VCE Chemistry Unit 3

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

Ms Lanna Derry & Edrolo 2014
We do our best to make these slides comprehensive and up-to-date, however there may be errors.
We'd appreciate it if you pointed these out to us!
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(
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.(
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)(
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&
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.

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&

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.(
(&
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(
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)(
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.(
((
(

11
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

12
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)(
13
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)(
(

14
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)

15
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
(VCAA Q3 June 2008)
16
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
(VCAA Q8 June 2005)

17
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

18
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)

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)

20
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
(VCAA Q4 June 2007)
0.0200 : 0.0600
1 : 3
21

CHEMISTRY
Chemical Analysis
Volumetric Analysis
Simple titrations

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(

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(

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.(
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(
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!((
27
Making(a(standard(solution(

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(

29
Correct(use(of(pipette

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.(
31
Correct(use(of(burette

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.(

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.(
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(

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(
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.(

Non-concordant values
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)(
(
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(

39
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(=((

n
V
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)(
41
(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.(
(
42

CHEMISTRY
Chemical Analysis
Volumetric Analysis
Titration Curves

43
Key(Knowledge(
volumetric(analysis(including(
(determination(of(excess(and(limiting(
reagents(and)(titration(curves:(simple((and(
back)(titrations,(acidPbase((and(redox)(
titrations(

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.(

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(

46

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.(

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&

49

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(((

51

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(
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(
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(
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(
56

https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/chemical-analysis-vol-analysis-back-titrations/key-knowledge /
CHEMISTRY
Chemical Analysis
Volumetric Analysis
Back Titrations
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(
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.(
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)&
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&

Total&
amount&
of&
strong&
base&
added&
initially&
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)(
&
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.(
&

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(
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
(
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

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
We do our best to make these slides comprehensive and up-to-date, however
there
may2008)
be errors.
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

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
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)

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)

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

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.

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)
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.

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)

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.

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

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

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

78

https://edrolo.com.au/vce/subjects/chemistry/vce-chemistry/aos-1-chemical-analysis/chemical-analysis-vol-analysis-oxidation-numbers/key-knowledge/
CHEMISTRY
Chemical Analysis
Volumetric Analysis
Oxidation Numbers and Partial Ionic Equations

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)(
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.(

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(
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.(

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.(
84
84

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)(
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(
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(

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(

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(
&

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(

91

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
Chemical Analysis
Volumetric Analysis
Redox Titrations

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.(
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(

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(
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(
(
(
(
Ms Lanna Derry
&
Edrolo
2014
(
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)(
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)

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

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.

(VCAA Q9 June 2007)
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

(VCAA Q7 June 2009)
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

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)

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

(VCAA Q18 June 2005)
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

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.

(1 mark)
(VCAA Q2 June 2005)
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)

(VCAA Q2 June 2005)
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.
(VCAA Q2 June 2005)
108
QUESTION 4(b)i (ANSWER)

(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

(VCAA Q2 June 2005)
109
QUESTION 4(b)ii
(ii) Calculate the amount, in mole, of vitamin C present in each 25.00 mL

aliquot.

(1 mark)
(VCAA Q2 June 2005)
110
QUESTION 4(b)ii (ANSWER)

(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

(VCAA Q2 June 2005)
111
QUESTION 4(b)iii
(iii) Calculate the concentration of vitamin C in the original (undiluted)

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

(VCAA Q2 June 2005)
112
QUESTION 4(b)iii (ANSWER)

(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.

(VCAA Q2 June 2005)
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
(VCAA Q2 June 2005)
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

Diluted Fruit
Juice
Standard I3Solution
25.00mL
pipette
Conical Flask
Original Fruit
Juice
(VCAA Q2 June 2005)
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.

(VCAA Q2 June 2008)
(1 mark)
116
QUESTION 5 (i) (ANSWER)

(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

(VCAA Q2 June 2008)
117
QUESTION 5 (ii)
(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)
(VCAA Q2 June 2008)
118
QUESTION 5 (ii) (ANSWER)

(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

(VCAA Q2 June 2008)
119
QUESTION 5 (iii)
(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.
(VCAA Q2 June 2008)
120
QUESTION 5 (iii) (ANSWER)

(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.

