Topic 10: Introduction to Organic

Chemistry - Hydrocarbons 1
Welcome to Topic 10. This topic begins our journey into organic chemistry. In this week’s material,
we will explore hydrocarbons – organic compounds containing only carbon and hydrogen atoms. We
will look at physical and chemical properties of hydrocarbons and learn how to name the many
different compounds that can form using an internationally accepted systematic approach (IUPAC
nomenclature).
How to work through this document

 Read through this document, work through the in-text problems as prompted and explore the
recommended supplementary materials. Answers to in-text problems are either written in blue
font inside blue shading or are hidden underneath a box. To unveil them select the shaded text
and change its font colour to anything other than blue or select the box and delete it.
 If you get stuck at any time, make sure you note it down so you can ask your tutor about it
during your workshop class.
 If you have plenty of time, try the “Practice Problems” located near the end of this document.
We anticipate, however, that most of you will not get through these all before your weekly
workshop class. You will be able to work through the practice problems during your workshop
class where you will have support from your tutor and fellow students. Your tutor will have a
copy of the answers during the workshop so you can check your progress during the class and
ask for any help you might need. These answers are posted on Blackboard but are time-
stamped to only become visible after the final workshop each week.
 Have this document and the Practice Problems available with you during class. You can print it
(black and white is cheaper and OK), or you are welcome to use your own device to access it
electronically.

Introduction
All living things on earth are formed mostly of carbon compounds. Early chemists regarded
substances isolated from organisms (plants and animals) as a different type of matter that could not
be synthesized artificially, and these substances were thus known as organic compounds. In 1828,
however, the German chemist Friedrich Wohler successfully synthesised urea in the laboratory from
non-living materials. Urea is a component of many body fluids and is responsible for the
characteristic pungent odour of urine. Since then, the classification of organic chemistry evolved to
include both natural and synthetic compounds that contain carbon as their principle element (Figure
1). Indeed the largest database of organic compounds lists about 10 million substances, which
include compounds originating from living organisms and those synthesized by chemists. The
number of potential organic compounds has been estimated at 1060— an exceedingly high number.

1
This document was created by Dr Vicky Barnett using her own materials and materials available through creative
commons access. There is significant overlap between the content in this document and documents developed previously
by Dr Barnett for the CHEM0006 unit at Curtin University.

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 Figure 1. All organic compounds contain carbon, and most are formed by living things, although they are also
formed by geological and artificial processes. (credit left: modification of work by Jon Sullivan; credit left middle:
modification of work by Deb Tremper; credit right middle: modification of work by “annszyp”/Wikimedia commons; credit
right: modification of work by George Shuklin).

The existence of so many organic molecules is a consequence of the ability of carbon atoms to
form up to four strong covalent bonds to other carbon atoms, resulting in chains and rings of
many different sizes, shapes, and complexities.

To simplify our understanding of organic chemistry, a systematic approach is required:

 Molecules are categorised based on what reactive groups (‘functional groups’) they contain.
 Simple molecules containing identical functional groups form a homologous series. Each
member of a homologous series has the same chemical properties and the same general
formula. They differ only in the size of their hydrocarbon ‘backbone’ or chain, with an
increase in length by one -CH2- group for each successive member.

Hydrocarbons
The simplest organic compounds are called hydrocarbons because they contain only the elements
carbon and hydrogen. Many hydrocarbons are found in plants, animals, and their fossils. Other
hydrocarbons have been prepared in the laboratory. We use hydrocarbons every day, mainly as
fuels, such as natural gas, acetylene, propane, butane, and the principal components of petrol,
diesel, and oils. Polyethylene, polypropylene, and polystyrene plastics are also hydrocarbons.

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All hydrocarbons are non-polar in nature, which means they only exhibit dispersion forces
between like-molecules. Small hydrocarbon molecules containing up to 4 C atoms exhibit
very weak dispersion forces and are gases at room temperature. Larger hydrocarbons exhibit
stronger dispersion forces and exist as liquids at room temperature, while even larger
hydrocarbons (~20+ C atoms) may exist as solids.
Because they are non-polar, all hydrocarbons are insoluble in water but can be dissolved in non-
polar solvents. There are an enormous number of hydrocarbon molecules, but we don’t need to
memorise them all because we can sort them into different categories based on the underlying
bonding patterns of their C atoms. Molecules within each different category will have the same
chemical properties. The remainder of this topic introduces the different types of hydrocarbons and
their characteristic physical and chemical properties.

