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Chem 7

This document is an exam question booklet focused on the structure, nomenclature, and properties of organic compounds, specifically designed for VCE Chemistry students. It includes various questions related to organic chemistry concepts such as bond energies, systematic naming, functional groups, and isomerism. The questions are structured to assess students' understanding of organic compound categorization and synthesis.

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0% found this document useful (0 votes)
40 views42 pages

Chem 7

This document is an exam question booklet focused on the structure, nomenclature, and properties of organic compounds, specifically designed for VCE Chemistry students. It includes various questions related to organic chemistry concepts such as bond energies, systematic naming, functional groups, and isomerism. The questions are structured to assess students' understanding of organic compound categorization and synthesis.

Uploaded by

s h r e y a
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Exam question booklet | Topic 7

7 Structure, nomenclature and


properties of organic compounds
Unit 4 How are carbon-based compounds designed for purpose?
Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.2 Characteristics of the carbon atom

To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].

Source: VCE 2022 Chemistry Exam, Section A, Q.29; © VCAA

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.

CH4 (g) + X2 (g) ⟶ CH3 X(g) + HX(g) ΔH < 0


catalyst

Which one of the following statements is true?


A. The strength of the bonds from weakest to strongest is C–Br < C–Cl < C–F.
B. Since hydrogen has the smallest atomic radius, the C–H bond is the weakest bond.
C. The C–Br bond is stronger than the C–H bond because of the size of the bromine atom.
D. The C–Br, C–Cl and C–F bonds are equal in strength because Br, Cl and F are halogens.

© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 1
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.2 Characteristics of the carbon atom

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.

Bond Bond energy (kJ mol–1 )


C–H 414
C–C 346
C=C 614

2 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.2 Characteristics of the carbon atom

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.

Hydrogen bonds Oxygen bonds


H–H 436 O–H 463
H–C 414 O–C 358
H–N 391 O–N 214
H–O 463 O–O 144
H–F 567 O–F 191
H–Cl 431 O–Cl 206

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)

c. Explain which molecule would be less stable. (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

Unit 4 How are carbon-based compounds designed for purpose?


Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.3 Structure and systematic naming

To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].

Source: VCE 2016 Chemistry Exam, Section A, Q.2; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.3 Structure and systematic naming

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

Source: VCE 2012 Chemistry Exam 1, Section A, Q.1; © VCAA

Question 3 (1 mark)

H H H Cl H

H C C C C C C H

H H H H H

The correct systematic name for the compound shown above is


A. 2-chlorohex-2-ene.
B. 3-chlorohex-2-ene.
C. 3-chlorohex-3-ene.
D. 4-chlorohex-5-ene.

© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 5
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.3 Structure and systematic naming

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)

c. State the molecular formula of the compound. (1 mark)

d. Name the homologous series that this compound belongs to. (1 mark)

e. What is the general formula for this homologous series? (1 mark)

6 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.3 Structure and systematic naming

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.

a. State the molecular formula of ibuprofen.

b. Calculate the molar mass of ibuprofen.

© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 7
Exam question booklet | Topic 7

Unit 4 How are carbon-based compounds designed for purpose?


Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.4 Functional groups

To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].

Source: VCE 2014 Chemistry Exam, Section B, Q.5.a; © VCAA

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.

Source: VCE 2013 Chemistry Exam, Section A, Q.9; © VCAA

Question 2 (1 mark)

O H H H
H
H C C C
C O C H
H
H H H

The systematic IUPAC name for the molecule shown above is


A. ethyl ethanoate.
B. ethyl propanoate.
C. propyl ethanoate.
D. methyl propanoate.

8 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.4 Functional groups

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

Which of the following statements is true?


A. P is an ester and its systematic name is propyl ethanoate.
B. R is a ketone and its systematic name is 3-hydroxy-3-methylbutan-2-one.
C. R, S and T are all ketones.
D. Q is a carboxylic acid and its systematic name is 2-methylbutanoic acid.

