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CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Gravimetric Analysis
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Outcome(1(
(
On(completion(of(this(unit(the(student(
should(be(able(to(evaluate(the(suitability(of(
techniques(and(instruments(used(in(
chemical(analyses.(
(
Key(Knowledge(
!Gravimetric(analysis(
!the(application(of(chemical(equations(to(
(volumetric(and)(gravimetric(analyses(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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Gravimetric(analysis(
This(form(of(quantitative(analysis(involves(
@ind(the(mass(of(a(part(of(the(sample(and(
relating(it(back(to(the(sample,(often(as(a(
percentage(by(mass(
The(part(of(the(sample(we(are(interested(
in(may(be(the(water(in(the(product,(or(
perhaps(we(might(be(focussing(on(a(
particular(ion(that(is(present.(
VCE Chemistry Unit 3
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Measuring(water(content(
Many(solids(have(a(high(proportion(of(water.(
Dehydration(removes(the(water(and(
decreases(the(mass(
This(may(be(heating(at(just(above(100(C(
Mass(loss(=(mass(of(water(originally(present(
%(water(content(=(m(water)((100(((((((((((((((((((((((((((
(((((((((((((((((((((((((((((((((((((((m(sample)(
VCE Chemistry Unit 3
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Weigh&the&
sample&
Heat&the&sample&
in&an&oven&just&
above&100&C&
Allow&the&
sample&to&cool&
in&a&desiccator&
This cycle is
repeated until
the sample
assumes a
constant mass
Reweigh&the&
sample&
VCE Chemistry Unit 3
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Finding(the(composition(of(a(
mixture(
1. Dissolve(the(mixture(in(water(
2. Add(an(ionic(solution(which(will(
form(a(precipitate(with(the(ion(
that(is(required((eg(SO42P).(
3. This(new(solid(is(then(@iltered(out,(
dried(and(weighed.
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The(most(common(precipitates&
Element'you'wish' Substance'that'is' Formula'of'
to'analyse'
added'to'create' precipitate'
precipitate'
Chlorine&&
Silver&nitrate&
AgCl&
Bromine&
Silver&nitrate&
AgBr&
Sulfur&
Barium&chloride&
BaSO4&
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Application(of(gravimetric(analysis(
! Gravimetric(analysis(is(used(in(the(
food(industry(to(determine(the(
amount(of(salt(in(products.(
! When(an(AgNO3(solution(is(added(((
((((to(the(dissolved(food,(chloride(ions(((
(((((present(as(NaCl)(are(precipitated(out((((
as(AgCl.(
(&
VCE Chemistry Unit 3
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Calculations(
m(AgCl)
Find(n(AgCl)(using:(n(AgCl)(=(( M(AgCl)
Then:&
n(AgCl)&=&n(Cl.)&=&n(NaCl)(
!Convert(n(NaCl)(to(m(NaCl)(using((
((((((m(NaCl)(=(n(NaCl)((M(NaCl)(
(
!%(NaCl)(=(m(NaCl)((100(
( ((((((((m(food)(((((1(
VCE Chemistry Unit 3
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Experiment((
(Analysis(of(Lawn(food(
Lawn(food(contains(many(nutrients(
required(by(plants(such(as(sulfate(ions,(
SO42P,(nitrate(ions,(NO3P(and(phosphate(
ions,(PO43B.&
&
Using&gravimetric&analysis&to&;ind&the&
amount&of&sulfate&ions&in&a&sample&of&
lawn&food&
1. Dissolve(lawn(food(in(water(
2. Add(barium(chloride(solution(
3. Sulfate(ions(precipitate(out(as(barium(
sulfate(
((((((((((BaCl2(aq)(+(SO42P((aq)((BaSO4(s)(+(2ClP(aq)(
VCE Chemistry Unit 3
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10
4. Filter,(wash(and(dry(the(BaSO4(to(obtain(a(pure(
sample(of(precipitate.(
(
5. During(washing(stages(@iltrate(is(tested(for(
presence(of(left(over(chloride(ions(by(adding(silver(
nitrate.(
(AgNO3(aq)+(ClP((AgCl(s)(+(NO3P(aq)(
(
(If(ions(are(in(the(@iltrate,(then(they(have(
probably(also(stuck(to(the(solid(and(its(mass(will(
be(too(high.(
((
(
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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
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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)(
VCE Chemistry Unit 3
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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)(
(
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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)
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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
VCE Chemistry Unit 3
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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
VCE Chemistry Unit 3
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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
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18
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19
QUESTION 3
When 2.54 g of solid iodine reacts with excess chlorine and the unreacted chlorine is
evaporated, 4.67 g of a yellow product remains.
The empirical formula of the product is
A. ICl2
B. ICl3
C. ICl4
D. ICl5
(VCAA Q4 June 2007)
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QUESTION 3 (ANSWER)
When 2.54 g of solid iodine reacts with excess chlorine and the unreacted chlorine is
evaporated, 4.67 g of a yellow product remains.
The empirical formula of the product is
A. ICl2
B. ICl3
C. ICl4
D. ICl5
2.54 2.13
:
126.9 35.5
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
0.0200 : 0.0600
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1 : 3
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21
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Simple titrations
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22
Key(Knowledge(
volumetric(analysis(including(determination(of(
excess(and(limiting(reagents((and(titration(
curves):(simple((and(back)(titrations,(acidPbase(
(and(redox(titrations)(
calculations(including(amount(of(solids,(liquids(
and(gases;(concentration;(volume,(pressure(and(
temperature(of(gases(
the(application(of(chemical(equations(to(
volumetric((and(gravimetric)(analyses(
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23
Key(skills((a(reminder)(
These(skills(include(the(ability(to:(
! conduct(investigations(that(include(collecting,(
processing,(recording(and(analysing(qualitative(
and(quantitative(data;(draw(conclusions(
consistent(with(the(question(under(investigation(
and(the(information(collected;(evaluate(
procedures(and(reliability(of(data(
! construct(questions((and(hypotheses);(plan(and/
or(design,(and(conduct(investigations;(identify(
and(address(possible(sources(of(uncertainty(
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24
Volumetric(analysis(
A(technique(in(which(two(solutions(are(
reacted(together.(
Typically(we(will(be(conducting(an(acidPbase(
reaction,(or(a(redox(reaction.(
Concentration(of(one(solution(must(be(
accurately(known((the(known)(
We(use(a(Primary(standard(to(make(up(a(
standard(solution(in(a(volumetric(or(
standard(@lask.(
VCE Chemistry Unit 3
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25
What(is(a(Primary(standard?(
Solid(at(room(temp(
Readily(obtainable(in(pure(form(
Known(formula((Does(not(react(with(
atmosphere)(
High(molar(mass((small(amount(has(a(
reasonable(mass(
Cheap(
eg(anhydrous(sodium(carbonate((Na2CO3)(
potassium(hydrogen(phthalate(KH(C8H4O4)(
NOT(NaOH(and(HCl(
VCE Chemistry Unit 3
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26
Standard(solution(
Made(up(in(standard((volumetric)(@lask(
So(volume(is(known(accurately((
Known(mass(of(solute(is(measured(and(
transferred(into(the(@lask(
Solution(will(have(an(accurately(known(
concentration(with(very(small(error(
amount
Remember:(concentration(=(
volume
Volume(must(be(in(litres!((
VCE Chemistry Unit 3
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27
Making(a(standard(solution(
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28
Volumetric(Pipette(
Used(to(very(accurately(dispense(a(known(
volume((aliquot)(of(the(standard(solution(
(accurately(known(concentration)(into(a(
conical(@lask.(
Uncertainty(is(usually(0.05mL,(although(
does(change(with(size(of(pipette(
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29
Correct(use(of(pipette
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30
BureDe&
Dispenses(a(volume((titre)(of(the(unknown(
solution((concentration(unknown)(into(the(
aliquot(that(is(already(in(the(conical(@lask.(
Burette(is(graduated,(so(volume(is(
determined(by(difference(between(initial(
reading(and(@inal(reading(
Uncertainty(is(usually(0.02(mL(per(reading,(
so(will(be(0.04(mL(for(one(volume(
delivered.(
VCE Chemistry Unit 3
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31
Correct(use(of(burette
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32
Titration(
The(addition(of(a(solution(from(the(burette(
into(a(conical(@lask(containing(an(aliquot(is(
called(a(titration.(
If(an(acidPbase(reaction(is(being(
performed,(an(acidPbase(indicator(is(used(
to(determine(the(end(of(the(titration.(
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33
The(end(of(a(titration((
The(equivalence(point(of(a(titration(is(the(
point(at(which(the(exact((stoichiometric)(
amount(of(acid(has(been(added(to(react(
with(the(base(in(the(conical(@lask.(
In(a(titration,(we(aim(to(stop(adding(the(
acid(from(the(burette(at(the(equivalence(
point.(This(is(called(the(end(point(and(is(
determined(by(the(indicator(changing(
colour.(
VCE Chemistry Unit 3
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34
Indicators(
An(indicator(is(usually(a(weak(acid(which(is(
a(different(colour(in(its(acidic(form(and(its(
basic(form.(
It(can(be(represented(as(HIn((acid(form)(
HIn(aq)((H+(aq)(+(InP(aq)(
((((((((((Colour(1(((((((((((((((colour(2(
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35
Considering(the(reaction:(
Na2CO3(aq)((+(2HCl(aq)((2NaCl(aq)(+((H2O(l)(+(CO2(aq)(
aliquot ((((titre(
The(methyl(orange(indicator(is(yellow(in(the(
sodium(carbonate(solution(because(it(was(in(its(
basic(form((InP)(
InP(aq)((+((H+(aq)(((HIn(aq)(
methyl(orange:yellow (
(pink(
The(HCl(reacted(with(the(sodium(carbonate(until(
none(was(left,(then(it(reacted(with(the(indicator(
which(gained(an(H+(and(turned(into(HIn(
(
This(colour(change(is(the(endpoint(
VCE Chemistry Unit 3
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36
Accuracy(
The(accuracy(of(volumetric(analysis(is(
obtained(by(repeating(the(titration(until(we(
obtain(3(concordant(results.((
Concordant(results(fall(within(a(range(of(
0.10mL(ie(The(smallest(titre(is(no(more(than(
0.10mL(less(than(the(largest(titre.(
Non-concordant values
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37
Acid(base(equations(which(MUST(be(
known(
! Acid&+&base&&salt&+&water&
((((((((((((((((((((eg(HCl(aq)(+(NaOH(aq)((NaCl(aq)((+(H2O(l)(
Ionic(equation:((H+((aq)(+(OHP((aq)(((H2O(l)(
(
! Acid&+&carbonate&&&&
& & &&&&&&&&salt&+&water&+&carbon&dioxide&
(((((((((((((((((eg((2HCl(aq)(+(Na2CO3(aq)((2NaCl(aq)(+(CO2(g)(+(H2O(l)(
Ionic(equation:(2H+((aq)(+(CO32P((aq)(((CO2(g)(+(H2O(l)(
(
! Acid&+&hydrogencarbonate&&
&& &&&&&&&&&&&&&&&&&salt&+&water&+&carbon&dioxide&
(((((((((((((((((((eg((HCl(aq)(+(NaHCO3(aq)((NaCl(aq)(+(CO2(g)(+(H2O(l)(
Ionic(equation:(H+((aq)(+(HCO3P((aq)((CO2(g)(+(H2O(l)(
(
VCE Chemistry Unit 3
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38
Using(titration(results(to(@ind(
concentration(of(unknown.(
1. Average(the(concordant(titres.(This(gives(
you(the(volume(of(solution(that(reacted(
with(the(aliquot.(
2. Use(the(known(concentration(of(the(
standard(solution(and(the(volume(of(the(
pipette((the(aliquot)(to(@ind(the(amount(of(
primary(standard(in(an(aliquot:(n(=(cV(
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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
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40
Sample(exam(question(based(on(a(simple(
titration(
Titration(between(standard(solution(of(HCl(and(NaHCO3.(
100.0(mL(of(1.00M(HCl(solution(was(to(be(diluted(to(0.100M(
in(1.00L(volumetric(@lask,(but(900(mL(of(0.0222M(NaOH(was(
added(instead(of(water.(
(a) Write(the(equation(for(the(reaction(that(occurs(in(the(
volumetric(@lask.(
(b)Calculate(the(concentration(of(the(HCl(in(the(volumetric(
@lask.(Correct(sig(@igs.(
(c) If(contaminated(HCl(is(used(in(the(titration,(will(the(
calculated(concentration(of(HCO3(be(greater(or(smaller(
than(the(true(value.(Justify(your(answer(
(VCAA(June(2009(Question(3)(
VCE Chemistry Unit 3
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(a)(In(the(volumetric(@lask:(
(((((((((HCl(aq)((+((NaOH(aq)(( NaCl(aq) + H2O(l)
(b) Calculate n(HCl) = cV = 1.00 0.100 = 0.100 mol
n(NaOH)added = cV = 0.0222((0.900 = 0.01998 mol
n(HCl)remaining after reaction = 0.100 0.01998 = 0.08002 mol
n
Concentration =
= 0.08002 M
(c) The(concentration(of(HCl(is(lower(than(we(are(
expecting,(((so(a(greater(volume(of(HCl(will(be(required(to(
react(with(the(NaHCO3.(This(will(make(it(seem(as(though(
the(NaHCO3(is(more(concentrated(than(it(actually(is,(so(the(
calculated(concentration(of(HCO3(will(be(greater(than(it(
actually(is.(
(
VCE Chemistry Unit 3
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42
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Titration Curves
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43
Key(Knowledge(
volumetric(analysis(including(
(determination(of(excess(and(limiting(
reagents(and)(titration(curves:(simple((and(
back)(titrations,(acidPbase((and(redox)(
titrations(
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44
TitraFon&curves&
As(an(acid(is(added(to(a(basic(solution,((or(a(
base(added(to(an(acidic(solution)(the(pH(of(
the(solution(changes.(
As(we(near(the((
(((equivalence(point,((
(((the(pH(changes((
(((more(rapidly.(
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45
A(titration(curve(tells(us((
whether(the(starting(solution(was(an(
acid(or(a(base(AND(whether(it(was(
strong(or(weak((
The(volume(of(the(second(solution(
added(when(neutralisation(occurred(
The(pH(at(the(equivalence(point(
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46
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47
Choice(of(indicator(
Each(different(indicator(has(a(particular(
pH(range(in(which(it(changes(colour.(
Methyl(orange(changes(colour(from((
((((pH(=(3.2(to(4.4.(
This(means(that(it(will(change(colour(
(have(an(endpoint)(near(the(equivalence(
point(of(the(reaction(between(HCl(and(
Na2CO3((a(strong(acid(and(a(weak(base.(
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48
Phenolphthalein(changes(colour(in(the(pH(
range(8.2(P(10.0(making(it(suitable(for(the(
titration(of(a(weak(acid(with(a(strong(base.(
See&data&booklet&table&11&
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49
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50
When(a(strong(acid(is(titrated(with(a(strong(
base,(the(equivalence(point(is(at(pH(=(7.(
Phenolphthalein(can(be(used,(or(even(
methyl(orange,(but(it(might(be(better(to(use(
another(indicator,(such(as(bromothymol(
blue(which(changes(colour(between(6.0(and(
7.6(((
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51
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52
Neutralising&strong&and&weak&acids&
Students(commonly(assume(that(a(strong(
acid(will(require(more(base(to(neutralise(it(
than(a(weak(acid,(but(this(is(NOT(true.(
Consider(the(equations(for(the(reactions:(
HCl(aq)((+((NaOH(aq)( NaCl(aq) + H2O(l)
Strong acid
CH3COOH(aq)((+((NaOH(aq)(
weak acid
CH3COONa(aq) + H2O(l)
Both(demonstrate(a(1:1(ratio(with(NaOH(
VCE Chemistry Unit 3
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53
Sample(exam(questions((pH(curves(
The(following(titration(curve(was(obtained(by(measuring(the(
pH(in(a(reaction(@lask(during(an(acidPbase(titration(
The(graph(represents(the(change(
in(pH(in(the(reaction(@lask(when(
(
(
(
A. A(weak(acid(is(added(to(a(strong(base(
B. A(weak(base(is(added(to(a(strong(acid(
C. A(strong(acid(is(added(t(a(weak(base(
D. A(strong(base(is(added(to(a(weak(acid.((
VCAA(June(2010(Q1(
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54
Which(one(of(the(following(is(a(suitable(indicator(for(
use(in(this(titration?(
A. Phenol(red(
B. Thymol(blue(
C. Phenolphthalein(
D. Bromophenol(blue((
(
(
(
VCAA(June(2010(Q2(
VCE Chemistry Unit 3
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55
Sample&exam&quesFon&&FtraFng&strong&and&weak&acids&
Two(titrations(were(performed(as(shown(below(
(
(
(
(
Which(one(of(the(following(statements(is(true?(
A. The(weak(acid(will(require(a(greater(volume(of(NaOH(solution(
than(the(strong(acid(to(reach(the(equivalence(point(
B. The(weak(acid(will(require(a(smaller(volume(of(NaOH(solution(
than(the(strong(acid(to(reach(the(equivalence(point(
C. The(weak(acid(will(require(the(same(amount(of(NaOH(solution(as(
the(strong(acid(to(reach(the(equivalence(point(
D. The(equivalence(point(in(a(titration(of(a(weak(monoprotic(acid(
with(NaOH(solution(cannot(be(determined.(
VCAA(June(2011(Q11(
VCE Chemistry Unit 3
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56
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Back Titrations
VCE Chemistry Unit 3
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57
Key(Knowledge(
volumetric(analysis(including(
determination(of(excess(and(limiting(
reagents((and(titration(curves):((simple(
and)(back(titrations,(acidPbase(and(redox(
titrations(
calculations(including(amount(of(solids,(
liquids(and(gases;(concentration;((volume,(
pressure(and(temperature(of(gases)(
the(application(of(chemical(equations(to(
volumetric((and(gravimetric)(analyses(
VCE Chemistry Unit 3
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58
Back(titrations(
The(reaction(between(a(weak(acid(and(a(
weak(base(does(not(give(a(sharp(change(in(
pH(at(the(end(point,(so(there(is(not(a(distinct(
colour(change.(
This(makes(it(impossible(to(perform(a(direct(
titration.(
Instead(a(back(titration(is(used.(
In(a(back(titration(two(reactions(occur,(one(
after(the(other.(
Both(reactions(are(likely(to(be(acidPbase(
reactions.(
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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)&
VCE Chemistry Unit 3
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60
The(distribution(of(added(strong(base(in(a(back(titration(
Amount&of&strong&base&that&
did¬&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&
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61
Calculations(associated(with(back(
titrations(
(1)(Total(amount(of(strong(base(added(
initially(=(volume((concentration(
(2)(Amount(of(strong(base(that(did&
not&react(with(the(weak(acid(is(found(
in(the(titration.(
! n(strong(acid)(=(cV(titre)(
! n(strong(base)(=(n(strong(acid)((for(
a(monoprotic(acid((most(common)(
VCE Chemistry Unit 3
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&
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62
Amount(of(strong(base(that(did&react&with(
the(weak(acid(is(found(by(subtraction:(
n(reacting)&=&n(added&initially)&&n(remaining)&
Amount(of(weak(acid(in(the(original(sample(is(then(
found(from(the(equation(for(the(reaction(between(
the(reacting(strong(base(and(the(original(weak(
acid.(
&
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63
Sample(exam(question((back(
titration(
0.415(g(of(a(pure(acid,(H2X(s)(is(added(to(exactly(100(mL(
of(0.105(M(NaOH(aq).(A(reaction(occurs(according(to:(
H2X(s)((+((2NaOH(aq)(( Na2X(aq) + 2H2O(l)
The NaOH is in excess. This excess NaOH requires 25.21
mL of 0.197M HCl(aq) for neutralisation.
