been accompanied by a metal ion, it is the carbonate content that needs to be measured, so AAS is not
valid. Alternative A refers to a metal (potassium) present in salt, so this is the correct answer.

(VCAA Q2 June 2007)

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182

QUESTION 2
A sodium lamp emits a yellow-coloured light. If the light from the lamp was passed
through a container of sodium vapour, it is likely that the light emerging from the
container would appear
A. brighter due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
B. brighter, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
C. duller, due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
D. duller, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.

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Q18 June
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183

QUESTION 2 (ANSWER)
A sodium lamp emits a yellow-coloured light. If the light from the lamp was passed
through a container of sodium vapour, it is likely that the light emerging from the
container would appear
A. brighter due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
B. brighter, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
C. duller, due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
D. duller, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.

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184

The correct answer is D: duller, due to electrons in atoms in the sodium vapour moving from
lower to higher energy levels.
The light being emitted by the sodium lamp has the energy that is needed by a sodium atom
to excite its electrons from lower energy levels to higher energy levels. When this light is
passed through a container of sodium vapour, the sodium atoms will absorb some of this
light energy and so the light emerging from the container will be duller. The reason is that
the atoms in the sodium vapour are using that light energy to move from lower to higher
energy levels.

(VCAA Q18 June 2007)

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185

QUESTION 3(a)
An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.

What is the concentration, in mgL-1, of


MnO4-(aq) in the diluted solution in the
100 mL volumetric flask?

Concentration =
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mgL-1

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(VCAAthere
Q2 June
2008)
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186

QUESTION 3(a) (ANSWER)


An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.

What is the concentration, in mgL-1, of


MnO4-(aq) in the diluted solution in the
100 mL volumetric flask?

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187

The concentration of MnO4-(aq) in the diluted solution in the 100 mL volumetric flask is
35 mgL-1
The calibration graph directly gives us the concentration, in mgL-1, of the diluted sample. You
need to find the absorbance (0.70) on the vertical axis and carefully draw a horizontal line
across to the calibration graph and from that point draw a vertical line down to the
concentration axis.
The value that you read should be 35 mgL-1.

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188

QUESTION 3(b)
An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.

Calculate the mass, in mg, of manganese


in the steel sample.

Mass =

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mg

(VCAA
Q2 June
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may2008)
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189

QUESTION 3(b) (ANSWER)


An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.

Calculate the mass, in mg, of manganese


in the steel sample.

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190

Note in reading the question that the g of steel was dissolved and made up to L ( mL). Then
100
mL of this solution was then diluted to mL (a dilution)25and it was for this diluted sample that
we found the concentration to be mgL-1
The mL of diluted0.140
solution contained MnO4- at a concentration of mgL-1.
0.140
- in the original solution is
The concentration
of
MnO
mgL-1
(54.9 + 4 16.0) 4 118.9
Since the volume of the original solution was L, the mass of MnO4- in the original solution =
mg
n(MnO4-) mol n(Mn) in the 1.00L of steel solution

(VCAA Q2 June 2008)

m(Mn) g mg

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191

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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Infrared Spectroscopy

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192

Key(Knowledge(
infrared(spectroscopy((IR)(including(use(
of(characteristic(absorption(bands(to(
identify(bonds(
mass(spectroscopy(including(
determination(of(molecular(ion(peak(and(
relative(molecular(mass,(and(identi@ication(
of(simple(fragments(
&
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193

Key(knowledge(continued(
proton(and(carbonP13(nuclear(magnetic(
resonance(spectroscopy((NMR)(including(spin,(
the(application(of(carbonP13(to(determine(
number(of(equivalent(carbon(environments;(
and(application(of(proton(NMR(to(determine(
structure:(chemical(shift,(areas(under(peak(and(
peak(splitting(patterns((excluding(coupling(
constants),(and(application(of(n+1(rule(to(
simple(compounds(

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194

Infrared((IR)(Spectroscopy((
Recall(that(infrared(radiation(has(a(longer(
wavelength(and(lower(energy(than(visible(
light.(
Infrared(radiation(can(be(absorbed(by(
molecules(and(makes(the(bonds(in(the(
molecules(vibrate(more(than(they(are(
already.(

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195

Bonds(within(molecules(can(vibrate(in(a((((((((((
variety(of(ways.(((
(Each(of(these(different(types(of(vibration(
result(when(infrared(radiation(of(different(
frequencies(is(absorbed.(

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196

How&an&infrared&spectrometer&
works&&

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197

Factors&which&affect&the&frequency&of&
radiation&absorbed&include:&
!'Strength(of(the(bond.&&&

&&&As(the(strength(of(the(bond(increases,((((
(((frequency(increases.(
!!Mass(of(atoms(in(the(bond.&&&
&&&&As(the(masses(of(the(atoms(increase,((((
((((the(frequency(decreases.(
&
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198

Reminders&about&waves:&
All(wavelengths(of(electromagnetic(
radiation(travel(at(the(same(speed(
Frequency((1(/(wavelength(
In(infrared(spectroscopy,(radiation(
absorbed(is(identi@ied(by(
wavenumber(which(is(measured(in(
cmP1((a(type(of(frequency)(

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199

Two&ways&in&which&an&infrared&
spectrum&may&be&used:&
!The(wavenumber(of(the(bands(
(peaks)(is(used(to(identify(
particular(functional(groups(
!The(@ingerprint(region(may(be(
matched(to(that(of(another(
infrared(spectrum.(
!An(unknown(compound(can(be(
identi@ied(if(its(spectrum(matches(
exactly(that(of(a(known(compound.(
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200

General'points'to'note'about'IR'
spectra'(eg'ethanol)'
'
yP
axis(

xPaxis(has(highest(wavenumber(on(the(left(
Bands(go(downward,(since(all(absorption(amounts(to(
less(than(100%(transmittance.(

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201

Identi;ication&of&functional&groups&&
See&Table&7&p7&VCE&Data&booklet&

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202

Identi;ication&of&functional&groups&
!Look(for(C=O(band(at(1670P1750(cmP1(
!If(C=O(band(is(missing,(then(it(is(not(a(
carboxylic(acid(or(ester(
!Look(for(OPH(band(at(2500P3300(cmP1((
(if(C=O(present)(or(at(3200P3550(cmP1((
(if(C=O(not(present(=(alcohol)(
!Expect(to(@ind(CPH(band(at((
(((2850P3300(cmP1(
!Maybe(CPCl(band(at(700P800(cmP1(

&

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203

The&;ingerprint&region&
This(is(the(region(of(a(spectrum(below(
1500(cmP1.(((
Lots(of(peaks(here((do(not(try(to(
identify(all!(
Use(this(region(to(identify(unknown(
compounds(by(matching(their(spectra(
with(those(of(known(ones.(

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204

Ethanoic'acid'

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205

Ethyl'ethanoate'(an'ester)'

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206

Infrared(spectra(cannot(usually(be(
used(in(isolation(to(completely(identify(
unknown(compounds.(
Instead,(they(are(used(in(combination(
with(other(techniques(such(as(mass(
spectroscopy(and(nuclear(magnetic(
resonance(spectroscopy.(

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207

What&functional&group/s&is/are&
present&here?&

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208

What&do&you&see&in&this&spectrum?&

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209

And&this&one?&

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210

IR(sample(exam(question(
When(a(sample(absorbs(infrared(radiation(
A. Covalent(bonds(are(broken(
B. Covalent(bonds(stretch(and(vibrate(
C. The(spin(alignment(of(certain(nuclei(
changes(
D. Electrons(in(atoms(move(to(higher(
energy(levels(
(VCAA(June(2010(Q8)(
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211

Answer(
B(is(the(answer(
Infrared(radiation(is(not(high(enough(in(
energy(to(break(covalent(bonds((alternative(
A),(but(it(will(cause(bonds(to(stretch((a(form(
of(vibration)(
UV(radiation(can(cause(electrons(to(change(
energy(levels((C)(
Radio(frequencies(cause(changes(to(the(spin(
alignment(of(nuclei((D)(
(

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212

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/mass-spectrometry/mass-spectrometry/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Mass Spectrometry

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213

Mass&Spectrometry&&

&
Mass(spectrometry(is(used(to(
describe(the(structure(of(a(molecule((
The(molecule(breaks(into(fragments(
in(the(mass(spectrometer.(
Previously(we(have(only(used(a(mass(
spectrometer(for(determining(the(
masses(and(abundances(of(isotopes.(

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214

Diagram&of&a&mass&spectrometer&

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215

How(are(fragments(formed?(
For(organic(compounds,(during(ionisation,(the(
high(energy(electrons(also(cause(parts(of(the(
molecule(to(break(off((fragments).(
There(will(be(some(whole(molecules(present(
as(ions((the(molecular(ion)(and(also(fragments(
which(correspond(to(parts(of(the(molecule(eg(
CH3+,(CH3CH2+(etc(
Each(positively(charged(fragment(appears(as(a(
peak(on(the(mass(spectrum(for(the(compound.(
&&
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216

A(mass(spectrum(

(Propanoic(acid)((

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217

Use'of'mass'spectra'in'analysis'
!The(sizes(of(the(fragments(can(help(us(
identify(the(structure(of(a(compound,(
!Other(information(is(used(in(
conjunction:(
((empirical(formula((from(calculations)(
((functional(groups(present((IR(((((
(((((spectroscopy)(
(details(of(the(arrangment(of(hydrogens(
in(the(compound((NMR(spectroscopy).(
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218

Useful(fragments(to(look(for(
!Molecular(ion((M+)(
This(is(usually(the(peak(with(the(greatest(
m/e(ratio(on(the(spectrum.(
It(gives(you(the(molecular(mass(of(the(
compound(which(can(be(combined(with(
the(empirical(formula(to(@ind(the(
molecular(formula.(

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219

!Peaks(due(to(common(groups(in(organic(
compounds(
!m/e(=(15( ( (CH3+(((methyl)(
!m/e(=(29( (CH3CH2+(((ethyl)(
!m/e(=(45( (COOH+(((carboxyl)(
(

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220

Mass(spectrum(of(propanP1Pol(

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221

Another(example((ethanol,(C2H5OH(

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222

Mass(spec(sample(exam(question(
A(sample(of(compound(M(is(analysed(in(a(mass(
spectrometer(where(it(forms(the(molecular(ion(M+(
according(to(
M((+((eP(((M+(+(2eP(
Some(of(the(molecular(ions(fragment(as(follows:(
M+((A+(+(B((and(M+(( A(+(B+(
The(mass(spectrum(would(show(peaks(due(to(the(
species(
A.((M+,(A,(A+,(B(and(B+(only(((B.(((M+,(A+(and(B+(only(
C.(((A+(and(B+(only(( (((((((((D.((A(and(B(only(
(VCAA(June(2009(Q2)(
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223

Answer(
B(is(the(answer(
This(is(the(only(alternative(with(parts(of(the(
answer(being(positively(charged(particles(

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224

QUESTION 1
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

Write an equation showing how either an ethanol molecule or a nitrogen dioxide


molecule becomes ionised in the mass spectrometer.
Please write down the equation on a piece of paper. You can self-mark it using the
answer on the next slide.
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(VCAA
June 2010
Section
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225

QUESTION 1 (ANSWER)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

Write an equation showing how either an ethanol molecule or a nitrogen dioxide


molecule becomes ionised in the mass spectrometer.