Alkanes
Alkanes contain only single bonds between carbon atoms. Hydrogen atoms are also bonded so that
each C atom contains four single bonds in a tetrahedral arrangement. Because the resulting
structure contains the maximum number of H atoms possible for a given number of C atoms, alkanes
are called saturated hydrocarbons. The molecular formula for noncyclic alkanes follows the general
pattern of CnH(2n+2). The molecular formula of any compound lists only its type and number of
constituent atoms, giving no indication of how they are connected. In organic chemistry, it is also
important to consider structural formulae, as these show not only the numbers and types of bonded
atoms, but also how they are arranged. There are several ways of representing structural formulae,
some of which are shown in Figure 2.

2-D Structural
formula

Ball and stick

3-D model

Space-filling
3-D model

Figure 2. Different representations to show the structural arrangement of atoms in the molecules of methane,
ethane, and pentane. Condensed structural and molecular formulae are also given beneath their names.

Representing the 3-D arrangement of atoms becomes quite complex for larger molecules, so
simplified 2-D sketches or condensed formulae are preferred. Another method simplifies these
representations even further by using skeletal or line structures where neither C nor H atoms are
drawn. Instead, C atoms are represented as the ends of lines and as the juncture between lines. H
atoms attached to the C atoms are not included at all because their numbers are easily determined
by remembering that each C atom must have 4 bonds in total. Figure 3 shows three equally valid
ways to represent the structural formula of the same molecule.

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Figure 3. Expanded formula, condensed formula and skeletal/line structures are commonly used to represent
structures of organic molecules. The molecule represented here is 3-ethyl-2-methylhexane, with a molecular
formula of C9H20. Its condensed formula could also be represented as CH3CH(CH3)CH(CH2CH3)CH2CH2CH3, with
branched groups shown in brackets.
Regardless of the representation used, we need to remember that each C atom in an
alkane has 4 single-bonded atoms around it and no lone or non-bonding electron
pairs. This means that each C atom will have a 3-D tetrahedral arrangement of
bonded atoms around it, with bond angles of 109.5°.

EXAMPLE 1: MOLECULAR AND STRUCTURAL FORMULA

For each molecule below i) write its molecular formula and ii) draw its line
structure.

Answer
i) The molecular formula shows the types and numbers of each atom
in the molecule. Both (a) and (b) have 7 C atoms and 16 H atoms, so
they both have the molecular formula C7H16. These two molecules
are an example of a pair of structural isomers – they have the same
molecular formula but are not the same molecule because their
atoms are arranged differently, giving different structural formulas.
ii) Each carbon atom is converted into the end of a line or the place
where lines intersect. All hydrogen atoms attached to the carbon
atoms are left out of the structure (although we still need to
remember they are there):

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 Check Your Learning
For each molecule below i) write its molecular formula and ii) draw its line structure.

Answer
i) The molecular formula for (a) is C7H14 and for (b) is C5H12.
ii)

EXAMPLE 2: MOLECULAR AND STRUCTURAL FORMULA

Identify the molecular formula of the molecule
represented to the right:
Answer
There are eight places where lines intersect or end,
meaning that there are eight carbon atoms in the molecule. Since we know that carbon
atoms tend to make four bonds, each carbon atom will have the number of hydrogen
atoms that are required for four bonds. This compound contains 16 hydrogen atoms for
a molecular formula of C8H16.