(a) Calculate the amount, in mol, of NaOH that is added to
the acid H2X initially.
(b) Calculate the amount, in mol, of NaOH that reacts with
the acid H2X.
(c) Calculate the molar mass, in gmol-1, of the acid H2X.
VCAA June 2008 Q8(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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64
Answer(
(a) n(NaOH)(=(cV(=(0.105((0.100(=(0.0105&mol&
&
b) NaOH(+(HCl((NaCl(+(H2O(
((((((((EXCESS(NaOH(was(titrated(with(HCl,(so(
n(NaOH)excess(=(n(HCl)(=(0.197((0.02521(=(0.004966(mol(
n(NaOH)reacting(with(H2X(=(0.0105(P(0.004966(=(0.00553&mol&
&
c) (H2X(s)((+((2NaOH(aq)(( Na2X(aq) + 2H2O(l)
((((((so(n(H2X)(=((n(NaOH)(=(0.002767(mol(
((((((0.002767(mol(H2X(has(a(mass(of(0.415g(
((((((so(1(mol(of(H2X(has(a(mass(of( ( 0.415
((((=(150(g(molP1(
0.002767
(
VCE Chemistry Unit 3
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65
QUESTION 1
1. The graph below shows the change in pH of a reaction solution during a titration of
0.10M NaOH with 0.10M CH3COOH
A suitable indicator for the titration and the colour change observed is
Indicator
Colour change
A. Methyl red
Yellow to red
B. Methyl red
Red to yellow
C. Phenolphthalein
Colourless to red
D. Phenolphthalein
Red to colourless
(VCAA
Q4 June
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66
QUESTION 1 (ANSWER)
1. The graph below shows the change in pH of a reaction solution during a titration of
0.10M NaOH with 0.10M CH3COOH
A suitable indicator for the titration and the colour change observed is
Indicator
Colour change
A. Methyl red
Yellow to red
B. Methyl red
Red to yellow
C. Phenolphthalein
Colourless to red
D. Phenolphthalein
Red to colourless
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67
Phenolphthalein suits this titration best because the equivalence point is at approximately pH
= 9. Phenolphthalein changes colour (according to the data book) between pH = 8.3 and
10.0, so would suit this equivalence point. The titration starts at a high pH, when
phenolphthalein is red and then it would become colourless.
(VCAA Q4 June 2008)
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68
QUESTION 2
2. 20.0 mL of 0.10 M hydrochloric acid (HCl) reacts with 20.0 mL of 0.30 M
potassium hydroxide (KOH) solution.
The concentration of potassium ions in the resultant solution, in mole per litre, is
A. 0.10
B. 0.15
C. 0.20
D. 0.30
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69
QUESTION 2 (ANSWER)
2. 20.0 mL of 0.10 M hydrochloric acid (HCl) reacts with 20.0 mL of 0.30 M
potassium hydroxide (KOH) solution.
The concentration of potassium ions in the resultant solution, in mole per litre, is
A. 0.10
B. 0.15
C. 0.20
D. 0.30
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70
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.
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71
QUESTION 3
3. Sulfuric acid (H2SO4) and nitric acid (HNO3) are both strong acids. Ethanoic acid
(CH3COOH) is a weak acid.
20.00 mL solutions of 0.10 M concentration of each of these three acids were
separately titrated with a 0.10 M solution of sodium hydroxide (NaOH).
In order to react completely
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72
QUESTION 3 (ANSWER)
3. Sulfuric acid (H2SO4) and nitric acid (HNO3) are both strong acids. Ethanoic acid
(CH3COOH) is a weak acid.
20.00 mL solutions of 0.10 M concentration of each of these three acids were
separately titrated with a 0.10 M solution of sodium hydroxide (NaOH).
In order to react completely
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73
H2SO4 is a diprotic acid, so it is not the strength of the acid, but its proticity that matters
here. For every one mol of H2SO4 reacting, two mol of NaOH would be required, while for
every one mol of CH3COOH or HNO3 reacting, only one mol of NaOH would be required.
Note that the fact that CH3COOH is a weak acid does not have any bearing on the acid.
Equal mol of strong or weak acids react with equal mol of NaOH.
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74
QUESTION 4(a)
4.(a) The hydrogen carbonate ion, (HCO3-) can act both as an acid and as a
base.
i. Write a chemical equation that shows HCO3- acting as an acid when it reacts with water.
ii. Write a chemical equation that shows HCO3- acting as an base when
water.
it reacts with
(2 marks)
Please write down your answer on a piece of paper. We will show you the answer
in the next section.
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75
it reacts with
Note that when HCO3- is acting as an base, it will accept an H+ from the water.
(2 marks)
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76
QUESTION 4(b)
4(b). The hydrogen ion concentration of a solution is described by the term pH. The
hydroxide ion concentration is described in the same way by the term pOH.
A solution has a pOH of 3 at 25C.
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77
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78
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Oxidation Numbers and Partial Ionic Equations
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79
79
Key(Knowledge(
volumetric(analysis(including(determination(of(
excess(and(limiting(reagents((and(titration(
curves):((simple(and(back(titrations,(acidPbase)(
and(redox(titrations(
calculations(including(amount(of(solids,(liquids(
and(gases;(concentration;((
the(writing(of(balanced(chemical(equations,(
including(the(use(of(oxidation(numbers(to(write(
redox(equations,(and(the(application(of(chemical(
equations(to(volumetric((and(gravimetric(
analyses)(
VCE Chemistry Unit 3
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80
80
Redox(reactions(
A(redox(reaction(involves(the(transfer(of(
electrons(from(a(reductant(to(an(oxidant.(
Reductants(are(usually(metals(eg(Mg,(Zn(or(nonP
metal(anions(eg(ClP,(BrP(
Oxidants(are(usually(nonPmetals(eg(Cl2,(O2(or(
metal(cations(eg(Cu2+,(Ag+(
A(redox(reaction(usually(results(in(the(formation(
of(an(ionic(compound.(
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81
81
Oxidation(is(the(loss(of(electrons(
An(oxidation(half(equation(has(electrons(on(
the(right(
Reductants(undergo(oxidation(
Mg((Mg2+(+(2eP(
(
Reduction(is(the(gain(of(electrons(
A(reduction(half(equation(has(electrons(on(
the(left(
Oxidants(undergo(reduction(
O2(+((4eP(((2O2P(
VCE Chemistry Unit 3
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82
82
Overall(equations(
An(oxidation(reaction(cannot(occur(without(
a(reduction(reaction(
When(two(half(equations(are(combined(the(
electrons(must(be(balanced(on(both(sides(of(
the(equation((no(left(over(electrons.(
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83
83
Oxidation(numbers(
Oxidation(numbers(are(used(to(judge(
whether(a(substance(is(undergoing(
reduction(or(oxidation.(
Follow(the(rules(to(assign(oxidation(
numbers((
While(oxidation(numbers(are(manPmade(
they(represent(the(charge(that(would(
appear(if(the(element(were(to(completely(
lose((or(gain)(electrons,(rather(than(just(
sharing(in(a(covalent(bond.(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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84
84
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85
85
! An(increase(in(oxidation(number(during(a(
chemical(reaction(indicates(that(the(substance(
has(been(oxidized.(
! A(decrease(in(oxidation(number(indicates(that(
the(substance(has(been(reduced.(
! eg((Fe(s)((+((Cu2+(aq)(((Fe2+(aq)((+((Cu(s)(
ONs(((0((((((((((((+2(((((((((((((((((((+2((((((((((((((((0(
(
Fe(has(increased(from(0(to(+2((has(been(
oxidised)(
Cu(has(decreased(from(+2(to(0((has(been(
reduced)(
VCE Chemistry Unit 3
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86
86
Sample(exam(question((oxidation(
numbers(
The(equation(for(a(reaction(that(occurs(during(the(
extraction(of(iron(from(iron(ore(is(
Fe2O3(s)((+((3CO(g)((((2Fe(l)((+((3CO2(g)(
(
During(this(reaction(the(oxidation(number(of(iron(changes(
from(
A. +(3(to(0,(and(CO(is(the(reductant(
B. +6(to(0,(and(CO(is(the(reductant(
C. +3(to(0(and(CO(is(the(oxidant(
D. +6(to(0(and(CO(is(the(oxidant(
VCAA(June(2006(Q14(
VCE Chemistry Unit 3
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87
87
Balancing(partial(ionic(equations(
Some(half(equations(are(not(as(simple(as(
((((Fe2+((+((2eP((((Fe(
They(may(involve(oxygen(atoms,(such(as(
when(H2SO4(is(reduced(to(form(H2S(
In(this(case(a(special(method(is(used(to(
balance(the(equation(
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88
88
Step&
Example&
ReducFon&of&Cr2O72B&to&Cr3+(
Balance&all&atoms&except&O&
and&H(
Cr2O72B&&&&&&&&&&Cr3+&
(
Balance&O&atoms&using&&
H2O(
Cr2O72B&&&&&&&&&&Cr3+&
(
Balance&H&atoms&using&&
H+(
Cr2O72B&&&&&&&&&&&&&&&&Cr3+&
(
Balance&charge&using&
electrons(
Cr2O72B&&&&&&&&&&&&&&&&&&&&&&&Cr3+&
(
Add&state&symbols(
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89
89
Sample(exam(question((balancing(
partial(ionic(equations&
When(this(half(equation(is(balanced(
correctly,((
VO2+(aq)(+(xH2O(l)((VO3P(aq)(+(yH+(aq)(+(zeP(
the(coef@icients,(x,(y(and(z(are(equal(to(
A. 1,(2,(4(
B. 2,(4,(1(
C. 2,(4,(2(
D. 3,(6,(2(
&
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90
VO2+(aq)(+(_H2O(l)((VO3P(aq)(+(_H+(aq)(+(_eP(
(
Balance(oxygen(using(H2O(
Balance(hydrogen(using(H+(
Balance(charge(using(eP(
The(answer(is(B(
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91
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Volumetric Analysis
Redox Titrations
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92
How(does(a(redox(titration(differ(to(an(
acidPbase(titration?(
Often(an(indicator(is(not(required(because(
the(reactant(and(product(have(different(
colours(
eg(Cr2O72P(is(orange(while(Cr3+(is(green(
In(other(redox(titrations(an( indicator (
such(as(starch(solution(is(added(near(the(
end(point.(It(will(react(with(the(excess(
titrant.(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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93
What(sort(of(reactants(can(be(analysed(
using(a(redox(titration?(
Sulfur(dioxide(P(a(preservative(used(in(wine:(
titrate(with(iodine(solution(
Ethanol((major(component(of(wine:(titrate(
with(thiosulfate(solution(after(reaction(with(
excess(dichromate(
Vitamin(C((in(fruit(juices:(titrate(with(iodine(
solution(
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94
Sample(exam(question((redox(titrations(
The(amount(of(iron(in(an(aluminium(alloy(is(to(be(
determined.(80.50(g(of(alloy(is(dissolved(in(HCl(and(iron(
atoms(convert(to(Fe2+((aq)(ions.(This(solution(is(transferred(
to(a(250.0(mL(volumetric(@lask(and(made(up(to(mark.(20.00(
mL(aliquots(of(this(solution(are(titrated(against(0.0400(M(
KMnO4(solution.(
5Fe2+(aq)(+(MnO4P(aq)(+(8H+(aq)((5Fe3+(aq)(+(Mn2+(aq)(+(4H2O(l)(
Four(titrations(were(carried(out:(
(
Titra:on'number'
1'
(
Vol&of&KMnO4&(mL)&
22.03&
2'
3'
4'
20.25&
21.97&
21.99&
VCAA((June(2010(Q1(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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95
(a)(Write(a(balanced(halfPequation,(including(states,(for(the(
conversion(of(MnO4P(in(an(acidic(solution(to(Mn2+(ions.(
Answer:((MnO4P((((((((((((((((((((((((((((((((((((((Mn2+(
(
(b)(Calculate(the(average(volume,(in(mL,(of(the(concordant(
titres(of(the(KMnO4(solution(
Answer:(20.25(mL(is(not(concordent,(so(do(not(include(in(
average(
Average(=((22.03(+(21.97(+(21.99)/3(=(22.00(mL(
(c)((Use(your(answer(to(part((b)(to(calculate(the(amount,(in(
mol,(of(MnO4P((aq)(ions(used(in(this(titration.(
Answer:(n(=(cV(=(0.0400((0.02200(=(8.80((10P4(mol(
(
(
(
VCE Chemistry Unit 3
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(
96
(d)((Calculate(the(amount,(in(mol,(of(Fe2+(ions(present(in(
the(250.0(mL(volumetric(@lask(
Answer:(n(Fe2+)(in(20.00(mL(=(5((n(MnO4P)(=(5((8.80((
10P4(=(4.40(10P3(mol(
250.0
n(Fe2+)(in(250.00(mL(=(4.40(10P3(( (=(0.0550(mol(
20.00
(
(e)((Calculate(the(percentage(by(mass,(of(iron(in(the(80.50(g(
sample(of(alloy.(Express(your(answer(to(the(correct(
number(of(signi@icant(@igures.(
Answer:(m(Fe)(=(n(Fe2+)((55.8(=(0.0550((55.8(=(3.069g(
100
%Fe(=(3.069((((((((((=(3.81%(
80.50 1
(
(Note(that(the(current(data(book(gives(Ar(Fe)(to(be(55.8,(
whereas(in(2010(it(was(given(as(55.9)(
VCE Chemistry Unit 3
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97
QUESTION 1&
Which one of the following is least likely to be a product of a redox reaction
between sulphuric acid and zinc metal?
A. H2
B. H2S
C. SO2
D. SO3
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98
QUESTION 1&
Which one of the following is least likely to be a product of a redox reaction
between sulphuric acid and zinc metal?
A. H2
B. H2S
C. SO2
D. SO3
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99
salt + hydrogen
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100
QUESTION 2&
When solid sodium hydride, NaH, is added to water, the hydride ion reacts
according to the following equation.
H-(aq) + H2O(l)
OH-(aq) + H2(g)
This reaction can be classified as
A. Acid-base only
B. Oxidation-reduction only
C. Both acid-base and oxidation-reduction
D. Neither acid-base nor oxidation-reduction
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101
QUESTION 2 (ANSWER)&
When solid sodium hydride, NaH, is added to water, the hydride ion reacts
according to the following equation.
H-(aq) + H2O(l)
OH-(aq) + H2(g)
This reaction can be classified as
A. Acid-base only
B. Oxidation-reduction only
C. Both acid-base and oxidation-reduction
D. Neither acid-base nor oxidation-reduction
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102
The 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.
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103
QUESTION 3&
In the following four substances, H2S2O7, N2O5, HIO3, Cl2O7, the atom with the
highest oxidation number is
A. I
B. S
C. N
D. Cl
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104
QUESTION 3 (ANSWER)&
In the following four substances, H2S2O7, N2O5, HIO3, Cl2O7, the atom with the
highest oxidation number is
A. I
B. S
C. N
D. Cl
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105
QUESTION 4(a)
For quality control, a chemist analyses the vitamin C (molecular formula C6H8O6)
content of a new brand of fruit juice. The reaction used is an oxidation-reduction
reaction in which I3- is the oxidant and vitamin C is the reductant.
The reaction is C6H8O6(aq) + I3-(aq)
C6H6O6(aq) + 2H+(aq) + 3I-(aq)
The half equation for the reduction of I3- to I- is I3-(aq) + 2e3I-(aq)
(1 mark)
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106
QUESTION 4(a)
For quality control, a chemist analyses the vitamin C (molecular formula C6H8O6)
content of a new brand of fruit juice. The reaction used is an oxidation-reduction
reaction in which I3- is the oxidant and vitamin C is the reductant.
The reaction is C6H8O6(aq) + I3-(aq)
C6H6O6(aq) + 2H+(aq) + 3I-(aq)
The half equation for the reduction of I3- to I- is I3-(aq) + 2e3I-(aq)
(1 mark)
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107
QUESTION 4(b)i
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.
(i) Calculate the amount of I3- present in the average titre, in mole.
(1 mark)
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For example, if your answer is 10.5 x 10-10, enter it as 10.50*10^(-10)
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108
(i) Calculate the amount of I3- present in the average titre, in mole.