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226

Many different equations were possible and acceptable as answers for this question.
CH3CH2OH(g) + e[CH3CH2OH]+(g) + 2eOr
Or

CH3CH2OH(g)
CH3CH2OH+(g) + eC2H6O(g)
C2H6O+(g) + e-

Or

NO2(g) + e-

[NO2]+(g) + 2e-

Or
NO2(g)
NO2+(g) + eThe important part of the question is that the molecule is being ionised, so an electron
must be given off as a product and the product particle must have a positive charge.
There is no need for the molecule to be fragmented (broken by the impact of the
electron), as the question asks for the equation to show how the ethanol or nitrogen
dioxide molecule is ionised, not fragmented.
It is important to show the states of the molecules as gaseous (g), since the first thing
that happens to a sample in the mass spectrometer is that it is vaporised to the gaseous
phase.

(VCAA Section B Q3 June 2010)


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227

QUESTION 2(a)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

Which mass spectrum cannot be that of nitrogen dioxide?


cannot be that of nitrogen dioxide.
(VCAA June 2010 Section B Q3)
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228

QUESTION 2(a) (ANSWER)


The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

Which mass spectrum cannot be that of nitrogen dioxide?

Spectrum A cannot be that of nitrogen dioxide.


(VCAA June 2010 Section B Q3)
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229

QUESTION 2(b)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

What evidence does the mass spectrum provide to support your answer?

Please write down your explanation on a piece of paper. You can self-mark it using
the answer on the next slide.
(VCAA June 2010 Section B Q3)
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230

QUESTION 2(b) (ANSWER)


The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

What evidence does the mass spectrum provide to support your answer?
There are only 3 possible peaks for NO2 m/e = 16 (O+), 30 (NO+) or 46(NO2+)
Peaks at m/e = 45 (or 31 or 29 or 27) will not result from fragmentation of NO2 or
the NO2 molecule.
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(VCAA June 2010 Section B Q3)

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231

QUESTION 3
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

What is the formula of the species that produces the peak seen at m/z 30 in
spectrum B?
Please write down the formula on a piece of paper. You can self-mark it using the
answer on the next slide.
(VCAA June 2010 Section B Q3)

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232

QUESTION 3 (ANSWER)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.

What is the formula of the species that produces the peak seen at m/z 30 in
spectrum B?
Spectrum B is the mass spectrum of NO2. The m/z value of 30 corresponds to one
N (14) and one O(16) 14 + 16 = 30, so the acceptable answers are [NO]+ or NO+ or
NO +
(VCAA June 2010 Section B Q3)

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233

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/nmr-spectroscopy-theory-spin-h-environments/nmr-spectroscopy/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
NMR Spectroscopy
Theory, Spin and H Environments
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234

Nuclear(magnetic(resonance((NMR)(
spectroscopy(

!This(is(used(to(identify(the(arrangement(
of(hydrogen(atoms(in(a(compound.(
It(is(possible(because(1H(nuclei(have(a(
spin(of((13C(also(has(a(spin(of((so(
can(also(be(analysed(using(NMR((also(
31P,(19F(and(15N)(

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235

What&is&Spin?&
Spin(is(a(fundamental(property(of(nature(
like(electrical(charge(or(mass.(
(Spin(comes(in(multiples(of(1/2(and(can(be(
+(or(P.(
A(nucleus(with(a((
(((nonPzero(spin((
(((behaves(like(a((
(((small(magnet((
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236

How&does&it&work?&
!An(NMR(spectrometer(applies(a(large(magnetic(
@ield((about(10(000(times(that(of(earths(magnetic(
@ield)(to(the(sample.(
!The(spinning(1H(nuclei(respond(by(either(aligning(
with(the(magnetic(@ield(or((opposing((it.(Spin(up(or(
spin(down)(

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237

Two(energy(levels((spin(states)(exist(
for(a(spinning(nucleus,(the(lower(one(
being(when(the(nucleus(is(aligned(
with(the(external(magnetic(@ield.(

opposed
to B

E=h

aligned
with B

B
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Bapp

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238

When(a(magnetic(@ield(is(being(applied(to(an(
1H(nucleus((a(proton)(the(difference(
between(the(spin(states(is(still(quite(small.(
So,(radiowaves((low(energy)(provide(
enough(energy(to(excite(a(proton(from(one(
spin(state(up(to(the(other((for(it(to(resonate)(
Only(1H(NMR(and(13C(NMR(have(to(be(
analysed(in(this(course(
13C(NMR(spectra(have(a(very(different(scale(
to(1H(NMR(spectra((
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239

Magnetic(in@luences(on(an(atom(in(a(
compound.(

The(applied(magnetic(@ield((Bapp)(comes(
from(the(actual(NMR(instrument(
A(local(magnetic(@ield(is(due(to(other(
atoms(in(the(compound.(
The(local(@ield((as(experienced(by(1H(
nuclei(in(a(compound)(depends(on(their(
environment(
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240

The(environment(of(the(1H(is(made(up(of(
the(atom(it(is(bonded(to,(as(well(as(other(
atoms(nearby.(
These(change(the(way(a(1H(nucleus(
responds(to(the(applied(magnetic(@ield.(
A(H(bonded(to(an(O(in(OH(will(resonate(at(
a(different(energy(to(one(bonded(to(a(C(
(eg(in(CH3)(

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241

Example&of&an&NMR&spectrum&

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242

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/analysing-nmr-spectra/how-can-we-use-nmr/#watch

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Analysing NMR Spectra

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243

How&can&we&use&NMR?&
The(NMR(spectrum(is(made(up(of(sets(
of(peaks(
The(position(of(a(peak(depends(on(the(
environment(of(the(1H(nuclei(
producing(that(peak.(
The(position(of(the(peak(along(the(
horizontal(axis(is(known(as(chemical(
shift.&
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244

The(location(of(an(NMR(signal(in(a(spectrum(is(
measured(relative(to(a(reference(signal(from(a(
reference(compound(added(to(the(sample.(
The(protons(in(the(reference(compound,(TMS,(
tetramethylsilane,(Si(CH3)4,(are(assigned(a(
chemical(shift(of(zero.(((
((((this(will(always(be((
((((present,(but(does(not(
(((( count (as(a(peak)(
A(chemical(shift(of((
(((1(ppm(means(that((
(((the(signal(is(shifted(by(200(Hz(on(a(200MHz(((
(((instrument.(
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245

H(atoms(bonded(to(more(
electronegative(atoms(will(have(a(
greater(shift((further(to(left)(than(those(
in(more(electron(dense(environments.(
Eg(a(H(bonded(to(an(O(will(have(a(
greater(shift(than(one(bonded(to(C(
Tables(of(chemical(shifts(help(us(to(
identify(a(H(atom((See(table(5(in(Data(
booklet(
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246

p5 of data booklet

Also see p6 of data booklet


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247

The(size(of(peaks(
The(size(of(peaks(relative(to(each(other(
is(often(indicated(by(an(integration(
trace.(
The(ratio(of(the(areas(under(the(peaks(
(from(the(integration(trace)(gives(the(
ratio(of(H(atoms(of(a(particular(type(

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248

example(
In(CH3CH2CH2CH3(there(are(two(
different(environments(for(Hs.(They(
may(either(be(part(of(a(CH3(group(or(a(
CH2(group.(
So(there(will(be(two(peaks(on(the(NMR(
spectrum(for(butane((one(at(chemical(
shift(of(0.9(ppm((for(CH3(groups)(and(
the(other(at(chemical(shift(of(1.3(ppm(
for(RPCH2PR(.(
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249

An(integration(trace(of(these(peaks(
will(show(a(ratio(of(peak(areas(of((
(((3(:(2(re@lecting(the(ratio(of(Hs(in(CH3(((
(((groups(to(Hs(in(CH2(groups.(

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250

Ethanol&&3&environments&

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251

SpliFng'of'peaks''
(high'resolu:on'NMR)'

The(effect(of(neighbouring(1H(nuclei(is(
to(split(the(peak(corresponding(to(a(
particular(group(of(Hs(into(several(
small(peaks.((
This(effect(is(called(a(splitting(pattern.(

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252

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253

Eg(If(the(Hs(in(a(CH3(group(on(the(end(
of(a(molecule(has(a(neighboring(C(with(
2Hs(on(it,(the(peak(for(the(CH3(Hs(will(
be(split(into(three((a(triplet).((n(+(1(
rule)(
Triplet would
represent
these Hs
Due to the 2
neighbouring
Hs

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254

In(the(example(of(butane,(the(peak(at(0.9ppm((CH3(
peak)(would(be(a(triplet(because(it(would(be(split(by(
the(neighboring(group(of(two(Hs(on(CH2(
The(peak(at((
1.3ppm((due(to((
CH2)(would(be(a((
multiplet(due(to((
the(3(neighboring((
CH3(Hs(AND(the((
2(neighbouring((
CH2(Hs(
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255

Chloroethane((2(environments,(one(
triplet(and(one(quartet(

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256

13C(NMR(

!13C(is(a(naturally(occurring,(but(very(low(
concentration(isotope(of(carbon.(
!It(can(be(used(for(identifying(the(
different(carbon(environments(in(a(
molecule.(
!Chemical(shifts(are(much(greater(for(13C(
NMR(than(1H(NMR((up(to(200(ppm)(
!13C(NMR(spectra(tend(to(be(simpler(than(
1H(due(to(the(smaller(differences(
between(Cs.(

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257

13C(NMR(of(ethanol(

!Notice(that(there(are(only(2(peaks(since(
there(are(only(2(different(Cs((one(on(end(
and(one(in(middle)(
!There(is(no(splitting(in(a(13C(NMR(

&

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258

In(summary(
!Chemical(shift(provides(information(
about(the(position(in(the(molecule(in(
which(the(H(is(found.(
!Number(of(peaks(=(number(of(different(
environments(
!Peak(area(gives(information(about(the(
ratio(of(equivalent(Hs(
!Peak(splitting(gives(information(about(
the(number(of(neighbouring(Hs.(
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259

NMR(Sample(exam(question(
A(sample(of(a(hydrocarbon(for(analysis(is(placed(in(a(
strong(magnetic(@iled(and(irradiated(with(
electromagnetic(radiation(of(radio(wave(frequency.(
This(is(most(likely(to(result(in(
(((((A. (ionisation(and(fragmentation(of(molecules(
(((((B.((An(increase(in(bond(vibrations(of(molecules(
(((((C.((The(promotion(of(electrons(to(higher(energy(((
(((((((((((levels(
(((((D.((A(change(in(the(energy(of(the(nuclei(of(the((
(((((((((((hydrogen(atoms.(
(VCAA(June(2008(Q(15)(
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260

Answer(
D(describes(NMR(
A(describes(mass(spectroscopy(
B(describes(IR(spectroscopy(
C(describes(atomic(emission(spectroscopy(

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261

QUESTION 1
The disease sickle cell anaemia is marked by the presence of an abnormal protein
in the blood of people with this disease. The sixth position in the normal protein
chain is occupied by the amino acid, glutamic acid. The sickle cell protein chain has
the amino acid, valine, in the sixth position. This is the only difference between the
two protein chains.
A section of each protein chain containing glutamic acid and valine is shown
below.

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262

It is possible to determine the molecular mass of these proteins in a mass


spectrometer. It is also possible to record their 1H NMR spectra. Which one of the
following alternatives is correct?

