Chem 7
Chem 7
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your learnON title at [Link].
Question 1 (1 mark)
One mole of methane, CH4 , reacts with one mole of halogen, X2 . X can be fluorine, F, chlorine, Cl, or
bromine, Br. The general equation for the reaction is given below.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 1
Exam question booklet | Topic 7
Question 2 (1 mark)
Which of the following statements is incorrect?
A. Single carbon-to-carbon bonds have a lower bond energy and longer bond length than double
carbon-to-carbon bonds.
B. Double carbon-to-carbon bonds have a higher bond energy and longer bond length than triple
carbon-to-carbon bonds.
C. Triple carbon-to-carbon bonds have a higher bond energy and shorter bond length than double
carbon-to-carbon bonds.
D. Double carbon-to-carbon bonds have a higher bond energy than single carbon to carbon bonds, but less
bond energy than triple carbon-to-carbon bonds.
Question 3 (1 mark)
Explain why C=C bonds are stronger than C−C bonds.
Question 4 (2 marks)
Use the following table to calculate the energy, in kJ, required to break all covalent bonds in 25.0 g of
C2 H4 gas.
2 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
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Question 5 (4 marks)
Water and hydrogen peroxide are both made up of the elements hydrogen and oxygen. Bond energies
(in kJ mol–1 ) for hydrogen and oxygen bonds are provided in the following table.
a. i. Calculate the energy required to separate the atoms in one mole of liquid water if the heat of
vaporisation for water is 40.8 kJ mol–1 . (1 mark)
ii. Explain why the bond energy is so high compared to the heat of vaporisation. (1 mark)
b. Which of the following is easier to break: the O–H bond in water, H2 O, or the O–O bond in hydrogen
peroxide, H2 O2 ? (1 mark)
Question 6 (2 marks)
The bond energy of H–Cl is 431 kJ mol–1 .
What is the total bond energy in 7.5 moles of HCl?
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 3
Exam question booklet | Topic 7
To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].
Question 1 (1 mark)
H C H
H H H H H
H C C C C C C H
H H H H H
H C H
H C H
What is the correct systematic name for the compound shown above?
A. 4-methyl-5-ethylhexane
B. 2-ethyl-3-methylhexane
C. 4,5-dimethylheptane
D. 3,4-dimethylheptane
4 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Source: VCE 2013 Chemistry Sample Exam for Units 3 and 4, Section A, Q.1; © VCAA
Question 2 (1 mark)
What is the correct systematic name for the following compound?
CH2 CH3
H3C CH CH CH3
CH2 CH3
A. 2-ethyl-3-methylpentane
B. 3-methyl-4-ethylpentane
C. 3,4-dimethylhexane
D. 2,3-diethylbutane
Question 3 (1 mark)
H H H Cl H
H C C C C C C H
H H H H H
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 5
Exam question booklet | Topic 7
Question 4 (1 mark)
Which of the following skeletal formulas is not represented by the molecular formula C5 H12 ?
A.
B.
C.
D.
Question 5 (6 marks)
A student identified a compound as 2-ethylbutane.
a. Draw this molecule. (1 mark)
b. Explain why the name given is incorrect and state the correct name. (2 marks)
d. Name the homologous series that this compound belongs to. (1 mark)
6 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 6 (1 mark)
Which of the following semi-structural formulas has the same molecular formula as butane?
A. CH3 CH2 CH2 CH2 CH3
B. CH3 CH(CH3 )2
C. CH2 C(CH3 )2
D. CH3 CH2 CHCH2
Question 7 (2 marks)
The skeletal structure of ibuprofen is shown below.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 7
Exam question booklet | Topic 7
To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].
Question 1 (1 mark)
A 2% solution of glycolic acid (2-hydroxyethanoic acid), CH2 (OH)COOH, is used in some skincare
products.
Draw the structural formula of glycolic acid.
Question 2 (1 mark)
O H H H
H
H C C C
C O C H
H
H H H
8 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Source: Adapted from VCE 2021 Chemistry Exam, Section B, Q.7; © VCAA
Question 3 (1 mark)
Five isomers with the molecular formula C5 H10 O2 are shown.