(1 mark)
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109
QUESTION 4(b)ii
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.
(1 mark)
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110
(1 mark)
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111
QUESTION 4(b)iii
A 20.00 mL sample of the fruit juice was made up to 250.0 mL with pure water
in a volumetric flask. 25.00 mL aliquots of the diluted fruit juice were then
placed in a conical flask and titrated with a solution in which [I3-] = 2.00 10-4
M. An average titre of 15.65 mL was obtained.
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112
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113
QUESTION 4(c)
During the analysis the chemist rinsed, but did not dry, each item of glassware.
She had available for use: pure water, the original fruit juice, the diluted fruit
juice and the standard I3- solution. For each item listed below, name the liquid
that should be used to rinse it by placing a tick in the appropriate box.
(4 marks)
Pure Water
Original Fruit
Juice
Diluted Fruit
Juice
Standard I3Solution
20.00 mL
pipette
250.00mL
Volumetric
Flask
25.00mL
pipette
Conical Flask
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Pure Water
20.00 mL
pipette
250.00mL
Volumetric
Flask
Diluted Fruit
Juice
Standard I3Solution
25.00mL
pipette
Conical Flask
Original Fruit
Juice
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115
QUESTION 5 (i)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).
(i)
(1 mark)
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116
(i)
(1 mark)
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117
QUESTION 5 (ii)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).
(ii) Give a half equation for the conversion of IO4-(aq) into IO3-(aq) in acid solution.
(1 mark)
Note: please follow this specific format while entering your answer:
Please do not leave any spaces.
If your answer is AAB+(I) + CCD-(aq) + 3-> EEF+(I) + GGH-(aq)
Please enter AAB(+)(I)+CCD(-)(aq)+3->EEF(+)(I)+GGH(-)(aq)
To make the arrow enter a hyphen (next to 0, at the top of the keyboard)
and then a greater than sign ([shift]+the second key right from M)
VCE Chemistry Unit 3
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118
(ii) Give a half equation for the conversion of IO4-(aq) into IO3-(aq) in acid solution.
(1 mark)
IO4-(aq) + 2H+(aq) + 2e- IO3-(aq) + H2O(l)
Balance Oxygens on LHS with water on RHS,
Balance Hydrogens on RHS with H+ on LHS,
Balance charge (+1 on LHS and -1 on RHS) with electrons
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119
QUESTION 5 (iii)
One method of analysing the manganese content of steel is to dissolve the steel in
nitric acid; producing a solution of manganese(II), Mn2+(aq).
The Mn2+(aq) ions are then treated with an excess of acidified solution of
periodate ions, IO4-(aq).
The products of this reaction are iodate ions, IO3-(aq), and the deeply purplecoloured permanganate ions, MnO4-(aq).
(iii) Is the IO4-(aq) ion acting as an oxidant or reductant? Explain your choice.
(1 mark)
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120
(iii) Is the IO4-(aq) ion acting as an oxidant or reductant? Explain your choice.
(1 mark)
IO4- is reduced in the above half equation (it gains electrons), so it is the oxidant. This is
because it causes the other reactant to be oxidised and the IO4- is reduced.
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121
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Chromatography
General Features and TLC
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122
Key(Knowledge:(
Principles(and(applications(of(chromatographic(
techniques((excluding(features(of(instrumentation(
and(operation),(and(interpretation(of(qualitative(and(
quantitative(data(from:(
(thin(layer(chromatography((TLC),(including(
calculation(of(Rf(
high(performance(liquid(chromatography((HPLC)(
gas(chromatography((GC)(including(Rt(and(the(use(
of(a(calibration(graph(to(determine(amount(of(
analyte.(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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123
General(features(of(chromatography(
A(technique(which(is(used(to(separate(parts(
of(a(mixture.(
There(are(always(two(phases((the(
stationary(phase(and(the(mobile(phase.(
Stationary(phase(does(not(move.((is(usually(
a(solid,(but(may(be(a(viscous(liquid(coated(
on(beads.((
Mobile(phase(is(a(liquid(or(gas(which(moves(
over(the(stationary(phase(
VCE Chemistry Unit 3
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124
Why(does(separation(occur?(
Components(have(different(structures,(so(
are(capable(of(different(degrees(of(
intermolecular(bonding(
Separation(occurs(due(to(the(difference(
in(solubility(in(the(mobile(phase(and(
difference(of(adsorption(to(stationary(
phase(of(the(components(of(the(mixture(
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125
How(does(it(work?(
Sample(is(placed(at(the(origin(
(on(the(stationary(phase)(
(
The(mobile(phase(is(added(
and(the(sample(starts(to(
move(along(the(stationary(
phase(as(the(mobile(phase(
moves((
VCE Chemistry Unit 3
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126
The(different(components(separate(as(
they(adsorb(onto(the(stationary(phase(
and(desorb(back(into(the(mobile(phase.(
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127
Thin(layer(chromatography((TLC)(
Stationary(phase((glass(or(plastic(
plate(with(thin(layer(of(aluminium(
oxide(powder(on(the(plate(
Mobile(phase((a(solvent(that(will(
dissolve(the(sample.((
eg(water,(NaCl(aq)(or(a(mixture(of(two(or(
more(liquids(eg(methylated(spirits(and(
acetone.(
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128
Interpreting(chromatograms(
A(chromatogram(is(the(pattern(of(bands(or(
spots(formed(on(the(plate.(
Each(component(of(the(mixture(travels(a(
different(distance(along(the(plate(or(paper.(
When(the(chromatogram(is(dried/
developed(a(spot(or(line(is(present(to(
represent(the(component.((
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129
Rf(values((Rf(=(retention(factor)(
Two(distances(are(measured(from(the(
origin:(
The(distance(that(the(solvent(has(travelled(
The(distance(that(the(component(has(
travelled(
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130
Qualitative(use(of(Rf(values(
The(Rf(value(is(used(
to(identify(a(
component(by(
comparing(it(to(Rf((
(((values(of(known((
(((substances(under((
((the(same(conditions.(
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131
TLC(Sample(exam(question(
1. Consider(the(following(TLC(plate(of(compounds,(X,(
Y(and(Z(developed(using(a(suitable(mobile(phase(on(
a(polar(stationary(phase(
(((((((The(Rf(value(of(the(most(polar(component(in(this((((
(((((((TLC(separation(is(
A.(0.29 (B.(0.62( (C.(0.78( (D.(0.80(
(VCAA(June(2010(Q6)(
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132
Answer(
A.((
The(most(polar(component(will(have(the(strongest(
attraction(to(the(stationary(phase,(so(will(have(the(
smallest(Rf(value.((
Spot(X(has(travelled(the(smallest(distance(and(its(
Rf(value(is(0.80/2.75(=(0.29(
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133
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Chromatography
HPLC and GLC
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134
Column(chromatography(
(The(basis(for(HPLC(and(GLC)(
In(the(simplest(form,(column((
(chromatography(is(carried((
(out(in(the(laboratory(
(in(a(glass(column(packed((
(with(a(solid(such(as((
(alumina,(Al2O3.(
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135
HPLC(
Separation(occurss(
in(a(short(column(
Stationary(phase:(
(very(@ine(solid((
(particles(tightly(
packed(eg(silica((
Mobile(phase:(liquid(under(high(pressure(to(
force(its(way(through(the(solid(
&
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136
The&Chromatogram&
Rt - retention time - determines sample identity
Rt
Rt
mAU
Area or height is
proportional to the
quantity of analyte.
Injection
VCE Chemistry Unit 3
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time
137
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137
HPLC(Applications((
HPLC(is(very(sensitive!(
Bioscience
Chemical
proteins
peptides
nucleotides
polystyrenes
dyes
phthalates
Pharmaceuticals
tetracyclines
corticosteroids
antidepressants
barbiturates
Consumer Products
lipids
antioxidants
sugars
Environmental
Clinical
polyaromatic hydrocarbons
Inorganic ions
herbicides
VCE Chemistry Unit 3
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amino acids
vitamins
homocysteine
138
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138
HPLC(Sample(exam(question(
HPLC(uses(a(nonPpolar(stationary(phase(together(
with(a(polar(mobile(phase.(Which(of(the(following(
molecules(will(have(the(greatest(retention(time(on(
such(a(column?(
((VCAA(June(2009(Q(5)(
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139
Answer((
The(answer(is(A(
Molecules(B,(C(and(D(are(all(polar.(To(see(this(
observe(the(OH(and(NH(groups(on(the(
hydrocarbon(chain(of(the(molecules.(
A(nonPpolar(molecule(will(have(the(greatest(
attraction(to(the(stationary(phase,(so(will(take(the(
longest(time(to(move(along(the(column(=(greatest(
retention(time.(
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140
GC(
Sample(and(the(solvent(it(is(dissolved(in(
must(be(volatile(as(they(are(heated(in(an(
oven(
Mobile(phase:(
(((Inert(gas(
Stationary(phase:(
((((porous(beads((
((((coated(with((
((((high(bpt(liquid(
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141
Most(sensitive(of(all(chromatography(
techniques(
Used(for(testing(urine(samples(for(drugs(
Compounds(must(be(able(to(be(vaporised(
without(decomposing((usually(low(
molecular(mass(<500(g(molP1(samples)(
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142
SeparaFon&of&mixture&
Sample(passes(along(column(with(mobile(
phase(
Passes(in(and(out(of(solution(in(stationary(
phase(
Component(which(is(least(soluble(in(
stationary(phase(will(be(eluted(@irst((moves(
quickest(along(column)(
As(components(are(eluted(they(are(detected(
by(@lame(ionisation(detector.(
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143
Chromatogram(
A(graph(with(peaks(which(correspond(to(
components(of(mixture(
Retention(time(=(time(taken(for(component(
to(pass(through(column(
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144
Quantitative(use(of(GC(
Run(a(series(of(standards(of(known(
concentration(under(the(same(
conditions(as(the(sample.(
The(area(under(the(peak(is(proportional(
to(the(amount(of(the(substance(present.(
Draw(a(calibration(graph(to(link(area(
under(peak(to(concentration(
Find(sample(concentration(using(graph.(
VCE Chemistry Unit 3
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145
145
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146
146
GC(Sample(exam(questions(&
1.Analysis(of(the(components(of(a(mixture(using(gasP
liquid(chromatography(normally(involves(measuring(
the(
(((((A.((Rf(values(of(components(using(a(gas(as(the(mobile((
phase(
(((((B.(Rf(values(of(components(using(a(liquid(as(the(mobile(
phase(
(((((C.((Retention(times(of(components,(using(a(gas(as(the(
mobile(phase.(
(((((D.(Retention(times(of(components,(using(a(liquid(as(the(
mobile(phase.(
( ( ( ((VCAA(June(2007(Q71)(
VCE Chemistry Unit 3
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147
2. This(diagram(shows(the(gas(chromatogram(of(a(sample(
containing(4(straight(chain(alkanes.(Which(of(the(
statements(that(follow(are(true?(
I.
The(boiling(points(of(the(compounds(arranged(from(
highest(to(lowest(are(Z>Y>X>W(
II. The(retention(times(will(stay(the(same(if(the(temperature(
at(which(the(chromatogram(is(recorded(is(increased(and(
all(other(conditions(remain(constant.(
III. Hydrogen(gas(could(have(been(used(as(a(carrier(gas(to(
obtain(this(chromatogram.(((((((((((((((((VCAA(June(2009(Q6)(
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148
148
Answers(
1. C(is(the(answer(
Rf(values(are(used(for(TLC(and(paper(
chromatography,(while(retention(times(are(used(for(
columnPbased(chromatography.(In(GC,(the(mobile(
phase(is(a(gas.(
2. Statements(I(and(III(are(correct(
Changing(the(temperature(will(change(the(retention(
time(of(all(of(the(alkanes(
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149
149
QUESTION 1
A student used paper chromatography to separate two components, I and II, in a
solution. A spot of the solution was initially placed at the origin. When the spot
corresponding to component I (Rf = 0.50) had advanced 4.0 cm, the spot
corresponding to component II was 1.0 cm behind. The Rf value of component II is
closest to
A. 0.68
B. 0.38
C. 0.25
D. 0.13
(VCAA Q6 June 2006)
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150
QUESTION 1 (ANSWER)
A student used paper chromatography to separate two components, I and II, in a
solution. A spot of the solution was initially placed at the origin. When the spot
corresponding to component I (Rf = 0.50) had advanced 4.0 cm, the spot
corresponding to component II was 1.0 cm behind. The Rf value of component II is
closest to A. 0.68
B. 0.38
C. 0.25
D. 0.13
The answer is alternative B
First we need to calculate the distance that the solvent had travelled.
Since Rf
We can calculate that the distance travelled by the solvent
So now we can find the Rf of component II which travelled only 3.0 cm =
(1.0 cm behind component I)
Rf =
4.0
= 8.0cm
0.50
(VCAA Q6 June 2006)
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151
QUESTION 2
Chromatogram 1 was obtained by analysis of a sample of a mixture of two sugars,
A and B, using high performance liquid chromatography (HPLC). Chromatogram 2
was obtained by analysing another sample of the same mixture by HPLC under
different conditions.
Consider the following changes, which could be made to the operating conditions
for HPLC.
I
decreasing the pressure of the mobile phase
II
decreasing the temperature
III
using a less tightly packed column
Which of the changes would be most likely to produce chromatogram 2?
A. I only
B. II only
C. III only
D. I and II only
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152
QUESTION 2 (ANSWER)
Chromatogram 1 was obtained by analysis of a sample of a mixture of two sugars,
A and B, using high performance liquid chromatography (HPLC). Chromatogram 2
was obtained by analysing another sample of the same mixture by HPLC under
different conditions.
Consider the following changes, which could be made to the operating conditions
for HPLC.
I
decreasing the pressure of the mobile phase
II
decreasing the temperature
III
using a less tightly packed column
Which of the changes would be most likely to produce chromatogram 2?
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153
A. I only
B. II only
C. III only
D. I and II only
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154
QUESTION 3
Consider the following TLC plate of compounds X, Y and Z developed using a
suitable mobile phase on a polar stationary phase.
The Rf value of the most polar component in this TLC separation is:
A. 0.29
B. 0.62
C. 0.78
D. 0.80
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155
QUESTION 3 (ANSWER)
Consider the following TLC plate of compounds X, Y and Z developed using a
suitable mobile phase on a polar stationary phase.
The Rf value of the most polar component in this TLC separation is:
A. 0.29
B. 0.62
C. 0.78
D. 0.80
The answer is alternative A
The question states that the stationary phase is polar, so the most polar component will
have the greatest attraction to the stationary phase and will take the longest to move
along the TLC plate. It will have the smallest Rf value.