A.

Molecular mass
Sickle cell protein chain has the
greater molecular mass.

1H

NMR spectrum
Both protein chains have the same 1H NMR
spectrum.

B.

Sickle cell protein chain has the


greater molecular mass.

The protein chains have different 1H NMR


spectra.

C.

Normal protein chain has the


greater molecular mass.

Both protein chains have the same 1H NMR


spectrum.

D.

Normal protein chain has the


greater molecular mass.

The protein chains have different 1H NMR


spectra.
(VCAA June 2008 Q5)

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263

QUESTION 1 (ANSWER)
The disease sickle cell anaemia is marked by the presence of an abnormal protein
in the blood of people with this disease. The sixth position in the normal protein
chain is occupied by the amino acid, glutamic acid. The sickle cell protein chain has
the amino acid, valine, in the sixth position. This is the only difference between the
two protein chains.
A section of each protein chain containing glutamic acid and valine is shown
below.

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264

It is possible to determine the molecular mass of these proteins in a mass


spectrometer. It is also possible to record their 1H NMR spectra. Which one of the
following alternatives is correct?

Molecular mass

1H

A.

Sickle cell protein chain has the


greater molecular mass.

Both protein chains have the same 1H NMR


spectrum.

B.

Sickle cell protein chain has the


greater molecular mass.

The protein chains have different 1H NMR


spectra.

C.

Normal protein chain has the


greater molecular mass.

Both protein chains have the same 1H NMR


spectrum.

D.

Normal protein chain has the


greater molecular mass.

The protein chains have different 1H


NMR spectra.

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265

The correct answer is D.


The difference between the two protein chains is the different amino acid in the 6th
position. Normal protein has glutamic acid and the sickle cell protein has valine.
From the Chemistry Data Book we see that the structures of the two differing amino acids
are

Glutamic acid has a larger molar mass than valine, so the Normal protein chain would have
a greater molecular mass.
Because the 1H environments are different in glutamic acid (3 environments) compared to
valine (2 environments), the protein chains would have different 1H NMR spectra.
(VCAA June 2008 Q5)
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266

QUESTION 2

The polymer polylactic acid, PLA, shown above, is used to make soluble stitches
which are absorbed by the body following surgery.
Other than the peak given by the TMS reference, the monomer from which PLA is
formed would give
A. one set of peaks in the 1H NMR spectrum
B. two sets of peaks in the 1H NMR spectrum
C. three sets of peaks in the 1H NMR spectrum
D. four sets of peaks in the 1H NMR spectrum
(VCAA June 2009 Q4)
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267

QUESTION 2 (ANSWER)

The polymer polylactic acid, PLA, shown above, is used to make soluble stitches
which are absorbed by the body following surgery.
Other than the peak given by the TMS reference, the monomer from which PLA is
formed would give
A. one set of peaks in the 1H NMR spectrum
B. two sets of peaks in the 1H NMR spectrum
C. three sets of peaks in the 1H NMR spectrum
D. four sets of peaks in the 1H NMR spectrum
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268

The section of the polymer, polylactic acid, shown in the question shows repeating ester groups COOwhich can be used to identify the monomer from which the condensation polymer is produced. The
ester groups form by reaction between carboxyl and hydroxyl groups, so we would expect a carboxyl
group on the right hand end of the monomer and a hydroxyl on the left hand end of the monomer.

The monomer would look like this:

It is lactic acid, although this knowledge is not necessary to answer the question correctly.
It would have four hydrogen environments.
Since each 1H environment is represented by a peak, the correct answer is D.
(VCAA June 2009 Q4)

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269

QUESTION 3(a)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

How many different proton environments are there in this molecule?


There are
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different proton environments.

(VCAA June 2009 Section B Q5 (modified))

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270

QUESTION 3(a) (ANSWER)


The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

How many different proton environments are there in this molecule?


Because there are two peaks in the NMR spectrum, there must be two different proton
(1H) environments.
(VCAA June 2009 Section B Q5 (modified))

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271

QUESTION 3(b)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Draw the structure of the unknown molecule, clearly showing all bonds.
Please draw your answer on a piece of paper. You can self-mark it using the answer on the next slide.
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(VCAA June 2009 Section B Q5 (modified))

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272

QUESTION 3(b) (ANSWER)


The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Draw the structure of the unknown molecule, clearly showing all bonds.

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273

(colour is not important for this answer)


(VCAA June 2009 Section B Q5 (modified))

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274

QUESTION 3(c)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Explain how the structure of the compound you have drawn in part (b) is
consistent with its IR spectrum.
Please write your explanation on a piece of paper. You can self-mark it using the answer on the next slide.
(VCAA June 2009 Section B Q5 (modified))

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275

QUESTION 3(c) (ANSWER)


The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Explain how the structure of the compound you have drawn in part (b) is
consistent with its IR spectrum.
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276

There is a strong band at 1750 cm-1 which indicates that there is a C=O (carbonyl) group.
And there is a broad band at 2500-3300 (cm-1) indicating an O-H bond.
Together these two bands confirm the existence of the carboxyl functional group.
(VCAA June 2009 Section B Q5 (modified))

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277

QUESTION 3(d)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Name the compound you have drawn in part (b).


Enter your answer here:

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(VCAA June 2009 Section B Q5 (modified))

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278

QUESTION 3(d) (ANSWER)


The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.

Name the compound you have drawn in part (b).


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279

Ethanoic acid
(Eth 2 carbons, -oic acid due to the carboxyl functional group)
(VCAA June 2009 Section B Q5 (modified))

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280

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/exam-question-combining-spectroscopic-techniques/exam-question/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Exam Question Combining Spectroscopic Techniques

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281

Exam(question(that(combines(all(
three(techniques(

The(structure(of(an(organic(molecule,(with(
empirical(formula(CH2O,(is(determined(
using(spectroscopic(techniques.(The(mass(
spectrum,(infrared(spectrum(and(1H(NMR(
spectrum(for(this(molecule(are(given(below.(
Use(the(information(provided(by(these(
spectra(to(answer(these(questions.(

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282

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283

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284

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285

a) What(is(the(molecular(formula(of(this(
molecule?(
b) How(many(different(proton(environments(
are(there(in(this(molecule?(
c) Draw(the(structure(of(the(unknown(
molecule,(clearly(showing(all(bonds.(

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286

Watch this lesson online:


https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/chemical-analysis-calculations/key-knowledge/

CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Calculations

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287

Key(Knowledge(
calculations(including(amount(of(solids,(
liquids(and(gases;(concentration;(volume,(
pressure(and(temperature(of(gases(

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288

Revision(of(Unit(2(
When(working(out(what(formula(to(use(
in(calculations(classify(the(reagents(in(
terms(of(their(state.(
If(the(mass(of(a(solid(is(required(or(given,(
use(
m
( (((((n(=((

If(a(solution(is(involved(use(((n(=(cV(
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289

Gases(
If(a(gas(is(involved,(then(the(general(gas(
equation(is(most(useful:(
( (PV(=(nRT((((R(=(8.31(J(KP1molP1)(
However,(keep(in(mind(that((((n(=( V
((((can(be(used(when(the(gas(is(
VM
(((((at(STP((0C,(1(atm(pressure)(or(
(((((at(SLC((25(C,(1(atm(pressure)(
(((((where(VM(=(22.4LmolP1(or(24.5(L(molP1(
See(the(Exam(data(book(p5(for(these(values(
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290

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291

Density(
Density(values(often(occur(as(part(of(a(
calculation(
Units:(g(mLP1((or(it(could(be(g(LP1(
Use(the(units(to(help(you(with(density((
eg(density(of(ethanol(is(0.785(g(mL,(so(
1mL(of(ethanol(has(a(mass(of(0.785g.((
So(50.0(mL(of(ethanol(has(a(mass(of((
(((0.785((50(=(39.25(g(
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292

Sample(exam(questionsPgases(
The(reaction(that(occurs(in(an(airbag(when(an(accident(
occurs(is(
10(NaN3(s)((+((2KNO3(s)(( 5Na2O(s) + K2O(s) + 16N2(g)
A particular car s airbag was found to inflate to a volume of
62.0L at a pressure of 100kPa when the temperature reached
36.6 C. The molar mass of NaN3 is 65.0 gmol-1. What was the
mass of sodium azide contained in the car s airbag?
A.97.9 g
B.156.6 g
C.250.6 g
D.828.1 g(
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293

Answer(
PV
PV(=(nRT,(so(n(=(
RT

(
100 62.0
n(= ( ((((((((((=(2.41(mol((
8.31 309.6
(
From(the(equation(N2(:((NaN3(
( ((((((((((((16(:(10(
10
( ((((((((2.41((: ( (=(1.51(mol(
2.41
16
m(NaN3)(=(1.51((65.0(
((((((((=(97.9(g(
The(answer(is(A(

(
&

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294

Sample(exam(questionsPdensity&
An(analysis(is(carried(out(on(a(sample(of(
unknown(gas.(The(density(of(the(gas(is(
2.86(gLP1(at(STP.(The(molecular(formula(of(
the(gas(is(
A. HCl(
B. Cl2(
C. NO2(
D. SO2(
VCAA(June(2011(Q14(
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295

Answer:(
Density(=(2.86(gLP1(
So,(1(Litre(of(gas(has(a(mass(of(2.86(g(
At(STP,(1(mole(of(gas(occupies(22.4(L(
So,(1(mole(of(gas(has(a(mass(of((
22.4((2.86(=(64.06(g(=(molar(mass((
Molar(mass(of(SO2(=(32.1(+(32.0(=(64.1(
D(is(the(answer.&
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296

QUESTION 1
The concentration of K+ ions in 100 mL of 0.0500 M K2CO3 solution, in gL-1, is

A. 0.196
B. 0.391
C. 1.96
D. 3.91
Note the careful reading required to make sure that you get the answer right here the
question is asking for gL-1 NOT molL-1
(VCAA Q12 June 2006)

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297

QUESTION 1 (ANSWER)
The concentration of K+ ions in 100 mL of 0.0500 M K2CO3 solution, in gL-1, is

A. 0.196
B. 0.391
C. 1.96
D. 3.91

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298

The concentration is 3.91 gL-1 (Alternative D)


Because concentration is being asked for, the volume is irrelevant.
[K+] = 2 0.0500 molL-1
= 0.100 molL-1
Convert mol to g
so m = n M(K+)
= 0.100 39.1
= 3.91 g

(VCAA Q12 June 2006)

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299

QUESTION 2
One possible reaction that occurs when trinitrotoluene (TNT), C7H5N3O6,
explodes is 2 C7H5N3O6(s)
2C(s) + 12CO(g) + 5H2(g) + 3N2(g)
When one mole of TNT explodes the total volume of the gases produced from this
reaction, measured at 27 C and 1.00 102 kPa, is closest to
A. 0.249 L
B. 22.7 L
C. 249 L
D. 274 L
(VCAA Q5 June 2010)

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300

QUESTION 2 (ANSWER)
One possible reaction that occurs when trinitrotoluene (TNT), C7H5N3O6,
explodes is 2 C7H5N3O6(s)
2C(s) + 12CO(g) + 5H2(g) + 3N2(g)
When one mole of TNT explodes the total volume of the gases produced from this
reaction, measured at 27 C and 1.00 102 kPa, is closest to
A. 0.249 L
B. 22.7 L
C. 249 L
D. 274 L

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301

The important term here in the question is the total volume of the gases .
We can see from the equation that when 2 mole of TNT explodes, 20 mole of gases are
produced (12CO + 5H2 + 3N2).
Therefore when one mole of TNT explodes, 10 mole of gases are produced, and now we
just need to convert to volume at 27 C and 1.00 102 kPa.
PV = nRT
nRT
10 8.31 (27 + 273)
V=
=
1.00 10 2
P
To 3 sig figs this answer is 249 L alternative C

=249.3L

(VCAA Q5 June 2010)

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302

QUESTION 3
A sample of the insecticide dichlorodiphenyltrichloroethane (DDT), C14H9Cl5, was
found to contain 0.120 g of carbon.
What mass of chlorine was present in the sample?