P Q R
H H H
H H H H H H
C O C O C H
H
H
H C C H C C H H C C
H
C O C C C O C C
O H
H H H
H H H H O
H H H H
H
S T
O H
H H
C O
O C
H
C C H C C H
H C H H C C
H C H
H H H
H H O H
HH H
Question 4 (1 mark)
The semi-structural formula for an isomer of C5 H13 NO is
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 9
Exam question booklet | Topic 7
Question 5 (3 marks)
The skeletal structure of an organic molecule is shown.
OH
Question 6 (1 mark)
An organic molecule with the molecular formula C4 H10 O is shown.
10 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 7 (1 mark)
Give a systematic name for the following compound.
Question 8 (1 mark)
The IUPAC name for the compound (CH3 )2 CHCH2 CH(NH2 )CH3 is:
A. 2-methylpentanamine.
B. 4-methylpentan-2-amine.
C. 2-methyl-4-pentanamine.
D. 4-methyl-2-pentanamine.
Question 9 (1 mark)
2−chloro−3−methylpentane and 2−chloro−3−methylhexane were dissolved together and the mixture was
analysed using gas chromatography.
Draw a structural formula of either 2−chloro−3−methylpentane or 2−chloro−3−methylhexane, clearly
showing all bonds.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 11
Exam question booklet | Topic 7
Question 10 (1 mark)
Which of the following structures represents 2-methylbutanoic acid?
A. B.
C. D.
12 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
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your learnON title at [Link].
Question 1 (1 mark)
C4 H8 reacts with HCl to form C4 H9 Cl.
The number of possible isomers is
A. 2
B. 3
C. 4
D. ≥ 5
Question 2 (1 mark)
How many structural isomers have the molecular formula C3 H6 BrCl?
A. 4
B. 5
C. 6
D. 7
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 13
Exam question booklet | Topic 7
Source: Adapted from VCE 2017 Chemistry Exam, Section B, Q.5.a.i, ii; © VCAA
Question 3 (2 marks)
There are a number of structural isomers for the molecular formula C3 H6 O. Three of these are propanal,
propanone and prop-2-en-1-ol.
a. Write the semi-structural formula for the ketone isomer propanone. (1 mark)
Question 4 (1 mark)
For which one of the following molecular formulas is there only one possible structure?
A. C2 HCl3
B. C2 H4 Cl2
C. C2 H2 Cl2
D. C4 H9 OH
Question 5 (1 mark)
Draw the full structural formula of an isomer of butan-2-ol.
14 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Source: VCE 2013 Chemistry Sample Exam for Units 3 and 4, Section A, Q.2; © VCAA
Question 6 (1 mark)
In a particular chlorination reaction, a single hydrogen atom of 2,2−dimethylbutane, C6 H14 , is replaced by
one chlorine atom. More than one compound of formula C6 H13 Cl will be formed.
A structure of 2,2-dimethylbutane is provided below.
The number of different carbon compounds that could be formed in this monosubstitution reaction is
A. 2
B. 3
C. 4
D. 5
Question 7 (1 mark)
How many structural isomers, each containing a double bond, have the molecular formula C5 H10 ?
A. 3
B. 4
C. 5
D. 6
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 15
Exam question booklet | Topic 7
Question 8 (4 marks)
A mixture contains several different organic liquids all of which boil at temperatures greater than 50 °C.
The compounds present in the mixture are separated and analysed.
Compound Y is an alkanol with a molecular formula of C4 H10 O.
Draw the structural formulas, showing all bonds, of the four possible alkanols with a molecular formula of
C4 H10 O.
Question 9 (1 mark)
The number of structural isomers that are carboxylic acids with the formula C4 H8 O2 is
A. 1
B. 2
C. 3
D. 4
16 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
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your learnON title at [Link].
Question 1 (1 mark)
The following table provides information about three organic compounds: X, Y and Z.
H O H
Z H O 60 ?
H C O C H
H
Which one of the following is the best estimate for the boiling point of Compound Z?
A. 31 °C
B. 101 °C
C. 114 °C
D. 156 °C
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 17
Exam question booklet | Topic 7
Question 2 (1 mark)
A student wants to use a physical property to distinguish between two alcohols, octan-1-ol and propan-1-ol.
Both alcohols are colourless liquids at standard laboratory conditions (SLC).