Check Your Learning

Identify the molecular formula of the molecule
represented to the right:

Answer
C9H20

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All alkanes have similar bonds, structures, and formulas:
 aliphatic alkanes are chain-based and have a formula of CnH2n+2
 alicyclic alkanes contain ring or cyclic arrangements and have the general formula of C nH2n
The number of carbon atoms present in an alkane has no limit. Greater numbers of atoms in the
molecules will lead to stronger intermolecular attractions (dispersion forces) and correspondingly
different physical properties of the molecules. Properties such as melting point and boiling point
(Table 1) usually increase in a predictable manner as the number of atoms in the molecules increase.
Table 1. Physical properties of the first 10 members of the alkane homologous series

Molecular Melting Boiling State at Room

Alkane
Formula Point (°C) Point (°C) Temperature

methane CH4 –182.5 –161.5 gas

ethane C2H6 –183.3 –88.6 gas

propane C3H8 –187.7 –42.1 gas

butane C4H10 –138.3 –0.5 gas

pentane C5H12 –129.7 36.1 liquid

hexane C6H14 –95.3 68.7 liquid

heptane C7H16 –90.6 98.4 liquid

octane C8H18 –56.8 125.7 liquid

nonane C9H20 –53.6 150.8 liquid

decane C10H22 –29.7 174.0 liquid

Organic molecules with the same molecular formula can have different structures. For example,
there are two alkanes with the molecular formula C4H10, and these are shown below:

Butane and 2-methylpropane are structural isomers. The have the

same molecular formula but different structures: Butane contains an unbranched chain, meaning
that no C atom is bonded to more than two other C atoms. 2–methylpropane has a branched chain
(the C atom in the centre of the structure is bonded to three other C atoms).

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 Structural isomers have the same molecular formula but different structural formulas.

Identifying isomers from

structural formulae is not always
easy because differently drawn
structures may represent the
same molecule rather than
different isomers. For example,
each structure on the left
represents butane.
Free rotation is possible around each single bond, meaning that these representations are
interconvertible. They are not isomers but simply the same molecule drawn differently on the page.

Nomenclature: Naming Alkanes

The International Union of Pure and Applied Chemistry (IUPAC) has devised a system of
nomenclature that begins with the names of the alkanes and can be adjusted from there to account
for more complicated structures. The nomenclature for alkanes is based on a series of rules:
1. First identify the longest chain of carbon atoms in the structure. This will determine the base of
the name in accordance with the alkane homologous series given in Table 1.
2. Add prefixes to the name of the longest chain to indicate the positions and names of any
substituents. Substituents are alkane-based branches (called alkyl branches) or functional
groups that have replaced hydrogen atoms along the base chain. The position of a substituent is
identified by the number of the carbon atom it is bonded to in the chain, with the carbon atoms
in the chain being numbered sequentially from the end closest to the substituents.
3. Alkyl branches are named in accordance with the number of C atoms they contained, with the
ending of -yl used to identify them as a branch (e.g. methyl for –CH3, ethyl for –CH2CH3, etc.).
4. Haloalkanes contain halogen atoms as substituents. In their naming, the ending –o is used (e.g.
a chlorine atom will be a ‘chloro’ substituent).
5. When more than one type of substituent is present, the substituents are listed alphabetically.
6. For multiple substituents of the same type, prefixes are used: di- (two), tri- (three), tetra- (four),
etc. (e.g. example, difluoro- indicates two fluorine substituents).

7. The prefix ‘cyclo’ is used to identify alicyclic compounds.

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 EXAMPLE 3: NAMING SUBSTITUTED ALKANES
Name the molecule whose structure is shown to the right:
Answer
The longest chain has 4 C atoms, so this is a substituted butane. The C on the right is closest to a
substituent, so the numbering of C atoms along the chain starts here.
The chlorine is on C-1 and bromine is on C-2, so both 1-chloro and 2-
bromo will be added as prefixes. Since bromo- comes before chloro-
alphabetically, it will be listed first. The resulting name of the
molecule is 2-bromo-1-chlorobutane.

Check Your Learning

Name the molecule to the right:

Answer:
3,3-dibromo-2-iodopentane

EXAMPLE 4: NAMING BRANCHED ALKANES

Name the molecule to the right:
Answer
The longest carbon chain runs horizontally across the page and contains six carbon atoms (this
makes the base of the name hexane). In this example, numbering along the carbon chain from
right to left gives the smallest numbering for substituents (this places the ethyl branch on C-3.
Numbering from the left would place the ethyl branch on C-4). The branch attached to position 3
of our chain contains two carbon atoms —so we take our name for two carbons eth- and attach –
yl at the end to signify we are describing a branch. Putting all the pieces together, this molecule is
3-ethylhexane.

