S A M P L E

Number of questions and mark allocations

may vary from the information indicated.

CHEMISTRYWritten examination

Tuesday 8 November 2016 Reading time: 9.00 am to 9.15 am (15 minutes) Writing time: 9.15 am to 11.45 am (2 hours 30 minutes)

QUESTION AND ANSWER BOOK

Structure of bookSection Number of

questionsNumber of questions

to be answeredNumber of

marks

A 30 30 30B 11 11 90

Total 120

• Students are permitted to bring into the examination room: pens, pencils, highlighters, erasers, sharpeners, rulers and one scientifi c calculator.

• Students are NOT permitted to bring into the examination room: blank sheets of paper and/or correction fl uid/tape.

Materials supplied• Question and answer book of 44 pages.• Data book.• Answer sheet for multiple-choice questions.Instructions• Write your student number in the space provided above on this page.• Check that your name and student number as printed on your answer sheet for multiple-choice

questions are correct, and sign your name in the space provided to verify this.• Unless otherwise indicated, the diagrams in this book are not drawn to scale.• All written responses must be in English.At the end of the examination• Place the answer sheet for multiple-choice questions inside the front cover of this book.• You may keep the data book.

Students are NOT permitted to bring mobile phones and/or any other unauthorised electronic devices into the examination room.

© VICTORIAN CURRICULUM AND ASSESSMENT AUTHORITY 2016

SUPERVISOR TO ATTACH PROCESSING LABEL HEREVictorian Certifi cate of Education2016

STUDENT NUMBER

Letter

2016 CHEMISTRY EXAM

S A M P L E

Number of questions and mark allocations

may vary from the information indicated.

SECTION A – Multiple-choice questions

Instructions for Section AAnswer all questions in pencil on the answer sheet provided for multiple-choice questions.Choose the response that is correct or that best answers the question.A correct answer scores 1; an incorrect answer scores 0. Marks will not be deducted for incorrect answers. No marks will be given if more than one answer is completed for any question.Unless otherwise indicated, the diagrams in this book are not drawn to scale.

SECTION B

Instructions for Section BAnswer all questions in the spaces provided. Write using blue or black pen.To obtain full marks for your responses, you should:• give simplifi ed answers, with an appropriate number of signifi cant fi gures, to all numerical questions; unsimplifi ed

answers will not be given full marks• show all working in your answers to numerical questions; no marks will be given for an incorrect answer unless

it is accompanied by details of the working• make sure chemical equations are balanced and that the formulas for individual substances include an indication

of state; for example, H2(g), NaCl(s).Unless otherwise indicated, the diagrams in this book are not drawn to scale.

Instructions

• Aquestionandanswerbookisprovidedwiththisdatabook.

Students are NOT permitted to bring mobile phones and/or any other unauthorised electronic devices into the examination room.

CHEMISTRYWritten examination

Tuesday 8 November 2016 Reading time: 9.00 am to 9.15 am (15 minutes) Writing time: 9.15 am to 11.45 am (2 hours 30 minutes)