(VCAA Q2 June 2008)
121

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CHEMISTRY
Chemical Analysis
Chromatography
General Features and TLC

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.(
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(
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(

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((
126
The(different(components(separate(as(
they(adsorb(onto(the(stationary(phase(
and(desorb(back(into(the(mobile(phase.(

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.(
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.((

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(

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.(

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(

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(

133

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CHEMISTRY
Chemical Analysis
Chromatography
HPLC and GLC

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.(

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(
&

136
The&Chromatogram&
Rt - retention time - determines sample identity
Rt
Rt
mAU
Area or height is
proportional to the
quantity of analyte.
Injection
time
137
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
amino acids
vitamins
homocysteine
138
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?(

((VCAA(June(2009(Q(5)(
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.(

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(
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)(

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.(
143
Chromatogram(
A(graph(with(peaks(which(correspond(to(
components(of(mixture(
Retention(time(=(time(taken(for(component(
to(pass(through(column(

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.(
145
145

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)(
147there may be errors.
Ms Lanna Derry
&
Edrolo
2014
We'd
appreciate
it
if
you
pointed
these
out
to
us!
(
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)(
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(

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)

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

4.0
= 8.0cm
0.50
(VCAA Q6 June 2006)
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)

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?

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)
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)

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
(VCAA Q6 June 2010)

156

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CHEMISTRY
Chemical Analysis
Atomic Absorption Spectroscopy

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(
158
The&electromagnetic&spectrum(
Radiation(in(the(electromagnetic(spectrum(
has(a(range(of(differing(energies.(
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.(
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.(

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(
162

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.(

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.(
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.((
166
Obtaining(Quantitative(results(
Standard(solutions(with(known(
concentrations(of(the(element(are(measured(
and(results(used(for(calibration(graph.(

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(

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(
169

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CHEMISTRY
Chemical Analysis
UV-Visible Spectroscopy

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.(

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.(
172

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.(

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.(
&

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.(
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(
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?(
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
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)

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.

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)

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
D. duller, due to electrons in atoms in the sodium vapour moving from lower to

(VCAAthere
Q18 June
may2007)
be errors.
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
B. brighter, due to electrons in atoms in the sodium vapour moving from lower to
C. duller, due to electrons in atoms in the sodium vapour moving from higher to
D. duller, due to electrons in atoms in the sodium vapour moving from lower to

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.

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 =
mgL-1

may
be errors.
(VCAAthere
Q2 June
2008)
186

What is the concentration, in mgL-1, of

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

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.

(VCAA Q2 June 2008)
188
QUESTION 3(b)
Calculate the mass, in mg, of manganese

in the steel sample.
Mass =

mg
(VCAA
Q2 June
there
may2008)
be errors.
189

Calculate the mass, in mg, of manganese

in the steel sample.

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

191

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CHEMISTRY
Chemical Analysis
Infrared Spectroscopy

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(
&
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(

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.(

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.(

196
How&an&infrared&spectrometer&
works&&

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.(
&
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)(

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.(
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.(

201
Identi;ication&of&functional&groups&&
See&Table&7&p7&VCE&Data&booklet&

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(
&

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.(

204
Ethanoic'acid'

205
Ethyl'ethanoate'(an'ester)'

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.(

207
What&functional&group/s&is/are&
present&here?&

208
What&do&you&see&in&this&spectrum?&

209
And&this&one?&

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(
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)(
(

212

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CHEMISTRY
Chemical Analysis
Mass Spectrometry

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.(

214
Diagram&of&a&mass&spectrometer&

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.(
&&
216
A(mass(spectrum(
(Propanoic(acid)((

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).(
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.(

219
!Peaks(due(to(common(groups(in(organic(
compounds(
!m/e(=(15( ( (CH3+(((methyl)(
!m/e(=(29( (CH3CH2+(((ethyl)(
!m/e(=(45( (COOH+(((carboxyl)(
(

220
Mass(spectrum(of(propanP1Pol(

221
Another(example((ethanol,(C2H5OH(

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(
223
Answer(
B(is(the(answer(
This(is(the(only(alternative(with(parts(of(the(
answer(being(positively(charged(particles(

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.
(VCAA
June 2010
Section
We do our best to make these slides comprehensive and up-to-date,
however
there
may BbeQ3)
errors.
225
QUESTION 1 (ANSWER)
Write an equation showing how either an ethanol molecule or a nitrogen dioxide

molecule becomes ionised in the mass spectrometer.

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)

227
QUESTION 2(a)
Which mass spectrum cannot be that of nitrogen dioxide?

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

Which mass spectrum cannot be that of nitrogen dioxide?
Spectrum A cannot be that of nitrogen dioxide.

229
QUESTION 2(b)
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.
230

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.
231
QUESTION 3
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.

232
QUESTION 3 (ANSWER)
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 +

233

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CHEMISTRY
Chemical Analysis
NMR Spectroscopy
Theory, Spin and H Environments
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)(

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((
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)(

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
Bapp
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((
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(
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)(

241
Example&of&an&NMR&spectrum&

242

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CHEMISTRY
Chemical Analysis
Analysing NMR Spectra

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.&
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.(
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(
246
p5 of data booklet
Also see p6 of data booklet

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(

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(.(
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.(

250
Ethanol&&3&environments&

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.(

252

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

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(
255
Chloroethane((2(environments,(one(
triplet(and(one(quartet(

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.(

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(
&

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.(
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)(
260
Answer(
D(describes(NMR(
A(describes(mass(spectroscopy(
B(describes(IR(spectroscopy(
C(describes(atomic(emission(spectroscopy(

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.