Check Your Learning

Name this molecule:

Answer
4-propyloctane

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 Want more practice naming alkanes? Watch this
video tutorial to review the nomenclature
process.

https://youtu.be/NRFPvLp3r3g (9:27min)

Chemical properties of alkanes

Alkanes are relatively stable molecules and do not react readily unless activated by large amounts of
heat or UV-light. There are two significant classes of reaction for alkanes, combustion and light-
induced substitution reactions. Combustion reactions were introduced in Workshop Activity 3:
 Complete combustion: hydrocarbon fuel + O2  CO2 + H2O
 Incomplete combustion: hydrocarbon fuel + O2  C, CO &/or CO2 + H2O.

Substitution reactions of alkanes (Not Examinable)

In a substitution reaction, one or more of the alkane’s hydrogen atoms is replaced with a different
atom or group of atoms. For alkanes, substitution reactions require high energy ultra-violet (UV)
light to occur. For example, the reaction between ethane and molecular chlorine depicted below is a
substitution reaction:

The product of this reaction is a haloalkane. The attached halogen is an example of a functional
group, the part of a molecule that imparts a specific chemical reactivity. The types of functional
groups present in an organic molecule are major determinants of its chemical properties and are
used as a means of classifying organic compounds.

Alkenes and alkynes

Hydrocarbons containing carbon-carbon double bonds (C=C) or triple bonds (C≡C) are described as
unsaturated because they contain fewer H atoms than their alkane counterpart. The C=C double
bond is called an alkene functional group, and the C≡C triple bond is an alkyne group.

Compounds containing these groups are named in a similar fashion to alkanes, but with the ending
of ‘-ene’ or ‘-yne’, respectively.

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Double and triple bonds also give
rise to a different geometry around
the carbon atom that participates in
them, leading to differences in their
localised molecular shapes.

In carbon chains with 4 or more C atoms, the position of the alkene (or alkyne) group can vary along
the chain, leading to different compounds that are structural isomers because their atoms are
arranged differently. This needs to be distinguished using a numbering system when we name these
compounds: The longest chain containing the alkene group is identified, and the terminal C atom
closest to the alkene group is numbered as C-1. The position of the alkene group is then identified by
the C atom closest to C-1 that is part of the alkene functional group, using a prefix system, as shown
below for 1-butene2 and 2-butene.

It should be noted that the numbering system for branched or substituted alkenes also has C-1 as
the terminal C atom closest to the alkene group.

Check Your Understanding

Name all the structural isomers of alkenes with the molecular formula of C5H10.
Answer

Geometric Isomers of Alkenes (To be revisited in Topic 12)

The compound 2-butene also forms a second type of isomer called a geometric isomer. Whilst
atoms connected by single bonds are able to rotate freely, those connected by double bonds cannot.
This makes it possible to have additional isomers of 2-butene, one with both methyl groups on the
same side of the double bond and one with each methyl group on opposite sides. The isomer in
which the two methyl groups are on the same side is called a cis-isomer; the one in which they are
on opposite sides is called a trans-isomer:

2
This nomenclature can also be written as but-1-ene; but-2-ene; etc.

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 Chemical properties of alkenes
Alkenes are much more reactive than alkanes due to the greater accessibility of electrons in one of
the electron pairs that make up the double bond, often referred to as -bonded electrons. Alkenes
undergo a characteristic reaction in which the π-bond of the C=C group is broken and replaced by
two additional single bonds, one on each of the adjacent C atoms, where incoming substituents
become attached. This reaction is called an addition reaction because two reactants combine to
produce only one product.
It should also be noted that the geometry of the carbon atoms in the double bond in an alkene also
changes from trigonal planar to tetrahedral during an addition reaction. For example, on reaction
with halogens the double bond is broken and the halogens add to the molecule via additional single
bonds that form. The addition reaction between ethene (CH2CH2) and chlorine (Cl2) is shown below:

Distinguishing between alkanes and alkenes (Not Examinable)