DATA BOOK

©VICTORIANCURRICULUMANDASSESSMENTAUTHORITY2016

Victorian Certificate of Education 2016

2016CHEMISTRYDATABOOK 2

Table of contents Page

1. Periodictableoftheelements 3

2. Theelectrochemicalseries 4

3. Physicalconstants 5

4. SIprefixes,theirsymbolsandvalues 5

5. 1HNMRdata 5–6

6. 13CNMRdata 7

7. Infraredabsorptiondata 7

8. 2-aminoacids(α-aminoacids) 8–9

9. Formulasofsomefattyacids 10

10. Structuralformulasofsomeimportantbiomolecules 10

11. Acid-baseindicators 11

12. Acidityconstants,Ka,ofsomeweakacidsat25°C 11

13. Valuesofmolarenthalpyofcombustionofsomecommonfuelsat298Kand101.3kPa 11

3 2016CHEMISTRYDATABOOK

TURN OVER

1. P

erio

dic t

able

of t

he el

emen

ts

1 H

1.0

hydrogen

2 He

4.0

helium

3 Li

6.9

lithium

4 Be

9.0

beryllium

5 B

10.8

boron

6 C

12.0

carbon

7 N

14.0

nitrogen

8 O

16.0

oxygen

9 F 19.0

fluorine

10

Ne

20.2

neon

11

Na

23.0

sodium

12

Mg

24.3

magnesium

13

Al

27.0

alum

inium

14

Si

28.1

silicon

15

P 31.0

phosphorus

16

S 32.1

sulfur

17

Cl

35.5

chlorine

18

Ar

39.9

argon

19

K

39.1

potassium

20

Ca

40.1

calcium

21

Sc

45.0

scandium

22

Ti

47.9

titanium

23

V

50.9

vanadium

24

Cr

52.0

chromium

25

Mn

54.9

manganese

26

Fe

55.8

iron

27

Co

58.9

cobalt

28

Ni

58.7

nickel

29

Cu

63.5

copper

30

Zn

65.4

zinc

31

Ga

69.7

gallium

32

Ge

72.6

germanium

33

As

74.9

arsenic

34

Se

79.0

selenium

35

Br

79.9

brom

ine

36

Kr

83.8

krypton

37

Rb

85.5

rubidium

38

Sr

87.6

strontium

39

Y

88.9

yttrium

40

Zr

91.2

zirconium

41

Nb

92.9

niobium

42

Mo

96.0

molybdenum

43

Tc

(98)

technetium

44

Ru

101.1

ruthenium

45

Rh

102.9

rhodium

46

Pd

106.4

palladium

47

Ag

107.9

silver

48

Cd

112.4

cadm

ium

49

In

114.8

indium

50

Sn

118.7

tin

51

Sb

121.8

antim

ony

52

Te

127.6

tellurium

53

I 126.9

iodine

54

Xe

131.3

xenon

55

Cs

132.9

caesium

56

Ba

137.3

barium

57–7

1 lanthanoids

72

Hf

178.5

hafnium

73

Ta

180.9

tantalum

74

W

183.8

tungsten

75

Re

186.2

rhenium

76

Os

190.2

osmium

77

Ir

192.2

iridium

78

Pt

195.1

platinum

79

Au

197.0

gold

80

Hg

200.6

mercury

81

Tl

204.4

thallium

82

Pb

207.2

lead

83

Bi

209.0

bism

uth

84

Po

(210)

polonium

85

At

(210)

astatine

86

Rn

(222)

radon

87

Fr

(223)

francium

88

Ra

(226)

radium

89–1

03

actinoids

104

Rf

(261)

rutherfordium

105

Db

(262)

dubnium

106

Sg

(266)

seaborgium

107

Bh

(264)

bohrium

108

Hs

(267)

hassium

109

Mt

(268)

meitnerium

110

Ds

(271)

darmstadtium

111

Rg

(272)

roentgenium

112

Cn

(285)

copernicium

114

Fl

(289)

flerovium

116

Lv

(292)

livermorium

57

La

138.9

lanthanum

58

Ce

140.1

cerium

59

Pr

140.9

praseodymium

60

Nd

144.2

neodym

ium

61

Pm

(145)

prom

ethium

62

Sm

150.4

samarium

63

Eu

152.0

europium

64

Gd

157.3

gadolinium

65

Tb

158.9

terbium

66

Dy

162.5

dysprosium

67

Ho

164.9

holmium

68

Er

167.3

erbium

69

Tm

168.9

thulium

70

Yb

173.1

ytterbium

71

Lu

175.0

lutetium

89

Ac

(227)

actinium

90

Th

232.0

thorium

91

Pa

231.0

protactinium

92

U

238.0

uranium

93

Np

(237)

neptunium

94

Pu

(244)

plutonium

95

Am

(243)

americium

96

Cm

(247)

curium

97

Bk

(247)

berkelium

98

Cf

(251)

californium

99

Es

(252)

einsteinium

100

Fm

(257)

fermium

101

Md

(258)

mendelevium

102

No

(259)

nobelium

103

Lr

(262)

lawrencium

Thevalueinbracketsindicatesthemassn

umberofthelongest-livedisotope.