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.

The protein chains have different 1H NMR

spectra.
C.
Normal protein chain has the


spectrum.
D.


spectra.
(VCAA June 2008 Q5)

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.

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.


spectrum.
B.


spectra.
C.


spectrum.
D.

The protein chains have different 1H

NMR spectra.

NMR spectrum
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)
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)
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
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)

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
different proton environments.
(VCAA June 2009 Section B Q5 (modified))
270

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.

271
QUESTION 3(b)
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.
272

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

273
(colour is not important for this answer)


274
QUESTION 3(c)
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.

275
QUESTION 3(c) (ANSWER)

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

277
QUESTION 3(d)
Name the compound you have drawn in part (b).

Enter your answer here:

278
QUESTION 3(d) (ANSWER)

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

279
Ethanoic acid
(Eth 2 carbons, -oic acid due to the carboxyl functional group)

280

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CHEMISTRY
Chemical Analysis
Exam Question Combining Spectroscopic Techniques

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.(

282

283

284

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.(

286

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CHEMISTRY
Chemical Analysis
Calculations

287
Key(Knowledge(
calculations(including(amount(of(solids,(
liquids(and(gases;(concentration;(volume,(
pressure(and(temperature(of(gases(

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(
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(
290

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(
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(
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(
(
&

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(
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.&
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

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

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

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)

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

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)

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)

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

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)

305

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CHEMISTRY
Organic Chemical Pathways
Alkanes and their Isomers

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(
&
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.(

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(

309
The(beginning((pre@ix)(of(the(name(of(any(
organic(compound(indicates(the(number(of(
carbon(atoms(in(that(compound(

310
The&rst&four&alkanes&

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.!
&
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.(

313
Isomers(
Structural(isomers(P(compounds(with(the(
same(molecular(formula(but(different(
structures.(
Note(that(formulas(can(be((represented(
((((in(several(
((((ways:(

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(

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.(

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.&
VCE
& Chemistry Unit 3
317
What(is(the(name(of(this(
compound?(

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(
319

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CHEMISTRY
Alkenes, Haloalkanes, Amines and Alkanols

320
Key(knowledge(
structure(including(molecular,(structural(
(alkanes),(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),((alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10)(

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.(

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(((

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(

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.&
&

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.(
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.(

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.(
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(

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.(

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(
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(
332

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CHEMISTRY
Alkanoic Acids and Esthers

333
Key(knowledge(
structure(including(molecular,(structural(
(alkanes,(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),)(alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10(

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(
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.(
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(

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(
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.(
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(
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.(

VCAA(June(
2010(Q19(
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(
&
342

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CHEMISTRY
Substitution Reactions of Alkanes and
Addition Reactions of Alkenes
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(

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)(
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.(

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.(
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.(
348
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(

349
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).(

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.(
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(

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(

353
examples&
CH2=CH2(+(HCl((CH3CH2Cl(
CH3CH=CHCH3+(HBr(CH3CH2CH2BrCH3(

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(
+

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(

VCAA(June(2006(Q1(
356

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CHEMISTRY
Substitution Reactions of Haloalkanes,
Oxidation of Alkanols and Esterification Reactions
357
Key&knowledge&
including(equations:(substitution(reactions(
of(primary(haloalkanes,(oxidation(of(
primary(alkanols,(and(esteri@ication)(

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(

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(

360
Equations:(
CH3Cl(+(OHP(((CH3OH(+(ClP(
C2H5Cl(+(H2O((C2H5OH(+(HCl(
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)(
362
Only(primary(alkanols(produce(carboxylic(acids(
when(oxidised:(
Secondary(alkanols(oxidise(to(ketones(and(
tertiary(alkanols(cannot(be(oxidised.(

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.&
&

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(

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

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(

367
General(equation(for(esteri@ication(

368
Equations(for(the(formation(of(esters(
1.(Ethyl(ethanoate(
CH3COOH((((((+(((((C2H5OH(( (
Ethanoic acid

ethanol
(((((CH3COOC2H5((((+(((((((H2O(((
ethyl ethanoate
water
369
2. Hexyl(propanoate(
Hexanol(+(propanoic(acid ((((((((hexyl(propanoate(+(water(
(
C6H13OH((+((C2H5COOH( ((((((C2H5COOC6H13((+(H2O(
&&&

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?(

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(
(

372

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CHEMISTRY
Reaction Pathways

373
Key(knowledge(
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(

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(
&
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.(