A. 0.127 g
B. 0.355 g
C. 0.994 g
D. 1.01 g
(VCAA Q6 June 2010)

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303

QUESTION 3 (ANSWER)
A sample of the insecticide dichlorodiphenyltrichloroethane (DDT), C14H9Cl5, was
found to contain 0.120 g of carbon.
What mass of chlorine was present in the sample?

A. 0.127 g
B. 0.355 g
C. 0.994 g
D. 1.01 g

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304

The answer is alternative A


The formula of the compound, C14H9Cl5, gives us the molar ratio of elements in the compound. If we
convert the mass of carbon into mole, we can find the amount
(in mole) of chlorine and hence the mass.
m
n(C)
= 0.120
M
12
C Cl (Hydrogen can be ignored for the purposes of this question)

0.01
5
14
m(Cl) =

(VCAA Q6 June 2010)

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkanes and their Isomers

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306

Key(Knowledge(
!structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
alkanes,((alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),(alkanoic(acids(
(CnH2n+1COOH)(and(esters)(up(to(C10(
&
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307

Families(of(carbon(compounds(
!Carbon(compounds(are(classi@ied(into(
homologous(series(according(to(their(
structure(and(the(atoms(that(make(them(up.(
(
!An(homologous(series(can(be(described(as(a(
group(of(compounds(which(have(the(same(
general(formula(and(similar(chemical(
properties.(

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308

Alkanes(
General(formula(CnH2n+2(
Single(bonds(occur(between(all(carbon(
atoms(=(saturated(hydrocarbons(
Alkane(molecules(are(always(nonPpolar(
The(systematic(names(of(all(alkanes(ends(
with(ane(

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309

The(beginning((pre@ix)(of(the(name(of(any(
organic(compound(indicates(the(number(of(
carbon(atoms(in(that(compound(

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310

The&rst&four&alkanes&

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311

!As(the(size(of(the((
alkane(increases,((
the(boiling(point((
increases,(due(to((
increased(strength((
of(dispersion(forces.(
!Remember&that!!
only!intermolecular!
forces!break!upon!!
boiling.!
&
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312

Other(molecules(to(be(aware(of(
! Cyclic(molecules(P(these(also(have(single((
(((CPC(bonds,(BUT(they(do(not(match(the(formula,(
CnH2n+2,(their(formula(is(CnH2n(
(
(
(

! Benzene(is(an(arene.(It(has(the(formula(C6H6(
and(is(carcinogenic.(Arenes(are(cyclic(molecules(
with(delocalised,(shared(electrons(in(a(ring.(
Naphthalene(is(also(an(arene.(

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313

Isomers(
Structural(isomers(P(compounds(with(the(
same(molecular(formula(but(different(
structures.(
Note(that(formulas(can(be((represented(
((((in(several(
((((ways:(

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314

Isomers(of(butane(
! The(molecular(formula(of(both(isomers(is(C4H10(
! The(semi(structural(formula(of(these(molecules(
would(be(
(((CH3CH2CH2CH3(and(CH3CH(CH3)CH3(

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315

These(isomers(would(have(the(same(
chemical(reactivity(because(they(are(both(
alkanes.(
Their(physical(properties(differ(slightly.(
Butane(has(a(higher(boiling(point(than(
methylpropane(because(the(linear(
butane(molecules(can(pack(together(
more(closely(than(the(branched(
methylpropane(molecules(and(stronger(
dispersion(forces(can(form.(

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316

Naming(hydrocarbons(

(
1. Identify(longest(chain(of(Cs((((main(part(of(name(
2. Look(for(any(branches(off(the(chain(
((((((branches(are(named(according(to(no.(of((Cs(eg(1(C(=(((
((((((((methyl,(2(Cs(=(ethyl)(
3. Indicate(the(position(of(branches(by(adding(a(number,(
working(from(the(end(nearest(to(the(branch(((lowest(
number)(
4. Numbers(are(separated(from(words(by(hyphens(and(
from(each(other(by(commas.&
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317
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What(is(the(name(of(this(
compound?(

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318

Sample(exam(question((naming(alkanes(
What(is(the(correct(systematic(name(for(the(
following(compound?(
(
(
(
(
A. 2PethylP3Pmethylpentane(
B. 3PmethylP4Pethylpentane(
C. 3,4Pdimethylhexane(
D. 2,3Pdiethylbutane(
VCAA(June(2010(Q10(
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319

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkenes, Haloalkanes, Amines and Alkanols

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320

Key(knowledge(
structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
(alkanes),(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),((alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10)(

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321

Alkenes(
Alkenes(always(have(one(CPC(double(bond.(
The(general(formula(of(the(alkene(family(is(
CnH2n(
They(are(more(reactive(than(alkanes(
The(shape(around(the(C=C(bond(is(trigonal(
planar,(not(tetrahedral(as(in(alkanes.(

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322

Naming(alkenes(
The(ending(of(any(alkene(will(be(ene(
The(position(of(the(double(bond(must(
be(indicated(from(C4H8(upwards.((
This(is(done(with(a(number((
(((eg(butP1Pene,(((((((((butP2Pene(((

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323

Functional(groups(
A(functional(group(is(an(atom(or(group(of(
atoms(which(in@luences(the(chemical(
properties(of(an(organic(compound.(
You(are(required(to(name(and(draw(
molecules(that(can(be(classi@ied(as(amines,(
alkanols((alcohols),(alkanoic(acids(
(carboxylic(acids),(haloalkanes(and(esters(

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324

Amines(
One(H(atom(is(replaced(by(a(PNH2(group(
General(formula(is(CnH2n+1(NH2(
The(amine(functional(group(is(basic((can(gain(an(
H+(ion.(
Amines(can(be(classi@ied(as(primary,(secondary(
or(tertiary,(according(to(how(many(alkyl(chains(
are(bonded(to(the(NH2(group.&

&

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325

Amines(are(named(with(the(suf@ix(amine(
Eg(ethanamine(C2H5NH2(
Isomers(are(named(according(to(the(
position(of(the(amine(group((
(((eg(butanP2Pamine(
Amines(are(polar(and(are(soluble(in(water(
due(to(their(ability(to(form(hydrogen(bonds.(
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326

Haloalkanes(
Members(of(this(homologous(series(are(
alkanes(with(a(halogen((F,(Cl,(Br,(I)(atom(
replacing(one(H(atom.(
General(formula(CnH2n+1X(
The(single(halogen(atom(makes(the(
molecule(polar(and(makes(it(susceptible(
to(further(reactions.(

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327

Naming:(Add(@luoroP,(or(chloroP(or(bromoP(
or(iodoP(as(a(pre@ix(
Eg(chloroethane(has(the(formula(C2H5Cl(
Isomers(are(possible:(
(((Isomers(of(Iodopropane(
((((((1Piodopropane(:(CH2ICH2CH3(
(2Piodopropane(:(CH3CHICH3(
(((((Numbers(are(used(to(indicate(the(position(((
(((((of(the(halogen(atom,(directly(in(front(of((
(((((the(pre@ix.(
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328

Alkanols((alcohols)(

One(H(is(replaced(by(OH(
General(formula(CnH2n+1OH(
The(name(of(an(alcohol(always(ends(in(ol(
Eg(ethanol(C2H5OH(
The(functional(group((POH)(is(called(a(
hydroxyl(group(

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329

Isomers(are(named(according(to(the(
position(of(the(POH(group(
(
Eg(butanP1Pol(:(CH3CH2CH2CH2OH(
and(butanP2Pol:(CH3CH2CH(OH)CH3(
The(presence(of(the(hydroxyl((POH)(group(
makes(the(molecule(polar(and(also(able(to(
hydrogen(bond(with(water(molecules((
((small(alcohols(can(dissolve(in(water.(

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330

Sample(exam(questions((
functional(groups(and(isomers(
For(which(one(of(the(following(molecular(
formulae(is(there(only(one(possible(structure?(
A. C2HCl3(
B. C2H4Cl2(
C. C2H2Cl2(
D. C4H9OH(
(
VCAA(June(2010(Q11(
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331

How(many(structural(isomers,(each(
containing(a(double(bond,(have(the(
molecular(formula(C5H10?(
A. 3(
B. 4(
C. 5(
D. 6(

(
VCAA(June(2008(Q16(
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332

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkanoic Acids and Esthers

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333

Key(knowledge(
structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
(alkanes,(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),)(alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10(

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334

Alkanoic((Carboxylic)(acids(
One((H(is(replaced(by(PCOOH(
(
(
(
Only(the(end(carbon(can(have(this(functional(
group(on(it,(so(few(structural(isomers(can(
occur,(although(dont(forget(branched(
structures.(
The(functional(group(is(called(a(carboxyl(group(
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335

General(formula(is(RCOOH(where(R(is(an(alkyl(group(
(methyl,(ethyl,(propyl(etc)(
The(name(of(a(carboxylic(acid(always(ends(in((
(((((oic(acid.(
The(total(number(of(Carbons(in(the(compound(gives(
us(the(name(so(C3H7COOH(with(4(Cs(is(butanoic(acid.(
(
(
(
These(compounds(are(acidic,(the(H(of(the((
(PCOOH(group(can(be(donated(in(an(acid(base(
reaction.(
Alkanoic(acids(are(the(most(common(weak(acids(
that(you(will(encounter.(
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336

Carboxylic(acids(are(polar(molecules(with(high(
melting(points(
The((formation(of(hydrogen(bonds(between(
carboxylic(acids(creates(dimers((so(their(melting(
point(becomes(effectively(equal(to(that(of(a(
molecule(with(double(the(molar(mass).((
Hydrogen(bonding(with(water(makes(them(soluble(
in(water(

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337

Esters(
Esters(have(a(functional(group(with(the(formula(
COPOP(
The(ending(oate(indicates(
((((an(ester(functional(group.(
Esters(are(formed(when(
((((alkanols(react(with(alkanoic(acids,(so(their(names(((
((((are(formed(from(these(two(compounds,(the(alkanol((
((((name(is(@irst(and(is(reduced(to( alkyl (eg(if(the((((
(((((alkanol(was(ethanol,(then(the(ester(name(would((
(((((start(with(ethyl.(
An(ester(that(is(formed(from(propanol(and(ethanoic(
acid(is(called(propyl(ethanoate(
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338

Naming(esters(from(their(
When(trying(to(name(an(ester(from(its(structure,(
structures(

you(need(to(locate(the(functional(group(@irst.(

(
(
The(alkyl(chain(which(included(the(C=O((carbonyl(
group)(has(come(from(the(carboxylic(acid,(and(the(
alkyl(chain(nearest(the(OP(has(come(from(the(
alkanol.(
Name(the(ester(with(the(alkanol(@irst:(this(one(is(
ethyl(ethanoate.(
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339