Unlike the substitution reaction of an alkane, alkenes react readily with halogens with no need for
high energy UV light. This gives us a useful chemical test to distinguish between alkanes (saturated
hydrocarbons) and alkenes (unsaturated hydrocarbons). Under normal laboratory conditions (i.e. in
the absence of high energy UV light), coloured halogen suspensions (such as orange Br 2(aq) or purple
I2(aq)) are mixed with the hydrocarbon to be tested. If there is no observed change under these
conditions the tested hydrocarbon is saturated. If the mixture becomes decolourised (i.e. becomes
colourless) the tested hydrocarbon is unsaturated.
- Under normal laboratory reaction conditions alkanes do NOT decolourise bromine water:

- Under normal laboratory reaction conditions alkenes readily decolourise bromine water:

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 This video demonstrates the use of bromine water to distinguish between alkenes and
alkanes. It’s relatively old, but I highly recommend it because the presenter gives really
good explanations for all observations made during this test.

https://youtu.be/ZXcS3oY9wQo
(4:28min)

EXAMPLE 5: ALKENE REACTIVITY AND NAMING

Provide the IUPAC names for the organic reactant and product of the reaction shown
below:

Answer
The reactant is a five-carbon chain that contains a carbon-carbon double bond, so the
base name will be pentene. We begin counting at the end of the chain closest to the
double bond - in this case, from the left—the double bond spans carbons 2 and 3, so
the name becomes 2-pentene. Since there are two carbon-containing groups
attached to the two carbon atoms in the double bond—and they are on the same side
of the double bond, this molecule is the cis-isomer, making the name of the starting
alkene cis-2-pentene.
The product of the addition reaction will be an alkane (as the double bond is broken)
with a chlorine atom attached to each of the adjacent carbon atoms that were a part
of the C=C double bond, i.e. a ‘dichloro’ alkane. The name of this product, following
IUPAC nomenclature is given below:

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 Check Your Understanding
Provide names for the organic reactant and product of the reaction shown:

Answer

Chemical properties of alkynes

The chemical properties of alkynes are like that of alkenes except the alkyne functional group has
two  bonds that readily undergo addition reactions. Depending on the amount of reactant
available, a single addition step will occur to produce a di-substituted alkene, or a complete addition
reaction will occur to produce a tetra-substituted alkane. For example:

Check Your Understanding

Provide the IUPAC names for the organic reactant and product for the reactions shown :

Answer

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Aromatic Hydrocarbons (NOT EXAMINABLE)
Benzene, C6H6, is the simplest member of a large family of hydrocarbons called aromatic
hydrocarbons. The term aromatic was originally given to these compounds because they mostly
exhibited characteristic odours.
Benzene has a 6-membered hexagonal ring structure and a formula that suggests
alternating double and single bonds within this structure. Benzene does not, however,
exhibit the characteristics typical of an alkene: It does NOT undergo addition reactions
at all. In fact, benzene is a very stable molecule that does not undergo any reaction
readily.
Benzene is so unreactive that it used to be used as a solvent for organic reactions – its non-polar
nature meant that it could readily dissolve other non-polar substances; it’s high stability meant it
would not react with them. Benzene use has been largely phased out, however, because it is toxic
and has been shown to be carcinogenic (cancer causing).
Benzene’s lack of chemical reactivity suggests that, unlike alkenes, the -electrons of the alternating
double bonds are not easily accessible for reaction:
 One theory to describe the stability of
the benzene ring proposes that the -
electrons of the double bonds move
rapidly between adjacent carbon
atoms (see diagram to the right). It is
proposed that the rapidly shifting
location of these electrons lowers
their accessibility for reaction, leading to
an unusually high degree of stability often
referred to as ‘resonance stabilisation’.
 Another proposal suggests that benzene does not contain C=C bonds at all,
but rather the 6 -electrons become delocalised among all 6 C atoms of the
ring, reducing their accessibility for reaction. Benzene is often represented by
the line structure on the left to show that the 6 -electrons are delocalised
within the ring structure and are not chemically reactive.

It is not necessary in this unit to describe why benzene is unusually stable, but it is important to
recognise that it is. Benzene does NOT undergo addition reactions.
The only chemical reactivity it has involves combustion reactions (like all other organic compounds)
or substitution reactions whereby the outer H atoms of the ring are replaced by other substituents.
Because of benzene’s high stability, its substitution reactions require very high energy, extremely
reactive electrophiles (the source of the incoming substituent), and/or catalysts to facilitate them.