It is component X that travels only 0.80 cm (BUT this is not its Rf)
Rf
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156
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Atomic Absorption Spectroscopy
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157
Key(Knowledge(
Principles(and(applications(of(spectroscopic(
techniques((excluding(features(of(instrumentation(
and(operation),(and(interpretation(of(qualitative(
and(quantitative(data(from:(
! atomic(absorption(spectroscopy((AAS)(including(
electron(transitions(and(use(of(calibration(graph(
to(determine(amount(of(analyte(
! visible(and(ultraviolet(spectroscopy((visiblePUV)(
including(electron(transitions(and(use(of(
calibration(graph(to(determine(amount(of(analyte(
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158
The&electromagnetic&spectrum(
Radiation(in(the(electromagnetic(spectrum(
has(a(range(of(differing(energies.(
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159
Wavelength&and&energy&
!Wavelength(is(the((
distance(between((
adjacent(crests(of(the((
electromagnetic(wave(
!The(shorter(the(wavelength,(the(greater(its(
energy(
hc
!Wavelength(is(related(to(energy(by((E =
((((Where(c(is(the(speed(of(light,(h(is(Plancks(constant(
and((is(the(wavelength.(
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160
Depending(on(its(energy,(radiation(
may(have(varying(effects(on(a(
substance(
Ultraviolet(and(visible(radiation(is(
absorbed(by(a(compound(and(excites(
the(electrons(of(a(molecule.((
The(absorption(of(infrared(radiation(
causes(a(molecule(to(vibrate.(
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161
Atomic&emission&spectra&
!Heat,(ligh(t(or(electricity(can(excite(the(
electrons(of(an(atom(to(higher(energy(
levels(
!An(emission(spectrum(is(formed(when(the(
excited(electrons(fall(back(from(higher(
energy(levels(to(the(2nd(electron(shell.(
!Each(line(corresponds(to(radiation(of(a(
speci@ic(energy((and(wavelength).(
!The(combination(and(energy(of(lines(is(
speci@ic(to(an(element,(like(a(@ingerprint(
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162
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163
Atomic(absorption(spectroscopy(
The(light(source((hollow(cathode(lamp)(is(
created(by(using(the(light(emitted(by(
excited(atoms(of(an(element,(making(it(
speci@ic(to(the(element.(
The(strongest(line(in(the(emission(
spectrum(is(chosen(for(analysis.(
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164
! Sample(solution(of(very(low(concentration(
is(aspirated(into(high(temperature(@lame(
where(it(meets(the(light(from(the(emission(
lamp.(
! Sample(absorbs(light(
! The(greater(the(concentration(of(the(
element(that(is(present,(the(more(light(is(
absorbed.(
! Light(that(passes(through(sample(is(
detected(and(compared(to(incident(light(
! Percentage(absorbance(is(recorded.(
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165
ApplicaFons&
!Analysis(of(metals(in(very(low(
concentrations.(
!Low(concentrations(are(measured(in(parts(
per(million((ppm)(=(mg(per(L(of(solution((
(or(parts(per(billion((ppb)(=(g(per(L(of(
solution(
!Eg(concentration(of(heavy(metal(such(as(
mercury(or(lead(in(water,(or(in(@ish,(or(
concentration(of(sodium(in(sports(drink(
!Is(a(speci@ic(form(of(analysis((you(have(to(
know(what(you(are(looking(for.((
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166
Obtaining(Quantitative(results(
Standard(solutions(with(known(
concentrations(of(the(element(are(measured(
and(results(used(for(calibration(graph.(
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167
AAS(sample(exam(question(
This(is(a(calibration(curve(for(Ba2+(ions(in(an(
Atomic(Absorption(Spectrometer(
(a) If(the(absorbance(of(a(
solution(is(0.11,(@ind(the(
concentration(of(Ba2+(
ions(in(the(solution(
(b)Calculate(the(mass(of(
Ba2+(ions(in(10(mL(of(
this(solution(
(VCAA(June(2009(Q10)(
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168
Answer(
a) Using(the(graph,(an(absorbance(of(0.11(
corresponds(to(a(concentration(of(19(
mgLP1(
mass
b) Concentration(=((
volume
((((((mass(=(concentration((volume(
(((((((((((((((((((((((((=(19((0.010(
((((((((((((((((((((((((((=((0.19(mg(
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169
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
UV-Visible Spectroscopy
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170
UVBVisible&Spectroscopy&
Radiation(in(the(UV(and(visible(parts(of(
the(spectrum(has(quite(high(energy(
It(is(able(to(be(absorbed(by(atoms,(ions(or(
molecules(and(excites(the(electrons(in(the(
compounds(from(low(energy(levels(to(
higher(energy(levels.(
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171
!Different(substances(have(many(different(
energy(levels,(so(the(energy(and(
wavelength(of(the(light(required(to(
promote(the(electrons(vary.(&
!If(a(substance(absorbs(visible(light,(it(will(
appear(coloured.(
!The(colour(of(light(that(is(absorbed(is(the(
complementary(colour(to(that(shown(by(
the(compound(eg(red(is(the(
complementary(colour(of(blue,(so(blue(
solutions(will(absorb(red(light.(
VCE Chemistry Unit 3
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172
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173
How(does(it(work?((
Light(of(a(selected(wavelength(is(shone(
through(a(sample.(
The(amount(of(light(that(is(transmitted(
(goes(through(the(sample)(is(measured:(%(
transmittance.(
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174
Quantitative(use(of(UVPVis(Spec(
!The(relative(absorbances(of(wavelengths(
from(200nm(to(800nm(is(measured(for(the(
compound.(
!Wavelength(of(light(that(is(strongly(
absorbed(by(compound(is(selected(for(
quantitative(use.(
&
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175
CalibraFon&graph&
As(for(AAS,(a(calibration(graph(is(created(by(
measuring(the(%(transmittance(of(a(series(
of(samples(of(known(concentration(and(
plotting(the(two(quantities(against(each(
other.(
A(straight(line(is(obtained.(
The(%(transmittance(of(the(sample(is(
measured(and(its(concentration(is(found(
from(the(calibration(graph.(
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ApplicaFons&of&UVBVis&
!Clinical(analysis(eg(determining(the(
haemoglobin(content(and(sugar(levels(in(blood(
!Identifying(the(presence(of(elements(by(
converting(them(into(coloured(compounds(if(
they(are(not(already(coloured(
!Determining(the(levels(of(nutrients,(additives(
and(contaminants(in(water(and(foods(
!Quantitative(analysis(of(DNA(and(proteins(
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177
UVPVis((sample(exam(question(
The(UVPvisible(absorption(spectrum(of(a(solution(of(
paracetamol(is(shown(below.(The(concentration(of(
paracetamol(in(the(solution(is15.1(g(mLP1(
(
(
(
(
(
(
The(absorbance(of(another(solution(of(paracetamol(is(
measured(under(the(same(conditions,(and(at(245(nm,(the(
absorbance(is(0.96.(What(is(the(concentration,(in(g(mLP1(
of(the(paracetamol(in(this(other(solution?(
(VCAA(June(2008(Q3)(
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178
Answer(
The(UVPvisible(spectrum(shows(an(
absorbance(of(1.6(for(the(concentration(of(
15.1g(mLP1(
Therefore,(if(the(absorbance(is(0.96,(we(can(
@ind(the(concentration( 15.1
x
=
(using(the(ratio(of((
1.6 0.96
concentration(to((
15.1
x = 0.96
absorbance(
1.6
(
= 9.1 gmL-1
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179
QUESTION 1
Which one of the following analyses is best performed using atomic absorption
spectroscopy?
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180
QUESTION 1
Which one of the following analyses is best performed using atomic absorption
spectroscopy?
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181
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182
QUESTION 2
A sodium lamp emits a yellow-coloured light. If the light from the lamp was passed
through a container of sodium vapour, it is likely that the light emerging from the
container would appear
A. brighter due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
B. brighter, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
C. duller, due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
D. duller, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
(VCAAthere
Q18 June
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183
QUESTION 2 (ANSWER)
A sodium lamp emits a yellow-coloured light. If the light from the lamp was passed
through a container of sodium vapour, it is likely that the light emerging from the
container would appear
A. brighter due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
B. brighter, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
C. duller, due to electrons in atoms in the sodium vapour moving from higher to
lower energy levels.
D. duller, due to electrons in atoms in the sodium vapour moving from lower to
higher energy levels.
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184
The correct answer is D: duller, due to electrons in atoms in the sodium vapour moving from
lower to higher energy levels.
The light being emitted by the sodium lamp has the energy that is needed by a sodium atom
to excite its electrons from lower energy levels to higher energy levels. When this light is
passed through a container of sodium vapour, the sodium atoms will absorb some of this
light energy and so the light emerging from the container will be duller. The reason is that
the atoms in the sodium vapour are using that light energy to move from lower to higher
energy levels.
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185
QUESTION 3(a)
An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.
Concentration =
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mgL-1
186
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187
The concentration of MnO4-(aq) in the diluted solution in the 100 mL volumetric flask is
35 mgL-1
The calibration graph directly gives us the concentration, in mgL-1, of the diluted sample. You
need to find the absorbance (0.70) on the vertical axis and carefully draw a horizontal line
across to the calibration graph and from that point draw a vertical line down to the
concentration axis.
The value that you read should be 35 mgL-1.
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188
QUESTION 3(b)
An experiment was carried out to determine the percentage of manganese in a particular
sample of steel. A 13.936g of steel was dissolved in acid and the manganese was converted to
MnO4-(aq) ions. The solution containing the MnO4-(aq) ions was filtered and made up to a
volume of 1.00 L. 25.00 mL of this solution was then further diluted to 100.0 mL in a volumetric
flask. The absorbance, at 525 nm, of this solution was 0.70.
Next, the absorbance, at 525 nm, of a
series of solutions of MnO4-(aq) ions of
known concentration was measured and
a calibration graph drawn.
Mass =
mg
(VCAA
Q2 June
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189
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190
Note in reading the question that the g of steel was dissolved and made up to L ( mL). Then
100
mL of this solution was then diluted to mL (a dilution)25and it was for this diluted sample that
we found the concentration to be mgL-1
The mL of diluted0.140
solution contained MnO4- at a concentration of mgL-1.
0.140
- in the original solution is
The concentration
of
MnO
mgL-1
(54.9 + 4 16.0) 4 118.9
Since the volume of the original solution was L, the mass of MnO4- in the original solution =
mg
n(MnO4-) mol n(Mn) in the 1.00L of steel solution
m(Mn) g mg
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191
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Infrared Spectroscopy
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192
Key(Knowledge(
infrared(spectroscopy((IR)(including(use(
of(characteristic(absorption(bands(to(
identify(bonds(
mass(spectroscopy(including(
determination(of(molecular(ion(peak(and(
relative(molecular(mass,(and(identi@ication(
of(simple(fragments(
&
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Key(knowledge(continued(
proton(and(carbonP13(nuclear(magnetic(
resonance(spectroscopy((NMR)(including(spin,(
the(application(of(carbonP13(to(determine(
number(of(equivalent(carbon(environments;(
and(application(of(proton(NMR(to(determine(
structure:(chemical(shift,(areas(under(peak(and(
peak(splitting(patterns((excluding(coupling(
constants),(and(application(of(n+1(rule(to(
simple(compounds(
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194
Infrared((IR)(Spectroscopy((
Recall(that(infrared(radiation(has(a(longer(
wavelength(and(lower(energy(than(visible(
light.(
Infrared(radiation(can(be(absorbed(by(
molecules(and(makes(the(bonds(in(the(
molecules(vibrate(more(than(they(are(
already.(
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195
Bonds(within(molecules(can(vibrate(in(a((((((((((
variety(of(ways.(((
(Each(of(these(different(types(of(vibration(
result(when(infrared(radiation(of(different(
frequencies(is(absorbed.(
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196
How&an&infrared&spectrometer&
works&&
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197
Factors&which&affect&the&frequency&of&
radiation&absorbed&include:&
!'Strength(of(the(bond.&&&
&&&As(the(strength(of(the(bond(increases,((((
(((frequency(increases.(
!!Mass(of(atoms(in(the(bond.&&&
&&&&As(the(masses(of(the(atoms(increase,((((
((((the(frequency(decreases.(
&
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198
Reminders&about&waves:&
All(wavelengths(of(electromagnetic(
radiation(travel(at(the(same(speed(
Frequency((1(/(wavelength(
In(infrared(spectroscopy,(radiation(
absorbed(is(identi@ied(by(
wavenumber(which(is(measured(in(
cmP1((a(type(of(frequency)(
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199
Two&ways&in&which&an&infrared&
spectrum&may&be&used:&
!The(wavenumber(of(the(bands(
(peaks)(is(used(to(identify(
particular(functional(groups(
!The(@ingerprint(region(may(be(
matched(to(that(of(another(
infrared(spectrum.(
!An(unknown(compound(can(be(
identi@ied(if(its(spectrum(matches(
exactly(that(of(a(known(compound.(
VCE Chemistry Unit 3
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200
General'points'to'note'about'IR'
spectra'(eg'ethanol)'
'
yP
axis(
xPaxis(has(highest(wavenumber(on(the(left(
Bands(go(downward,(since(all(absorption(amounts(to(
less(than(100%(transmittance.(
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201
Identi;ication&of&functional&groups&&
See&Table&7&p7&VCE&Data&booklet&
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202
Identi;ication&of&functional&groups&
!Look(for(C=O(band(at(1670P1750(cmP1(
!If(C=O(band(is(missing,(then(it(is(not(a(
carboxylic(acid(or(ester(
!Look(for(OPH(band(at(2500P3300(cmP1((
(if(C=O(present)(or(at(3200P3550(cmP1((
(if(C=O(not(present(=(alcohol)(
!Expect(to(@ind(CPH(band(at((
(((2850P3300(cmP1(
!Maybe(CPCl(band(at(700P800(cmP1(
&
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203
The&;ingerprint®ion&
This(is(the(region(of(a(spectrum(below(
1500(cmP1.(((
Lots(of(peaks(here((do(not(try(to(
identify(all!(
Use(this(region(to(identify(unknown(
compounds(by(matching(their(spectra(
with(those(of(known(ones.(
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204
Ethanoic'acid'
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205
Ethyl'ethanoate'(an'ester)'
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206
Infrared(spectra(cannot(usually(be(
used(in(isolation(to(completely(identify(
unknown(compounds.(
Instead,(they(are(used(in(combination(
with(other(techniques(such(as(mass(
spectroscopy(and(nuclear(magnetic(
resonance(spectroscopy.(
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207
What&functional&group/s&is/are&
present&here?&
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208
What&do&you&see&in&this&spectrum?&
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209
And&this&one?&
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210
IR(sample(exam(question(
When(a(sample(absorbs(infrared(radiation(
A. Covalent(bonds(are(broken(
B. Covalent(bonds(stretch(and(vibrate(
C. The(spin(alignment(of(certain(nuclei(
changes(
D. Electrons(in(atoms(move(to(higher(
energy(levels(
(VCAA(June(2010(Q8)(
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211
Answer(
B(is(the(answer(
Infrared(radiation(is(not(high(enough(in(
energy(to(break(covalent(bonds((alternative(
A),(but(it(will(cause(bonds(to(stretch((a(form(
of(vibration)(
UV(radiation(can(cause(electrons(to(change(
energy(levels((C)(
Radio(frequencies(cause(changes(to(the(spin(
alignment(of(nuclei((D)(
(
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212
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Mass Spectrometry
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213
Mass&Spectrometry&&
&
Mass(spectrometry(is(used(to(
describe(the(structure(of(a(molecule((
The(molecule(breaks(into(fragments(
in(the(mass(spectrometer.(
Previously(we(have(only(used(a(mass(
spectrometer(for(determining(the(
masses(and(abundances(of(isotopes.(
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214
Diagram&of&a&mass&spectrometer&
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215
How(are(fragments(formed?(
For(organic(compounds,(during(ionisation,(the(
high(energy(electrons(also(cause(parts(of(the(
molecule(to(break(off((fragments).(
There(will(be(some(whole(molecules(present(
as(ions((the(molecular(ion)(and(also(fragments(
which(correspond(to(parts(of(the(molecule(eg(
CH3+,(CH3CH2+(etc(
Each(positively(charged(fragment(appears(as(a(
peak(on(the(mass(spectrum(for(the(compound.(
&&
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216
A(mass(spectrum(
(Propanoic(acid)((
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217
Use'of'mass'spectra'in'analysis'
!The(sizes(of(the(fragments(can(help(us(
identify(the(structure(of(a(compound,(
!Other(information(is(used(in(
conjunction:(
((empirical(formula((from(calculations)(
((functional(groups(present((IR(((((
(((((spectroscopy)(
(details(of(the(arrangment(of(hydrogens(
in(the(compound((NMR(spectroscopy).(
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218
Useful(fragments(to(look(for(
!Molecular(ion((M+)(
This(is(usually(the(peak(with(the(greatest(
m/e(ratio(on(the(spectrum.(
It(gives(you(the(molecular(mass(of(the(
compound(which(can(be(combined(with(
the(empirical(formula(to(@ind(the(
molecular(formula.(
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219
!Peaks(due(to(common(groups(in(organic(
compounds(
!m/e(=(15( ( (CH3+(((methyl)(
!m/e(=(29( (CH3CH2+(((ethyl)(
!m/e(=(45( (COOH+(((carboxyl)(
(
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220
Mass(spectrum(of(propanP1Pol(
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221
Another(example((ethanol,(C2H5OH(
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222
Mass(spec(sample(exam(question(
A(sample(of(compound(M(is(analysed(in(a(mass(
spectrometer(where(it(forms(the(molecular(ion(M+(
according(to(
M((+((eP(((M+(+(2eP(
Some(of(the(molecular(ions(fragment(as(follows:(
M+((A+(+(B((and(M+(( A(+(B+(
The(mass(spectrum(would(show(peaks(due(to(the(
species(
A.((M+,(A,(A+,(B(and(B+(only(((B.(((M+,(A+(and(B+(only(
C.(((A+(and(B+(only(( (((((((((D.((A(and(B(only(
(VCAA(June(2009(Q2)(
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223
Answer(
B(is(the(answer(
This(is(the(only(alternative(with(parts(of(the(
answer(being(positively(charged(particles(
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224
QUESTION 1
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
(VCAA
June 2010
Section
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however
there
may BbeQ3)
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225
QUESTION 1 (ANSWER)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
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226
Many different equations were possible and acceptable as answers for this question.
CH3CH2OH(g) + e[CH3CH2OH]+(g) + 2eOr
Or
CH3CH2OH(g)
CH3CH2OH+(g) + eC2H6O(g)
C2H6O+(g) + e-
Or
NO2(g) + e-
[NO2]+(g) + 2e-
Or
NO2(g)
NO2+(g) + eThe important part of the question is that the molecule is being ionised, so an electron
must be given off as a product and the product particle must have a positive charge.
There is no need for the molecule to be fragmented (broken by the impact of the
electron), as the question asks for the equation to show how the ethanol or nitrogen
dioxide molecule is ionised, not fragmented.
It is important to show the states of the molecules as gaseous (g), since the first thing
that happens to a sample in the mass spectrometer is that it is vaporised to the gaseous
phase.
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227
QUESTION 2(a)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
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228
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229
QUESTION 2(b)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
What evidence does the mass spectrum provide to support your answer?
Please write down your explanation on a piece of paper. You can self-mark it using
the answer on the next slide.
(VCAA June 2010 Section B Q3)
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230
What evidence does the mass spectrum provide to support your answer?
There are only 3 possible peaks for NO2 m/e = 16 (O+), 30 (NO+) or 46(NO2+)
Peaks at m/e = 45 (or 31 or 29 or 27) will not result from fragmentation of NO2 or
the NO2 molecule.
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231
QUESTION 3
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
What is the formula of the species that produces the peak seen at m/z 30 in
spectrum B?
Please write down the formula on a piece of paper. You can self-mark it using the
answer on the next slide.
(VCAA June 2010 Section B Q3)
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232
QUESTION 3 (ANSWER)
The molecules ethanol and nitrogen dioxide have the same molar mass
(M = 46 g mol1). They can be easily distinguished by mass spectrometry.
The mass spectra of the two molecules are shown below.
What is the formula of the species that produces the peak seen at m/z 30 in
spectrum B?