Source: VCE 2018 Chemistry NHT Exam, Section A, Q.12; © VCAA

Question 4 (1 mark)
The semi-structural formula for an isomer of C5 H13 NO is

NH2 CH2 CH2 CH (CH3 ) CH2 OH

The correct systematic name for this molecule is


A. 4-amino-pentan-1-ol
B. 4-amino-2-methyl-butan-1-ol
C. 4-hydroxy-3-methyl-butan-1-amine
D. 1-hydroxy-2-methyl-4-amino-butane

© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 9
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.4 Functional groups

Question 5 (3 marks)
The skeletal structure of an organic molecule is shown.

OH

a. Draw its structural formula. (1 mark)

b. Write its molecular formula. (1 mark)

c. Write its semi-structural formula. (1 mark)

Question 6 (1 mark)
An organic molecule with the molecular formula C4 H10 O is shown.

Which of the following statements about the molecule is true?


A. It is a primary alcohol and its systematic name is butan-2-ol.
B. It is a primary alcohol and its systematic name is butan-3-ol.
C. It is a secondary alcohol and its systematic name is butan-2-ol.
D. It is a secondary alcohol and its name is butan-3-ol.

10 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.4 Functional groups

Source: VCE 2008 Chemistry Exam 1, Section B, Q.6.a.i; © VCAA

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.

Source: VCE 2009 Chemistry Exam 1, Section B, Q.1.a; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.4 Functional groups

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
Exam question booklet | Topic 7

Unit 4 How are carbon-based compounds designed for purpose?


Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.5 Isomers

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)
C4 H8 reacts with HCl to form C4 H9 Cl.
The number of possible isomers is
A. 2
B. 3
C. 4
D. ≥ 5

Source: VCE 2020 Chemistry Exam, Section A, Q.7; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.5 Isomers

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)

b. Draw the structural formula for the isomer prop-2-en-1-ol. (1 mark)

Source: VCE 2010 Chemistry Exam 1, Section A, Q.11; © VCAA

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

Source: VCE 2015 Chemistry Exam, Section B, Q.5.b; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.5 Isomers

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

Source: VCE 2008 Chemistry Exam 1, Section A, Q.16; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.5 Isomers

Source: VCE 2008 Chemistry Exam 1, Section B, Q.4.b.i; © VCAA

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.

Source: VCE 2006 Chemistry Exam 1, Section A, Q.9; © VCAA

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
Exam question booklet | Topic 7

Unit 4 How are carbon-based compounds designed for purpose?


Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.6 Trends in physical properties

To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].

Source: VCE 2020 Chemistry Exam, Section A, Q.16; © VCAA

Question 1 (1 mark)
The following table provides information about three organic compounds: X, Y and Z.

Compound Structural formula Molar mass (g mol–1 ) Boiling point (°C)


X H H H 60 97
H C C C O H
H H H
Y H O 60 118
H C C

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

Unit 4 AOS 1 Topic 7 Subtopic 7.6 Trends in physical properties

Source: VCE 2018 Chemistry Exam, Section A, Q.21; © VCAA

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.

Source: VCE 2011 Chemistry Exam 1, Section A, Q.1; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.6 Trends in physical properties

Source: VCE 2010 Chemistry Exam 1, Section B, Q.9.c; © VCAA

Question 4 (3 marks)
The boiling points of several alkanols are provided in the following table.

Alkanol methanol ethanol propan-l-ol butan-l-ol pental-l-ol


Boiling point (°C) 64.5 78.3 97.2 117.2 138.0

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

Unit 4 AOS 1 Topic 7 Subtopic 7.6 Trends in physical properties

Question 6 (1 mark)
Consider the compounds shown.
I. II.

III. IV.

Which of the following statements regarding these compounds is incorrect?


A. Compounds II and III are non-polar.
B. Compounds I and IV would be involved in hydrogen bonding.
C. Compound I would have the lowest boiling point.
D. Compound III would have larger dispersion forces than compound II.

20 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 How are carbon-based compounds designed for purpose?


Area of Study 1 How are organic compounds categorised and synthesised?
Topic 7 Structure, nomenclature and properties of organic compounds
Subtopic 7.7 Review

To answer questions online and to receive immediate feedback and sample responses for every question, go to
your learnON title at [Link].