79

Au

197.0

gold

atom

icnum

ber

relativeatom

icmass

symbolofelement

nameofelement

2016CHEMISTRYDATABOOK 4

2. The electrochemical series

Reaction Standard electrode potential (E0) in volts at 25 °C

F2(g)+2e–⇌ 2F–(aq) +2.87

H2O2(aq)+2H+(aq)+2e–⇌ 2H2O(l) +1.77

Au+(aq)+e–⇌ Au(s) +1.68

Cl2(g)+2e–⇌ 2Cl–(aq) +1.36

O2(g)+4H+(aq)+4e–⇌ 2H2O(1) +1.23

Br2(l)+2e–⇌ 2Br–(aq) +1.09

Ag+(aq)+e–⇌ Ag(s) +0.80

Fe3+(aq)+e–⇌ Fe2+(aq) +0.77

O2(g)+2H+(aq)+2e–⇌ H2O2(aq) +0.68

I2(s)+2e–⇌ 2I–(aq) +0.54

O2(g)+2H2O(l)+4e–⇌ 4OH–(aq) +0.40

Cu2+(aq)+2e–⇌ Cu(s) +0.34

Sn4+(aq)+2e–⇌ Sn2+(aq) +0.15

S(s)+2H+(aq)+2e–⇌ H2S(g) +0.14

2H+(aq)+2e–⇌ H2(g) 0.00

Pb2+(aq)+2e–⇌ Pb(s) –0.13

Sn2+(aq)+2e–⇌ Sn(s) –0.14

Ni2+(aq)+2e–⇌ Ni(s) –0.23

Co2+(aq)+2e–⇌ Co(s) –0.28

Fe2+(aq)+2e–⇌ Fe(s) –0.44

Zn2+(aq)+2e–⇌ Zn(s) –0.76

2H2O(l)+2e–⇌ H2(g)+2OH–(aq) –0.83

Mn2+(aq)+2e–⇌ Mn(s) –1.03

Al3+(aq)+3e–⇌ Al(s) –1.67

Mg2+(aq)+2e–⇌ Mg(s) –2.34

Na+(aq)+e–⇌ Na(s) –2.71

Ca2+(aq)+2e–⇌ Ca(s) –2.87

K+(aq)+e–⇌ K(s) –2.93

Li+(aq)+e–⇌ Li(s) –3.02

5 2016CHEMISTRYDATABOOK

TURN OVER

3. Physical constants

Avogadro’sconstant(NA) 6.02×1023mol–1

chargeononeelectron –1.60×10–19C

Faradayconstant(F) 96500Cmol–1

gasconstant(R) 8.31JK–1mol–1

ionicproduct(self-ionisationconstant)forwater(Kw)at298K 1.00×10–14mol2L–2

molarvolume(Vm)ofanidealgasat273K,101.3kPa(STP) 22.4Lmol–1

molarvolume(Vm)ofanidealgasat298K,101.3kPa(SLC) 24.5Lmol–1

specificheatcapacity(c)ofwater 4.18Jg–1K–1

density(d)ofwaterat25°C 1.00gmL–1

1atm 101.3kPa=760mmHg

0°C 273K

4. SI prefixes, their symbols and values

SI prefix Symbol Value

giga G 109

mega M 106

kilo k 103

deci d 10–1

centi c 10–2

milli m 10–3

micro μ 10–6

nano n 10–9

pico p 10–12

5. 1H NMR dataTypicalprotonshiftvaluesrelativetoTMS=0Thesecandifferslightlyindifferentsolvents.Wheremorethanoneprotonenvironmentisshownintheformula,theshiftreferstotheonesinboldletters.