Spectrum B is the mass spectrum of NO2. The m/z value of 30 corresponds to one
N (14) and one O(16) 14 + 16 = 30, so the acceptable answers are [NO]+ or NO+ or
NO +
(VCAA June 2010 Section B Q3)
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233
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
NMR Spectroscopy
Theory, Spin and H Environments
VCE Chemistry Unit 3
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234
Nuclear(magnetic(resonance((NMR)(
spectroscopy(
!This(is(used(to(identify(the(arrangement(
of(hydrogen(atoms(in(a(compound.(
It(is(possible(because(1H(nuclei(have(a(
spin(of((13C(also(has(a(spin(of((so(
can(also(be(analysed(using(NMR((also(
31P,(19F(and(15N)(
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235
What&is&Spin?&
Spin(is(a(fundamental(property(of(nature(
like(electrical(charge(or(mass.(
(Spin(comes(in(multiples(of(1/2(and(can(be(
+(or(P.(
A(nucleus(with(a((
(((nonPzero(spin((
(((behaves(like(a((
(((small(magnet((
VCE Chemistry Unit 3
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236
How&does&it&work?&
!An(NMR(spectrometer(applies(a(large(magnetic(
@ield((about(10(000(times(that(of(earths(magnetic(
@ield)(to(the(sample.(
!The(spinning(1H(nuclei(respond(by(either(aligning(
with(the(magnetic(@ield(or((opposing((it.(Spin(up(or(
spin(down)(
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237
Two(energy(levels((spin(states)(exist(
for(a(spinning(nucleus,(the(lower(one(
being(when(the(nucleus(is(aligned(
with(the(external(magnetic(@ield.(
opposed
to B
E=h
aligned
with B
B
VCE Chemistry Unit 3
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Bapp
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238
When(a(magnetic(@ield(is(being(applied(to(an(
1H(nucleus((a(proton)(the(difference(
between(the(spin(states(is(still(quite(small.(
So,(radiowaves((low(energy)(provide(
enough(energy(to(excite(a(proton(from(one(
spin(state(up(to(the(other((for(it(to(resonate)(
Only(1H(NMR(and(13C(NMR(have(to(be(
analysed(in(this(course(
13C(NMR(spectra(have(a(very(different(scale(
to(1H(NMR(spectra((
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239
Magnetic(in@luences(on(an(atom(in(a(
compound.(
The(applied(magnetic(@ield((Bapp)(comes(
from(the(actual(NMR(instrument(
A(local(magnetic(@ield(is(due(to(other(
atoms(in(the(compound.(
The(local(@ield((as(experienced(by(1H(
nuclei(in(a(compound)(depends(on(their(
environment(
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240
The(environment(of(the(1H(is(made(up(of(
the(atom(it(is(bonded(to,(as(well(as(other(
atoms(nearby.(
These(change(the(way(a(1H(nucleus(
responds(to(the(applied(magnetic(@ield.(
A(H(bonded(to(an(O(in(OH(will(resonate(at(
a(different(energy(to(one(bonded(to(a(C(
(eg(in(CH3)(
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241
Example&of&an&NMR&spectrum&
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242
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Analysing NMR Spectra
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243
How&can&we&use&NMR?&
The(NMR(spectrum(is(made(up(of(sets(
of(peaks(
The(position(of(a(peak(depends(on(the(
environment(of(the(1H(nuclei(
producing(that(peak.(
The(position(of(the(peak(along(the(
horizontal(axis(is(known(as(chemical(
shift.&
VCE Chemistry Unit 3
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244
The(location(of(an(NMR(signal(in(a(spectrum(is(
measured(relative(to(a(reference(signal(from(a(
reference(compound(added(to(the(sample.(
The(protons(in(the(reference(compound,(TMS,(
tetramethylsilane,(Si(CH3)4,(are(assigned(a(
chemical(shift(of(zero.(((
((((this(will(always(be((
((((present,(but(does(not(
(((( count (as(a(peak)(
A(chemical(shift(of((
(((1(ppm(means(that((
(((the(signal(is(shifted(by(200(Hz(on(a(200MHz(((
(((instrument.(
VCE Chemistry Unit 3
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245
H(atoms(bonded(to(more(
electronegative(atoms(will(have(a(
greater(shift((further(to(left)(than(those(
in(more(electron(dense(environments.(
Eg(a(H(bonded(to(an(O(will(have(a(
greater(shift(than(one(bonded(to(C(
Tables(of(chemical(shifts(help(us(to(
identify(a(H(atom((See(table(5(in(Data(
booklet(
VCE Chemistry Unit 3
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246
p5 of data booklet
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247
The(size(of(peaks(
The(size(of(peaks(relative(to(each(other(
is(often(indicated(by(an(integration(
trace.(
The(ratio(of(the(areas(under(the(peaks(
(from(the(integration(trace)(gives(the(
ratio(of(H(atoms(of(a(particular(type(
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248
example(
In(CH3CH2CH2CH3(there(are(two(
different(environments(for(Hs.(They(
may(either(be(part(of(a(CH3(group(or(a(
CH2(group.(
So(there(will(be(two(peaks(on(the(NMR(
spectrum(for(butane((one(at(chemical(
shift(of(0.9(ppm((for(CH3(groups)(and(
the(other(at(chemical(shift(of(1.3(ppm(
for(RPCH2PR(.(
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249
An(integration(trace(of(these(peaks(
will(show(a(ratio(of(peak(areas(of((
(((3(:(2(re@lecting(the(ratio(of(Hs(in(CH3(((
(((groups(to(Hs(in(CH2(groups.(
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250
Ethanol&&3&environments&
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251
SpliFng'of'peaks''
(high'resolu:on'NMR)'
The(effect(of(neighbouring(1H(nuclei(is(
to(split(the(peak(corresponding(to(a(
particular(group(of(Hs(into(several(
small(peaks.((
This(effect(is(called(a(splitting(pattern.(
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252
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253
Eg(If(the(Hs(in(a(CH3(group(on(the(end(
of(a(molecule(has(a(neighboring(C(with(
2Hs(on(it,(the(peak(for(the(CH3(Hs(will(
be(split(into(three((a(triplet).((n(+(1(
rule)(
Triplet would
represent
these Hs
Due to the 2
neighbouring
Hs
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254
In(the(example(of(butane,(the(peak(at(0.9ppm((CH3(
peak)(would(be(a(triplet(because(it(would(be(split(by(
the(neighboring(group(of(two(Hs(on(CH2(
The(peak(at((
1.3ppm((due(to((
CH2)(would(be(a((
multiplet(due(to((
the(3(neighboring((
CH3(Hs(AND(the((
2(neighbouring((
CH2(Hs(
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255
Chloroethane((2(environments,(one(
triplet(and(one(quartet(
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256
13C(NMR(
!13C(is(a(naturally(occurring,(but(very(low(
concentration(isotope(of(carbon.(
!It(can(be(used(for(identifying(the(
different(carbon(environments(in(a(
molecule.(
!Chemical(shifts(are(much(greater(for(13C(
NMR(than(1H(NMR((up(to(200(ppm)(
!13C(NMR(spectra(tend(to(be(simpler(than(
1H(due(to(the(smaller(differences(
between(Cs.(
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257
13C(NMR(of(ethanol(
!Notice(that(there(are(only(2(peaks(since(
there(are(only(2(different(Cs((one(on(end(
and(one(in(middle)(
!There(is(no(splitting(in(a(13C(NMR(
&
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258
In(summary(
!Chemical(shift(provides(information(
about(the(position(in(the(molecule(in(
which(the(H(is(found.(
!Number(of(peaks(=(number(of(different(
environments(
!Peak(area(gives(information(about(the(
ratio(of(equivalent(Hs(
!Peak(splitting(gives(information(about(
the(number(of(neighbouring(Hs.(
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259
NMR(Sample(exam(question(
A(sample(of(a(hydrocarbon(for(analysis(is(placed(in(a(
strong(magnetic(@iled(and(irradiated(with(
electromagnetic(radiation(of(radio(wave(frequency.(
This(is(most(likely(to(result(in(
(((((A. (ionisation(and(fragmentation(of(molecules(
(((((B.((An(increase(in(bond(vibrations(of(molecules(
(((((C.((The(promotion(of(electrons(to(higher(energy(((
(((((((((((levels(
(((((D.((A(change(in(the(energy(of(the(nuclei(of(the((
(((((((((((hydrogen(atoms.(
(VCAA(June(2008(Q(15)(
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Answer(
D(describes(NMR(
A(describes(mass(spectroscopy(
B(describes(IR(spectroscopy(
C(describes(atomic(emission(spectroscopy(
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261
QUESTION 1
The disease sickle cell anaemia is marked by the presence of an abnormal protein
in the blood of people with this disease. The sixth position in the normal protein
chain is occupied by the amino acid, glutamic acid. The sickle cell protein chain has
the amino acid, valine, in the sixth position. This is the only difference between the
two protein chains.
A section of each protein chain containing glutamic acid and valine is shown
below.
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262
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.
C.
D.
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263
QUESTION 1 (ANSWER)
The disease sickle cell anaemia is marked by the presence of an abnormal protein
in the blood of people with this disease. The sixth position in the normal protein
chain is occupied by the amino acid, glutamic acid. The sickle cell protein chain has
the amino acid, valine, in the sixth position. This is the only difference between the
two protein chains.
A section of each protein chain containing glutamic acid and valine is shown
below.
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264
Molecular mass
1H
A.
B.
C.
D.
NMR spectrum
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265
Glutamic acid has a larger molar mass than valine, so the Normal protein chain would have
a greater molecular mass.
Because the 1H environments are different in glutamic acid (3 environments) compared to
valine (2 environments), the protein chains would have different 1H NMR spectra.
(VCAA June 2008 Q5)
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266
QUESTION 2
The polymer polylactic acid, PLA, shown above, is used to make soluble stitches
which are absorbed by the body following surgery.
Other than the peak given by the TMS reference, the monomer from which PLA is
formed would give
A. one set of peaks in the 1H NMR spectrum
B. two sets of peaks in the 1H NMR spectrum
C. three sets of peaks in the 1H NMR spectrum
D. four sets of peaks in the 1H NMR spectrum
(VCAA June 2009 Q4)
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267
QUESTION 2 (ANSWER)
The polymer polylactic acid, PLA, shown above, is used to make soluble stitches
which are absorbed by the body following surgery.
Other than the peak given by the TMS reference, the monomer from which PLA is
formed would give
A. one set of peaks in the 1H NMR spectrum
B. two sets of peaks in the 1H NMR spectrum
C. three sets of peaks in the 1H NMR spectrum
D. four sets of peaks in the 1H NMR spectrum
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268
The section of the polymer, polylactic acid, shown in the question shows repeating ester groups COOwhich can be used to identify the monomer from which the condensation polymer is produced. The
ester groups form by reaction between carboxyl and hydroxyl groups, so we would expect a carboxyl
group on the right hand end of the monomer and a hydroxyl on the left hand end of the monomer.
It is lactic acid, although this knowledge is not necessary to answer the question correctly.
It would have four hydrogen environments.
Since each 1H environment is represented by a peak, the correct answer is D.
(VCAA June 2009 Q4)
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269
QUESTION 3(a)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.
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270
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271
QUESTION 3(b)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.
Draw the structure of the unknown molecule, clearly showing all bonds.
Please draw your answer on a piece of paper. You can self-mark it using the answer on the next slide.
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272
Draw the structure of the unknown molecule, clearly showing all bonds.
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273
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274
QUESTION 3(c)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.
Explain how the structure of the compound you have drawn in part (b) is
consistent with its IR spectrum.
Please write your explanation on a piece of paper. You can self-mark it using the answer on the next slide.
(VCAA June 2009 Section B Q5 (modified))
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275
Explain how the structure of the compound you have drawn in part (b) is
consistent with its IR spectrum.
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276
There is a strong band at 1750 cm-1 which indicates that there is a C=O (carbonyl) group.
And there is a broad band at 2500-3300 (cm-1) indicating an O-H bond.
Together these two bands confirm the existence of the carboxyl functional group.
(VCAA June 2009 Section B Q5 (modified))
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277
QUESTION 3(d)
The structure of an organic molecule, with empirical formula CH2O, is determined
using spectroscopic techniques. The molecular formula of this molecule is C2H4O2.
The infrared spectrum and 1H NMR spectrum for this molecule are given below.
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278
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279
Ethanoic acid
(Eth 2 carbons, -oic acid due to the carboxyl functional group)
(VCAA June 2009 Section B Q5 (modified))
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280
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Exam Question Combining Spectroscopic Techniques
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281
Exam(question(that(combines(all(
three(techniques(
The(structure(of(an(organic(molecule,(with(
empirical(formula(CH2O,(is(determined(
using(spectroscopic(techniques.(The(mass(
spectrum,(infrared(spectrum(and(1H(NMR(
spectrum(for(this(molecule(are(given(below.(
Use(the(information(provided(by(these(
spectra(to(answer(these(questions.(
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282
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283
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284
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285
a) What(is(the(molecular(formula(of(this(
molecule?(
b) How(many(different(proton(environments(
are(there(in(this(molecule?(
c) Draw(the(structure(of(the(unknown(
molecule,(clearly(showing(all(bonds.(
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286
CHEMISTRY
Unit 3, Area of Study 1:
Chemical Analysis
Calculations
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287
Key(Knowledge(
calculations(including(amount(of(solids,(
liquids(and(gases;(concentration;(volume,(
pressure(and(temperature(of(gases(
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288
Revision(of(Unit(2(
When(working(out(what(formula(to(use(
in(calculations(classify(the(reagents(in(
terms(of(their(state.(
If(the(mass(of(a(solid(is(required(or(given,(
use(
m
( (((((n(=((
If(a(solution(is(involved(use(((n(=(cV(
VCE Chemistry Unit 3
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289
Gases(
If(a(gas(is(involved,(then(the(general(gas(
equation(is(most(useful:(
( (PV(=(nRT((((R(=(8.31(J(KP1molP1)(
However,(keep(in(mind(that((((n(=( V
((((can(be(used(when(the(gas(is(
VM
(((((at(STP((0C,(1(atm(pressure)(or(
(((((at(SLC((25(C,(1(atm(pressure)(
(((((where(VM(=(22.4LmolP1(or(24.5(L(molP1(
See(the(Exam(data(book(p5(for(these(values(
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290
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291
Density(
Density(values(often(occur(as(part(of(a(
calculation(
Units:(g(mLP1((or(it(could(be(g(LP1(
Use(the(units(to(help(you(with(density((
eg(density(of(ethanol(is(0.785(g(mL,(so(
1mL(of(ethanol(has(a(mass(of(0.785g.((
So(50.0(mL(of(ethanol(has(a(mass(of((
(((0.785((50(=(39.25(g(
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292
Sample(exam(questionsPgases(
The(reaction(that(occurs(in(an(airbag(when(an(accident(
occurs(is(
10(NaN3(s)((+((2KNO3(s)(( 5Na2O(s) + K2O(s) + 16N2(g)
A particular car s airbag was found to inflate to a volume of
62.0L at a pressure of 100kPa when the temperature reached
36.6 C. The molar mass of NaN3 is 65.0 gmol-1. What was the
mass of sodium azide contained in the car s airbag?
A.97.9 g
B.156.6 g
C.250.6 g
D.828.1 g(
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293
Answer(
PV
PV(=(nRT,(so(n(=(
RT
(
100 62.0
n(= ( ((((((((((=(2.41(mol((
8.31 309.6
(
From(the(equation(N2(:((NaN3(
( ((((((((((((16(:(10(
10
( ((((((((2.41((: ( (=(1.51(mol(
2.41
16
m(NaN3)(=(1.51((65.0(
((((((((=(97.9(g(
The(answer(is(A(
(
&
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294
Sample(exam(questionsPdensity&
An(analysis(is(carried(out(on(a(sample(of(
unknown(gas.(The(density(of(the(gas(is(
2.86(gLP1(at(STP.(The(molecular(formula(of(
the(gas(is(
A. HCl(
B. Cl2(
C. NO2(
D. SO2(
VCAA(June(2011(Q14(
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295
Answer:(
Density(=(2.86(gLP1(
So,(1(Litre(of(gas(has(a(mass(of(2.86(g(
At(STP,(1(mole(of(gas(occupies(22.4(L(
So,(1(mole(of(gas(has(a(mass(of((
22.4((2.86(=(64.06(g(=(molar(mass((
Molar(mass(of(SO2(=(32.1(+(32.0(=(64.1(
D(is(the(answer.&
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296
QUESTION 1
The concentration of K+ ions in 100 mL of 0.0500 M K2CO3 solution, in gL-1, is
A. 0.196
B. 0.391
C. 1.96
D. 3.91
Note the careful reading required to make sure that you get the answer right here the
question is asking for gL-1 NOT molL-1
(VCAA Q12 June 2006)
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297
QUESTION 1 (ANSWER)
The concentration of K+ ions in 100 mL of 0.0500 M K2CO3 solution, in gL-1, is
A. 0.196
B. 0.391
C. 1.96
D. 3.91
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298
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299
QUESTION 2
One possible reaction that occurs when trinitrotoluene (TNT), C7H5N3O6,
explodes is 2 C7H5N3O6(s)
2C(s) + 12CO(g) + 5H2(g) + 3N2(g)
When one mole of TNT explodes the total volume of the gases produced from this
reaction, measured at 27 C and 1.00 102 kPa, is closest to
A. 0.249 L
B. 22.7 L
C. 249 L
D. 274 L
(VCAA Q5 June 2010)
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300
QUESTION 2 (ANSWER)
One possible reaction that occurs when trinitrotoluene (TNT), C7H5N3O6,
explodes is 2 C7H5N3O6(s)
2C(s) + 12CO(g) + 5H2(g) + 3N2(g)
When one mole of TNT explodes the total volume of the gases produced from this
reaction, measured at 27 C and 1.00 102 kPa, is closest to
A. 0.249 L
B. 22.7 L
C. 249 L
D. 274 L
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301
The important term here in the question is the total volume of the gases .
We can see from the equation that when 2 mole of TNT explodes, 20 mole of gases are
produced (12CO + 5H2 + 3N2).
Therefore when one mole of TNT explodes, 10 mole of gases are produced, and now we
just need to convert to volume at 27 C and 1.00 102 kPa.
PV = nRT
nRT
10 8.31 (27 + 273)
V=
=
1.00 10 2
P
To 3 sig figs this answer is 249 L alternative C
=249.3L
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302
QUESTION 3
A sample of the insecticide dichlorodiphenyltrichloroethane (DDT), C14H9Cl5, was
found to contain 0.120 g of carbon.
What mass of chlorine was present in the sample?
A. 0.127 g
B. 0.355 g
C. 0.994 g
D. 1.01 g
(VCAA Q6 June 2010)
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303
QUESTION 3 (ANSWER)
A sample of the insecticide dichlorodiphenyltrichloroethane (DDT), C14H9Cl5, was
found to contain 0.120 g of carbon.