Source: VCE 2022 Chemistry Exam, Section A, Q.16; © VCAA

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

Source: VCE 2020 Chemistry Exam, Section A, Q.4; © VCAA

Question 2 (1 mark)

H H
H H

O H
N C
H C C
H
H
H H C
C H

H
H

What is the IUPAC name of the molecule shown above?


A. 3-hydroxy-3-ethyl-propan-1-amine
B. 3-amino-1-methylpropan-1-ol
C. 3-hydroxypentan-1-amine
D. 1-aminopentan-3-ol

© John Wiley & Sons Australia, Ltd Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition 21
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

Source: VCE 2019 Chemistry Exam, Section A, Q.3; © VCAA

Question 3 (1 mark)
A compound has the following skeletal formula.

The molar mass of the compound is


A. 71 g mol–1
B. 74 g mol–1
C. 85 g mol–1
D. 86 g mol–1

Source: VCE 2012 Chemistry Exam 1, Section A, Q.9; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

Source: VCE 2018 Chemistry NHT Exam, Section A, Q.5; © VCAA

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.

Source: VCE 2011 Chemistry Exam 1, Section A, Q.4; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

Source: VCE 2011 Chemistry Exam 1, Section A, Q.3; © VCAA

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

III. CH3 CH3


H3C CH CH2 C CH3
CH3

IV. CH3 CH3


H3C CH CH2 CH2 C H
CH3
Which of the structures is that of 2,2,4-trimethylpentane?
A. I and III only
B. I and IV only
C. II and III only
D. II and IV only

Source: VCE 2012 Chemistry Exam 1, Section A, Q.2; © VCAA

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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

Source: VCE 2018 Chemistry Exam, Section B, Q.1.a; © VCAA

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)

b. Give the molecular formula of but-2-yne. (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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

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.

Carboxylic acid Melting point (°C)


heptanoic acid –11
pentanoic acid –34.5
2-methylhexanoic acid –56

With reference to their structure and bonding, explain the difference in melting points between
a. heptanoic acid and pentanoic acid (2 marks)

b. heptanoic acid and 2-methylhexanoic acid. (2 marks)

28 Jacaranda Chemistry 2 VCE Units 3 and 4 Third Edition © John Wiley & Sons Australia, Ltd
Exam question booklet | Topic 7

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

Question 14 (6 marks)
Cyclohexane and cyclohexene are examples of cyclic hydrocarbons.
a. Draw the structures of cyclohexane and cyclohexene (2 marks)

b. Draw a straight-chain structure of a non-cyclic isomer of each. (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

Unit 4 AOS 1 Topic 7 Subtopic 7.7 Review

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)

b. What is the name of the functional group? (1 mark)

c. Is this a primary, secondary or tertiary alcohol? Justify your answer. (1 mark)

d. Write the semi-structural formula of 2-methylpropan-2-ol. (1 mark)

e. Draw the skeletal structure 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

Answers and marking guide


7.2 Characteristics of the carbon atom
Question 1
A. Bond energy depends on the type of atoms involved in the bond, the bond length and the number of
bonds between the atoms.
The greater the size of the atom, the greater the bond length and the lesser the bond dissociation energy; that
is, the lesser the bond strength. The smaller the halogen atom, the shorter the bond length and the stronger
the bond. Also, the higher the electronegativity of the halogen, the stronger the polarity of the bond, and the
greater the strength of the bond. So alternative A is correct.
For alternatives B and C, a shorter bond in C–H would probably result in a stronger bond, not a weaker
bond.
Bond strength decreases from C–F to C–Cl to C–Br because of the increase in bond length, so alternative D
is incorrect.
VCAA Assessment Report note:
54% of students answered this correctly.
Question 2
B. Double carbon-to-carbon bonds have a lower bond energy and longer bond length than triple
carbon-to-carbon bonds. This is because double bonds involve four electrons and triple bonds involve six
electrons. An increased number of shared electrons shortens the bond length and strengthens the bond,
which requires more energy to break.
Single bonds are longer and require less energy to break than double bonds (options A and D are correct).
Double bonds are longer and require less energy to break than triple bonds (options C and D are correct).
Question 3
C=C bonds are stronger than C−C bonds because they have twice the number of electrons between the
nuclei. This causes a shorter, stronger and more stable bond. [1 mark]

n(C2 H4 ) =
Question 4
m
M

=
(2 × 12.0 + 4 × 1.0)
25.0

=
25.0

= 0.893 mol [1 mark]