Amides(
Although(this(functional(group(is(not(on(the(key(
knowledge(list,(it(occurs(in(proteins(and(is(often(
used(in(past(exam(questions.(
The(amide(functional(group(can(appear((
(((((as ( ( ( (or(
(
(
depending(on(whether(it(is(on(the(end(or(in(the(
middle(of(a(compound(
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340

Sample&exam&quesFons&&alkanoic&
acids,&esters&and&amides&
The(structure(of(tami@lu,((
an(anti@lu(drug(is(shown((
opposite.(
The(names(of(the(
functional(groups(
labelled(I,(II(and(III(are(
I&

II&

III&

A.(

Amide(

Amino(

Carboxylic(acid(

B.(

Amino(

Amide(

ester(

C.(

Amide(

Amino(

ester(

Amino(

Amide(

Carboxylic(acid(

D.(

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341

The(number(of(structural(isomers(that(
are(carboxylic(acids(with(the(formula(
C4H8O2(is(
A. 1(
B. 2(
C. 3(
D. 4(
(
VCAA(June(2006(Q9(
&
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342

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Substitution Reactions of Alkanes and
Addition Reactions of Alkenes
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343

Key&knowledge&
common(reactions(of(organic(compounds(
including(equations:(addition(reactions(of(
alkenes((addition(of(hydrogen(halides(and(
water(limited(to(symmetrical(alkenes),(
substitution(reactions(of(alkanes(

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344

&
Combustion(reactions(

! Most(hydrocarbons(will(undergo(combustion(
in(the(presence(of(oxygen.(
! There(are(two(types(of(combustion(reactions(
(complete(combustion(and(incomplete(
combustion.(
! The(products(of(complete(combustion(are(CO2(
and(H2O,(while(incomplete(combustion(may(
form(CO(and/or(C(and(H2O(
! Eg(CH4(g)(+(2O2(g)((CO2(g)(+(2H2O(l)(
((((2CH4(g)(+(3O2(g)((2CO(g)(+(4H2O(l)(
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345

Substitution(reactions(of(alkanes(
In(a(substitution(reaction,(one(or(more(of(the(
hydrogen(atoms(on(the(alkane(is(replaced(by(
another(atom(or(functional(group.(
Heat(or(UV(light(is(needed(to(start(a(substitution(
reaction(when(the(bond(in(the(halogen(molecule(is(
broken(and(two(free(radicals(are(formed.(
Haloalkanes(are(made(when(alkanes(react(with(
halogens(such(as(chlorine(and(bromine(in(this(way.(

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346

Formation(of(a(haloalkane(
! Alkane(+(halogen((haloalkane(+(hydrogen(
halide((
UV((((((((((CH
light
eg(CH4((+((Cl2((((((((((((((
!!!!
3Cl((+((HCl(
(
! After(the(substitution(of(one(chlorine(onto(the(
alkane,(another(can(be(substituted:(
(CH3Cl((+((Cl2((((CH2Cl2((+((HCl(
! If(enough(chlorine(is(present,(this(can(continue(
right(up(to(CCl4(
! This(applies(to(other(halogens(reacting(in(the(
same(way.(
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347

Addition(reactions(of(Alkenes(
! The(CPC(double(bond,(is(more(reactive(than(the(
CPC(single(bond(so(alkenes(are(more(reactive(
than(alkanes.((
! Addition(reactions(involve(the(CPC(double(bond(
becoming(a(single(bond((breaking)(and(extra(
atoms(or(functional(groups(adding(onto(the(
molecule.(
! The(new(atoms(or(functional(groups(always(add(
across(the(double(bond((with(one(atom((or(
functional(group)(on(each(side(of(what(used(to(
be(the(double(bond.(
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Some(typical(addition(reactions(
(all(follow(the(same(pattern)(
1.
2.
3.
4.
5.

Reaction(with(a(halogen(
Reaction(with(hydrogen((hydrogenation)(
Reaction(with(a(hydrogen(halide(
Reaction(with(water((steam)(
Addition(polymerisation(

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1.(Reaction(with(a(halogen(
Alkene(+(bromine((((dibromoalkane(
Eg(CH2=CH2((+((((((Br2((((((((CH2BrCH2Br(
((((((colourless((redPbrown(colourless(
This(reaction(is(used(to(identify(the(presence(of(
unsaturation((double(bonds)(in(a(hydrocarbon.(
The(redPbrown(colour(of(bromine(disappears(
when(it(reacts(with(an(alkene,(but(not(with(an(
alkane((unless(UV(light(is(present).(

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350

An(alkane(will(not(react(with(bromine(
unless(UV(light(is(present,(whereas(an(
alkene(will(instantly(react(with(bromine(and(
the(brown(colour(disappears.(
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351

2.(Reaction(with(hydrogen(
! This(is(used(to(decrease(the(number(of(double(
bonds(in(an(unsaturated(hydrocarbon((in(
particular(in(making(margarine.(
! Alkene(+(hydrogen((((((alkane(
(
! Eg(CH2=CH2(+(H2((((CH3CH3(

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352

3.(Reaction(with(a(hydrogen(halide(
While(the(reaction(with(a(halogen(produces(a(
dihaloalkane,(this(reaction(adds(just(one(halogen(
atom(onto(the(alkane,(making(a(haloalkane.(
Only(symmetrical(alkenes((with(the(double(bond(
exactly(in(the(middle(of(the(molecule)(need(to(be(
used(as(examples(
Alkene(+(hydrogen(chloride((chloroalkane(

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353

examples&
CH2=CH2(+(HCl((CH3CH2Cl(

CH3CH=CHCH3+(HBr(CH3CH2CH2BrCH3(

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354

4.(Reaction(with(water(
This(is(an(easy(method(for(making(an(alkanol(
A(catalyst(is(used((phosphoric(acid(
Alkene(+(steam((alcohol(
( ( ( ( (((((((H3PO4(
Eg(CH2=CH2(g)(+(H2O(g)((((((CH3CH2OH(l)(
(catalyst(is(always(written(over(the(arrow)&
Only(symmetrical(alkenes(need(to(be(used(
+

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355

Sample(exam(questionP(
substitution(and(addition(reactions(
A(student(was(given(four(colourless(liquids(that(were(
labelled(A,(B,(C(and(D.(They(were(known(to(be(ethanol,(
ethanoic(acid,(pentane(and(hexene,(but(the(exact(identity(
of(each(liquid(was(unknown.(The(student(tested(the(
properties(of(each(liquid(and(obtained(the(results(shown(
below.(
A&
B&
C&
D&
(

Solubility(in(
water(

insoluble(

soluble(

soluble(

insoluble(

Addition(of(Br2(
solution(

Colour(
disappears(

No(
immediate(
reaction(

No(
immediate(
reaction(

No(
immediate(
reaction(

Addition(of(
Na2CO3(powder(

No(reaction(

Gas(evolved(

No(reaction(

No(reaction(

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356

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Substitution Reactions of Haloalkanes,
Oxidation of Alkanols and Esterification Reactions
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357

Key&knowledge&
common(reactions(of(organic(compounds(
including(equations:(substitution(reactions(
of(primary(haloalkanes,(oxidation(of(
primary(alkanols,(and(esteri@ication)(

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358

Primary&haloalkanes&
Haloalkanes(are(named(according(to(the(number(
of(carbon(atoms(that(are(bonded(to(the(carbon(on(
which(the(halogen(is(bonded.(
A(primary(haloalkane(has(the(halogen(atom(
bonded(to(a(carbon(that(is(on(the(end(of(the(
carbon(chain((it(is(only(bonded(to(one(other(
carbon((hence(primary)(
eg((CH3CH2CH2Cl(

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359

Substitution(reactions(of(haloalkanes(
In(this(case(the(substitution(reaction(involves(
the(replacement(of(one(functional(group(with(
another.(
The(halogen(atom(makes(the(carbon(atom(
into(a(positive(charge(centre,(so(nucleophiles(
(functional(groups(with(a(nonPbonding(pair(
of(electrons(or(a(negative(charge)(are(
attracted(to(it.(
Hydroxide(ions,(water((and(ammonia(are(all(
nucleophiles(

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360

Equations:(
CH3Cl(+(OHP(((CH3OH(+(ClP(

C2H5Cl(+(H2O((C2H5OH(+(HCl(
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361

Oxidation(reactions(of(alkanols(
Oxidation(of(a(primary(alkanol(produces(a(carboxylic(
acid(
NB(The(oxidant(used(is(either(the(permanganate(ion,(or(
the(dichromate(ion.(In(addition,(heat(is(required(and(
acid((eg(H2SO4)(

This(is(how(vinegar(is(made(from(wine!(
When(wine( goes (off,(we(often(say(it(has(gone(
vinegary ((because(ethanoic(acid(has(been(made(by(
the(oxidation(of(the(ethanol(by(oxygen(in(the(air((and(
bacteria)(
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362

Only(primary(alkanols(produce(carboxylic(acids(
when(oxidised:(

Secondary(alkanols(oxidise(to(ketones(and(
tertiary(alkanols(cannot(be(oxidised.(

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363

Alkanoic(acids(as(weak(acids(
Alkanoic&acids&ionise&to&a&limited&extent&in&water,&
producing&a&weakly&acidic&soluFon.&
&
Watch&for&opportuniFes&in&which&acidBbase&reacFons&
may&occur&between&an&alkanoic&acid&and&a&base,&such&
as&sodium&hydroxide.&

&

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364

Esteri@ication(reactions(
Esteri@ication(is(a(condensation(reaction(in(
which(an(ester(is(produced(
The(reaction(occurs(between(an(alkanoic(acid(
and(an(alkanol.(
(Alkanol(+(alkanoic(acid(((ester(+(water(
An(acid(catalyst((eg(H2SO4(is(required(for(this(
reaction(to(work(and(the(mixture(must(be(
heated(

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365

The(name(of(an(ester(is(taken(from(the(names(
of(the(alcohol(and(carboxylic(acid(from(which(it(
is(formed.(
The(name(of(an(ester(ends(in((Poate(
(eg(the(ester(made(from(ethanol(and(propanoic(
acid(would(be(ethyl(propanoate((note(the(
alcohol(name(comes(@irst)(
From the

carboxylic acid
From the
alcohol

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366

Properties(of(esters(
Many(esters(have(a(strong(smell(or(@lavour.(
Many(arti@icial(@lavourings((eg(banana(essence)(
are(esters.(
Small(molecular(esters(are(volatile((become(
vapour(easily)(and(are(smelly.(
Large(molecular(esters(include(waxes(and(oils(

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367

General(equation(for(esteri@ication(

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368

Equations(for(the(formation(of(esters(
1.(Ethyl(ethanoate(

CH3COOH((((((+(((((C2H5OH(( (
Ethanoic acid

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ethanol

(((((CH3COOC2H5((((+(((((((H2O(((
ethyl ethanoate

water

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369

2. Hexyl(propanoate(
Hexanol(+(propanoic(acid ((((((((hexyl(propanoate(+(water(
(
C6H13OH((+((C2H5COOH( ((((((C2H5COOC6H13((+(H2O(

&&&

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370

Sample(exam(question((substitution,(oxidation(and(
esteri@ication(
Which(one(of((
the(following((
organic(reactions((
does(not(result(in((
the(product((
shown(on(the((
rightPhand(side((
of(the(reaction?(