The student should use
A. density because propan-1-ol has a much higher density than octan-1-ol.
B. boiling point because octan-1-ol has a higher boiling point than propan-1-ol.
C. electrical conductivity because octan-1-ol has a higher conductivity than propan-1-ol.
D. spectroscopy because it is not possible to distinguish between the alcohols using their physical
properties.
Question 3 (1 mark)
Which one of the following compounds is least soluble in water at room temperature?
A. ethane
B. ethanol
C. ethylamine
D. ethanoic acid
18 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 4 (3 marks)
The boiling points of several alkanols are provided in the following table.
Butane and propan-1-ol have similar molar masses. The boiling point of butane is −138.4 °C and that of
propan-1-ol is 97.2 °C.
Explain, in terms of intermolecular forces, the difference between the boiling points of these two
compounds.
Question 5 (5 marks)
Two compounds have the molecular formula C2 H6 O.
Use the following data to draw the structures of compound A and compound B.
Compound A Compound B
Boiling point –24 °C 78 °C
–1
Solubility in water at SLC 71 g L Miscible
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 19
Exam question booklet | Topic 7
Question 6 (1 mark)
Consider the compounds shown.
I. II.
III. IV.
20 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
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Question 1 (1 mark)
The correct IUPAC name for CH3 CH2 CHClCHOHCH3 is
A. 3-chloropentan-4-ol
B. 3-chloropentan-2-ol
C. 2,3-chloro-pentanol
D. 3,2-chloro-pentanol
Question 2 (1 mark)
H H
H H
O H
N C
H C C
H
H
H H C
C H
H
H
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 21
Exam question booklet | Topic 7
Question 3 (1 mark)
A compound has the following skeletal formula.
Question 4 (1 mark)
H H
O
H C C C H H
H H O C C H
H H
Which one of the following is the correct systematic name of this compound?
A. ethyl propanoate
B. ethyl ethanoate
C. propyl ethanoate
D. propyl pentanoate
22 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 5 (1 mark)
Pentane, hexane, heptane and octane are non-branched alkanes.
Which one of the following statements gives a valid comparison?
A. Octane has a greater viscosity and a higher boiling point than hexane.
B. Pentane has a greater viscosity and a lower boiling point than octane.
C. Heptane has a lower viscosity and a higher boiling point than octane.
D. Heptane has a lower viscosity and a lower boiling point than pentane.
Question 6 (1 mark)
The compound that is not an isomer of 2,2,4-trimethylpentane is
A. octane.
B. 3-ethylhexane.
C. 2,4-dimethylpentane.
D. 2,4-dimethylhexane.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 23
Exam question booklet | Topic 7
Question 7 (1 mark)
Consider the following structures.
I. CH3
H C CH2 CH2 CH CH3
CH3 CH3
II. CH3
H3C C CH2 CH CH3
CH3 CH3
Question 8 (1 mark)
The number of structural isomers of C4 H9 Cl is
A. 2
B. 3
C. 4
D. 5
24 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 9 (1 mark)
The structural arrangement of 2,2-dimethylbutan-1-ol is
A. H CH3 CH3 H
H C C C C OH
H H H H
B. H H CH3 H
H C C C C OH
H H CH3 H
C. H H CH3 H
HO C C C C H
H H CH3 H
D. H H
H C C OH
CH3 CH3
Question 10 (1 mark)
What is the IUPAC name of the following molecule?
HO NH2
A. 1-amino-2-methylbutan-4-ol
B. 2-aminobutan-4-ol
C. 4-amino-3-methylbutan-1-ol
D. 3-aminobutan-1-ol
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 25
Exam question booklet | Topic 7
Question 11 (3 marks)
Organic compounds are numerous and diverse due to the nature of the carbon atom. There are international
conventions for the naming and representation of organic compounds.
a. Draw the structural formula of 2-methyl-propan-2-ol. (1 mark)
H C H
Br C H
H C Br
H H H
H C C C C H
H O H H
c. Give the IUPAC name of the compound that has the structural formula shown above. (1 mark)
26 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Source: Adapted from VCE 2019 Chemistry Exam, Section B, Q.2.a; © VCAA
Question 12 (4 marks)
A sequence of reactions can be applied to pent-2-ene to produce a variety of desirable products.
a. Draw the skeletal formula for pent-2-ene. (1 mark)
Two structural isomers are possible when pent-2-ene is reacted with water at a high temperature in the
presence of an acid catalyst. Each isomer is a secondary alcohol with the formula C5 H11 OH.
b. Give the IUPAC name of both isomers. (2 marks)
c. When one of these isomers is reacted with acidified dichromate ions, pentan-2-one is formed.