376
Reaction(pathways(can(be(represented(visually(
as(a(web(of(reactions.((

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(

378
Similarly(propanoic(acid(can(be(made(by(a(reaction(
pathway(from(propane(

379
&
The(two(pathways(join(to(make(ethyl(
propanoate&
&

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(((
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(
382

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CHEMISTRY
Proteins: Formation and Structure

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(

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.(

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.((
386
The&side&chains&
The(20(different(side(chains(are(shown(in(the(data(
book((table(8)(
(

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.(
388

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.(
&

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.(

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.(

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.(

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.(

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)(

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.(

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.(

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.(
398
Answer(
(i)(
(
(
(
(
(
(
(
(ii)((Zwitterion:(
399

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CHEMISTRY
Proteins: Tertiary Structure and Enzymes

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(
&
401
The&four&levels&of&protein&structure&

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(
(
403
The&catalase&enzyme&

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(

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.(
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.(
407
The(lock(and(key(mechanism(of(enzyme(
action(

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.(

409

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.(

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.(
&

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.(
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(
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!(
415

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CHEMISTRY
Lipids

416
Key(Knowledge(
appropriate(equations(and(reagents:(
(condensation(reactions(that(produce(lipids(
(limited(to(triglycerides)(

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.((

418
FormaFon&of&a&triglyceride&
Fatty(acids(are(carboxylic(acids(with(a(long(
hydrocarbon(chain(eg(H3C(CH2)16COOH(
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.(
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(
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(
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(

423
Table(9(from(the(data(book(

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.(
&

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.(

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.(

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(

Carboxyl(and(
hydroxyl(
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.(

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(
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.((
431

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CHEMISTRY
Carbohydrates

432
Key(Knowledge(
(condensation(and(polymerisation(reactions(
that(produce(large(biomolecules(including(
carbohydrates,((proteins(and(DNA)(

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.(

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:(
&&&&
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.(
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.(
&&

437
Glucose(+(galactose((lactose(
Glucose(+(fructose((sucrose(
The(monomers(are(joined(by(a(glycosidic(
linkage,(also(known(as(an(ether(functional(
group.(
&
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.(
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.((

440
Cellulose(
Cellulose(is(a(linear(polymer(of(Pglucose(
and(Pglucose.(
Individual(bundles(of(cellulose(molecules(
are(joined(by(hydrogen(bonds(

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).(
&

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(
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.(
(

444

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CHEMISTRY
DNA

445
Key&Knowledge&
!chemical(bonding:(
(primary(and(secondary(structure(of(DNA(
!organic(reaction(pathways(including(
(condensation(and(polymerisation((
((((reactions(that(produce(large(biomolecules((
(((((including((carbohydrates,(proteins(and)((((
(((((DNA(
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(

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(

448
Structure(of(the(bases(is(in(the(VCE(Chemistry(
data(book(
Adenine(and(guanine(are(
purine(bases(

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

450
Condensation(reactions(to(form(the(
polynucleotide(chain(

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.(
452
Hydrogen(bonding(between(the(bases(

453

454
Tertiary(structure((negative(charge(due(to(
phosphate(groups(allows(DNA(to(supercoil(around(
proteins(called(histones.(
This(tight(packaging(creates(a(chromosome.(

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?(
(
VCAA(June(2008(Q10(456
Use&the&data&booklet!&
Piece(most(readily( Strand(of(highest(
separated(by(
molecular(mass(
heating(

A.(
1(
X(
B.(
2(
W(
C.(
2(
X(
D.(
1(
W(
457

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CHEMISTRY
Biochemical Fuels

458
Key(Knowledge(
!organic(reaction(pathways(including(
(production(of(biochemical(fuels(including(
the(fermentation(of(sugars(to(produce(
ethanol(

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.(

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)(

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(
462
Distillation(

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(

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.(
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.(

466
Equation(for(the(formation(of(
biodiesel(

467
Biogas&
Equal(mix(of(CO2(and(methane(((CH4)(
Generated(when(organic(material(decomposes(in(
the(absence(of(oxygen.(
Particularly(suited(to(farms(

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(

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(
(
470

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CHEMISTRY
The Design and Synthesis of Medicines including Aspirin

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.(

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.(
473
Preparation(of(Aspirin(
Aspirin(can(be(made(by(two(different(
pathways(
Salicylic(acid(+(ethanoic(acid(

474
Or(salicylic(acid(+(ethanoic(anhydride(

475
Alkaline(hydrolysis(breaks(aspirin(down(
Aspirin(can(be(made((
soluble(by(creating(a((
sodium(salt.(
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.(

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.(
&

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.(

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(
&

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(

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
482
(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.(
(
483
(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.(
(
484

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VCE Chemistry Unit 3

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