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371

Answer(
Alternative(A(is(a(substitution(reaction(
between(sodium(hydroxide(and(1P
chlorobutane(to(make(butanP1Pol.(
Alternative(B(is(an(addition(reaction(between(
butP2Pene(and(HCl(which(should(make(2P
chlorobutane,(however(the(product(given(is(
1Pchlorobutane(which(is(impossible.(
Alternative(C(is(an(esteri@ication(reaction(
between(methanol(and(ethanoic(acid(forming(
methyl(ethanoate(
Alternative(D(is(an(addition(reaction(between(
propene(and(steam(forming(propanP2Pol(
(

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372

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Reaction Pathways

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373

Key(knowledge(
common(reactions(of(organic(compounds(
including(equations:(addition(reactions(of(
alkenes((addition(of(hydrogen(halides(and(water(
limited(to(symmetrical(alkenes),(substitution(
reactions(of(alkanes(and(primary(haloalkanes,(
oxidation(of(primary(alkanols,(and(esteri@ication(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:((
(production(of(esters(from(alkenes(

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374

Reaction(Pathways((
In(the(previous(sections(we(have(found(a(range(of(
ways(to(produce(certain(chemicals.(
eg(Ethanol(can(be(produced(by((
1. the(addition(reaction(between(ethene(and(
steam((
2. the(substitution(reaction(between(
chloroethane(and(sodium(hydroxide(

&
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375

These(different(methods,(sometimes(with(many(
stages,(are(known(as(reaction(pathways.(
It(is(important(to(be(aware(of(the(principles(of(
green(chemistry(including(the(minimisation(of(
waste(materials,(of(energy(use(and(the(use(of(
environmentally(friendly(solvents.(

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376

Reaction(pathways(can(be(represented(visually(
as(a(web(of(reactions.((

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377

The(synthesis(of(ethyl(propanoate(
Ethyl(propanoate(is(an(ester(which(is(made(
from(ethanol(and(propanoic(acid(
Ethanol(can(be(made(by(two(different(reaction(
pathways(

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378

Similarly(propanoic(acid(can(be(made(by(a(reaction(
pathway(from(propane(

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379

&
The(two(pathways(join(to(make(ethyl(
propanoate&
&

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380

Sample(exam(question((reaction(
pathways(
The(ester(methyl(propanoate(has(a(characteristic(fruity(odour(
and(has(been(isolated(from(many(fruits(including(pineapple.(A(
sample(of(this(ester(is(to(be(prepared(in(the(laboratory.(A(partly(
completed(reaction(pathway(for(this(preparation(is(shown(
below.(
C3H7Cl(
((((((((reagent(X(
(
(
(
2Cr
2O7
Compound(K ( !!!
((((((((C
((((((methyl (
( ( ( (
3H6O2 (
concentrated
+
H 2SO4 catalyst
( ((((((((( ( and
( H ( ( ( ( ((((((((((((((propanoate(
!!!!!

(
( (((((((((((compound(L(((
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381

(i) Write(a(structural(formula,(showing(all(bonds,(for(
methyl(propanoate(

(ii) Write(structural(formulae,(showing(all(bonds,(for(
compounds(K(and(L(

(iii)Write(the(formula(of(reagent(X(
(
(
VCAA(June(2008(Q6(
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382

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Proteins: Formation and Structure

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383

Key(Knowledge(
organic(reaction(pathways(including(appropriate(
equations(and(reagents:(
((((P(condensation(and(polymerisation(reactions((((
(((((((that(produce(large(biomolecules(including(((
((((((((carbohydrates),(proteins((and(DNA)(
chemical(bonding:(
(primary,(secondary(and(tertiary(structures(of(proteins(
(the(role(of(the(tertiary(structure(of(proteins(in(enzyme(
action(
(denaturing(of(proteins:(effect(of(changes(in(pH(and(
temperature(on(bonding(

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384

Proteins&
Proteins(are(fundamental(to(the(structure(of(cells(
as(well(as(their(operation.(
They(may(be(structural,(such(as(proteins(in(
muscle,(hair,(nails(etc(
Enzymes(are(proteins(which(catalyze(many(
reactions(that(occur(in(the(human(body.(
Hormones(are(proteins,(as(is(haemoglobin(which(
carries(oxygen(around(in(the(blood.(

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385

Amino(acids(
The(monomers(from(which(proteins(are(
built(are(called(2Pamino(acids((or(Pamino(
acids).(
They(consist(of(a(central(C(atom(which(has(
bonded(to(it(a(carboxyl((COOH)(group(and(
an(amine((NH2)(group(as(well(as(a(H(atom(
and(a(side(chain(denoted(((
(((as(Z(which(may(be(one(of(20(
(((different(groups.((
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386

The&side&chains&
The(20(different(side(chains(are(shown(in(the(data(
book((table(8)(
(

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387

The(functional(groups(
The(carboxyl(group(allows(an(amino(acid(to(behave(
in(solution(as(an(acid.(
When(the(pH(is(high,(the(amino(acid(donates(an(H+(
ion(to(the(solution(and(it(becomes(negatively(
charged.(
The(amine(group(allows(an(
((((amino(acid(to(behave(as(a((
((((base(in(solution.(
When(the(pH(is(low,(the((
((((amino(acid(can(accept(an((
((((H+(ion(from(the(solution((
((((and(it(becomes(positively((
(((charged.(
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388

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389

In(an(approximately(neutral(solution,(an(amino(
acid(will(have(both(gained(and(lost(an(H+,(so(will(
have(a(positive(and(a(negative(charge.(
This(is(called(a(Zwitterion.(
The(pH(at(which(the(amino(acid(exists(as(a(
zwitterion(is(called(its(isoelectric(point(and(
depends(on(the(side(chain(of(the(amino(acid.(

&

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390

Formation(of(proteins(
Amino(acids(undergo(condensation(reactions(
with(other(amino(acids(to(form(dipeptides,(
polypeptides(and(proteins.(
(((An(amide(functional(group(joins(the(residues(of(
the(alkanoic(acid(and(amine.(
((((This(functional(group(may(also(be(called(a(
peptide(link.(

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391

Forming(a(dipeptide(
A(condensation(reaction(causes(a(molecule(of(water(to(
be(formed(each(time(two(amino(acids(join(via(an(
amide(functional(group(or(peptide(link.(

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392

Structure(of(proteins(
The(structure(of(proteins(is(very(involved(and(may(
be(described(at(different(levels(of(complexity.(
These(levels(are(known(as(the(primary,(secondary,(
tertiary(and(quaternary(structures(of(a(protein.(

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393

Primary(structure(
This(is(the(type,(number(and(the(sequence(of(
amino(acids(in(a(protein(chain.(
The(bonding(involved(here(is(covalent(bonding.(

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394

Secondary(structure(
A(protein(chain(is(very(long((more(than(50(
amino(acids)(and(coils(up(due(to(hydrogen(
bonds(between(different(parts(of(the(chain.(
The(chain(may(form(a(spiral((Phelix)(or(a(
pleated(sheet((like(corrugated(cardboard)(

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395

Tertiary(structure(
The(coiled(protein(chain(is(still(long(and(folds(up(
to(form(the(operational(shape(of(the(protein.((
This(is(the(tertiary(structure.(
Bonds(form(between(ZPgroups(of(the(amino(acids.(
These(may(be(dispersion(forces,(hydrogen(bonds,(
ionic(bonds,(or(even(covalent((disul@ide(bridge)(
bonds.(

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396

This(overall(threePdimensional(shape(helps(to(
determine(the(function(of(a(protein.(
Many(proteins(have(a(metal(ion(as(part(of(their(
structure,(or(may(be(made(up(of(several(protein(
chains(bound(together.(
This(fully(working(shape(of(the(protein(is(its(
quaternary(structure.(

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397

Sample(exam(question(P(proteins(
The(following(structure(shows(part(of(a(polypeptide(
(
(
(
(
(i) Name(the(amino(acids(that(make(up(this(section(of(
the(polypeptide(
At(a(particular(pH,(an(amino(acid(in(solution(can(exist(
as(ions(that(have(both(a(negative(and(positive(charge.(
These(ions(are(called(zwitterions.(
((ii)((Choose(one(of(the(amino(acids(in(this(section(of((((
((((((((((polypeptide(and(draw(the(structure(of(its((
((((((((((zwitterion(clearly(showing(all(bonds.(
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398

Answer(
(i)(
(
(
(
(
(
(
(
(ii)((Zwitterion:(
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399

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Proteins: Tertiary Structure and Enzymes

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400

Key(Knowledge(
chemical(bonding:(
(primary,(secondary(and(tertiary(
structures(of(proteins(
(the(role(of(the(tertiary(structure(of(
proteins(in(enzyme(action(
(denaturing(of(proteins:(effect(of(changes(
in(pH(and(temperature(on(bonding(
&
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401

The&four&levels&of&protein&structure&

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402

Enzymes(
Enzymes(are(proteins(that(act(as(
biological(catalysts((increase(the(rate(of((
biological(reactions).(
An(example(of(a(most(ef@icient(enzyme(is(
catalase.((
Each(catalase(molecule(can(decompose(
millions(of(hydrogen(peroxide(molecules(
every(second(
((((((((((((((((((2H2O2(( (2H2O((+((O2(
(
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403

The&catalase&enzyme&

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404

Compared(to(inorganic(catalysts,(
enzymes(are:(
More(ef@icient((resulting(in(much(
faster(reactions(
More(speci@ic((may(only(work(for(one(
reaction(
Able(to(act(only(in(a(narrow(
temperature(range((body(temperature(
Able(to(act(only(in(a(narrow(pH(range(

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405

Enzyme(action(
The(tertiary(structure(of(the(enzyme(enables(
it(to(form(intermolecular(bonds(with(speci@ic(
reactants((the(substrate)(and(so(determines(
the(catalytic(ability(of(an(enzyme.(
The(enzyme(has(an(active(site(which(is(where(
the(substrate((reactants)(binds(by(
intermolecular(bonding.(
The(active(site(@its(the(required(molecules(
exactly(and(this(is(where(the(reaction(occurs.(
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406

When(the(products(are(released(from(the(
active(site,(the(enzyme(is(able(to(accept(
another(substrate(and(so(on.(
It(is(not(changed(by(the(reaction(it(is(
catalysing.(
Enzymes(are(thought(to(act(according(to(
the(lock(and(key(mechanism.(
This(describes(the(enzymes(active(site(as(
@itting(the(substrate(perfectly.(
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407

The(lock(and(key(mechanism(of(enzyme(
action(

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408

Denaturation(of(enzymes(
When(enzymes(are(heated(to(a(
temperature(above(their(normal(
operation(temperature,(or(when(the(pH(of(
the(solution(is(changed,(their(structure(is(
disrupted,(intermolecular(bonds(are(
broken(and(the(enzyme(is(denatured.(

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409

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410

After(denaturation,(the(protein(
chains(may(come(together(again,(but(
the(working(shape(has(been(lost(and(
the(chains(just(clump.((
This(is(coagulation.(

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411

Examples(of(coagulation((cooking(eggs:(
clear(egg(white(becomes(hard(and(white(
(P(cooking(meat((becomes(brown(and(
harder(
(P(Curdling(milk(with(lemon(juice(or(
vinegar.(
&