Give the semi-structural formula of pentan-2-one. (1 mark)
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 27
Exam question booklet | Topic 7
Source: Adapted from VCE 2017 Chemistry Exam, Section B, Q.7a; © VCAA
Question 13 (4 marks)
A table of carboxylic acids and their melting points is shown below.
With reference to their structure and bonding, explain the difference in melting points between
a. heptanoic acid and pentanoic acid (2 marks)
28 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 14 (6 marks)
Cyclohexane and cyclohexene are examples of cyclic hydrocarbons.
a. Draw the structures of cyclohexane and cyclohexene (2 marks)
c. Name the homologous series to which the isomers in part b belong. (2 marks)
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 29
Exam question booklet | Topic 7
Question 15 (5 marks)
The diverse nature of organic compounds can be attributed to carbon and its unique chemical properties. In
fact, there are millions of organic compounds found in nature and synthesised in the laboratory. To be able
to identify these molecules, IUPAC has developed naming conventions and models.
Consider the alcohol 2-methylpropan-2-ol.
a. Draw the structural formula of 2-methylpropan-2-ol. (1 mark)
30 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
n(C2 H4 ) =
Question 4
m
M
=
(2 × 12.0 + 4 × 1.0)
25.0
=
25.0
= 966.8
= 967 kJ mol−1 [1 mark]
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 31
Exam question booklet | Topic 7
ii. To vaporise the water, the hydrogen bonds between the water molecules must be broken; however, to
separate the hydrogen atoms the much stronger covalent bonds must be broken, which requires
considerably more energy. [1 mark]
b. O–H bond energy = 463 kJ mol–1
O–O bond energy = 144 kJ mol–1
It is easier to break the O–O bond. [1 mark]
c. The hydrogen peroxide molecule would be less stable because the O–O bond is easier to break. [1 mark]
5 CH2 CH3
6
VCAA Assessment Report note:
70% of students answered this correctly.
Question 3
B. Positions of functional groups must be numbered starting from the end that will result in the lowest
possible sum.
VCAA Assessment Report note:
92% of students answered this correctly.
Question 4
D. C5 H12 has five carbon atoms. These are represented by the vertices of the skeletal formula.
Options A to C each have five carbons. Option D has six carbons and is the molecule hexane, C6 H14 .
Question 5
a. 2-ethylbutane can be drawn as a four-chain alkane (butane) with an ethyl group from C2.
H
H C H
H C H
H H H
H C C C C H
H H H H [1 mark]
32 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
b. The longest chain has five carbons and there is a methyl group attached to the third carbon. [1 mark] The
correct name is 3-methylpentane. [1 mark]
c. C6 H14 [1 mark]
d. Alkanes is the homologous series. [1 mark]
It is composed only of C and H, and has only single bonds.
e. Cn H2n + 2 is the general formula for alkanes. [1 mark]
Question 6
The molecular formula of butane is C4 H10 . The semi-structural formula CH3 CH(CH3 )2 also
represents C4 H10 .
Question 7
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 33
Exam question booklet | Topic 7
Question 4
B. The hydroxyl functional group has a higher priority than the amino group, so the suffix ‘-ol’ is used and
the carbons are numbered from this end of the molecule. The hydroxyl group is attached to C1, the methyl
branch is attached to C2 and the amino group is attached to C4.
Question 5
a. H
H H
H C H
H H
H C C C H
C C
H O H
H H
H
[1 mark]
b. C6 H14 O [1 mark]
c. CH3 CH2 C(CH3 )OHCH2 CH3 [1 mark]
Question 6
The longest carbon chain is C4 and the hydroxyl group is coming off C2, so its name is butan-2-ol.
The carbon atom bonded to the –OH is bonded to two other carbon atoms, therefore the alcohol is classified
as a secondary (2°) alcohol.