28.0

Energy in C2 H4 bonds = (4 × C–H + C=C)


= (4 × 414) + 614
= 2270 kJ mol−1
Energy in 0.89 mol C2 H4 = 0.893 × 2270
= 2026.8 kJ
= 2.03 × 103 kJ [1 mark]
Question 5
a. i. The water must be vaporised first, so the energy required to do this is 40.8 kJ. There are two O–H

Total energy = 926 + 40.8


bonds in water so this requires 2 × 463 kJ = 926 kJ.

= 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]

Energy = n(HCl) × 431 kJ mol –1


Question 6

= 7.5 mol × 431 kJ mol –1


= 3232.5 kJ [1 mark]
= 3.2 × 103 kJ (to 2 sig. figs.) [1 mark]

7.3 Structure and systematic naming


Question 1
D. The longest unbroken carbon chain in this compound is 7, making it a branched heptane. Number the
positions of the two methyl branches so that the sum of the locants (numbers) is as small as possible: hence,
3,4-dimethylheptane.
VCAA Assessment Report note:
73% of students answered this correctly.
Question 2
C. The longest unbroken chain is a six-membered chain as shown below. Methyl groups are attached at
carbons 3 and 4.
2 1
CH2 CH3
4 3
H3C CH CH CH3

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

b. Molar mass = 13 × 12.0 + 18 × 1.0 + 2 × 16.0


a. Molecular formula: C13 H18 O2 [1 mark]

= 206 g mol−1 [1 mark]

7.4 Functional groups


Question 1
H O
C C
H
O H
O
H

[1 mark for correct structural formula]


VCAA Assessment Report note:
The O–H bond was overlooked in a number of responses.
Question 2
C.
O H H H
H
H C C C
C O C H
H
H H H
ethanoate propyl

VCAA Assessment Report note:


73% of students answered this correctly.
Question 3
B. Molecule R is a ketone (with a C=O functional group) and the systematic name is
3-hydroxy-3-methylbutan-2-one. This option is correct.
Molecule P is an ester, but the first part of the molecule (originally from the alcohol) is branched, so the
systematic name is not simply propyl ethanoate.
Molecule R and T are ketones, but molecule S is an aldehyde. Molecule Q is a carboxylic acid but the
carboxyl group takes priority when numbering the carbons, so the methyl branch is attached to C3 and its
systematic name is 3-methylbutanoic acid.

© 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

[1 mark for one correct structure showing all bonds]


Question 10
In 2-methylbutanoic acid, the methyl group branches off the second carbon in the chain. In carboxylic acids,
the carbon in the carboxyl group is always carbon number 1.

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

[1 mark for one of the above structures]


VCAA Assessment Report note:
It was evident that many students read the question as the isomer butan-2-ol rather than a different
compound that is isomeric with (has the same molecular formula as) butan-2-ol. When asked to draw a full
structural formula, students are reminded that all bonds including the O–H bond must be shown.
Question 6
Three compounds can be formed: 1-chloro-3,3-dimethylbutane, 2-chloro-3,3-dimethylbutane and
1-chloro-2,2-dimethylbutane.
VCAA Assessment Report note:
As the words ‘different compounds’ could be interpreted in two ways, two answers were accepted for this
question. The first sentence of the question referred to ‘compound of formula C6 H13 Cl’. 2,2-dimethylbutane
can react with Cl2 to produce three different monochloro compounds:1-chloro-3,3-dimethylbutane,
2-chloro-3,3-dimethylbutane and 1-chloro-2,2-dimethylbutane.
However, each substitution reaction also produces hydrogen chloride, HCl, so a total of four different
compounds will be formed.
It was determined that ‘The number of different compounds that could be formed in this monosubstitution
reaction ...’ could be interpreted as referring to either ‘the compounds of formula C6 H13 Cl’ or ‘all the
compounds including HCl. Students are reminded that it is extremely rare that more than one
multiple-choice answer is accepted and this should not be seen as a precedent.
Question 7
Structural isomers refer to compounds that have the same molecular formula but different structural
formulas; that is, atom connectivities.
The options for C5 H10 are:
CH3 CH2 CH2 CH=CH2 : 1-pentene
CH3 CH2 CH=CHCH3 : 2-pentene
CH3 CH2 C(CH3 )=CH2 : 2-methyl-1-butene
(CH3 )2 CHCH=CH2 : 3-methyl-1-butene
(CH3 )2 C=CHCH3 : 2-methyl-2-butene.
Therefore, there are five structural isomers containing a double bond.
VCAA Assessment Report note:
31% of students answered this correctly.