Type of proton Chemical shift (ppm)

R–CH3 0.8–1.0

R–CH2–R 1.2–1.4

RCH=CH–CH3 1.6–1.9

R3–CH 1.4–1.7

2016CHEMISTRYDATABOOK 6

Type of proton Chemical shift (ppm)

or CH3

ORC

OCH3

NHR

CO

2.0

CH3R

C

O

2.1–2.7

R–CH2–X(X=F,Cl,BrorI) 3.0–4.5

R–CH2–OH,R2–CH–OH 3.3–4.5

R

NHCH2R

CO

3.2

R—O—CH3 or R—O—CH2R 3.3

O C

O

CH32.3

R

OCH2R

CO

4.1

R–O–H 1–6(variesconsiderablyunderdifferentconditions)

R–NH2 1–5

RHC CH2 4.6–6.0

OH 7.0

H 7.3

R

NHCH2R

CO

8.1

R

H

CO

9–10

R

OC

H

O9–13

7 2016CHEMISTRYDATABOOK

TURN OVER

6. 13C NMR data

Type of carbon Chemical shift (ppm)

R–CH3 8–25

R–CH2–R 20–45

R3–CH 40–60

R4–C 36–45

R–CH2–X 15–80

R3C–NH2 35–70

R–CH2–OH 50–90

RC CR 75–95

R2C=CR2 110–150

RCOOH 160–185

7. Infrared absorption dataCharacteristicrangeforinfraredabsorption

Bond Wave number (cm–1)

C–Cl 700–800

C–C 750–1100

C–O 1000–1300

C=C 1610–1680

C=O 1670–1750

O–H(acids) 2500–3300

C–H 2850–3300

O–H(alcohols) 3200–3550

N–H(primaryamines) 3350–3500

2016CHEMISTRYDATABOOK 8

8. 2-amino acids (α-amino acids)