Primary alcohols have the general formula R–CH2 –OH because the carbon bonded to the –OH is bonded to
one other carbon atom only. [1 mark]
Question 7
Any one of:
• aminoethane
• ethylamine
• ethanamine
[1 mark for any one of the above]
Question 8
Numbering starts from the end that gives the amino functional group the lowest number. The longest chain
is C5, with a methyl group coming off C4.
Option D would also be acceptable, but it is not the preferred IUPAC name.
Question 9
34 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
7.5 Isomers
Question 1
C. There are four isomers of C4 H9 Cl; two unbranched chlorobutane structures and two branched
chloropropane structures.
H H H H H Cl H H
H C C C C Cl H C C C C H
H H H H H H H H
1-chloropropane 2-chloropropane
H CH3 H H CH3 H
H C C C H H C C C H
H Cl H Cl H H
1-chloro-2-methylpropane 1-chloro-2-methylpropane
Question 2
B.
CH3 CH2 CHBrCl; 1-bromo-1-chloropropane
CH3 CHClCH2 Br; 1-bromo-2-chloropropane
CH2 ClCH2 CH2 Br; 1-bromo-3-chloropropane
CH3 CHBrCH2 Cl; 2-bromo-1-chloropropane
CH3 CBrClCH3 ; 2-bromo-2-chloropropane
VCAA Assessment Report note:
46% of students answered this correctly.
Question 3
a. CH3 COCH3 [1 mark]
b. H H
H H
C C
C C H H C H
H C O O
H
H
H H
[1 mark for either of the above orientations of the structure]
Question 4
A. Drawing of structural isomers shows only one possibility for option A.
VCAA Assessment Report note:
79% of students answered this correctly.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 35
Exam question booklet | Topic 7
Question 5
Acceptable structures include:
H H H
H
C C
H C C H
O
H H
H H
H H
H
C C
H C H
H O
C H
H
HH
H
H H
O
C C
H C H
H H
C
H
HH
36 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 8
[1 mark for each of the four structures shown; all bonds must be drawn to receive a mark]
VCAA Assessment Report note:
This question was generally well done. The main concerns were:
• repetition of structures
• not drawing out the O–H link.
Question 9
There are two carboxylic acids with molecular formula C4 H8 O2 :
• CH3 CH2 CH2 COOH (butanoic acid)
• (CH3 ) 2 CHCOOH (methylpropanoic acid).
VCAA Assessment Report note:
45% of students answered this correctly.
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 37
Exam question booklet | Topic 7
Question 3
A. Ethanol (CH3 CH2 OH) ethylamine (CH2 CH2 NH2 ), and ethanoic acid (CH3 COOH) all dissolve in water
via hydrogen bonding. Ethane (CH3 CH3 ) is non-polar and is less soluble in water.
VCAA Assessment Report note:
75% of students answered this correctly.
Question 4
Responses may include:
• correctly describing the bonding (dispersion force attraction) between butane molecules
• correctly describing the bonding (hydrogen bonding) between propan-1-ol molecules
• indicating that the higher boiling point of propan-1-ol is due to the hydrogen bonding between
propan-1-ol molecules being stronger than the dispersion forces bonding between butane molecules.
[1 mark for each of three key points in a valid explanation]
VCAA Assessment Report note:
Some responses showed good understanding of bonding and included points such as the relative polarity of
butane and 1-propanol molecules, and the role of the —OH group in hydrogen bonding between 1-propanol
molecules. However, overall performance on this question suggested that many students were perhaps not
expecting a ‘bonding’-related question.
While the boiling point of butane is stated in the question, −138.4 °C is its melting temperature (the correct
boiling temperature is −0.5 °C); this did not affect student performance.
Common errors included:
• reading the data as butane having the higher boiling point
• relating the boiling point to the bonds within the molecules
• describing the hydrogen bonding in propan-1-ol as the bond between O and H in the hydroxyl group
• referring to hydrogen bonding between propan-1-ol and water.
There was clear evidence that many students were not familiar with, or were confused by, the term
‘intermolecular’.
Question 5
H H H
O H C C O
H3C CH3
H H
Compound A Compound B
The weaker intermolecular dipole–dipole attractions holding dimethyl ether molecules together means a
lower temperature is required to reach its boiling point compared to the hydrogen bonds between the
ethanol molecules.