Aromatic rings (benzene) are very unreactive. They do NOT undergo addition reactions. The
only reactions they can undergo is combustion or substitution reactions. Like alkanes,
substitution reactions for benzene require very specific reaction conditions.

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KEY CONCEPTS AND SUMMARY
Strong, stable bonds between carbon atoms produce complex molecules containing chains,
branches, and rings. The chemistry of these compounds is called organic chemistry. Hydrocarbons
are organic compounds composed of only carbon and hydrogen.
A homologous series consists of compounds that have the same functional group but differ in the
size of their carbon chain. As such, members of a homologous series have similar chemical
properties. Their physical properties change, however, with the larger members being more
influenced by the non-polar hydrocarbon chains. This leads to increasing non-polar properties and
stronger dispersion forces between molecules.
The alkanes are saturated hydrocarbons—that is, hydrocarbons that contain only single bonds. The
molecular shape around each C atom is tetrahedral, but sketches commonly used to represent these
molecules are usually simplified and do not show the true 3-D arrangement. Alkenes contain one or
more carbon-carbon double bonds, with a trigonal planar bonding arrangement around the C atoms
in the C=C bond. Alkynes contain one or more carbon-carbon triple bonds, with a linear arrangement
around the C atoms in the C≡C bond. Aromatic hydrocarbons contain ring structures with unreactive
delocalized π electron systems. Due to the trigonal planar bonding arrangement of each aromatic C
atom, these rings are flat hexagonal rings.
All hydrocarbons undergo combustion reactions. Otherwise alkanes are relatively stable and require
high energy (e.g. as UV light) to react. When reacted they undergo substitution reactions.
Alkenes and alkynes readily undergo addition reactions across the C=C double or C≡C triple bonds.
Benzene is very stable and does not readily react. Like alkanes, benzene can react under high energy
or catalytic conditions. When reacted the type of reaction that occurs is a substitution reaction that
replaces a ring H atom with a different substituent. The benzene ring itself remains intact.

Glossary
addition reaction: reactions of alkenes and alkynes where two reactants combine to form one
product. The double bond is broken and replaced by 2 single bonds that allow incoming atoms to
become bonded to the organic reactant
alicyclic hydrocarbon: molecule consisting of only carbon and hydrogen atoms that contains ring, or
cyclic structures (that are not aromatic in nature, see below)
aliphatic hydrocarbon: molecule consisting of only carbon and hydrogen atoms arranged in chains
or branched chains
alkane: saturated hydrocarbons. Alkanes contain C and H atoms, with only single bonds between
adjacent C atoms
alkene: organic molecule containing at least one carbon-carbon double bond
alkyl group: branched alkane-like substituent attached to a larger structure
alkyne: organic molecule containing at least one carbon-carbon triple bond
aromatic hydrocarbon: cyclic molecule consisting of a benzene ring (6 carbon and hydrogen atoms
with alternating carbon-carbon single and double bonds). The benzene group has an unusually high
stability and does not react readily

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complete combustion: the reaction of an organic molecule with oxygen gas to form only carbon
dioxide gas and water as its products. Heat energy is also produced, making combustion reactions an
excellent source of energy

Page 16 of 20
functional group: part of an organic molecule that exhibits a specific chemical reactivity
geometric isomers: isomers of alkenes where substituents on the alkene group are located either on
the same side of the C=C double bond (cis) or opposite sides of the C=C bond (trans)
homologous series: a family of molecules that each have the same functional group and thus have
similar chemical properties. Each successive member differs only by the length of its carbon chain
hydrocarbon: non-polar organic molecules consisting of only C and H atoms.
incomplete combustion: the reaction of an organic molecule with insufficient oxygen gas for
complete combustion. A range of products can form, including water, CO2(g), CO(g), &/or C(s)
saturated hydrocarbon: molecule containing carbon and hydrogen that has only single bonds
between carbon atoms
skeletal or line structure: shorthand method of drawing organic molecules in which carbon atoms
are represented by the ends of lines and junctures between lines, and hydrogen atoms attached to
the carbon atoms are not shown (but are understood to be present by the context of the structure)
structural isomers: molecules that have the same molecular formula but different structural formula
as the arrangement of their atoms differ
substituent: branch or functional group that replaces hydrogen atoms in a larger hydrocarbon chain
substitution reaction: reaction in which one atom replaces another in a molecule. Substitution
reactions occur for alkanes but require high energy UV-light. They can also occur for aromatic
hydrocarbons under very specific reaction conditions
unsaturated hydrocarbon: molecule containing carbon and hydrogen that has at least one double
and/or triple bond between carbon atoms