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412

Below(normal(operating(temperatures,(
enzymes(become(inactive.((
They(may(work(very(slowly(or(not(at(all.((
If(the(temperature(increases(again,(their(
structure(is(still(intact.(
SO,(in(summary,(denaturation(stops(the(
enzyme(from(working(altogether(because(
the(tertiary(structure(is(changed,(while(
deactivating(slows(it(right(down,(but(the(
enzyme(can(become(active(again.(
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413

Sample(exam(question(P(enzymes(
Which(one(of(the(following(statements(about(enzymes(
is(not(true?(
A. Enzymes(can(only(be(denatured(by(an(increase(in(
temperature(
B. Enzymes(may(form(temporary(ionPdipole(bonds(
with(substrate(molecules(
C. Enzymes(speed(up(reactions(by(holding(substrate(
molecules(in(positions(necessary(for(reaction.(
D. The(tertiary(structure(of(an(enzyme(may(be(altered(
if(one(amino(acid(in(its(primary(structure(is(
substituted(for(another,(different((amino(acid.(
VCAA(June(2009(Q(17(
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414

Answer(
A. Is(not(true,(as(a(change(in(pH(also(causes(
enzymes(to(be(denatured.(
B. Is(true,(as(ionPdipole(bonds(may(indeed(be(
formed(between(substrates(and(enzymes(
C. Is(true.(This(is(the(method(by(which(
enzymes(work.(
D. Is(true,(since(a(change(in(the(primary(
structure(may(indeed(have(an(effect(on(the(
tertiary(structure.(
A(is(the(answer!(
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415

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Lipids

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416

Key(Knowledge(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(reactions(that(produce(lipids(
(limited(to(triglycerides)(

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417

Lipids(
Lipids(are(a(class(of(molecules(that(include(
fats,(oils,(steroids((including(cholesterol)(
and(waxes.(
Fats(and(oils(are(triglycerides.(
Each(triglyceride(molecule(is(formed(by(
the(condensation(reaction(between(one(
glycerol(molecule(and(three(fatty(acids.((

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418

FormaFon&of&a&triglyceride&

Fatty(acids(are(carboxylic(acids(with(a(long(
hydrocarbon(chain(eg(H3C(CH2)16COOH(
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419

The(difference(between(fats(and(oils(is(
that(fats(are(solid(at(room(temperature(
whereas(oils(are(liquid.(
Fats(tend(to(come(from(animal(sources(
whereas(oils(tend(to(come(from(plants.(
There(are(other(lipids(such(as(
phospholipids((used(to(make(the(
membrane(of(cells)(and(steroids(
(including(cholesterol),(but(in(this(course(
we(will(only(discuss(triglycerides.(
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420

Types(of(fats(
A(fat((or(oil)(is(named(according(to(the(
type(of(fatty(acids(in(it.(
Saturated(fats(are(made(from(fatty(acids(
with(only(carbonPcarbon(single(bonds.(
They(are(generally(considered(to(be(
unhealthy.(
They((saturated(fatty(acids)(have(the(
general(formula(CnH2nO2(
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421

Unsaturated(fats(
A(monoPunsaturated(fat(is(made(from(fatty(acids(
with(only(one(carbonPcarbon(double(bond(per(fatty(
acid.(
General(formula(CnH2nP2O2(
The(reduced(number(of(hydrogens(is(due(to(the(
presence(of(the(double(bond.(
PolyPunsaturated(fats(are(found(in(vegetable(oils.(
They(have(more(than(one(carbonPcarbon(double(
bond(per(fatty(acid.(
General(formula(may(be(one(of((
(CnH2nP4O2((two(double(bonds)((
or(CnH2nP6O2((three(double(bonds)((etc(
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422

&
Type&of&
Name&of&
fat&
fatty&acid&
&

Semi.structural&formula&

Molecular&
formula&

saturated( Stearic(

CH3(CH2)16COOH(

C18H36O2(

MonoP
unsaturated(

Oleic(

CH3(CH2)7CH=CH(CH2)7COOH(

C18H34O2(

PolyP(
unsaturated(

Linoleic(

CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH(

C18H32O2(

PolyP(
unsaturated(

Linolenic(

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH(

C18H30O2(

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423

Table(9(from(the(data(book(

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424

Melting(point(of(triglycerides(
The(presence(of(CPC(double(bonds(in(the(fatty(
acid(chains(creates(kinks(in(the(chain.(
This(prevents(them(from(packing(closely(and(
reduces(the(strength(of(the(dispersion(forces(
between(the(chains.(
This(lowers(the(melting(point(of(the(
unsaturated(fat.(
So(unsaturated(fats,(with(double(bonds((and(
kinks)(are(liquids(and(have(lower(melting(
points(than(saturated(fats((solids)(with(only(
single(bonds(with(only(single(CPC(bonds.(

&

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425

Digestion(of(triglycerides(
Fats(are(emulsi@ied(by(bile(in(the(small(intestine,(
then(enzymes(catalyse(the(alkaline(hydrolysis(of(
the(ester(linkages(to(form(fatty(acids(and(
glycerol.(
These(small(molecules(are(absorbed(into(the(
blood(stream(and(are(reassembled(into(
triglycerides(which(are(transported(in(
lipoproteins(to(adipose(tissue(where(the(fats(are(
stored.(

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426

Condensation(Polymerisation((a(
summary(
If(a(monomer(has(a(functional(group(on(each(
end,(it(can(react(with(other(monomers(in(a(
series(of(condensation(reactions(to(form(a(
condensation(polymer.(
Condensation(polymers(occur(in(
biomolecules(as(well(as(synthetic(@ibres(
such(as(nylon(and(polyesters.(

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427

Functional(groups(and(their(
polymers
(
Polymer&
Functional&
Other&name&
Formed&from&
group&

these&
functional&
groups&

Proteins(
(dipeptides(and(
polypeptides)(
Nylon(

Amide(

Peptide(linkage(

Amino(and(
carboxyl((

Carbohydrate(

Ether(

Glycosidic(
linkage(

Two(hydroxyl(

Triglyceride((not(
really(a(polymer)(
Polyester(

Ester(

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Carboxyl(and(
hydroxyl(

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428

Sample(exam(question(P(triglycerides(
(a)((i)(A(long(chain(carboxylic(acid(can(be(represented(by(
the(general(formula(RCOOH(where(R(represents(a(
hydrocarbon(group.(Draw(the(structure(of(a(fat(formed(by(
the(reaction(between(glycerol(and(three(molecules(of(
RCOOH.(Clearly(show(the(structure(of(all(ester(groups(in(
the(fat.(

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429

(ii)(Palmitic(acid((C16H32O2)(and(oleic(acid((C18H34O2)(are(both(
long(chain(carboxylic(acids.(Which(one(of(them(is(classi@ied(as(an(
unsaturated(carboxylic(acid?(
Answer:(
General(formula:(CnH2nO2(
(
(
(
(
(b) Unsaturated(fats(can(be(converted(into(saturated(fats(by(
reaction(with(hydrogen(gas(in(the(presence(of(a(metallic(
catalyst.(In(one(such(conversion,(2.50(mole(of(an(unsaturated(
fat(is(converted(to(a(saturated(fat(by(reaction(with(15.0(g(of(
H2(gas.(Calculate(the(number(of(carbon(to(carbon(double(
bonds(present(in(a(molecule(of(the(unsaturated(fat.(
(
VCAA(Nov(2006(Q9(
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430

Answer((b)(
n(H2)(=( 15.0 = 7.50mol
2.02

(
n(fat)(=(2.50(mol(
1(mol(of(H2(reacts(with(1(mol(of(double(
bonds(
7.50
So(n(double(bonds)(=( 2.50 = 3 mol
(
There(are(3(double(bonds(in(each(molecule(
of(the(unsaturated(fat.((
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431

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Carbohydrates

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432

Key(Knowledge(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(and(polymerisation(reactions(
that(produce(large(biomolecules(including(
carbohydrates,((proteins(and(DNA)(

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433

Carbohydrates(
Carbohydrates(are(our(primary(energy(
source.(
They(include(monosaccharides(such(as(
glucose,(disaccharides(such(as(sucrose,(and(
polysaccharides(such(as(starch(and(
cellulose.(

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434

Monosaccharides(
All(have(the(general(formula(CH2O(
They(are(the(simplest(sugars(
Glucose(has(the(formula(C6H12O6(and(can(
occur(in(solution(as(one(of(two(cyclic(
molecules(((and((glucose)(or(a(straight(
chain(version.(
This(is((glucose:(
&&&&
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435

Fructose(and(galactose(are(also(common(
monosaccharides.(
Fructose:(

All(are(very(soluble(in(water(due(to(the(
presence(of(a(large(number(of(hydroxyl(
groups(and(the(consequent(hydrogen(
bonding(that(is(possible(between(the(
hydroxyl(groups(and(the(water(molecules.(
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436

Disaccharides(
A(condensation(reaction(between(hydroxyl(
groups(on(adjacent(monosaccharides(will(
result(in(a(disaccharide.(
Maltose(is(formed(when(two(glucose(
molecules(join(in(a(condensation(reaction(
with(a(water(molecule(being(released.(
&&

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437

Glucose(+(galactose((lactose(
Glucose(+(fructose((sucrose(

The(monomers(are(joined(by(a(glycosidic(
linkage,(also(known(as(an(ether(functional(
group.(
&
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438

Polysaccharides(
!There(are(three(different(types(of(
polysaccharides(that(can(be(formed(from(
glucose(
Starch(
" The(molecule(that(plants(use(to(store(energy(
Cellulose(
" A(structural(molecule(used(in(plant(cell(walls((
" Cannot(be(digested(by(humans((dietary(@ibre)(
Glycogen(
" The(molecule(that(animals(use(to(store(energy.(
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439

Starch(
This(is(made(up(of(long(chains(of(Pglucose.(
There(is(little(branching(in(starch(making(it(slow(
to(be(hydrolysed((broken(down(into(glucose(
molecules)(/(digested(by(enzymes(in(presence(of(
water.((

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440

Cellulose(
Cellulose(is(a(linear(polymer(of(Pglucose(
and(Pglucose.(
Individual(bundles(of(cellulose(molecules(
are(joined(by(hydrogen(bonds(

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441

Glycogen(
This(is(a(branched(polymer(of(Pglucose.(
The(branches(make(it(easier(for(enzymes(
to(hydrolyse(the(ether(linkages(and(
release(the(glucose(for(respiration((and(
the(production(of(energy).(
&

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442

Sample(exam(question(P(carbohydrates(
Amylase(is(an(enzyme(that(speci@ically(digests(
starch(in(humans.(A(major(product(of(this(starch(
hydrolysis(reaction(is(
A. Maltose(
B. Glycogen(
C. Cellulose(
D. Glycerol(
(
VCAA(June(2006(Q(14(
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443

Answer(
Starch(is(a(condensation(polymer(of(glucose(
((((When(it(is(hydrolysed,(it(breaks(down(into(((
(((((smaller(molecules,(such(as(the(disaccharide,(((
(((((maltose.(
Glycogen(and(cellulose(are(both(also(condensation(
polymers(of(glucose,(but(one(polymer(will(not(be(
hydrolysed(to(make(a(different(polymer.(
Glycerol(is(a(small(molecule(that(is(produced(when(
fats(are(hydrolysed.(
The(answer(is(A.(
(