What mass of chlorine was present in the sample?
A. 0.127 g
B. 0.355 g
C. 0.994 g
D. 1.01 g
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304
0.01
5
14
m(Cl) =
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305
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkanes and their Isomers
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306
Key(Knowledge(
!structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
alkanes,((alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),(alkanoic(acids(
(CnH2n+1COOH)(and(esters)(up(to(C10(
&
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307
Families(of(carbon(compounds(
!Carbon(compounds(are(classi@ied(into(
homologous(series(according(to(their(
structure(and(the(atoms(that(make(them(up.(
(
!An(homologous(series(can(be(described(as(a(
group(of(compounds(which(have(the(same(
general(formula(and(similar(chemical(
properties.(
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308
Alkanes(
General(formula(CnH2n+2(
Single(bonds(occur(between(all(carbon(
atoms(=(saturated(hydrocarbons(
Alkane(molecules(are(always(nonPpolar(
The(systematic(names(of(all(alkanes(ends(
with(ane(
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309
The(beginning((pre@ix)(of(the(name(of(any(
organic(compound(indicates(the(number(of(
carbon(atoms(in(that(compound(
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310
The&rst&four&alkanes&
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311
!As(the(size(of(the((
alkane(increases,((
the(boiling(point((
increases,(due(to((
increased(strength((
of(dispersion(forces.(
!Remember&that!!
only!intermolecular!
forces!break!upon!!
boiling.!
&
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312
Other(molecules(to(be(aware(of(
! Cyclic(molecules(P(these(also(have(single((
(((CPC(bonds,(BUT(they(do(not(match(the(formula,(
CnH2n+2,(their(formula(is(CnH2n(
(
(
(
! Benzene(is(an(arene.(It(has(the(formula(C6H6(
and(is(carcinogenic.(Arenes(are(cyclic(molecules(
with(delocalised,(shared(electrons(in(a(ring.(
Naphthalene(is(also(an(arene.(
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Isomers(
Structural(isomers(P(compounds(with(the(
same(molecular(formula(but(different(
structures.(
Note(that(formulas(can(be((represented(
((((in(several(
((((ways:(
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314
Isomers(of(butane(
! The(molecular(formula(of(both(isomers(is(C4H10(
! The(semi(structural(formula(of(these(molecules(
would(be(
(((CH3CH2CH2CH3(and(CH3CH(CH3)CH3(
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315
These(isomers(would(have(the(same(
chemical(reactivity(because(they(are(both(
alkanes.(
Their(physical(properties(differ(slightly.(
Butane(has(a(higher(boiling(point(than(
methylpropane(because(the(linear(
butane(molecules(can(pack(together(
more(closely(than(the(branched(
methylpropane(molecules(and(stronger(
dispersion(forces(can(form.(
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316
Naming(hydrocarbons(
(
1. Identify(longest(chain(of(Cs((((main(part(of(name(
2. Look(for(any(branches(off(the(chain(
((((((branches(are(named(according(to(no.(of((Cs(eg(1(C(=(((
((((((((methyl,(2(Cs(=(ethyl)(
3. Indicate(the(position(of(branches(by(adding(a(number,(
working(from(the(end(nearest(to(the(branch(((lowest(
number)(
4. Numbers(are(separated(from(words(by(hyphens(and(
from(each(other(by(commas.&
VCE
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What(is(the(name(of(this(
compound?(
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Sample(exam(question((naming(alkanes(
What(is(the(correct(systematic(name(for(the(
following(compound?(
(
(
(
(
A. 2PethylP3Pmethylpentane(
B. 3PmethylP4Pethylpentane(
C. 3,4Pdimethylhexane(
D. 2,3Pdiethylbutane(
VCAA(June(2010(Q10(
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CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkenes, Haloalkanes, Amines and Alkanols
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Key(knowledge(
structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
(alkanes),(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),((alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10)(
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321
Alkenes(
Alkenes(always(have(one(CPC(double(bond.(
The(general(formula(of(the(alkene(family(is(
CnH2n(
They(are(more(reactive(than(alkanes(
The(shape(around(the(C=C(bond(is(trigonal(
planar,(not(tetrahedral(as(in(alkanes.(
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322
Naming(alkenes(
The(ending(of(any(alkene(will(be(ene(
The(position(of(the(double(bond(must(
be(indicated(from(C4H8(upwards.((
This(is(done(with(a(number((
(((eg(butP1Pene,(((((((((butP2Pene(((
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323
Functional(groups(
A(functional(group(is(an(atom(or(group(of(
atoms(which(in@luences(the(chemical(
properties(of(an(organic(compound.(
You(are(required(to(name(and(draw(
molecules(that(can(be(classi@ied(as(amines,(
alkanols((alcohols),(alkanoic(acids(
(carboxylic(acids),(haloalkanes(and(esters(
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324
Amines(
One(H(atom(is(replaced(by(a(PNH2(group(
General(formula(is(CnH2n+1(NH2(
The(amine(functional(group(is(basic((can(gain(an(
H+(ion.(
Amines(can(be(classi@ied(as(primary,(secondary(
or(tertiary,(according(to(how(many(alkyl(chains(
are(bonded(to(the(NH2(group.&
&
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325
Amines(are(named(with(the(suf@ix(amine(
Eg(ethanamine(C2H5NH2(
Isomers(are(named(according(to(the(
position(of(the(amine(group((
(((eg(butanP2Pamine(
Amines(are(polar(and(are(soluble(in(water(
due(to(their(ability(to(form(hydrogen(bonds.(
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326
Haloalkanes(
Members(of(this(homologous(series(are(
alkanes(with(a(halogen((F,(Cl,(Br,(I)(atom(
replacing(one(H(atom.(
General(formula(CnH2n+1X(
The(single(halogen(atom(makes(the(
molecule(polar(and(makes(it(susceptible(
to(further(reactions.(
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327
Naming:(Add(@luoroP,(or(chloroP(or(bromoP(
or(iodoP(as(a(pre@ix(
Eg(chloroethane(has(the(formula(C2H5Cl(
Isomers(are(possible:(
(((Isomers(of(Iodopropane(
((((((1Piodopropane(:(CH2ICH2CH3(
(2Piodopropane(:(CH3CHICH3(
(((((Numbers(are(used(to(indicate(the(position(((
(((((of(the(halogen(atom,(directly(in(front(of((
(((((the(pre@ix.(
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328
Alkanols((alcohols)(
One(H(is(replaced(by(OH(
General(formula(CnH2n+1OH(
The(name(of(an(alcohol(always(ends(in(ol(
Eg(ethanol(C2H5OH(
The(functional(group((POH)(is(called(a(
hydroxyl(group(
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329
Isomers(are(named(according(to(the(
position(of(the(POH(group(
(
Eg(butanP1Pol(:(CH3CH2CH2CH2OH(
and(butanP2Pol:(CH3CH2CH(OH)CH3(
The(presence(of(the(hydroxyl((POH)(group(
makes(the(molecule(polar(and(also(able(to(
hydrogen(bond(with(water(molecules((
((small(alcohols(can(dissolve(in(water.(
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330
Sample(exam(questions((
functional(groups(and(isomers(
For(which(one(of(the(following(molecular(
formulae(is(there(only(one(possible(structure?(
A. C2HCl3(
B. C2H4Cl2(
C. C2H2Cl2(
D. C4H9OH(
(
VCAA(June(2010(Q11(
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331
How(many(structural(isomers,(each(
containing(a(double(bond,(have(the(
molecular(formula(C5H10?(
A. 3(
B. 4(
C. 5(
D. 6(
(
VCAA(June(2008(Q16(
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332
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Alkanoic Acids and Esthers
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333
Key(knowledge(
structure(including(molecular,(structural(
and(semiPstructural(formulae,(and(
International(Union(of(Pure(and(Applied(
Chemistry((IUPAC)(nomenclature(of(
(alkanes,(alkenes,(amines,(haloalkanes,(
alkanols((CnH2n+1OH),)(alkanoic(acids(
(CnH2n+1COOH)(and(esters(up(to(C10(
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334
Alkanoic((Carboxylic)(acids(
One((H(is(replaced(by(PCOOH(
(
(
(
Only(the(end(carbon(can(have(this(functional(
group(on(it,(so(few(structural(isomers(can(
occur,(although(dont(forget(branched(
structures.(
The(functional(group(is(called(a(carboxyl(group(
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335
General(formula(is(RCOOH(where(R(is(an(alkyl(group(
(methyl,(ethyl,(propyl(etc)(
The(name(of(a(carboxylic(acid(always(ends(in((
(((((oic(acid.(
The(total(number(of(Carbons(in(the(compound(gives(
us(the(name(so(C3H7COOH(with(4(Cs(is(butanoic(acid.(
(
(
(
These(compounds(are(acidic,(the(H(of(the((
(PCOOH(group(can(be(donated(in(an(acid(base(
reaction.(
Alkanoic(acids(are(the(most(common(weak(acids(
that(you(will(encounter.(
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336
Carboxylic(acids(are(polar(molecules(with(high(
melting(points(
The((formation(of(hydrogen(bonds(between(
carboxylic(acids(creates(dimers((so(their(melting(
point(becomes(effectively(equal(to(that(of(a(
molecule(with(double(the(molar(mass).((
Hydrogen(bonding(with(water(makes(them(soluble(
in(water(
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337
Esters(
Esters(have(a(functional(group(with(the(formula(
COPOP(
The(ending(oate(indicates(
((((an(ester(functional(group.(
Esters(are(formed(when(
((((alkanols(react(with(alkanoic(acids,(so(their(names(((
((((are(formed(from(these(two(compounds,(the(alkanol((
((((name(is(@irst(and(is(reduced(to( alkyl (eg(if(the((((
(((((alkanol(was(ethanol,(then(the(ester(name(would((
(((((start(with(ethyl.(
An(ester(that(is(formed(from(propanol(and(ethanoic(
acid(is(called(propyl(ethanoate(
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338
Naming(esters(from(their(
When(trying(to(name(an(ester(from(its(structure,(
structures(
you(need(to(locate(the(functional(group(@irst.(
(
(
The(alkyl(chain(which(included(the(C=O((carbonyl(
group)(has(come(from(the(carboxylic(acid,(and(the(
alkyl(chain(nearest(the(OP(has(come(from(the(
alkanol.(
Name(the(ester(with(the(alkanol(@irst:(this(one(is(
ethyl(ethanoate.(
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339
Amides(
Although(this(functional(group(is(not(on(the(key(
knowledge(list,(it(occurs(in(proteins(and(is(often(
used(in(past(exam(questions.(
The(amide(functional(group(can(appear((
(((((as ( ( ( (or(
(
(
depending(on(whether(it(is(on(the(end(or(in(the(
middle(of(a(compound(
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340
Sample&exam&quesFons&&alkanoic&
acids,&esters&and&amides&
The(structure(of(tami@lu,((
an(anti@lu(drug(is(shown((
opposite.(
The(names(of(the(
functional(groups(
labelled(I,(II(and(III(are(
I&
II&
III&
A.(
Amide(
Amino(
Carboxylic(acid(
B.(
Amino(
Amide(
ester(
C.(
Amide(
Amino(
ester(
Amino(
Amide(
Carboxylic(acid(
D.(
VCAA(June(
2010(Q19(
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341
The(number(of(structural(isomers(that(
are(carboxylic(acids(with(the(formula(
C4H8O2(is(
A. 1(
B. 2(
C. 3(
D. 4(
(
VCAA(June(2006(Q9(
&
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342
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Substitution Reactions of Alkanes and
Addition Reactions of Alkenes
VCE Chemistry Unit 3
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343
Key&knowledge&
common(reactions(of(organic(compounds(
including(equations:(addition(reactions(of(
alkenes((addition(of(hydrogen(halides(and(
water(limited(to(symmetrical(alkenes),(
substitution(reactions(of(alkanes(
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344
&
Combustion(reactions(
! Most(hydrocarbons(will(undergo(combustion(
in(the(presence(of(oxygen.(
! There(are(two(types(of(combustion(reactions(
(complete(combustion(and(incomplete(
combustion.(
! The(products(of(complete(combustion(are(CO2(
and(H2O,(while(incomplete(combustion(may(
form(CO(and/or(C(and(H2O(
! Eg(CH4(g)(+(2O2(g)((CO2(g)(+(2H2O(l)(
((((2CH4(g)(+(3O2(g)((2CO(g)(+(4H2O(l)(
VCE Chemistry Unit 3
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345
Substitution(reactions(of(alkanes(
In(a(substitution(reaction,(one(or(more(of(the(
hydrogen(atoms(on(the(alkane(is(replaced(by(
another(atom(or(functional(group.(
Heat(or(UV(light(is(needed(to(start(a(substitution(
reaction(when(the(bond(in(the(halogen(molecule(is(
broken(and(two(free(radicals(are(formed.(
Haloalkanes(are(made(when(alkanes(react(with(
halogens(such(as(chlorine(and(bromine(in(this(way.(
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346
Formation(of(a(haloalkane(
! Alkane(+(halogen((haloalkane(+(hydrogen(
halide((
UV((((((((((CH
light
eg(CH4((+((Cl2((((((((((((((
!!!!