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.

7.6 Trends in physical properties


Question 1
A. Boiling points of molecular compounds such as X, Y and Z are related to the strength of the
intermolecular bonding.
Since all three are polar molecules, the intermolecular bonding will have contributions from both dispersion
forces and dipole–dipole attractions.
All three molecules have the same molar mass, so the contribution from dispersion forces will be similar
for all.
Compounds X and Y will both have hydrogen bonding, due to the –OH groups.
Since compound Z does not have intermolecular hydrogen bonding, it would have the lowest boiling point.
VCAA Assessment Report note:
20% of students answered this correctly.
Question 2
B. Propan-1-ol and octan-1-ol both have a single –OH group and have both hydrogen bonding and
dispersion forces as intermolecular attractions.
Octan-1-ol has stronger intermolecular bonding due to its molecules having a larger hydrocarbon tail than
propan-1-ol.
Octan-1-ol has higher density and a higher boiling point than propan-1-ol.
VCAA Assessment Report note:
78% 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

CH3 COCH(CH3 )2 → C5 H10 O → M = 86.0 g mol−1


D. The skeletal formula translates to the following semi-structural formula:

VCAA Assessment Report note:


83% of students answered this correctly.
Question 4
A. The parent alkanol and alkanoic acid are respectively ethanol and propanoic acid.
VCAA Assessment Report note:
83% of students answered this correctly.
Question 5
A. Octane has the longest chain, therefore it has the strongest intermolecular attraction (dispersion forces).
Question 6
C. The molecular formula of 2,2,4-trimethylpentane is C8 H18 . There are nine carbon atoms in compound C.
VCAA Assessment Report note:
73% of students answered this correctly.
Question 7
C. The longest unbroken chain is five carbon atoms long (hence pentane), and there are three methyl side
chains (trimethyl) at positions 2, 2 and 4.
VCAA Assessment Report note:
95% of students answered this correctly.

© 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

b. Pentan-2-ol/2-pentanol [1 mark] and pentan-3-ol/3-pentanol [1 mark]


VCAA Assessment Report note:
Chemical names must be spelt and represented accurately.
c. CH3 COCH2 CH2 CH3 [1 mark]
Question 13
a. Heptanoic and pentanoic acids are both straight-chain carboxylic acids, but pentanoic acid molecules
(CH3 (CH2 )3 COOH) have shorter hydrocarbon chains than heptanoic acid molecules
(CH3 (CH2 )5 COOH). [1 mark]
Thus, pentanoic acid has weaker dispersion force attraction between its molecules and hence, a lower
melting point
OR
heptanoic acid has a higher molecular mass than pentanoic acid and hence, stronger intermolecular
dispersion forces and a higher melting point. [1 mark]
b. Heptanoic and 2-methylhexanoic molecules have the same molecular formula (C8 H13 COOH), but
heptanoic acid molecules are straight chains and 2-methylhexanoic acid molecules are branched.
[1 mark]
The branch in the 2-methylhexanoic acid hydrocarbon chain prevents the 2-methylhexanoic acid
molecules from packing together as effectively as heptanoic acid molecules, hence the intermolecular
forces are much weaker than in heptanoic acid, and 2-methylhexanoic acid has a lower melting point.
[1 mark]

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

HC C CH2 CH2 CH2 CH3

[1 mark for each correct structure]


c. Alkene [1 mark]
Alkyne [1 mark]

© 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

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