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444

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
DNA

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445

Key&Knowledge&
!chemical(bonding:(
(primary(and(secondary(structure(of(DNA(
!organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(and(polymerisation((
((((reactions(that(produce(large(biomolecules((
(((((including((carbohydrates,(proteins(and)((((
(((((DNA(
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446

Biological(Importance(of(DNA(
Chromosomes(are(found(in(the(nucleus(of(almost(
all(cells.(
Chromosomes(contain(sections(called(genes(
Genes(are(made(of(DNA(
Genes(blueprint(the(production(of(proteins(

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447

The(bonding(and(structure(of(DNA(
DNA((deoxyribonucleic(acid)(is(a(condensation(
polymer(
There(are(four(nucleotide(monomers(
Nucleotides(are(made(up(of(three(molecules(joined(
by(condensation(reactions((a(sugar((deoxyribose)(
a(phosphate(group(and(one(of(four(different(
organic(bases((adenine,(thymine,(cytosine(and(
glycine(

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448

Structure(of(the(bases(is(in(the(VCE(Chemistry(
data(book(

Adenine(and(guanine(are(
purine(bases(

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cytosine(and(thymine(are(
pyramidine(bases(

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449

Formation(of(nucleotides(
Carbon(1(of(the(sugar(bonds(to(the(organic(base(
and(carbon(5(of(the(sugar(bonds(to(the(
phosphate(group(in(condensation(reactions(
(water(released).(
These(structures(are(in(the(data(book((table(10)(
1

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450

Condensation(reactions(to(form(the(
polynucleotide(chain(

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451

Degrees(of(DNA(structure(
Primary(structure((order(of(nucleotides(
Held(together(by(covalent(bonding(
(
Secondary(structure((held(together(by(
hydrogen(bonding.(
DNA(is(made(up(of(two(strands(
Organic(bases(pair(up(with(corresponding(
base(on(second(DNA(strand(using(HP
bonding.(
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452

Hydrogen(bonding(between(the(bases(

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453

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454

Tertiary(structure((negative(charge(due(to(
phosphate(groups(allows(DNA(to(supercoil(around(
proteins(called(histones.(
This(tight(packaging(creates(a(chromosome.(

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455

Sample(exam(question(P(DNA(
In(the(piece(of(doublePstranded(DNA(shown,(the(letters(
A,C,(G(and(T(represent(the(bases(adenine,(cytosine,(
guanine(and(thymine(respectively.(Each(vertical(line(
represents(a(sugarPphosphate(backbone.(
(
Which(of(the(following((
alternatives(correctly(
identi@ies(the(DNA(piece(
that(is(most(readily((
separated(by(heating(
and(the(strand(of(the(
highest(molecular(mass?(
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(
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VCAA(June(2008(Q10(456

Use&the&data&booklet!&

Piece(most(readily( Strand(of(highest(
separated(by(
molecular(mass(
heating(

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A.(

1(

X(

B.(

2(

W(

C.(

2(

X(

D.(

1(

W(

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457

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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Biochemical Fuels

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458

Key(Knowledge(
!organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(production(of(biochemical(fuels(including(
the(fermentation(of(sugars(to(produce(
ethanol(

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459

Biochemical(fuels((biofuels)(
! These(are(fuels(derived(from(plant(materials(
such(as(grains,(sugarcane(or(vegetable(waste(
(biomass),(and(vegetable(oils.(
! They(may(be(used(alone(or(mixed(with(fossil(
fuels.(
! Ethanol(and(biodiesel(
((((are(the(most(common(
(((((biofuels.(

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460

! Biofuels(are(considered(carbon(neutral(because(
they(are(made(from(plants(which(used(CO2(for(
photosynthesis,(so(when(they(are(burnt(that(same(
CO2(is(returned.(
! Recall(the(equation(for(photosynthesis:(
sunlight
6CO2(g)(+(6H2O(l) !!!
( ((C6H12O6(aq)((+(6O2(g)(
(
! Combustion(of(ethanol:(
(((((C2H5OH(l)((+((O2(g)((((2CO2(g)((+((3H2O(l)(

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461

Ethanol(
! Made(by(the(fermentation(of(sugars(
! This(is(an(anaerobic((in(the(absence(of(O2)(
process(
C6H12O6(aq)( !!!
( enzymes
((2(C2H5OH(aq)((+(2CO2(g)(
&
! The(product(is(not(pure(ethanol((only(about(
20%,(so(must(be(distilled(to(purify.(
! Recall(that(distillation(uses(the(difference(in(
boiling(points(of(liquids(to(separate(them(
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462

Distillation(

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463

Production(of(ethanol(as(a(green(
process(
CO2(from(the(fermentation(is(sold(to(soft(drink(
manufacturers.(
5%(petrol(is(added(to(prevent(people(drinking(it.(
Waste(water(used(for(irrigating(crops(
Remains(of(fermentation(used(for(feedstock.(
Recycle(byproducts(as(fertiliser(

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464

Biodiesel(
This(is(a(mixture(of(esters(produced(by(a(chemical(
reaction(between(vegetable(oil(and(an(alcohol(such(
as(methanol.(
The(properties(of(biodiesel(are(very(similar(to(
those(of(diesel,((
In(virtually(all(models(of(equipment(and(vehicles(
currently(in(production,(a(biodiesel(blended(fuel(is(
compatible.((
Raw(materials:(fresh(vegetable(oils(or(recycled(
vegetable(oil(or(animal(fats.(
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465

How(biodiesel(is(made:(
The(triglyceride(is(hydrolysed&by(warming(it(with(
KOH(aq).(
KOH(also(acts(as(a(catalyst(
Overall(the(triglyceride(breaks(down(to(three(fatty(
acid(molecules,(plus(glycerol.(
Methanol(is(added(and(reacts(with(the(fatty(acid(to(
make(biodiesel.(

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466

Equation(for(the(formation(of(
biodiesel(

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467

Biogas&
Equal(mix(of(CO2(and(methane(((CH4)(
Generated(when(organic(material(decomposes(in(
the(absence(of(oxygen.(
Particularly(suited(to(farms(

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468

Lots(of(sources(of(organic(waste(can(be(adapted(to(
biogas(generation.(
eg(Werribee(waste(treatment(plant(
Rubbish(tips(
Chicken(farms(
Piggeries(
Food(processing(plants(

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469

Sample(exam(question(P(biofuels(
A(product(derived(from(palm(tree(oil(is(used(as(an(alternative(fuel(in(
diesel(engines.(Palm(oil(is(converted(to(biodiesel(by(the(following(
reaction(
(
(
(
(
(
(
Glycerol(is(separated(from(the(reaction(mixture.(The(mixture(of(the(
compounds(labelled(X,(Y(and(Z(is(used(as(palm(oil(biodiesel.(The(term(
that(best(describes(the(mixture(of(compounds(in(palm(oil(biodiesel(is(
A. Methyl(esters ( (B.((carbohydrates(((
C. Carboxylic(acids ( (D.((monoglycerides(
VCAA(June(2009(Q18(
(
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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
The Design and Synthesis of Medicines including Aspirin

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471

Key(Knowledge(
organic(reaction(pathways(including(appropriate(
equations(and(reagents:(
P function(of(organic(molecules(in(the(design(and(
synthesis(of(medicines(including(the(production(of(
aspirin(from(salicylic(acid.(

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472

Aspirin((
Aspirin(is(an(ester.(
It(is(derived(from(salicylic(acid(which(was(
known(as(a(pain(killer(and(reduced(fever(but(
caused(irritation(to(the(lining(of(the(stomach(
and(the(mouth.(
The(full(name(of(aspirin(is(acetyl(salicylic(acid.(
Aspirin(is(much(less(irritating(to(the(stomach(
and(mouth(than(salicylic(acid.(
It(is(broken(down(into(salicylic(acid(in(the(
alkaline(surroundings(of(the(small(intestine.(
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473

Preparation(of(Aspirin(
Aspirin(can(be(made(by(two(different(
pathways(
Salicylic(acid(+(ethanoic(acid(

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474

Or(salicylic(acid(+(ethanoic(anhydride(

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475

Alkaline(hydrolysis(breaks(aspirin(down(

Aspirin(can(be(made((
soluble(by(creating(a((
sodium(salt.(
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476

Another(example(P(Penicillin(
An(example(of(a(drug(developed(after(chance(observations(
in(the(lab.(
A(culture(of(staph(bacteria(was(growing(and(a(mould(which(
grew(on(the(plate(by(mistake(was(found(to(kill(the(bacteria.(
Isolation/extraction(of(the(mould(was(dif@icult(when(it(was(
@irst(discovered.&
Increased(need(for(the(drug((WW2)(and(improved(
methods(extraction(12(years(later((1940)(
Initially(tested(on(mice,(but(quickly(moved(to(humans(due(
to(the(need(to(save(the(lives(of(soldiers(who(were(suffering(
from(infections(after(surgery(on(the(battle(@ield.(

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477

Eect&of&changing&the&structure&slightly&
Different(side(chains(are(possible(in(penicillin.(
Stomach(acid((
broke(penicillin((
down.((
Change(of(side(
chain(improved((
stability.(

&

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478

Resistance&to&drugs&
Bacteria(reproduce(very(rapidly(
Those(bacteria(that(are(slightly(different(and(can(
survive(the(drug,(get(to(reproduce(and(so(a(strain(
of(drug(resistant(bacteria(are(created.(
Taking(a(full(course(of(antibiotics(minimises(the(
chance(of(bacteria(surviving.(

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479

Developing(a(new(drug(
Lead(compounds(can(potentially(be(made(into(

drugs.(
Sources(may(be(herbal(or(traditional(
((remedies.(eg(aspirin.((
Computer(modelling(is(used(for(design(of(speci@ic(
drugs(

&

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480

Steps(in(drug(design(
Computer(modelling(
Development(of(synthetic(pathway(
Formulation(for(administering(drug(is(required(
Testing(is(needed((clinical(trials(
Comparison(with(placebos(to(see(how(effective(the(
drug(actually(is.(
Analysis(of(the(drug(tests(purity(

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481

Sample(exam(question((functional(
groups(in(drugs(
The(compound(salicin(can(be(converted(into(aspirin(using(
the(steps(below:(
(
(
(
(
(
(
(
(
VCAA((June(2010(Q(8(
(3
VCE Chemistry Unit
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(a)(What(type(of(linkage(is(circled(in(the(structure(of(
salicin?(
(b)In(step(1,(salicyl(alcohol(and(another(compound(is(
produced.((
(((((((i)What(group(of(biomolecules(does(this(compound((
(belong(to?(
((((((ii)(The(structure(of(this(other(compound(is(not(
(complete.(Write(the(formula(of(the(atom(or(group(of(
(atoms(represented(by(A(in(the(reaction(scheme( (above.(
(c) Step(2(involves(the(conversion(of(salicyl(alcohol(into(
salicylic(acid.(
(i) What(type(of(reaction(is(step(2?(
(ii) Suggest(a(suitable(reagent(to(carry(out(the(reaction.(
(
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(d)(Step(3(requires(sulfuric(acid(catalyst(and(another(
reagent.(Name(this(reagent.(

(
(
(e)(Aspirin(reacts(with(a(strong(base(according(to(the(
equation(
(
(
(
(
Draw(the(structure(of(the(product(B.(

(
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484