3Cl((+((HCl(
(
! After(the(substitution(of(one(chlorine(onto(the(
alkane,(another(can(be(substituted:(
(CH3Cl((+((Cl2((((CH2Cl2((+((HCl(
! If(enough(chlorine(is(present,(this(can(continue(
right(up(to(CCl4(
! This(applies(to(other(halogens(reacting(in(the(
same(way.(
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347
Addition(reactions(of(Alkenes(
! The(CPC(double(bond,(is(more(reactive(than(the(
CPC(single(bond(so(alkenes(are(more(reactive(
than(alkanes.((
! Addition(reactions(involve(the(CPC(double(bond(
becoming(a(single(bond((breaking)(and(extra(
atoms(or(functional(groups(adding(onto(the(
molecule.(
! The(new(atoms(or(functional(groups(always(add(
across(the(double(bond((with(one(atom((or(
functional(group)(on(each(side(of(what(used(to(
be(the(double(bond.(
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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(
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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).(
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350
An(alkane(will(not(react(with(bromine(
unless(UV(light(is(present,(whereas(an(
alkene(will(instantly(react(with(bromine(and(
the(brown(colour(disappears.(
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351
2.(Reaction(with(hydrogen(
! This(is(used(to(decrease(the(number(of(double(
bonds(in(an(unsaturated(hydrocarbon((in(
particular(in(making(margarine.(
! Alkene(+(hydrogen((((((alkane(
(
! Eg(CH2=CH2(+(H2((((CH3CH3(
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352
3.(Reaction(with(a(hydrogen(halide(
While(the(reaction(with(a(halogen(produces(a(
dihaloalkane,(this(reaction(adds(just(one(halogen(
atom(onto(the(alkane,(making(a(haloalkane.(
Only(symmetrical(alkenes((with(the(double(bond(
exactly(in(the(middle(of(the(molecule)(need(to(be(
used(as(examples(
Alkene(+(hydrogen(chloride((chloroalkane(
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353
examples&
CH2=CH2(+(HCl((CH3CH2Cl(
CH3CH=CHCH3+(HBr(CH3CH2CH2BrCH3(
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354
4.(Reaction(with(water(
This(is(an(easy(method(for(making(an(alkanol(
A(catalyst(is(used((phosphoric(acid(
Alkene(+(steam((alcohol(
( ( ( ( (((((((H3PO4(
Eg(CH2=CH2(g)(+(H2O(g)((((((CH3CH2OH(l)(
(catalyst(is(always(written(over(the(arrow)&
Only(symmetrical(alkenes(need(to(be(used(
+
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355
Sample(exam(questionP(
substitution(and(addition(reactions(
A(student(was(given(four(colourless(liquids(that(were(
labelled(A,(B,(C(and(D.(They(were(known(to(be(ethanol,(
ethanoic(acid,(pentane(and(hexene,(but(the(exact(identity(
of(each(liquid(was(unknown.(The(student(tested(the(
properties(of(each(liquid(and(obtained(the(results(shown(
below.(
A&
B&
C&
D&
(
Solubility(in(
water(
insoluble(
soluble(
soluble(
insoluble(
Addition(of(Br2(
solution(
Colour(
disappears(
No(
immediate(
reaction(
No(
immediate(
reaction(
No(
immediate(
reaction(
Addition(of(
Na2CO3(powder(
No(reaction(
Gas(evolved(
No(reaction(
No(reaction(
VCAA(June(2006(Q1(
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356
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Substitution Reactions of Haloalkanes,
Oxidation of Alkanols and Esterification Reactions
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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357
Key&knowledge&
common(reactions(of(organic(compounds(
including(equations:(substitution(reactions(
of(primary(haloalkanes,(oxidation(of(
primary(alkanols,(and(esteri@ication)(
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358
Primary&haloalkanes&
Haloalkanes(are(named(according(to(the(number(
of(carbon(atoms(that(are(bonded(to(the(carbon(on(
which(the(halogen(is(bonded.(
A(primary(haloalkane(has(the(halogen(atom(
bonded(to(a(carbon(that(is(on(the(end(of(the(
carbon(chain((it(is(only(bonded(to(one(other(
carbon((hence(primary)(
eg((CH3CH2CH2Cl(
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359
Substitution(reactions(of(haloalkanes(
In(this(case(the(substitution(reaction(involves(
the(replacement(of(one(functional(group(with(
another.(
The(halogen(atom(makes(the(carbon(atom(
into(a(positive(charge(centre,(so(nucleophiles(
(functional(groups(with(a(nonPbonding(pair(
of(electrons(or(a(negative(charge)(are(
attracted(to(it.(
Hydroxide(ions,(water((and(ammonia(are(all(
nucleophiles(
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360
Equations:(
CH3Cl(+(OHP(((CH3OH(+(ClP(
C2H5Cl(+(H2O((C2H5OH(+(HCl(
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361
Oxidation(reactions(of(alkanols(
Oxidation(of(a(primary(alkanol(produces(a(carboxylic(
acid(
NB(The(oxidant(used(is(either(the(permanganate(ion,(or(
the(dichromate(ion.(In(addition,(heat(is(required(and(
acid((eg(H2SO4)(
This(is(how(vinegar(is(made(from(wine!(
When(wine( goes (off,(we(often(say(it(has(gone(
vinegary ((because(ethanoic(acid(has(been(made(by(
the(oxidation(of(the(ethanol(by(oxygen(in(the(air((and(
bacteria)(
VCE Chemistry Unit 3
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362
Only(primary(alkanols(produce(carboxylic(acids(
when(oxidised:(
Secondary(alkanols(oxidise(to(ketones(and(
tertiary(alkanols(cannot(be(oxidised.(
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363
Alkanoic(acids(as(weak(acids(
Alkanoic&acids&ionise&to&a&limited&extent&in&water,&
producing&a&weakly&acidic&soluFon.&
&
Watch&for&opportuniFes&in&which&acidBbase&reacFons&
may&occur&between&an&alkanoic&acid&and&a&base,&such&
as&sodium&hydroxide.&
&
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364
Esteri@ication(reactions(
Esteri@ication(is(a(condensation(reaction(in(
which(an(ester(is(produced(
The(reaction(occurs(between(an(alkanoic(acid(
and(an(alkanol.(
(Alkanol(+(alkanoic(acid(((ester(+(water(
An(acid(catalyst((eg(H2SO4(is(required(for(this(
reaction(to(work(and(the(mixture(must(be(
heated(
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365
The(name(of(an(ester(is(taken(from(the(names(
of(the(alcohol(and(carboxylic(acid(from(which(it(
is(formed.(
The(name(of(an(ester(ends(in((Poate(
(eg(the(ester(made(from(ethanol(and(propanoic(
acid(would(be(ethyl(propanoate((note(the(
alcohol(name(comes(@irst)(
From the
carboxylic acid
From the
alcohol
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366
Properties(of(esters(
Many(esters(have(a(strong(smell(or(@lavour.(
Many(arti@icial(@lavourings((eg(banana(essence)(
are(esters.(
Small(molecular(esters(are(volatile((become(
vapour(easily)(and(are(smelly.(
Large(molecular(esters(include(waxes(and(oils(
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367
General(equation(for(esteri@ication(
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368
Equations(for(the(formation(of(esters(
1.(Ethyl(ethanoate(
CH3COOH((((((+(((((C2H5OH(( (
Ethanoic acid
ethanol
(((((CH3COOC2H5((((+(((((((H2O(((
ethyl ethanoate
water
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369
2. Hexyl(propanoate(
Hexanol(+(propanoic(acid ((((((((hexyl(propanoate(+(water(
(
C6H13OH((+((C2H5COOH( ((((((C2H5COOC6H13((+(H2O(
&&&
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370
Sample(exam(question((substitution,(oxidation(and(
esteri@ication(
Which(one(of((
the(following((
organic(reactions((
does(not(result(in((
the(product((
shown(on(the((
rightPhand(side((
of(the(reaction?(
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371
Answer(
Alternative(A(is(a(substitution(reaction(
between(sodium(hydroxide(and(1P
chlorobutane(to(make(butanP1Pol.(
Alternative(B(is(an(addition(reaction(between(
butP2Pene(and(HCl(which(should(make(2P
chlorobutane,(however(the(product(given(is(
1Pchlorobutane(which(is(impossible.(
Alternative(C(is(an(esteri@ication(reaction(
between(methanol(and(ethanoic(acid(forming(
methyl(ethanoate(
Alternative(D(is(an(addition(reaction(between(
propene(and(steam(forming(propanP2Pol(
(
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372
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Reaction Pathways
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373
Key(knowledge(
common(reactions(of(organic(compounds(
including(equations:(addition(reactions(of(
alkenes((addition(of(hydrogen(halides(and(water(
limited(to(symmetrical(alkenes),(substitution(
reactions(of(alkanes(and(primary(haloalkanes,(
oxidation(of(primary(alkanols,(and(esteri@ication(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:((
(production(of(esters(from(alkenes(
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374
Reaction(Pathways((
In(the(previous(sections(we(have(found(a(range(of(
ways(to(produce(certain(chemicals.(
eg(Ethanol(can(be(produced(by((
1. the(addition(reaction(between(ethene(and(
steam((
2. the(substitution(reaction(between(
chloroethane(and(sodium(hydroxide(
&
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375
These(different(methods,(sometimes(with(many(
stages,(are(known(as(reaction(pathways.(
It(is(important(to(be(aware(of(the(principles(of(
green(chemistry(including(the(minimisation(of(
waste(materials,(of(energy(use(and(the(use(of(
environmentally(friendly(solvents.(
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376
Reaction(pathways(can(be(represented(visually(
as(a(web(of(reactions.((
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377
The(synthesis(of(ethyl(propanoate(
Ethyl(propanoate(is(an(ester(which(is(made(
from(ethanol(and(propanoic(acid(
Ethanol(can(be(made(by(two(different(reaction(
pathways(
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378
Similarly(propanoic(acid(can(be(made(by(a(reaction(
pathway(from(propane(
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379
&
The(two(pathways(join(to(make(ethyl(
propanoate&
&
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380
Sample(exam(question((reaction(
pathways(
The(ester(methyl(propanoate(has(a(characteristic(fruity(odour(
and(has(been(isolated(from(many(fruits(including(pineapple.(A(
sample(of(this(ester(is(to(be(prepared(in(the(laboratory.(A(partly(
completed(reaction(pathway(for(this(preparation(is(shown(
below.(
C3H7Cl(
((((((((reagent(X(
(
(
(
2Cr
2O7
Compound(K ( !!!
((((((((C
((((((methyl (
( ( ( (
3H6O2 (
concentrated
+
H 2SO4 catalyst
( ((((((((( ( and
( H ( ( ( ( ((((((((((((((propanoate(
!!!!!
(
( (((((((((((compound(L(((
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381
(i) Write(a(structural(formula,(showing(all(bonds,(for(
methyl(propanoate(
(ii) Write(structural(formulae,(showing(all(bonds,(for(
compounds(K(and(L(
(iii)Write(the(formula(of(reagent(X(
(
(
VCAA(June(2008(Q6(
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382
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Proteins: Formation and Structure
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383
Key(Knowledge(
organic(reaction(pathways(including(appropriate(
equations(and(reagents:(
((((P(condensation(and(polymerisation(reactions((((
(((((((that(produce(large(biomolecules(including(((
((((((((carbohydrates),(proteins((and(DNA)(
chemical(bonding:(
(primary,(secondary(and(tertiary(structures(of(proteins(
(the(role(of(the(tertiary(structure(of(proteins(in(enzyme(
action(
(denaturing(of(proteins:(effect(of(changes(in(pH(and(
temperature(on(bonding(
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384
Proteins&
Proteins(are(fundamental(to(the(structure(of(cells(
as(well(as(their(operation.(
They(may(be(structural,(such(as(proteins(in(
muscle,(hair,(nails(etc(
Enzymes(are(proteins(which(catalyze(many(
reactions(that(occur(in(the(human(body.(
Hormones(are(proteins,(as(is(haemoglobin(which(
carries(oxygen(around(in(the(blood.(
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385
Amino(acids(
The(monomers(from(which(proteins(are(
built(are(called(2Pamino(acids((or(Pamino(
acids).(
They(consist(of(a(central(C(atom(which(has(
bonded(to(it(a(carboxyl((COOH)(group(and(
an(amine((NH2)(group(as(well(as(a(H(atom(
and(a(side(chain(denoted(((
(((as(Z(which(may(be(one(of(20(
(((different(groups.((
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386
The&side&chains&
The(20(different(side(chains(are(shown(in(the(data(
book((table(8)(
(
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387
The(functional(groups(
The(carboxyl(group(allows(an(amino(acid(to(behave(
in(solution(as(an(acid.(
When(the(pH(is(high,(the(amino(acid(donates(an(H+(
ion(to(the(solution(and(it(becomes(negatively(
charged.(
The(amine(group(allows(an(
((((amino(acid(to(behave(as(a((
((((base(in(solution.(
When(the(pH(is(low,(the((
((((amino(acid(can(accept(an((
((((H+(ion(from(the(solution((
((((and(it(becomes(positively((
(((charged.(
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388
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389
In(an(approximately(neutral(solution,(an(amino(
acid(will(have(both(gained(and(lost(an(H+,(so(will(
have(a(positive(and(a(negative(charge.(
This(is(called(a(Zwitterion.(
The(pH(at(which(the(amino(acid(exists(as(a(
zwitterion(is(called(its(isoelectric(point(and(
depends(on(the(side(chain(of(the(amino(acid.(
&
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390
Formation(of(proteins(
Amino(acids(undergo(condensation(reactions(
with(other(amino(acids(to(form(dipeptides,(
polypeptides(and(proteins.(
(((An(amide(functional(group(joins(the(residues(of(
the(alkanoic(acid(and(amine.(
((((This(functional(group(may(also(be(called(a(
peptide(link.(
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391
Forming(a(dipeptide(
A(condensation(reaction(causes(a(molecule(of(water(to(
be(formed(each(time(two(amino(acids(join(via(an(
amide(functional(group(or(peptide(link.(
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392
Structure(of(proteins(
The(structure(of(proteins(is(very(involved(and(may(
be(described(at(different(levels(of(complexity.(
These(levels(are(known(as(the(primary,(secondary,(
tertiary(and(quaternary(structures(of(a(protein.(
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393
Primary(structure(
This(is(the(type,(number(and(the(sequence(of(
amino(acids(in(a(protein(chain.(
The(bonding(involved(here(is(covalent(bonding.(
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394
Secondary(structure(
A(protein(chain(is(very(long((more(than(50(
amino(acids)(and(coils(up(due(to(hydrogen(
bonds(between(different(parts(of(the(chain.(
The(chain(may(form(a(spiral((Phelix)(or(a(
pleated(sheet((like(corrugated(cardboard)(
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395
Tertiary(structure(
The(coiled(protein(chain(is(still(long(and(folds(up(
to(form(the(operational(shape(of(the(protein.((
This(is(the(tertiary(structure.(
Bonds(form(between(ZPgroups(of(the(amino(acids.(
These(may(be(dispersion(forces,(hydrogen(bonds,(
ionic(bonds,(or(even(covalent((disul@ide(bridge)(
bonds.(
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396
This(overall(threePdimensional(shape(helps(to(
determine(the(function(of(a(protein.(
Many(proteins(have(a(metal(ion(as(part(of(their(
structure,(or(may(be(made(up(of(several(protein(
chains(bound(together.(
This(fully(working(shape(of(the(protein(is(its(
quaternary(structure.(
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397
Sample(exam(question(P(proteins(
The(following(structure(shows(part(of(a(polypeptide(
(
(
(
(
(i) Name(the(amino(acids(that(make(up(this(section(of(
the(polypeptide(
At(a(particular(pH,(an(amino(acid(in(solution(can(exist(
as(ions(that(have(both(a(negative(and(positive(charge.(
These(ions(are(called(zwitterions.(
((ii)((Choose(one(of(the(amino(acids(in(this(section(of((((
((((((((((polypeptide(and(draw(the(structure(of(its((
((((((((((zwitterion(clearly(showing(all(bonds.(
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398
Answer(
(i)(
(
(
(
(
(
(
(
(ii)((Zwitterion:(
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399
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Proteins: Tertiary Structure and Enzymes
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400
Key(Knowledge(
chemical(bonding:(
(primary,(secondary(and(tertiary(
structures(of(proteins(
(the(role(of(the(tertiary(structure(of(
proteins(in(enzyme(action(
(denaturing(of(proteins:(effect(of(changes(
in(pH(and(temperature(on(bonding(
&
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401
The&four&levels&of&protein&structure&
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402
Enzymes(
Enzymes(are(proteins(that(act(as(
biological(catalysts((increase(the(rate(of((
biological(reactions).(
An(example(of(a(most(ef@icient(enzyme(is(
catalase.((
Each(catalase(molecule(can(decompose(
millions(of(hydrogen(peroxide(molecules(
every(second(
((((((((((((((((((2H2O2(( (2H2O((+((O2(
(
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403
The&catalase&enzyme&
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404
Compared(to(inorganic(catalysts,(
enzymes(are:(
More(ef@icient((resulting(in(much(
faster(reactions(
More(speci@ic((may(only(work(for(one(
reaction(
Able(to(act(only(in(a(narrow(
temperature(range((body(temperature(
Able(to(act(only(in(a(narrow(pH(range(
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405
Enzyme(action(
The(tertiary(structure(of(the(enzyme(enables(
it(to(form(intermolecular(bonds(with(speci@ic(
reactants((the(substrate)(and(so(determines(
the(catalytic(ability(of(an(enzyme.(
The(enzyme(has(an(active(site(which(is(where(
the(substrate((reactants)(binds(by(
intermolecular(bonding.(
The(active(site(@its(the(required(molecules(
exactly(and(this(is(where(the(reaction(occurs.(
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406
When(the(products(are(released(from(the(
active(site,(the(enzyme(is(able(to(accept(
another(substrate(and(so(on.(
It(is(not(changed(by(the(reaction(it(is(
catalysing.(
Enzymes(are(thought(to(act(according(to(
the(lock(and(key(mechanism.(
This(describes(the(enzymes(active(site(as(
@itting(the(substrate(perfectly.(
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407
The(lock(and(key(mechanism(of(enzyme(
action(
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408
Denaturation(of(enzymes(
When(enzymes(are(heated(to(a(
temperature(above(their(normal(
operation(temperature,(or(when(the(pH(of(
the(solution(is(changed,(their(structure(is(
disrupted,(intermolecular(bonds(are(
broken(and(the(enzyme(is(denatured.(
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409
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410
After(denaturation,(the(protein(
chains(may(come(together(again,(but(
the(working(shape(has(been(lost(and(
the(chains(just(clump.((
This(is(coagulation.(
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411
Examples(of(coagulation((cooking(eggs:(
clear(egg(white(becomes(hard(and(white(
(P(cooking(meat((becomes(brown(and(
harder(
(P(Curdling(milk(with(lemon(juice(or(
vinegar.(
&
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412
Below(normal(operating(temperatures,(
enzymes(become(inactive.((
They(may(work(very(slowly(or(not(at(all.((
If(the(temperature(increases(again,(their(
structure(is(still(intact.(
SO,(in(summary,(denaturation(stops(the(
enzyme(from(working(altogether(because(
the(tertiary(structure(is(changed,(while(
deactivating(slows(it(right(down,(but(the(
enzyme(can(become(active(again.(
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413
Sample(exam(question(P(enzymes(
Which(one(of(the(following(statements(about(enzymes(
is(not(true?(
A. Enzymes(can(only(be(denatured(by(an(increase(in(
temperature(
B. Enzymes(may(form(temporary(ionPdipole(bonds(
with(substrate(molecules(
C. Enzymes(speed(up(reactions(by(holding(substrate(
molecules(in(positions(necessary(for(reaction.(
D. The(tertiary(structure(of(an(enzyme(may(be(altered(
if(one(amino(acid(in(its(primary(structure(is(
substituted(for(another,(different((amino(acid.(
VCAA(June(2009(Q(17(
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414
Answer(
A. Is(not(true,(as(a(change(in(pH(also(causes(
enzymes(to(be(denatured.(
B. Is(true,(as(ionPdipole(bonds(may(indeed(be(
formed(between(substrates(and(enzymes(
C. Is(true.(This(is(the(method(by(which(
enzymes(work.(
D. Is(true,(since(a(change(in(the(primary(
structure(may(indeed(have(an(effect(on(the(
tertiary(structure.(
A(is(the(answer!(
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415
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Lipids
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416
Key(Knowledge(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(reactions(that(produce(lipids(
(limited(to(triglycerides)(
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417
Lipids(
Lipids(are(a(class(of(molecules(that(include(
fats,(oils,(steroids((including(cholesterol)(
and(waxes.(
Fats(and(oils(are(triglycerides.(
Each(triglyceride(molecule(is(formed(by(
the(condensation(reaction(between(one(
glycerol(molecule(and(three(fatty(acids.((
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418
FormaFon&of&a&triglyceride&
Fatty(acids(are(carboxylic(acids(with(a(long(
hydrocarbon(chain(eg(H3C(CH2)16COOH(
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419
The(difference(between(fats(and(oils(is(
that(fats(are(solid(at(room(temperature(
whereas(oils(are(liquid.(
Fats(tend(to(come(from(animal(sources(
whereas(oils(tend(to(come(from(plants.(
There(are(other(lipids(such(as(
phospholipids((used(to(make(the(
membrane(of(cells)(and(steroids(
(including(cholesterol),(but(in(this(course(
we(will(only(discuss(triglycerides.(
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420
Types(of(fats(
A(fat((or(oil)(is(named(according(to(the(
type(of(fatty(acids(in(it.(
Saturated(fats(are(made(from(fatty(acids(
with(only(carbonPcarbon(single(bonds.(
They(are(generally(considered(to(be(
unhealthy.(
They((saturated(fatty(acids)(have(the(
general(formula(CnH2nO2(
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421
Unsaturated(fats(
A(monoPunsaturated(fat(is(made(from(fatty(acids(
with(only(one(carbonPcarbon(double(bond(per(fatty(
acid.(
General(formula(CnH2nP2O2(
The(reduced(number(of(hydrogens(is(due(to(the(
presence(of(the(double(bond.(
PolyPunsaturated(fats(are(found(in(vegetable(oils.(
They(have(more(than(one(carbonPcarbon(double(
bond(per(fatty(acid.(
General(formula(may(be(one(of((
(CnH2nP4O2((two(double(bonds)((
or(CnH2nP6O2((three(double(bonds)((etc(
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422
&
Type&of&
Name&of&
fat&
fatty&acid&
&
Semi.structural&formula&
Molecular&
formula&
saturated( Stearic(
CH3(CH2)16COOH(
C18H36O2(
MonoP
unsaturated(
Oleic(
CH3(CH2)7CH=CH(CH2)7COOH(
C18H34O2(
PolyP(
unsaturated(
Linoleic(
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH(
C18H32O2(
PolyP(
unsaturated(
Linolenic(
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH(
C18H30O2(
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423
Table(9(from(the(data(book(
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424
Melting(point(of(triglycerides(
The(presence(of(CPC(double(bonds(in(the(fatty(
acid(chains(creates(kinks(in(the(chain.(
This(prevents(them(from(packing(closely(and(
reduces(the(strength(of(the(dispersion(forces(
between(the(chains.(
This(lowers(the(melting(point(of(the(
unsaturated(fat.(
So(unsaturated(fats,(with(double(bonds((and(
kinks)(are(liquids(and(have(lower(melting(
points(than(saturated(fats((solids)(with(only(
single(bonds(with(only(single(CPC(bonds.(
&
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425
Digestion(of(triglycerides(
Fats(are(emulsi@ied(by(bile(in(the(small(intestine,(
then(enzymes(catalyse(the(alkaline(hydrolysis(of(
the(ester(linkages(to(form(fatty(acids(and(
glycerol.(
These(small(molecules(are(absorbed(into(the(
blood(stream(and(are(reassembled(into(
triglycerides(which(are(transported(in(
lipoproteins(to(adipose(tissue(where(the(fats(are(
stored.(
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426
Condensation(Polymerisation((a(
summary(
If(a(monomer(has(a(functional(group(on(each(
end,(it(can(react(with(other(monomers(in(a(
series(of(condensation(reactions(to(form(a(
condensation(polymer.(
Condensation(polymers(occur(in(
biomolecules(as(well(as(synthetic(@ibres(
such(as(nylon(and(polyesters.(
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427
Functional(groups(and(their(
polymers
(
Polymer&
Functional&
Other&name&
Formed&from&
group&
these&
functional&
groups&
Proteins(
(dipeptides(and(
polypeptides)(
Nylon(
Amide(
Peptide(linkage(
Amino(and(
carboxyl((
Carbohydrate(
Ether(
Glycosidic(
linkage(
Two(hydroxyl(
Triglyceride((not(
really(a(polymer)(
Polyester(
Ester(
Carboxyl(and(
hydroxyl(
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428
Sample(exam(question(P(triglycerides(
(a)((i)(A(long(chain(carboxylic(acid(can(be(represented(by(
the(general(formula(RCOOH(where(R(represents(a(
hydrocarbon(group.(Draw(the(structure(of(a(fat(formed(by(
the(reaction(between(glycerol(and(three(molecules(of(
RCOOH.(Clearly(show(the(structure(of(all(ester(groups(in(
the(fat.(
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429
(ii)(Palmitic(acid((C16H32O2)(and(oleic(acid((C18H34O2)(are(both(
long(chain(carboxylic(acids.(Which(one(of(them(is(classi@ied(as(an(
unsaturated(carboxylic(acid?(
Answer:(
General(formula:(CnH2nO2(
(
(
(
(
(b) Unsaturated(fats(can(be(converted(into(saturated(fats(by(
reaction(with(hydrogen(gas(in(the(presence(of(a(metallic(
catalyst.(In(one(such(conversion,(2.50(mole(of(an(unsaturated(
fat(is(converted(to(a(saturated(fat(by(reaction(with(15.0(g(of(
H2(gas.(Calculate(the(number(of(carbon(to(carbon(double(
bonds(present(in(a(molecule(of(the(unsaturated(fat.(
(
VCAA(Nov(2006(Q9(
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430
Answer((b)(
n(H2)(=( 15.0 = 7.50mol
2.02
(
n(fat)(=(2.50(mol(
1(mol(of(H2(reacts(with(1(mol(of(double(
bonds(
7.50
So(n(double(bonds)(=( 2.50 = 3 mol
(
There(are(3(double(bonds(in(each(molecule(
of(the(unsaturated(fat.((
VCE Chemistry Unit 3
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431
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Carbohydrates
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432
Key(Knowledge(
organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(and(polymerisation(reactions(
that(produce(large(biomolecules(including(
carbohydrates,((proteins(and(DNA)(
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433
Carbohydrates(
Carbohydrates(are(our(primary(energy(
source.(
They(include(monosaccharides(such(as(
glucose,(disaccharides(such(as(sucrose,(and(
polysaccharides(such(as(starch(and(
cellulose.(
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434
Monosaccharides(
All(have(the(general(formula(CH2O(
They(are(the(simplest(sugars(
Glucose(has(the(formula(C6H12O6(and(can(
occur(in(solution(as(one(of(two(cyclic(
molecules(((and((glucose)(or(a(straight(
chain(version.(
This(is((glucose:(
&&&&
VCE Chemistry Unit 3
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435
Fructose(and(galactose(are(also(common(
monosaccharides.(
Fructose:(
All(are(very(soluble(in(water(due(to(the(
presence(of(a(large(number(of(hydroxyl(
groups(and(the(consequent(hydrogen(
bonding(that(is(possible(between(the(
hydroxyl(groups(and(the(water(molecules.(
VCE Chemistry Unit 3
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436
Disaccharides(
A(condensation(reaction(between(hydroxyl(
groups(on(adjacent(monosaccharides(will(
result(in(a(disaccharide.(
Maltose(is(formed(when(two(glucose(
molecules(join(in(a(condensation(reaction(
with(a(water(molecule(being(released.(
&&
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437
Glucose(+(galactose((lactose(
Glucose(+(fructose((sucrose(
The(monomers(are(joined(by(a(glycosidic(
linkage,(also(known(as(an(ether(functional(
group.(
&
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438
Polysaccharides(
!There(are(three(different(types(of(
polysaccharides(that(can(be(formed(from(
glucose(
Starch(
" The(molecule(that(plants(use(to(store(energy(
Cellulose(
" A(structural(molecule(used(in(plant(cell(walls((
" Cannot(be(digested(by(humans((dietary(@ibre)(
Glycogen(
" The(molecule(that(animals(use(to(store(energy.(
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439
Starch(
This(is(made(up(of(long(chains(of(Pglucose.(
There(is(little(branching(in(starch(making(it(slow(
to(be(hydrolysed((broken(down(into(glucose(
molecules)(/(digested(by(enzymes(in(presence(of(
water.((
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440
Cellulose(
Cellulose(is(a(linear(polymer(of(Pglucose(
and(Pglucose.(
Individual(bundles(of(cellulose(molecules(
are(joined(by(hydrogen(bonds(
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441
Glycogen(
This(is(a(branched(polymer(of(Pglucose.(
The(branches(make(it(easier(for(enzymes(
to(hydrolyse(the(ether(linkages(and(
release(the(glucose(for(respiration((and(
the(production(of(energy).(
&
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442
Sample(exam(question(P(carbohydrates(
Amylase(is(an(enzyme(that(speci@ically(digests(
starch(in(humans.(A(major(product(of(this(starch(
hydrolysis(reaction(is(
A. Maltose(
B. Glycogen(
C. Cellulose(
D. Glycerol(
(
VCAA(June(2006(Q(14(
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443
Answer(
Starch(is(a(condensation(polymer(of(glucose(
((((When(it(is(hydrolysed,(it(breaks(down(into(((
(((((smaller(molecules,(such(as(the(disaccharide,(((
(((((maltose.(
Glycogen(and(cellulose(are(both(also(condensation(
polymers(of(glucose,(but(one(polymer(will(not(be(
hydrolysed(to(make(a(different(polymer.(
Glycerol(is(a(small(molecule(that(is(produced(when(
fats(are(hydrolysed.(
The(answer(is(A.(
(
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444
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
DNA
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445
Key&Knowledge&
!chemical(bonding:(
(primary(and(secondary(structure(of(DNA(
!organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(condensation(and(polymerisation((
((((reactions(that(produce(large(biomolecules((
(((((including((carbohydrates,(proteins(and)((((
(((((DNA(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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446
Biological(Importance(of(DNA(
Chromosomes(are(found(in(the(nucleus(of(almost(
all(cells.(
Chromosomes(contain(sections(called(genes(
Genes(are(made(of(DNA(
Genes(blueprint(the(production(of(proteins(
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447
The(bonding(and(structure(of(DNA(
DNA((deoxyribonucleic(acid)(is(a(condensation(
polymer(
There(are(four(nucleotide(monomers(
Nucleotides(are(made(up(of(three(molecules(joined(
by(condensation(reactions((a(sugar((deoxyribose)(
a(phosphate(group(and(one(of(four(different(
organic(bases((adenine,(thymine,(cytosine(and(
glycine(
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448
Structure(of(the(bases(is(in(the(VCE(Chemistry(
data(book(
Adenine(and(guanine(are(
purine(bases(
cytosine(and(thymine(are(
pyramidine(bases(
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449
Formation(of(nucleotides(
Carbon(1(of(the(sugar(bonds(to(the(organic(base(
and(carbon(5(of(the(sugar(bonds(to(the(
phosphate(group(in(condensation(reactions(
(water(released).(
These(structures(are(in(the(data(book((table(10)(
1
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450
Condensation(reactions(to(form(the(
polynucleotide(chain(
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451
Degrees(of(DNA(structure(
Primary(structure((order(of(nucleotides(
Held(together(by(covalent(bonding(
(
Secondary(structure((held(together(by(
hydrogen(bonding.(
DNA(is(made(up(of(two(strands(
Organic(bases(pair(up(with(corresponding(
base(on(second(DNA(strand(using(HP
bonding.(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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452
Hydrogen(bonding(between(the(bases(
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453
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454
Tertiary(structure((negative(charge(due(to(
phosphate(groups(allows(DNA(to(supercoil(around(
proteins(called(histones.(
This(tight(packaging(creates(a(chromosome.(
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455
Sample(exam(question(P(DNA(
In(the(piece(of(doublePstranded(DNA(shown,(the(letters(
A,C,(G(and(T(represent(the(bases(adenine,(cytosine,(
guanine(and(thymine(respectively.(Each(vertical(line(
represents(a(sugarPphosphate(backbone.(
(
Which(of(the(following((
alternatives(correctly(
identi@ies(the(DNA(piece(
that(is(most(readily((
separated(by(heating(
and(the(strand(of(the(
highest(molecular(mass?(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
(
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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(
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457
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
Biochemical Fuels
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458
Key(Knowledge(
!organic(reaction(pathways(including(
appropriate(equations(and(reagents:(
(production(of(biochemical(fuels(including(
the(fermentation(of(sugars(to(produce(
ethanol(
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459
Biochemical(fuels((biofuels)(
! These(are(fuels(derived(from(plant(materials(
such(as(grains,(sugarcane(or(vegetable(waste(
(biomass),(and(vegetable(oils.(
! They(may(be(used(alone(or(mixed(with(fossil(
fuels.(
! Ethanol(and(biodiesel(
((((are(the(most(common(
(((((biofuels.(
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460
! Biofuels(are(considered(carbon(neutral(because(
they(are(made(from(plants(which(used(CO2(for(
photosynthesis,(so(when(they(are(burnt(that(same(
CO2(is(returned.(
! Recall(the(equation(for(photosynthesis:(
sunlight
6CO2(g)(+(6H2O(l) !!!
( ((C6H12O6(aq)((+(6O2(g)(
(
! Combustion(of(ethanol:(
(((((C2H5OH(l)((+((O2(g)((((2CO2(g)((+((3H2O(l)(
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461
Ethanol(
! Made(by(the(fermentation(of(sugars(
! This(is(an(anaerobic((in(the(absence(of(O2)(
process(
C6H12O6(aq)( !!!
( enzymes
((2(C2H5OH(aq)((+(2CO2(g)(
&
! The(product(is(not(pure(ethanol((only(about(
20%,(so(must(be(distilled(to(purify.(
! Recall(that(distillation(uses(the(difference(in(
boiling(points(of(liquids(to(separate(them(
VCE Chemistry Unit 3
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462
Distillation(
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463
Production(of(ethanol(as(a(green(
process(
CO2(from(the(fermentation(is(sold(to(soft(drink(
manufacturers.(
5%(petrol(is(added(to(prevent(people(drinking(it.(
Waste(water(used(for(irrigating(crops(
Remains(of(fermentation(used(for(feedstock.(
Recycle(byproducts(as(fertiliser(
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464
Biodiesel(
This(is(a(mixture(of(esters(produced(by(a(chemical(
reaction(between(vegetable(oil(and(an(alcohol(such(
as(methanol.(
The(properties(of(biodiesel(are(very(similar(to(
those(of(diesel,((
In(virtually(all(models(of(equipment(and(vehicles(
currently(in(production,(a(biodiesel(blended(fuel(is(
compatible.((
Raw(materials:(fresh(vegetable(oils(or(recycled(
vegetable(oil(or(animal(fats.(
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465
How(biodiesel(is(made:(
The(triglyceride(is(hydrolysed&by(warming(it(with(
KOH(aq).(
KOH(also(acts(as(a(catalyst(
Overall(the(triglyceride(breaks(down(to(three(fatty(
acid(molecules,(plus(glycerol.(
Methanol(is(added(and(reacts(with(the(fatty(acid(to(
make(biodiesel.(
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466
Equation(for(the(formation(of(
biodiesel(
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467
Biogas&
Equal(mix(of(CO2(and(methane(((CH4)(
Generated(when(organic(material(decomposes(in(
the(absence(of(oxygen.(
Particularly(suited(to(farms(
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468
Lots(of(sources(of(organic(waste(can(be(adapted(to(
biogas(generation.(
eg(Werribee(waste(treatment(plant(
Rubbish(tips(
Chicken(farms(
Piggeries(
Food(processing(plants(
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469
Sample(exam(question(P(biofuels(
A(product(derived(from(palm(tree(oil(is(used(as(an(alternative(fuel(in(
diesel(engines.(Palm(oil(is(converted(to(biodiesel(by(the(following(
reaction(
(
(
(
(
(
(
Glycerol(is(separated(from(the(reaction(mixture.(The(mixture(of(the(
compounds(labelled(X,(Y(and(Z(is(used(as(palm(oil(biodiesel.(The(term(
that(best(describes(the(mixture(of(compounds(in(palm(oil(biodiesel(is(
A. Methyl(esters ( (B.((carbohydrates(((
C. Carboxylic(acids ( (D.((monoglycerides(
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(
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470
CHEMISTRY
Unit 3, Area of Study 2:
Organic Chemical Pathways
The Design and Synthesis of Medicines including Aspirin
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471
Key(Knowledge(
organic(reaction(pathways(including(appropriate(
equations(and(reagents:(
P function(of(organic(molecules(in(the(design(and(
synthesis(of(medicines(including(the(production(of(
aspirin(from(salicylic(acid.(
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472
Aspirin((
Aspirin(is(an(ester.(
It(is(derived(from(salicylic(acid(which(was(
known(as(a(pain(killer(and(reduced(fever(but(
caused(irritation(to(the(lining(of(the(stomach(
and(the(mouth.(
The(full(name(of(aspirin(is(acetyl(salicylic(acid.(
Aspirin(is(much(less(irritating(to(the(stomach(
and(mouth(than(salicylic(acid.(
It(is(broken(down(into(salicylic(acid(in(the(
alkaline(surroundings(of(the(small(intestine.(
VCE Chemistry Unit 3
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473
Preparation(of(Aspirin(
Aspirin(can(be(made(by(two(different(
pathways(
Salicylic(acid(+(ethanoic(acid(
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474
Or(salicylic(acid(+(ethanoic(anhydride(
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475
Alkaline(hydrolysis(breaks(aspirin(down(
Aspirin(can(be(made((
soluble(by(creating(a((
sodium(salt.(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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476
Another(example(P(Penicillin(
An(example(of(a(drug(developed(after(chance(observations(
in(the(lab.(
A(culture(of(staph(bacteria(was(growing(and(a(mould(which(
grew(on(the(plate(by(mistake(was(found(to(kill(the(bacteria.(
Isolation/extraction(of(the(mould(was(dif@icult(when(it(was(
@irst(discovered.&
Increased(need(for(the(drug((WW2)(and(improved(
methods(extraction(12(years(later((1940)(
Initially(tested(on(mice,(but(quickly(moved(to(humans(due(
to(the(need(to(save(the(lives(of(soldiers(who(were(suffering(
from(infections(after(surgery(on(the(battle(@ield.(
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477
Eect&of&changing&the&structure&slightly&
Different(side(chains(are(possible(in(penicillin.(
Stomach(acid((
broke(penicillin((
down.((
Change(of(side(
chain(improved((
stability.(
&
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478
Resistance&to&drugs&
Bacteria(reproduce(very(rapidly(
Those(bacteria(that(are(slightly(different(and(can(
survive(the(drug,(get(to(reproduce(and(so(a(strain(
of(drug(resistant(bacteria(are(created.(
Taking(a(full(course(of(antibiotics(minimises(the(
chance(of(bacteria(surviving.(
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Developing(a(new(drug(
Lead(compounds(can(potentially(be(made(into(
drugs.(
Sources(may(be(herbal(or(traditional(
((remedies.(eg(aspirin.((
Computer(modelling(is(used(for(design(of(speci@ic(
drugs(
&
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480
Steps(in(drug(design(
Computer(modelling(
Development(of(synthetic(pathway(
Formulation(for(administering(drug(is(required(
Testing(is(needed((clinical(trials(
Comparison(with(placebos(to(see(how(effective(the(
drug(actually(is.(
Analysis(of(the(drug(tests(purity(
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481
Sample(exam(question((functional(
groups(in(drugs(
The(compound(salicin(can(be(converted(into(aspirin(using(
the(steps(below:(
(
(
(
(
(
(
(
(
VCAA((June(2010(Q(8(
(3
VCE Chemistry Unit
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482
Ms Lanna Derry & Edrolo 2014
(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.(
(
VCE Chemistry Unit 3
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483
Ms Lanna Derry & Edrolo 2014
(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.(
(
VCE Chemistry Unit 3
Ms Lanna Derry & Edrolo 2014
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484