Name Symbol Structure

alanine Ala

H2N CH COOH

CH3

arginine Arg

H2N CH COOH

CH2 CH2 CH2 NH

NH

C NH2

asparagine Asn

H2N CH COOH

CH2

O

C NH2

asparticacid Asp

H2N CH COOH

CH2 COOH

cysteine Cys

H2N CH COOH

CH2 SH

glutamine Gln

H2N CH COOH

CH2 CH2

O

C NH2

glutamicacid Glu

H2N CH COOH

CH2 CH2 COOH

glycine Gly H2N CH2 COOH

histidine His

H2N CH COOH

CH2 NH

N

isoleucine Ile

H2N CH COOH

CH3 CH CH2 CH3

9 2016CHEMISTRYDATABOOK

TURN OVER

Name Symbol Structure

leucine Leu

H2N CH COOH

CH2

CH3 CH CH3

lysine Lys

H2N CH COOH

CH2 CH2 CH2 CH2 NH2

methionine Met

H2N CH COOH

CH2 CH2 S CH3

phenylalanine Phe

H2N CH

CH2

COOH

proline ProHN

COOH

serine Ser

H2N CH COOH

CH2 OH

threonine Thr

H2N CH COOH

CH3 CH OH

tryptophan Trp

H2N CH

CH2

COOH

HN

tyrosine Tyr OH

H2N CH

CH2

COOH

valine Val

H2N CH COOH

CH3 CH CH3

2016CHEMISTRYDATABOOK 10

9. Formulas of some fatty acids

Name Formula

lauric C11H23COOH

myristic C13H27COOH

palmitic C15H31COOH

palmitoleic C15H29COOH

stearic C17H35COOH

oleic C17H33COOH

linoleic C17H31COOH

linolenic C17H29COOH

arachidic C19H39COOH

arachidonic C19H31COOH

10. Structural formulas of some important biomolecules

OH

OH

OH

OH HO

O O

O

H H

H

H H

H

H H

CH2OH

CH2OH

HOCH2

sucrose

OH

HO

O

H H H H

H

HOCH2

deoxyribose phosphate

O

O

P OO

C

C

C

H

H

OH

OH

OH

H

H

H

glycerol

adenine guanine cytosine thymine

NH2 NH2

CC

CCH

CH

C

CCHC

HN HN

H2N

N N

N

C C

CO

C N N

O

C

C

O

ONH

CH

CH3CH

CHNH

NHN

HN

11 2016CHEMISTRYDATABOOK

END OF DATA BOOK

11. Acid-base indicators

Name pH range Colour change Ka

Acid Basethymolblue 1.2–2.8 red yellow 2×10–2

methylorange 3.1–4.4 red yellow 2×10–4

bromophenolblue 3.0–4.6 yellow blue 6×10–5

methylred 4.2–6.3 red yellow 8×10–6

bromothymolblue 6.0–7.6 yellow blue 1×10–7

phenolred 6.8–8.4 yellow red 1×10–8

phenolphthalein 8.3–10.0 colourless red 5×10–10

12. Acidity constants, Ka, of some weak acids at 25 °C

Name Formula Ka

ammoniumion NH4+ 5.6×10–10

benzoic C6H5COOH 6.4×10–5

boric H3BO3 5.8×10–10

ethanoic CH3COOH 1.7×10–5

hydrocyanic HCN 6.3×10–10

hydrofluoric HF 7.6×10–4

hypobromous HOBr 2.4×10–9

hypochlorous HOCl 2.9×10–8

lactic HC3H5O3 1.4×10–4

methanoic HCOOH 1.8×10–4

nitrous HNO2 7.2×10–4

propanoic C2H5COOH 1.3×10–5

13. Values of molar enthalpy of combustion of some common fuels at 298 K and 101.3 kPa

Substance Formula State ΔHc(kJ mol–1)hydrogen H2 g –286carbon(graphite) C s –394methane CH4 g –889ethane C2H6 g –1557propane C3H8 g –2217butane C4H10 g –2874pentane C5H12 1 –3509hexane C6H14 1 –4158octane C8H18 1 –5464ethene C2H4 g –1409methanol CH3OH 1 –725ethanol C2H5OH 1 –13641-propanol CH3CH2CH2OH 1 –20162-propanol CH3CHOHCH3 1 –2003glucose C6H12O6 s –2816

0

1

2

3

4

5

6

7

8

9

0

1

2

3

4

5

6

7

8

9

0

1

2

3

4

5

6

7

8

9

0

1

2

3

4

5

6

7

8

9

6

7

8

9

6

7

8

9

6

7

8

9

6

7

8

9

0

1

2

3

4

5

0

1

2

3

4

5

0

1

2

3

4

5

0

1

2

3

4

5

R

T

W

X

A

E

F

G

J

L

STUDENT NUMBER

Please DO NOT fold, bend or staple this form.

STUDENTNAME:

© N

CS

Pear

son

18

84

0

Shade the “ABSENT” boxif the student was absentfrom the examination.ABSENT

SUPERVISORUSE ONLY

SUPERVISOR’SINITIALS

USE PENCIL ONLY

VCE CHEMISTRYWritten Examination

INSTRUCTIONS:

SIGNATURE:

SIGN HERE IF YOUR NAME AND NUMBER ARE PRINTED CORRECTLY.

USE PENCIL ONLY

If your name or number on this sheet is incorrect, notify the Supervisor.Use a PENCIL for ALL entries. For each question, shade the box which indicates your answer. All answers must be completed like THIS example:Marks will NOT be deducted for incorrect answers.NO MARK will be given if more than ONE answer is completed for any question.If you make a mistake, ERASE the incorrect answer – DO NOT cross it out.

A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

A B C D A B C D

11

12

13

14

15

16

17

18

19

20

ONE ANSWER PER LINE

A B C D

A B C D

A B C D

A B C D

A B C D

A B C D

A B C D

A B C D

A B C D

A B C D

21

22

23

24

25

26

27

28

29

30

ONE ANSWER PER LINEONE ANSWER PER LINE

1

2

3

4

5

6

7

8

9

10

ANSWER SHEET –

OFFICE USEONLY

2016