Attributions
Parts of this document are adapted from https://courses.lumenlearning.com/chemistryformajors/

Page 17 of 20
Practice Problems
1. Give the molecular formula, condensed structural formula, structural formula and line
drawings for a hydrocarbon belonging to each of the following homologous series that
contains 5 carbon atoms.
a. an alkane
b. an alkene
c. an alkyne
2. What is the difference between the localised shape around the central carbon in saturated
hydrocarbons and the functional groups of unsaturated hydrocarbons?
3. How does the reaction of bromine with a saturated hydrocarbon differ from its reaction with
an unsaturated hydrocarbon?
4. How does the reaction of bromine with an alkyne differ from its reaction with an alkene?
5. Explain why alkenes can form geometric isomers while alkanes cannot.
6. Explain why the following two molecules are not isomers:

7. Explain why the following two molecules are not isomers:

8. Write the molecular formula and draw structural formula for each of the following
hydrocarbons:
a. hexane
b. 3-methylpentane
c. cis-3-hexene
d. 4-methyl-1-pentene
e. 3-hexyne
f. 4-methyl-2-pentyne

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 9. Give the IUPAC name for each of the following compounds:
a. CH3CH2CBr2CH3
b. C(CH3)3Cl
c.

d. CH3CH2C≡CH
e.

f. CH3CH(CH3)CH2CH=CH2
10. Butane is used as a fuel in disposable lighters. Draw structural formulae and write the IUPAC
name for each isomer of butane.
11. Draw the structures and write the IUPAC name for each geometric isomer of CH3CH=CHCl.
12. Draw structures for the three isomers of the aromatic hydrocarbon xylene, C6H4(CH3)2.
13. Isooctane (drawn below) is the common name of the isomer of C8H18 used as the standard of
100 for the octane rating for petrol.

a. What is the IUPAC name for the compound?

b. Write a balanced equation for the complete combustion of isooctane.
c. Write a balanced equation for an incomplete combustion of isooctane.
14. Draw structures and write IUPAC names for the alkyne isomers of C4H6.
15. Draw the structural formula and describe the molecular geometry at each carbon atom in the
following compounds:
a. cis-3-hexene
b. cis-2-bromo-1-chloroethene
c. 2-pentyne
d. trans–6-ethyl-7-methyl-2-octene
16. Teflon is prepared by the polymerization of tetrafluoroethene.
a. Write a balanced equation for the production of tetrafluoroethene from
difluoroethyne and molecular fluorine.
b. What is the name given for the type of reaction described above?

Page 19 of 20
 17. Write balanced equations for each of the following reactions:
a. 1 mol of 1-butyne reacts with 2 mol of iodine.
b. Pentane is burned in air (assume complete combustion).
18. What mass of 2-bromopropane could be prepared from 25.5 g of propene? Assume a 100%
yield of product.
19. Ethene can be produced by the pyrolysis of ethane:
C2H6 → C2H4 + H2.
a. How many kilograms of ethene is produced by the complete pyrolysis of 1.0 × 103 kg
of ethane?
b. Both ethene and ethane can be reacted with bromine (Br2), but the reactions are very
different in nature. Write an equation to show each of these reactions and give the
IUPAC names for the organic product(s). Also describe any special reactions conditions
required and give the name for the type of reaction involved in each case.
20. Ethanol can be produced synthetically by reaction of ethene with water in the presence of a
catalyst:
H2C=CH2 + H2O  CH3CH2OH
What is the name given to this type of reaction involving the alkene functional group?

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