Compound A (dimethyl ether) is polar due to the angular shape of the molecule and polarised C−O−C
bonds. This allows it to form hydrogen bonds with water but nowhere near as effectively as the hydrogen
bonds that form between water and ethanol, which is compound B.
Question 6
Compound I would exhibit hydrogen bonding between molecules due to the polar N–H bond. This would
give it a higher boiling point than a small hydrocarbon like compound II, which has only dispersion forces
operating between its molecules. Likewise, compound IV would also exhibit hydrogen bonding between
molecules due to its O–H bond, making its boiling point higher than compound II.
38 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
7.7 Review
Question 1
B. The compound is an alcohol with five carbon atoms, so it is pentanol. The hydroxyl group for the alcohol
is attached to the second carbon (as it must have the lowest number) and the name is therefore pentan-2-ol.
The chlorine atom is attached to the third carbon atom and so the prefix 3-chloro is used. The compound is
3-chloropentan-2-ol.
Hint: Remember to draw organic structures where possible.
VCAA Assessment Report note:
87% of students answered this correctly.
Question 2
D.
H H
H H
2 H
N C 3 O
H C C
1
H
H
H H C
4 C H
5
H
H
The –OH functional group is of higher priority than the –NH2 functional group, hence it is an alcohol with
an amino functional group attached and not an amine with a hydroxy functional group attached.
VCAA Assessment Report note:
63% of students answered this correctly.
Question 3
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 39
Exam question booklet | Topic 7
Question 8
C.
1-chlorobutane, CH3 CH2 CH2 CH2 Cl
2-chlorobutane, CH3 CH2 CHClCH3
1-chloro-2-methylpropane, (CH3 )2 CHCH2 Cl
2-chloro-2-methylpropane, (CH3 )3 CCl
VCAA Assessment Report note:
66% of students answered this correctly.
Question 9
B. The 2,2-dimethyl indicates the two CH3 groups are coming off the same carbon and the one next to the
hydroxyl (–OH) functional group on C1.
Option A is 2,3-dimethylbutan-1-ol.
Option C is 3,3-dimethylbutan-1-ol.
Option D is butan-2-ol.
Question 10
D. The hydroxyl (–OH) functional group takes priority over the amino (NH2 ) functional group, so
numbering starts at the carbon with the –OH, making the ending -1-ol. Due to this, the amino group is
at C3.
Question 11
a. H
H H
O
C C
H C H
H H
C
H
H
H
[1 mark]
VCAA Assessment Report note:
The most common error was not showing the O–H bond. Missing and/or extra H atoms was also
relatively common.
b. C4 H6 [1 mark]
VCAA Assessment Report note:
The molecular formula shows the symbol and numbers of atoms of each element present in the molecule
only. Structural or semi-structural formulas were not appropriate.
c. 2,3-dibromo-4-methylhexane [1 mark]
VCAA Assessment Report note:
The following logical steps in determining nomenclature proved challenging for many students:
• longest carbon chain — 6 — hence, hexane
• number carbons to give functional groups lowest possible numbers — 2,3-dibromo; 4-methyl
This question was not answered well, suggesting that systematic naming of compounds is an area
needing further attention.
Question 12
a.
[1 mark for either of the above structures]
VCAA Assessment Report note:
Strong performance on this question indicated skeletal structures are well appreciated.
40 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7
Question 14
a. H H
H H
H H
C H
H C H C H
C H C C
H C C H H C C H
C C
H H H
H H H H
[1 mark for each correct structure]
b. Any straight-chain isomer of hexene and any isomer of hexadiene or hexyne. For example:
H H H H
C6H12: H C C C C C C H
H H H H H H
H H H H H H
1 6
C6H10: H C C C C C C H
2 3 4 5
H H
© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 41
Exam question booklet | Topic 7
Question 15
a. H
H C H
H H
H C C C H
H H
O
H
[1 mark]
b. The functional group in 2-methylpropan-2-ol is a hydroxyl group. [1 mark]
c. This is a tertiary alcohol because the carbon bonded to the –OH group is attached to three other carbon
atoms (alkyl groups). [1 mark]
d. CH3 C(CH3 )OHCH3
e. OH
42 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd