Chem 30 Unit A PDF

Chemistry 30
Student Module Book

Unit A: Organic Chemistry
Module 1 : Structure and Properties of Hydrocarbons

Module 2 : Organic Reactions of Hydrocarbons and
Hydrocarbon Derivatives
Table of Contents

Introduction................................................................................................................................................ i
Module 1: Structure and Properties of Hydrocarbons.............................................................................. 1
Module 2: Organic Reactions of Hydrocarbons and Hydrocarbon Derivatives...................................... 43
Appendix................................................................................................................................................. 97
Glossary................................................................................................................................................ 121
ADLC | Chemistry 30 Unit A – Introduction
Unit A
Organic Chemistry
Introduction
Organic chemistry is a major branch of chemistry that deals with the study of organic compounds. In
the early study of chemistry, organic compounds were defined as only those compounds produced
by living things (hence the name “organic”). Today, however, we regard organic chemistry to be the
chemistry of carbon and its compounds. This definition includes carbon compounds produced by
living things and carbon compounds that are manufactured, such as plastics. Realize, however, that
most manufactured carbon compounds are derived from fossil fuels. Recall from previous courses that
fossil fuels resulted from decaying plant and animal matter (that is, previously living matter).
pumpjack organic molecule plastics
Unit A consists of two modules:
Module 1 Module 2
Organic Reactions
Structure and Properties of
of Hydrocarbons and
Hydrocarbons
i
Unit A – Introduction ADLC | Chemistry 30
Key Concepts
Organic molecules are carbon-containing compounds.
Organic molecules that contain only carbon and hydrogen are known as hydrocarbons. Examples are
shown below.
methane ethane
Other organic compounds contain atoms in addition to

carbon and hydrogen. These compounds are known
as hydrocarbon derivatives. As an example, study the
hydrocarbon derivative shown below. In addition to carbon
and hydrogen, notice the oxygen atoms. Hydrocarbon
derivatives can also contain other atoms such as halogen
atoms, sulfur and nitrogen (for example). You will learn much
more about hydrocarbon derivatives in Module 2.
hydrocarbon derivative
You should be aware that some carbon-containing compounds are not considered to be organic. It is
best to commit the names of these inorganic compounds to memory:
oxides, such as CO ^g h and CO2 ^g h
ionic compounds of carbon, such as those that contain carbonate, cyanide, and carbide ions
i.e. K2 CO3 ] s g , LiCN ] s g , and Be2 C ] s g
ii
ADLC | Chemistry 30 Unit A – Introduction
Check Your Understanding
Can you identify organic compounds? Complete Section 9.1, Question 1 on page 361 of the textbook,
Nelson Chemistry. Check your work with the solutions provided in the Appendix.
Virtual Investigation
1. Log in to your Chemistry 30 course in Moodle.
2. Click on Virtual Investigations.
3. Choose “Properties of Organic and Inorganic Compounds.” You will find it under Unit A.
Answer associated questions in your Module 1 Summative Assessment.
iii
ADLC | Chemistry 30 Unit A – Module 1
Module 1
Structure and Properties of Hydrocarbons
Introduction
You learned in the Unit A Introduction that one broad category of organic compounds is made up
entirely of molecules that contain only carbon and hydrogen atoms. We refer to these molecules as
hydrocarbons. Some common examples of hydrocarbons include the following:
natural gas mothballs gasoline
Hydrocarbons are classified as either aliphatic or aromatic. In Module 1, you will investigate the
structures and properties of these two main classes of hydrocarbons. You will also learn about the
extraction, refining, modification, and manipulation of naturally occurring hydrocarbon molecules.
Module 1 contains three lessons:
Lesson 1 Aliphatic Hydrocarbons

Lesson 2 Aromatic Hydrocarbons
Lesson 3 Hydrocarbons and Alberta’s Oil and Gas Industry
1
Unit A – Module 1 ADLC | Chemistry 30
Lesson 1
Aliphatic Hydrocarbons
Introduction
The aliphatic hydrocarbons are a broad class of hydrocarbons including alkanes, alkenes, and alkynes.
Some of these structures are straight chains, some are branched, and some are cyclical.
Aliphatic hydrocarbons can be divided into two main groups: saturated and unsaturated.
Saturated hydrocarbons contain only carbon-carbon single covalent bonds with the maximum
number of hydrogen atoms bound to each carbon. The alkanes are saturated hydrocarbons.
Unsaturated hydrocarbons contain carbon-carbon double or triple covalent bonds. This group
includes the alkenes and the alkynes. These compounds have fewer hydrogen atoms than
compounds with carbon-carbon single bonds.
Saturated Hydrocarbons Unsaturated Hydrocarbons
Alkanes Alkenes and Alkynes
2
Lesson 1.1
Introducing the Alkanes
Key Concepts
The alkanes are a class of hydrocarbons that contain only single bonds. Because they contain single
bonds only, alkanes are classified as “saturated”.
A homologous series is a progression of organic compounds that differ only in the number of repeating
units.
Log in to your Moodle course and click on Animations. Under Unit A, choose “Alkanes”.
In the homologous series shown in the animation, each alkane has one more CH2
group than the preceding alkane. Keep clicking on the green arrow to see the various
compounds included in this homologous series.
Study the following table displaying the first ten alkanes.
IUPAC Name Molecular Formula

methane CH4 ^g h
ethane C 2 H 6 ^g h
propane C 3 H 8 ^g h
Learning Tip:
butane C4 H10 ^g h The molecular formula shows the number of
pentane C5 H12 ] l g each type of atom in a compound.
hexane C6 H14 ] l g The prefixes indicating one to ten carbon

C 7 H16 ] l g
heptane atoms (shown in red) are the same for all
hydrocarbons. Commit them to memory!
octane C8 H18 ] l g
nonane C 9 H20 ] l g
decane C10 H22 ] l g
3
Did you notice a pattern between the number of carbon atoms and the number of hydrogen atoms?
The general formula for an alkane is C n H2n + 2 . Knowing this pattern can help you identify the family to
which a hydrocarbon belongs. This is quite handy for large molecules. For example, is the compound
with the molecular formula C17 H36 an alkane? The answer is yes!
Note that some alkanes form cyclical structures called cycloalkanes. In these structures, the carbon
chain forms a closed ring. Study the examples below depicting cyclopentane and cyclohexane. Count
the carbons and hydrogens in each molecule. What do you notice about these molecular formulae?
Do they fit the regular pattern for alkanes?
H H
H H
C C
CH2
CH2 CH2 H H
C C
H H
CH2 CH2
C C
H H
H H
cyclopentane cyclohexane
Although these compounds are classified as saturated, they have a different general formula than
other alkanes. Instead of C n H2n + 2 , they have the general formula C n H2n . Can you see why the general
formula of cycloalkanes shows two less hydrogen per molecule?
Read pages 366 to 367 in your textbook, Nelson Chemistry.
4
Lesson 1.2
Naming the Alkanes
Key Concepts
When you are provided with a diagram of an organic molecule, you have to be able to name it
correctly. Three types of diagrams are used to represent organic molecules - structural, condensed
structural, and line.
For example, study the illustrations below. All three diagrams depict hexane ]C 6 H14g.
A structural diagram shows all carbon and hydrogen atoms and all bonds.
H H H H H H
H C C C C C C H
H H H H H H
hexane
A condensed structural diagram shows all carbon and hydrogen atoms and all carbon-carbon
bonds. However, it does not show carbon-hydrogen bonds.
Learning Tip
CH3 CH2 CH2 CH2 CH2 CH3 Longer hydrocarbon chains can be
condensed further by combining
hexane
the repeating units, such as
CH3- ]CH2g4- CH3
A line diagram shows only carbon-carbon bonds. The intersections and ends of the line drawing
indicate carbon atoms.
2 4 6
1 3 5
hexane
5
I. Naming Unbranched Alkanes and/or Cycloalkanes
A diagram of an unbranched alkane is quite straightforward to name. Just follow these steps:
1. Count the number of carbons in the chain or ring.
2. Choose the appropriate prefix from the table shown in the section “Introducing the
Alkanes”. Remember that the prefix corresponds to the number of carbon atoms.
3. Add the suffix “ane”.
4. If the alkane is in a closed ring, add the prefix “cyclo” to the front of the name.
CH2
H H H H H H H H
CH2 CH2
H C C C C C C C C H
H H H H H H H H CH2 CH2
octane cyclopentane

Watch
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “Naming
Unbranched Alkanes and Cyckloalkanes.”
6
II. Naming Branched Alkanes and/or Cycloalkanes
The ability of a carbon atom to form four bonds allows for branching along the length of a
hydrocarbon molecule. An alkyl branch is not part of the parent chain and contains only
singly-bonded carbon and hydrogen atoms.
Naming branched alkanes is trickier than naming unbranched alkanes! Fortunately, the
IUPAC (International Union of Pure and Applied Chemists) has set standards relating to organic
nomenclature.
To name branched alkanes, follow the steps below:
1. Identify the longest continuous chain of carbon atoms. This is the parent chain (also
referred to as the main chain).
2. Number the carbon atoms in the parent chain such that the branches have the lowest set
of numbers. The lowest set of numbers is defined by IUPAC as being the set that starts
with the lowest number. If you are comparing two sets of numbers and both sets start with
the same number, compare the second numbers in the sets. Start numbering the longest
continuous chain from the end with the closest branch!
3. Identify any alkyl branches. Count the number of carbon atoms in the branch, use the
appropriate prefix, and add the ending yl (methyl, ethyl, propyl, etc.). List the alkyl branches
in alphabetical order.
4. Indicate the locations of the alkyl branches using numbers. If there is more than one branch
of the same type, use additional prefixes di, tri, etc. Please note that these additional
prefixes do not affect the alphabetical order of the branches.
5. When naming a branched cycloalkane, keep the following in mind:
Because the cyclic structure is the parent chain, the prefix “cyclo” is placed in front of
the alkane name.
Number the branches in order to obtain the lowest possible carbon numbers. Begin
with the location of one of the branches.
If there is only one branch present, omit the “1” from the name.
Watch
Branched Alkanes and Cycloalkanes”.
7
Examples of Branched Alkanes and Cycloalkanes
Diagram of Molecule IUPAC Name
CH3
2-methylpentane
CH3 CH2 CH2 CH CH3
CH3
CH3 CH2 CH2 CH CH3 2,2-dimethylbutane
CH3
CH3
CH2
CH3 CH2
CH3 CH2 C C CH2 CH3 3,4-diethyl-3-methyl-4-propylheptane
CH2 CH2
CH3 CH2
CH3
1-ethyl-3-methylcyclopentane
Read pages 367 to 372 of the textbook, Nelson Chemistry, giving close attention to the
sample problems and communication examples.
8
Go to your textbook, Nelson Chemistry, and complete Practice Questions 9 and 11 on page 371 and
Section 9.2 Question 6 on page 373. Check your work with the answers provided in the Appendix.
9
Lesson 1.3
Drawing the Alkanes
Key Concepts
You have been studying how to name various types of alkanes when provided with diagrams.
However, you also need to know how to diagram the molecule when provided with only its name or
molecular formula.
Drawing an unbranched alkane (“straight chain”) is quite straightforward. The name of the parent chain
indicates the number of carbons in the molecule. Simply draw a straight chain containing the correct
number of carbon atoms. Next, add sufficient hydrogen atoms to provide each carbon with four single
bonds.
Drawing branched alkanes can be more difficult.
To draw a branched alkane, follow these steps:
1. Study the name of the molecule. How many carbons are contained in the parent chain? Draw a
straight chain containing this number of carbons.
2. Number the carbons from left to right.
3. Draw in the alkyl branches, attaching them to their numbered locations on the parent chain (as
stipulated in the molecule’s name).
4. Add hydrogen atoms to give each carbon four single bonds.
5. When drawing a cycloalkane, connect the parent chain into a continuous loop. See
Communication Example 3 on page 372 of your textbook, Nelson Chemistry.
Watch
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “Drawing
Unbranched/Branched Alkanes and Cyckloalkanes”.
10
Read pages 369 to 371 in the textbook, Nelson Chemistry, paying special attention to
the sample problems and communication examples.
Go to your textbook, Nelson Chemistry, and complete Practice Questions 7 (a to g) and 10 on

pages 370 and 371 and Section 9.2 Question 5 on page 373. Check your work with the solutions
provided in the Appendix.
11
Lesson 1.4
Structural Isomerism in Alkanes
Key Concepts
If you are drawing methane, ethane, or propane, you probably noticed that the carbon and hydrogen
atoms can be arranged in only one way.
H H H H H H
H C H H C C H H C C C H
H H H H H H
methane ethane propane
What about drawing diagrams for larger organic molecules? For example, consider the molecular
formula C4 H10 . What would your diagram look like?
Perhaps you would draw this:
H H H H
H C C C C H
H H H H
butane
Does the following structural diagram also represent C4 H10 ? Count the number of carbon atoms and
hydrogen atoms.
H C H
H H
H C C C H
H H H
2-methylpropane
12
The compounds shown above have quite different structures although they have the same molecular
formula. Each structure is named differently and is considered a different entity. Chemists refer to
these compounds as structural isomers.
Because structural isomers have differing structures, they have different physical and chemical
properties. For example, a branched alkane has a lower boiling point than the corresponding straight
chain alkane does. Why does branching decrease boiling point?
Branching decreases boiling point because branched chains are shorter and fatter than straight
chains. The “bulky” branched molecules cannot lie as close together as can long, thin straight chain
alkanes. Therefore, the intermolecular forces between the branched isomers are not as strong. Recall
from Chemistry 20 that London dispersion forces are formed as a result of the attraction between the
positively charged atomic nuclei and negatively charged electrons of a neighbouring molecule. The
further away the neighbouring molecule is, the weaker the London dispersion forces.
To see how the boiling points of structural isomers can differ, log in to your Moodle
course and click on Animations. Under Unit A, choose “Alkanes in crude oil.”
Read pages 366 to 368 in the textbook, Nelson Chemistry, to learn more about the
rules for naming and drawing structural isomers.
Complete Section 9.2 Question 7 on page 373 in the textbook, Nelson Chemistry. Check your answers
with the solutions provided in the Appendix.
13
Lesson 1.5
Introducing the Alkenes and Alkynes
Key Concepts
The alkenes and alkynes are hydrocarbons that contain double or triple covalent bonds, respectively.
The presence of a double or triple bond has a direct effect on the chemical and physical properties of
these hydrocarbons.
Because of the double or triple bond, alkenes and alkynes have less hydrogen atoms than
alkanes.
Empirical evidence has demonstrated that alkenes and alkynes are much more reactive than
alkanes. You will look much more closely at this in Module 2.
Alkenes and alkynes occur in low quantities in crude oil and natural gas, but they are very important
because they represent the starting materials for many hydrocarbon derivatives (which you will study
in Module 2). Because they exist only naturally in small quantities, alkenes and alkynes are often
manufactured during chemical refining processes.
The alkenes contain at least one double bond. Alkenes possess the general formula C n H2n . Alkenes
have less hydrogen atoms per carbon than alkanes. This is because a double bond requires two pairs
of electrons.
For example, consider ethene, the simplest alkene.
Ethene ]C2 H4g only contains four hydrogen atoms. Therefore in order for each carbon to still form four
bonds, each carbon must bond to two hydrogen atoms and form a double bond with the other carbon
atom.
H C C H
H H
ethene
Note that some alkenes form closed rings. In this case, the molecules are known as cycloalkenes
and have the general formula C 2 H2n - 2 . Compared to the straight chain alkenes, the cycloalkenes do
not have as many hydrogen atoms per carbon atom. This is due to the ring structure. For example,
consider the structure of cyclohexene shown on the following page.
14
H H
H H
C
H C C
H C C
C
H H
H H
cyclohexene
Count the carbons and hydrogens in the molecule. Notice that the compound reflects the general
formula C 2 H2n - 2 .
The alkynes contain at least one triple bond. Alkynes possess the general formula C n H2n - 2 . Alkynes
have less hydrogen atoms per carbon than alkenes. This is because a triple bond is composed of
three pairs of electrons.
For example, consider ethyne ]C2 H2g, the simplest alkyne.
H C C H
ethyne
Ethyne only contains two hydrogen atoms. Therefore, in order for each carbon to still form four bonds,
each carbon atom must bond to one hydrogen atom and form a triple bond with the other carbon
atom.
Note that some alkynes form closed rings. In this case, the molecules are known as cycloalkynes and
have the general formula C 2 H2n - 4 . Compared to the straight chain alkynes, the cycloalkynes do not
have as many hydrogens per carbon atom. This is due to the ring structure. For example, consider
the structure of cyclooctyne shown below. Count the carbons and the hydrogens in the molecule.
Remember that each carbon can only form four bonds. You will see that the compound reflects the
general formula, C 2 H2n - 4 .
cyclooctyne
Because alkenes and alkynes have fewer hydrogen atoms attached than alkanes, these molecules are
classified as unsaturated.
15
Read pages 374 to 377 in the textbook, Nelson Chemistry, to learn more about the
structure of alkenes/alkynes, including cycloalkenes and cycloalkynes.
Go to your textbook, Nelson Chemistry, and complete Practice Question 1 on page 377. Check your
answers with the solutions provided in the Appendix.
16
Lesson 1.6
Naming the Alkenes and Alkynes
Key Concepts
As was the case for alkanes, three types of diagrams can be used to depict the structure of alkanes
and alkenes: structural diagrams, condensed structural diagrams, and line diagrams. You may be
given any of these three types of diagrams and asked to assign an IUPAC name to an alkene or
alkyne.
To name alkenes and alkynes:
1. Beginning at the end closest to the multiple bond, number the longest chain of carbons
(otherwise known as the “parent chain”). This will give the multiple bond the lowest possible
number.
H H H H H
Learning Tip:
C1 C2 C3 C4 C5 H When naming branched

alkenes/alkynes, the
position of the double
bond takes priority,
H H H H not the location of the
pent-1-ene branches.
H H H H H
H C5 C4 C3 C2 C1
H H H H
pent-1-ene
2. Determine the appropriate prefix to use in the name, based on the number of carbons in the
parent chain. You will use the same prefixes that are used to name the alkanes. If you have
forgotten what these prefixes are, refer back to Table 3 on page 366 of your textbook, Nelson
Chemistry. The prefixes are shown in red.
17
3. The ending of the name will be “ene” if there is a double bond or “yne” if there is a triple bond.
H H H
H C C C C C H
H H H H H
pent-2-ene
H H H H H
H C C C C C C C H
H H H H H
hept-2-yne
4. Next, identify the type and location of each branch. List the branches in alphabetical order.
5. Now, write the IUPAC name using this format:
(Branch location) – (branch name)(prefix) – (multiple bond location) – ene/yne
6. If the alkene or alkyne is in a closed ring, add “cyclo” to the front of the parent chain name.
Remember that the double or triple bond should be assigned the lowest carbon number. In
other words, the carbons of the multiple bond in the cyclical structure automatically become
carbons 1 and 2. Finally, number any branches to give them the lowest possible carbon
numbers.
Watch
Alkenes and Alkynes.”
18
Examples of Organic Compounds Containing Multiple Bonds

H H H
H
H C C C C
H 3-methylbut-1-ene
H
H C H
CH3 CH2 CH3

C C 3-methylpent-2-ene
CH3 H
hex-1-yne
3-methylcyclohexene
Complete Practice Questions 4 and 5 on page 377 of the textbook, Nelson Chemistry. Check your
work with the answers provided in the Appendix.
19
Lesson 1.7
Drawing the Alkenes and Alkynes
Key Concepts
To draw alkenes and alkynes:
1. Study the molecule’s name to determine the number of carbon atoms in the parent chain. Draw
the parent chain.
2. Next, number the parent chain from left to right. Then, use the number in front of the ending
to locate the proper position for the multiple bond. If the name ends in “ene”, the molecule
contains a double bond. If the name ends in “yne”, the molecule contains a triple bond.
3. Add the branches listed in the name of the molecule.
4. Add hydrogen atoms to give each carbon atom four bonds.
Watch
Alkenes and Alkynes”.
Go to your textbook, Nelson Chemistry, and complete Practice Questions 2 and 3 on page 377. Check
your work with the answers provided in the Appendix.
20
Lesson 1.8
Isomers of Alkenes and Alkynes
Key Concepts
You will recall from your study of alkanes that a structural isomer is a compound with the same
molecular formula but a different structure. Alkenes and alkynes can form structural isomers, also. For
example, if the multiple bond changes position, an isomer is produced.
H H H H H H H
H C C C C C H H C C C C C H
H H H H H H H H H
pent-2-ene, C5 H10 pent-1-ene, C5 H10
Similarly, an isomer is also produced if a straight chain hydrocarbon is changed into a branched
hydrocarbon or a cyclic hydrocarbon. All the isomers of a molecule have the same number of carbons
and the same number of hydrogens. However, the atoms are arranged differently. Refer to page 377 in
your textbook, Nelson Chemistry.
H H
H
H H
H
H C H
C C C C
H
C H H H
H H C C C
H C
H H H
H
H C C
hex-1-ene, C6 H12
H H
H H
cyclohexane, C6 H12
Hex-1-ene and cyclohexane both have the same molecular formulae (same number of carbon atoms
and hydrogen atoms). Therefore, they are isomers of one another.
21
H H H H
H C C C C C C H
H H H H
hex-1-yne, C6 H10
H H
H H
C
H C C
H C C
C
H H
H H
cyclohexene, C6 H10
Study the two diagrams above. Hex-1-yne and cyclohexene have the same molecular formulae (same
number of carbon atoms and hydrogen atoms). Therefore, they are isomers of one another.
Learning Tip:
Alkenes and cycloalkanes that have the same number of carbons and hydrogens are isomers
of one another. Similarly, alkynes and cycloalkenes that have the same number of carbons and
hydrogens are isomers of one another.
22
Watch
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “Structural
Isomers of Alkenes and Alkynes”.
Go to your textbook, Nelson Chemistry, and complete Section 9.3 Questions 2 and 5 on page 380.
Check your answers with the solutions provided in the Appendix.
Lesson Assignment
Log in to your Chemistry 30 course in Moodle and click on Autograded Lesson
Assignments. Complete the Module 1 Lesson 1 Assignment online.
23
Lesson 2
Aromatic Hydrocarbons
Introduction
Aromatic hydrocarbons are defined as benzene and all compounds that contain a benzene ring.
Benzene and other aromatic compounds are found naturally in crude oil and natural gas and can be
separated during the refining process. Benzene can be formed during the incomplete combustion of
organic materials. Despite its link to cancer, benzene is used in many chemical processes. Below are
images of some everyday products that contain aromatic hydrocarbons.
aspirin TNT vanillin
24
Lesson 2.1
Introducing Benzene
Key Concepts
The molecular formula for benzene is C 6 H 6 , but its structural diagram is much more complex. In
fact, the unique structure of benzene puzzled scientists for years because the molecule displayed
properties that were very difficult to explain. For example, benzene has a relatively high melting point
and boiling point and demonstrates chemical reactions similar to an alkane.
X-ray diffraction demonstrates that benzene’s carbon-carbon bond lengths are all the same; however,
they are neither single nor double bonds. In other words, six unbonded electrons are shared equally
around a ring structure.
Learning Tip:
Aromatic compounds are not classified as either saturated or
unsaturated.
The inner circle in the diagram above illustrates that there are not three specific double bond locations;
rather, the six valence electrons appear to be shared equally among the six carbon atoms. Although
the above diagram of benzene is the most widely used, sometimes you will see benzene depicted in a
manner that shows the carbon and hydrogen atoms.
Read through pages 381 and 382 in your textbook, Nelson Chemistry, to learn more
about the evidence that eventually led to the development of a structure that accurately
represented benzene. Study Figure 2 at the bottom of page 381 in your textbook,
Nelson Chemistry. You will see how models of benzene evolved over the years until
scientists arrived eventually at the line structural diagram shown above.
Log in to your Moodle course and click on Animations. Under Unit A, choose
“Benzene.”
25
Go to your textbook, Nelson Chemistry, and complete Section 9.4 Questions 1, 7, 8, and 9 on page
385. Check your answers with the solutions provided in the Appendix.
26
Lesson 2.2
Naming Aromatic Compounds
Key Concepts
To name aromatic hydrocarbons:
1. When naming branched aromatics, consider the benzene ring to be the parent chain (unless
the benzene ring is attached to a larger molecule).
2. If you have more than one alkyl branch attached, they are listed in alphabetical order. Always
number the benzene ring so that the branch numbers are the lowest possible. (In other words,
you will always have a branch numbered 1). If you have a choice between two sets of lowest
numbers, choose the set that is in both numerical and alphabetical order. Refer to
Sample Problem 9.3 on page 383 of your textbook, Nelson Chemistry.
3. If there is a benzene ring attached to a larger molecule (usually one that contains four or
more carbon atoms), the larger molecule is considered to be the parent chain and benzene is
considered to be the branch. In these cases, benzene is referred to as a phenyl branch.
Watch
Aromatic Compounds”.
Read the section “Naming Aromatics” on pages 382 and 383 in the textbook, Nelson
Chemistry. For practice naming aromatics, refer to the Communication Example on
page 383 of your textbook, Nelson Chemistry.
27
Examples of Aromatic Compounds

CH3
methylbenzene (toluene)
The molecular formula of this compound is C 7 H8 . Recall that the

molecular formula of benzene is C 6 H 6 . Therefore, for every alkyl
branch substituted onto a benzene ring, a hydrogen atom must
be removed!
1-ethyl-3-methylbenzene
2-methyl-3-phenylbutane
Go to your textbook, Nelson Chemistry, and complete Section 9.4 Question 5 on page 385. Check
your answers with the solutions provided in the Appendix.
28
Lesson 2.3
Drawing Aromatic Compounds
Key Concepts
To draw aromatic hydrocarbons…
1. When drawing a structural formula from a name, first look at the ending of the name to
determine if the parent chain is benzene or an aliphatic compound. Draw the parent chain first.
2. Number the carbons on the parent chain such that the branches fall on the lowest carbon
numbers. If the parent chain is a benzene ring, number the carbons such that the branches
have the lowest possible numbers. Note that the branch that is first alphabetically should be
placed at carbon 1.
Watch
Aromatic Compounds”.
Read the section on drawing aromatics in the textbook, Nelson Chemistry. The section
begins at the bottom of page 382.
29
Go to your textbook, Nelson Chemistry, and complete Section 9.4 Questions 2, 3, and 6 on page 385.
Module 1 – Lesson 2 Assignment

Important!
When entering names for the organic compounds, be very careful not to introduce any
spaces, commas, or dashes that do not belong. If you do, the computer will mark your
answer as incorrect!
30
Lesson 3
Hydrocarbons and Alberta’s Oil/Gas Industry
Introduction
There are six main raw sources of hydrocarbons: natural gas, coalbed methane, crude oil, heavy oil,
oil sands, and coal. These naturally occurring hydrocarbons are known as “fossil fuels”. You probably
recall from previous courses that fossil fuels are formed from the accumulated remains of previously
living plants/animals. Besides being burned to produce heat and energy, these hydrocarbons are also
used to synthesize vast numbers of organic compounds, such as specific fuels, plastics, and synthetic
fibres.
gas plant, west of Calgary Alberta oil sand refinery pumpjack, near Calgary
Alberta has an abundance of fossil fuels. Refer to Figure 2 on page 359 of the textbook, Nelson
Chemistry, to see a map depicting the fossil fuel reserves in our province. This abundance drives
Alberta’s economy and is at the core of many industries in Alberta, especially the petroleum industry.
Petroleum is a mixture of hydrocarbons obtained from oil or natural gas. The petroleum industry is
focused on locating, extracting, and refining these natural resources.
In this section of Module 1, you will explore Alberta’s oil and gas industries and look more closely
at the physical, chemical, and technological processes used to separate organic compounds from
natural mixtures of hydrocarbons. In addition, you will examine the effect of the petroleum industry on
the environment.
31
Lesson 3.1
Natural Gas
Key Concepts
Natural gas is a rich source of hydrocarbon molecules. Refineries, such as the one pictured in the
photograph below, separate components of natural gas. The refining of natural gas in Alberta occurs
at more than 800 gas plants.
natural gas refinery, Southern Alberta
Read pages 362 and 363 in the textbook, Nelson Chemistry, to learn more about the
composition and refinement of natural gas. Note that some steps in the refinement
process involve chemical reactions and some steps involve physical changes.
Go to your textbook, Nelson Chemistry, and complete Section 9.2 Questions 1, 2, 3, 4, and 10(a) on
pages 372 and 373. Check your answers with the solutions provided in the Appendix.
32
Lesson 3.2
Crude Oil
Key Concepts
Crude oil, a complex mixture of hydrocarbons, is pumped from the ground by thousands of
“pump jacks” located all over Alberta.
pump jack
Crude oil is of various types. Read pages 386 and 387 in the textbook, Nelson
Chemistry, to learn more about the types of crude oil, the property that determines its
grade, and the refining process.
33
The refining of crude oil involves both physical processes and chemical processes.
I. Physical Refining Processes
Fractional distillation and solvent extraction are two of the physical processes used to refine
crude oil.
A. Fractional Distillation
This physical process separates molecules using their boiling points.
In a furnace, crude oil is heated to 500cC . At this temperature, most components of the
crude oil will vaporize. The vapours then rise up the fractionation tower, which is very
hot at the bottom and cooler at the top. As the vapours rise, they cool and condense
into liquids. Because different molecules have different boiling points, they condense at
different temperatures. In other words, the various substances condense at various levels
in the tower. As each substance condenses, the liquid is collected by a tray. Each liquid
separated in this manner is known as a fraction.
Recall from Chemistry 20 that smaller molecules have fewer electrons and thus weaker
London Forces. This results in a lower boiling point. Therefore, these smaller molecules
rise higher in the tower and are collected at the top where the temperature is cooler. Larger
molecules, which have a greater number of electrons (and thus stronger London forces),
have higher boiling points and, therefore, condense closer to the bottom of the fractionation
tower where the temperature is higher.
“Fractional Distillation”. View slides 1 to 10.
Use this animation about fractional distillation to enhance your understanding
of the principles and processes involved in oil refining. As you move your
mouse over the alternatives in each question, a pop-up window will appear to
allow you to self-score and see where you chose incorrectly.
B. Solvent Extraction
Solvent extraction is a physical process in which a solvent is added to a mixture to

selectively dissolve and remove an impurity or to separate some useful product. In other
words, it is a procedure used to separate compounds based on differences in their
solubility. For instance, a given mixture may contain both polar and non-polar compounds.
If you want to separate the polar compounds, you could add a polar solvent. This is
because “like dissolves like.” The polar solvent dissolves the polar compounds but not the
non-polar compounds.
34
Go to your textbook, Nelson Chemistry, and complete Practice Questions 2, 4, and 6 on page 388.
II. Chemical Refining Process
A. Cracking
Cracking is a process in which heat or a catalyst is used to break larger molecules into
smaller molecules.
C17 H36 ]1 g $ C 9 H20 ]1 g + C 7 H16 ] s g
B. Hydrocracking
Hydrocracking is similar to cracking, but it involves the addition of hydrogen. During this
process, no coke is produced. This is an improvement over cracking because coke is an
undesirable side product.
For example:
H H H H H H H
H C C C C C C C H H2
H H H H H H H
H H H H H H H
H C C C C H H C C C H
H H H H H H H
35
C. Alkylation
Alkylation converts a straight chain alkane into a branched alkane. This process is used to
increase the octane rating of gasoline.
H H
H C H H C H
H H H
CH3 (CH2)6 CH3 H C C C C C H
H H H H
H C H
D. Catalytic Reforming
This chemical process involves converting alkanes into aromatic molecules. The reason for
this conversion is that aromatic gasoline molecules combust better in car motors.
CH3 CH3
CH2
CH2 CH3
4H2
CH2 CH2
CH2
Now that you have learned about some of the processes used in oil refining, log back in to your
Moodle course, click on the Animations, and once again choose “Fractional Distillation.” This
time, view slides 11 to 15. Select the “i” shown in each frame to view simulations of the processes
described.
36
Go to your textbook, Nelson Chemistry, and complete Practice Questions 8, 9, 10, 11, and 12 on
page 391. Check your answers with the solutions provided in the Appendix.
37
Lesson 3.3
Oil Sands
Key Concepts
Alberta has immense oil reserves. Most of these reserves, however, are not in the form of liquid crude
oil, but rather they are in the form of bitumen. Bitumen is a mixture of hydrocarbons that covers the
sand grains of Alberta’s oil sands. This hydrocarbon mixture contains a large proportion of large
aromatic hydrocarbons whereas crude oil contains a higher proportion of aliphatic hydrocarbons. The
hydrocarbons in bitumen undergo so many changes during the refining process that the product is
termed “synthetic oil”. Many people consider the synthetic crude oil sold by Alberta to be “dirty oil”
because of the environmental damage caused by extracting and refining bitumen.
oil-rich sand of Fort McMurray, AB oilsands refinery, Fort McMurray
Watch
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “Oil Sand
Separation Demonstration © Government of Alberta”.
38
Complete Section 9.5 Questions 6 and 7 on page 397 of the textbook, Nelson Chemistry. Check your
answers with the solutions provided in the Appendix.
Module 1 – Lesson 3 Assignment

Assignments. Complete the Moodle 1 Lesson 3 Assignment online.
Module 1 Summative Assessment

Log in to your Chemistry 30 course in Moodle and click on Module Summative
Assessments. Download and complete the Module 1 Summative Assessment. You
may complete electronically or by hand. Submit your work electronically using the
“Add submission” button (scroll down to see this button). Once your assessment has
been marked, you may see your graded work, view feedback and access the module
test password by scrolling down on this same page until you see an area entitled
“Feedback.”
Module 1 Test
Log in to your Chemistry 30 course in Moodle and click on Module Tests. Complete
the Module 1 Test online, using the password provided in your Module 1 Summative
Assessment feedback.
39
Module 1 : Structure and Properties of Hydrocarbons

Module 2 : Organic Reactions of Hydrocarbons and
Module 2
Organic Reactions of Hydrocarbons and Hydrocarbon Derivatives
Introduction
Organic compounds occur in two main groups: hydrocarbons and hydrocarbon derivatives. As you
learned in the previous module, hydrocarbons are organic compounds consisting only of carbon
atoms and hydrogen atoms.
In contrast, a hydrocarbon derivative is an organic compound composed of carbon, hydrogen

(usually), and at least one other element. Some common hydrocarbon derivatives include the
following:
teflon antifreeze vinegar
Module 2 contains three lessons:
Lesson 1 Families of Hydrocarbon Derivatives

Lesson 2 Further Reactions of Organic Compounds
Lesson 3 Polymers
43
Lesson 1
Families of Hydrocarbon Derivatives
Introduction
Recall from Module 1 that hydrocarbons are grouped into categories based on whether they possess
single bonds, multiple bonds or benzene rings.
In contrast, hydrocarbon derivatives are categorized based on their functional group.
A functional group is a characteristic arrangement of atoms or bonds within a molecule that

determines the most important chemical and physical properties of that particular family. The
functional group refers to the characteristic arrangement of atoms within the molecules.
Refer to the table below for a list of the hydrocarbon derivatives that will be discussed in this lesson.
IUPAC Name Molecular Formula

Halogenated Hydrocarbons Halogen atom ^F, Cl, Br, I, Ath
Alcohols Hydroxyl group ]OHg
Carboxylic Acids Carboxyl group ]COOHg
Esters Ester linkage ]COOg
44
Lesson 1.1
Introducing the Halogenated Hydrocarbons (Alkyl Halides)
Key Concepts
Halogenated hydrocarbons, also known as organic halides and alkyl halides, are organic compounds
in which one or more hydrogen atoms have been substituted by a halogen atom (X). R represents a
hydrocarbon.
R X Learning Tip:
Halogenated hydrocarbons are known as
General formula of an alkyl halide
alkyl halides and organic halides.
Recall that the halogen atoms are found in Group 17 atoms of the periodic table.
45
Many common products contain halogenated hydrocarbons. Examples include the following:
Cl
H C Cl
Cl
chloroform
F C Br
halon-1301 (fire suppression agent)
Cl C F
Cl
refrigerant
Read pages 417 and 418 in the textbook, Nelson Chemistry, to learn more about
halogenated hydrocarbons.
46
Lesson 1.2
Properties of the Halogenated Hydrocarbons (Alkyl Halides)
Key Concepts
The physical properties of the halogenated hydrocarbons differ considerably from those of
corresponding alkanes. The presence of the halogen functional group is responsible for the unique
physical and chemical properties of this family.
I. Physical Properties of Halogenated Hydrocarbons
A. Boiling Point
Halogenated hydrocarbons have higher boiling points than alkanes with the same number
of carbons. Why is this?
Consider the following molecules:
Methane CFC Molecule

Chemical Formula CH4 CCl2 F2
Boiling Point ]cCg - 161 - 29.8
Methane is a non-polar molecule and, as such, exhibits only London Dispersion forces.
In contrast, dichlorodifluoromethane is a polar molecule, thanks to its electronegative
halogen atoms. Because it is a polar molecule, dichlorodifluoromethane possesses
the relatively strong “dipole-dipole” forces. In addition, because it has more electrons,
dichlorodifluoromethane demonstrates stronger London forces than methane. Remember
that the stronger the intermolecular forces, the higher the boiling point!
B. Solubility
Because they are more polar, halogenated hydrocarbons are more soluble in water than
are alkanes. However, generally speaking, their solubility in water is relatively low due to
the fact that halogenated hydrocarbons are unable to form hydrogen bonds with water
molecules. However, halogenated hydrocarbons tend to have good solubility in non-polar
solvents such as hexane.
II. Chemical Properties of Halogenated Hydrocarbons
The presence of the halogen atom determines the chemical properties of halogenated
hydrocarbons. Which reactions involve halogenated hydrocarbons? You will explore this
question in Lesson 2.
47
Complete Practice Question 3 on page 419 and Practice Question 10 on page 423 of the textbook,
Nelson Chemistry. Check your work using the answers provided in the Appendix.
48
Lesson 1.3
Naming the Halogenated Hydrocarbons (Alkyl Halides)
Key Concepts
Naming halogenated hydrocarbons is similar to naming branched hydrocarbons. Simply consider the
halogen atoms to be branches (i.e. “halide” branches). Keep the following points in mind:
1. When identifying the main or parent chain, keep in mind that the parent chain must contain the
carbon to which the halide branch is attached.
2. When numbering the carbons of the parent chain, assign the alkyl branches and halide
branch(es) the lowest possible number(s). Halide branches do not receive priority.
3. If more than one type of halide branch is present, list the halide branches alphabetically. The
halide branches are named by shortening the halogen names.
Chemical symbol Prefix

-F fluoro
- Cl chloro
- Br bromo
-I iodo
4. If more than one atom of the same halide is present, use the prefixes di, tri, tetra, etc. Realize
that these prefixes do not affect the alphabetical listing of the halides.
Examples of Halogenated Hydrocarbons
Cl Cl
1,2-dichloro-1,2-difluoroethane
F CH CH F
F F
Cl F
F 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane
F
Cl F
49
Examples of Halogenated Hydrocarbons (continued)

F F
1,1-difluorocyclopentane
F F
C C tetrafluoroethene
F F
Br Br
1,4-dibromo-2-chlorobenzene
Cl
Learning Tip:
When writing molecular formulae for halogenated hydrocarbons, list halogen atoms in increasing
order of electronegativity ^i.e. I, Br, Cl, Fh .
Examples:
C4 H2 Cl2 F6, C4 H4 Br2 ClF3, C5 H8 F2, C3 Br2 F4, C6 H3 Br2 Cl
Complete Practice Question 2 on page 419 of the textbook, Nelson Chemistry. Check your work using
the solution provided in the Appendix.
50
Lesson 1.4
Drawing the Halogenated Hydrocarbons (Alkyl Halides)
Key Concepts
When drawing halogenated hydrocarbons, follow the steps below. Refer to Sample Problem 10.1 and
Communication Example 2 on page 418 of the textbook, Nelson Chemistry.
1. Draw and number the parent chain (also known as the main chain).
2. Add the halogen atom(s) at the location(s) specified in the IUPAC name.
3. If you are drawing a structural diagram, complete the bonding by adding H atoms to the
carbon atoms. If you are drawing a line structural diagram, remember that the intersections and
ends of the lines represent the carbon atoms. Hydrogen atoms are not indicated, but halogen
atoms are shown. Refer to Communication Example 2 on page 418 of the textbook, Nelson
Chemistry.
Learning Tip
Remember that each carbon forms four bonds.
Watch
Log in to your Chemistry 30 Moodle course and click on Instructional Videos. Choose “Drawing Alkyl
Halides.”
Complete Practice Question 1 on page 418 and Practice Questions 4 and 5 on page 419 of the
textbook, Nelson Chemistry. Check your work using the solutions provided in the Appendix.
51
Lesson 1.5
Introducing the Alcohols
Key Concepts
Alcohols are a family of organic compounds containing one or more hydroxyl functional groups
]- OHg. The general formula for an alcohol is R - OH . R represents a hydrocarbon.
R OH
General formula of an alcohol
Alcohols can be produced by chemical synthesis, or, as is the case in ethanol production, by
fermentation.
Alcohols can contain one or more hydroxyl groups.
For example, ethanol contains a single hydroxyl group. It is an important organic compound with many
industrial/technological applications. For example, ethanol is added to gasoline to increase the fuel’s
octane number.
H H H
H C C O
H H
ethanol
52
Alcohols that contain a single hydroxyl functional group can be classified as primary, secondary, or
tertiary depending on the position of the hydroxyl group and the bonding of the structure.
Primary alcohols – The hydroxyl group is attached to a terminal carbon.
Secondary alcohols – The hydroxyl group is attached to a carbon that is bonded to two other
carbon atoms.
Tertiary alcohols – The hydroxyl group is bonded to a carbon atom that is bonded to three other
carbon atoms.
H H H H
H C C C C O H CH3 CH CH2 CH3
H H H H OH
butan-1-ol (primary alcohol) butan-2-ol (secondary alcohol)
H OH H
H C C C H
H H
H C H
H
methylpropan-2-ol (tertiary alcohol)
Some alcohols contain more than one - OH group and are referred to as polyalcohols. For example,
ethylene glycol (found in antifreeze) is a polyalcohol.
H H
HO C C OH
H H
ethylene glycol
Read pages 425 to 430 in the textbook, Nelson Chemistry, to learn more about
alcohols.
53
Lesson 1.6
Properties of the Alcohols
Key Concepts
Alcohols display very different properties compared to similarly sized hydrocarbons. The presence of
the hydroxyl ]- OHg functional group determines the unique physical and chemical properties of this
family.
I. Physical Properties
A. Boiling Point
Alcohols boil at a much higher temperature than hydrocarbons of similar molar mass. For
example, C2 H 6 (ethane) has a much lower boiling point than C2 H5 OH . Whereas the ethane
molecule exhibits only London forces, the - OH group allows for hydrogen bonding to
occur between neighbouring ethanol molecules.
Study the table below. How does the boiling point change as the size of the alcohol
increases?
Alcohol Boiling point Solubility in water

(°C) (g/100 mL)
methanol 65 miscible
ethanol 79 miscible
propan-1-ol 97 miscible
butan-1-ol 117 8.0
pentan-1-ol 137 2.7
The increase in boiling point can be explained by the fact that larger molecules possess
more electrons. The more electrons, the stronger the London forces between neighbouring
alcohol molecules. In contrast, the dipole-dipole forces and hydrogen bonds stay
approximately the same for all five alcohols.
54
B. Solubility
The - OH end of the alcohol promotes solubility in water whereas the hydrocarbon portion
of the molecule resists solubility. The solubility of alcohols in water varies, depending
on the length of the carbon chain. Short-chain alcohols tend to be very soluble in water
because of their size, polarity, and hydrogen bonding. However, larger alcohols, with their
predominant non-polar hydrocarbon portion, are not as soluble in water. In fact, larger
alcohols often are used as solvents for non-polar compounds.
“Hydrogen Bonding.”
II. Chemical Properties
The presence of the hydroxyl group determines the chemical properties of alcohols. In which
reactions are alcohols involved? You will explore this question in Lesson 2.
Complete Practice Questions 8, 9, 10, and 11 on page 430 of the textbook, Nelson Chemistry. Check
your work using the solutions provided in the Appendix.
55
Lesson 1.7
Naming the Alcohols
Key Concepts
Keep the following points in mind when naming alcohols.
1. Find the longest continuous hydrocarbon chain and number the carbon atoms, starting from
the end that will give the hydroxyl group the lowest carbon position number.
2. Name the parent chain (main chain) as if it were an alkane. Drop the “e” from the parent chain
name and add the location of the hydroxyl group. Complete the parent chain name with “ol” to
indicate that the compound is an alcohol.
OH
OH
H3C CH
CH2 CH3
butan-2-ol hexan-3-ol
3. Some alcohols, referred to as polyalcohols, contain more than one hydroxyl group. If more
than one hydroxyl functional group occurs, the “e” is not dropped from the parent chain name;
rather, add the carbon position numbers following the parent chain name. Finally, add the
appropriate suffix (diol, triol, etc.).
H H
C C OH
HO
H H
ethane-1,2-diol

56
Watch
Alcohols”.
More Examples of Alcohols

OH
H
H
H O H
H C OH
H C C C H
H
H H H
OH
methanol propan-2-ol butane-2,3-diol
OH OH
phenol cyclopentanol
the answers provided in the Appendix.
57
Lesson 1.8
Drawing the Alcohols
Key Concepts
When drawing alcohols from an IUPAC name, follow the steps below.
1. Draw and number the carbon atoms of the parent chain.
2. Add the hydroxyl group(s) at the locations specified in the IUPAC name.
3. If you are drawing a structural diagram, complete the bonding by adding H atoms to the
carbon atoms so that each carbon atom forms four bonds. If you are drawing a line structural
diagram, remember that the intersections and ends of the lines represent the carbon atoms.
Hydrogen atoms are not indicated, but the hydroxyl groups are shown.
Watch
Alcohols”.
Complete Practice Questions 6 and 7 on page 430 in the textbook, Nelson Chemistry. Check your
answers using the solutions provided in the Appendix.
58
Lesson 1.9
Introducing the Carboxylic Acids
Key Concepts
Carboxylic acids are a family of organic compounds

characterized by a carboxyl functional group ]- COOHg. As O (carbonyl)
illustrated below, the carboxyl functional group is composed
of a carbonyl functional group ]C = Og attached to a hydroxyl R C
functional group ]- OHg . The carboxyl group is always at
the end of a hydrocarbon chain. The general formula for a OH (hydroxyl)
carboxylic acid is R - COOH . R represents a hydrocarbon or
a hydrogen atom. General formula of a carboxylic acid
Some carboxylic acids contain two, three, or more carboxyl

groups.
H
O
HO C COOH
HO C
C OH HO C COOH
O H
oxalic acid tartaric acid
OH
O O
C CH2 C CH2 C
HO OH
C
HO O
citric acid
59
Carboxylic acids have a sour, tangy taste and a distinctive odour. They occur naturally in citrus fruits,
crab apples, rhubarb, and other foods. Many common products contain carboxylic acids. Some
common examples include the following:
H OH
methanoic acid (formic acid)
H O
H C C
H O H
ethanoic acid (acetic acid or vinegar)
HO C
C OH
oxalic acid
Read pages 436 and 437 in the textbook, Nelson Chemistry, to learn more about
carboxylic acids.
60
Lesson 1.10
Properties of the Carboxylic Acids
Key Concepts
The presence of the carboxyl (-COOH) functional group determines the unique physical and chemical
properties of this family.
A. Boiling Point
Study the table below. The earlier section discussed how the boiling points of alcohols
increase with size. Now, consider how boiling point increases within a homologous series
of carboxylic acids. Study the last three columns of the table below.
Boiling Solubility in water Boiling Solubility in water

Alcohol Carboxylic acid
Point (°C) (g/100 mL) Point (°C) (g/100 mL)
methanol 65 miscible methanoic acid 101 miscible
ethanol 79 miscible ethanoic acid 118 miscible
propan-1-ol 97 miscible propanoic acid 141 miscible
butan-1-ol 117 8.0 buanoic acid 164 miscible
pentan-1-ol 137 2.7 pentanoic acid 186 2.4
Comparing Boiling Points and Solubilities of Alcohols vs. Carboxylic Acids
Methanoic acid has one carbon atom whereas pentanoic acid has five carbon atoms.
In a pattern similar to the alcohols, the boiling point increases steadily as the size of the
carboxylic acid increases. This trend is due to the fact that larger molecules possess a
greater number of electrons and, therefore, display stronger London forces. The dipole-
dipole forces and the hydrogen bonding remain approximately the same for all the acids
shown.
A carboxylic acid has a higher boiling point than does an alcohol with the same number of
carbon atoms. This is partially due to the fact that the carboxyl group is more polar than
the hydroxyl group is, resulting in stronger dipole-dipole forces. Carboxylic acids also have
more locations where hydrogen bonding can occur.
61
B. Solubility
As well as forming hydrogen bonds with each other, carboxylic acids can form hydrogen
bonds with water molecules, which increases their solubility. In fact, carboxylic acids
exhibit the same solubility pattern as alcohols do. The smaller carboxylic acids are the most
soluble in water whereas the larger carboxylic acids are virtually insoluble. The more - CH2
groups added to the parent chain, the greater the non-polar part of the acid and the lower
its solubility.
The presence of the carboxyl group determines the chemical properties of this family. What
reactions involve carboxylic acids? You will explore this question in Lesson 2.
62
Lesson 1.11
Naming the Carboxylic Acids
Key Concepts
To name a carboxylic acid, identify the parent chain (main chain). Drop the “e” in the alkane name and
add “oic acid”.
Study the structures and names of the following carboxylic acids.
Carboxylic Acids
O OH
H O
O
C H C C
H OH O H
H
methanoic acid ethanoic acid benzoic acid
H H H O H H O
H C C C C H C C C
H H H O H H H O H
butanoic acid propanoic acid
OH
octanoic acid
63
Learning Tip:
When determining whether a compound is saturated or unsaturated, only the presence of
carbon-carbon double or triple bonds makes a compound unsaturated. Double bonds within a
functional group do not characterize a compound as unsaturated. For example, propanoic
acid is classified as a saturated compound because all of its carbon atoms are joined to each other
by single bonds. The double bond between carbon and oxygen does not make propanoic acid
unsaturated.
the solutions provided in the Appendix.
64
Lesson 1.12
Drawing the Carboxylic Acids
Key Concepts
When drawing a carboxylic acid from an IUPAC name, follow the steps below:
1. Draw the correct number of carbon atoms (refer to the prefix of the parent chain name).
2. On a terminal carbon, add a double bonded O and an - OH .
3. Complete the diagram by adding the correct number of hydrogen atoms so that each
carbon ends up with four bonds. If you drawing a line structural diagram, remember that
the intersections and ends of the lines represent the carbon atoms. Hydrogen atoms are not
indicated, however the carboxyl group is shown.
Watch
Carboxylic Acids”.
65
Lesson 1.13
Introducing the Esters
Key Concepts
Esters are organic compounds that naturally occur in fruits, flowers,

essential oils and pheromones. They are commonly used to enhance
the taste and aroma of foods. Esters are also used in cosmetics,
perfumes and solvents.
Esters are formed by the reaction of a carboxylic acid and an alcohol, a

process that will be discussed in more detail later.
The organic family of esters contains the ester linkage (-COO-).

This functional group resembles the carboxyl group, except that
the hydrogen atom of the carboxyl group has been replaced with a naturally occurring esters
hydrocarbon branch.
O
R is the hydrocarbon branch from the carboxylic acid.
C R´ is the hydrocarbon branch from the alcohol.
R OR´
General formula of an ester
Study the line structures below. They represent the esters responsible for the odour of rum and the
odour of apple.
O O
H O O
odour of rum odour of apple
Read pages 439 to 442 in the textbook, Nelson Chemistry, to learn more about esters.
66
Lesson 1.14
Properties of the Esters
Key Concepts
The presence of the ester linkage functional group determines the unique physical and chemical
properties of this family.
A. Boiling Point
Unlike the alcohols and carboxylic acids, esters cannot hydrogen bond with themselves.
In general, boiling points of esters increase as CH2 groups are added to the parent chain.
This occurs because the number of electrons increases, strengthening the London forces.
However, note that the smaller esters demonstrate higher boiling points than similarly sized
alkanes. This is because esters are polar and, therefore, exhibit a small additional dipole-
dipole force. In large esters, however, the non-polar portion of the molecule becomes
predominant and dipole-dipole forces contribute much less to the total intermolecular
forces present.
B. Solubility
Small esters are fairly soluble in water. While small esters cannot form hydrogen bonds
between themselves, they can hydrogen-bond to water molecules. This occurs when one
of the slightly positive hydrogen atoms in a water molecule becomes attracted to one of the
ester’s oxygen atoms. As chain length increases, however, the hydrocarbon portion of the
ester molecule begins to interfere with hydrogen bonding. This decreases solubility.
The presence of the ester linkage determines the chemical properties of the esters. What
reactions involve esters? You will explore this question in Lesson 2.
67
Lesson 1.15
Naming the Esters
Key Concepts
When naming esters, keep in mind that the ester is named opposite to the way it is drawn.
1. The name has two parts. The first part is an alkyl name given to the carbon chain that is
attached to the single bonded oxygen atom.
2. The second part represents the carbon chain that contains the carbonyl group. This chain is
given the corresponding alkane name; however, the “e” is dropped and “oate” is added.
Examples of Esters
ethyl heptanoate
CH3 (CH2)5 COO CH2 CH3
(grape-like aroma)
H H H O
H C C C C H H
ethyl butanoate
(banana-like aroma)
H H H O C C H
H H
H O
H C C H H H
propyl ethanoate
(pear-like aroma)
H O C C C H
H H H
68
Watch
Esters”.
the answers provided in the Appendix.
69
Lesson 1.16
Drawing the Esters
Key Concepts
Recall from Lesson 1.13 that esters are organic molecules with the following general formula:
O
R is the branch from the carboxylic acid.
C R´ is the branch from the alcohol.
R OR´
General formula of an ester
When drawing esters from an IUPAC name, follow the steps below.
1. The second word in the IUPAC name identifies the R group. Draw this group first, keeping in
mind that the last carbon atom forms a double bond with an oxygen atom and a single bond
with another oxygen atom.
2. The first word of the ester’s name identifies the R’ group. Attach this group to the bond that
ordinarily holds the “H” atom of the carboxyl group.
Watch
Esters.”
70
Draw the following esters. Check your answers using the solutions provided in the Appendix.
a. ethyl methanoate
b. ethyl benzoate
c. methyl butanoate
Lesson 1 Assignment
71
Lesson 2
Further Reactions of Organic Compounds
Introduction
In Module 1, you learned about some of the organic reactions involved in producing the hydrocarbons
that are in demand by society. In this lesson, you will expand your study of organic reactions to also
include reactions that involve hydrocarbon derivatives.
In Alberta, 95% of refined crude oil and natural gas is burned to release stored chemical energy, a
process known as combustion. The other 5% is used to produce petrochemicals. Petrochemicals
are examples of hydrocarbon derivatives. Common examples of petrochemicals include polyester,
antifreeze, and polystyrene.
72
Lesson 2.1
Combustion Reactions
Key Concepts
Combustion
Combustion, or burning, is the reaction of a chemical with oxygen to produce oxides and energy.
When organic compounds undergo combustion, certain chemical products and large quantities of
energy will be produced. The exact nature of the chemicals produced by the combustion reaction
will depend on the amount of available oxygen and the composition of the fuel being combusted. In
general, two types of combustion occur, complete combustion and incomplete combustion.
Read Section 9.6 on pages 398 to 400 of the textbook, Nelson Chemistry.
73
I. Complete Combustion
Complete combustion involves a fuel reacting with excess oxygen to produce carbon
dioxide and water vapour. In the complete combustion of a hydrocarbon, only two chemical
compounds are formed. Energy is produced also.
CH3 H
CH3 C CH2 C CH3 O O O C O O
CH3 CH3 H H
Hydrocarbon derivatives also can undergo complete combustion. For example, methanol can
be used as a fuel.
H H
H C O O O O O C O
H H H
Methanol is considered a clean-burning fuel because, similar to a hydrocarbon, the only

products of its complete combustion are carbon dioxide, water vapour, and energy.
Many fuels are not as clean burning as methanol. For example, gasoline may be contaminated
with sulfur. When sulfur undergoes complete combustion, sulfur dioxide is produced. This is a
very undesirable product because it reduces air quality and can result in acid deposition (such
as acid rain).
In Canada, a federal mandate requires the reduction of sulfur in gasoline. Refineries in

Alberta have upgraded their equipment to reduce sulfur content in their products.
II. Incomplete Combustion
Incomplete combustion of a hydrocarbon or hydrocarbon derivative occurs when the supply of

oxygen is limited. During incomplete combustion, various products are possible, including
C (carbon - known as soot), carbon monoxide, carbon dioxide, and water vapour. The
respective amounts of these products depend primarily on the proportion of oxygen available.
Hydrocarbon + ]insufficientg O2 ^g h " xC ] s g + y CO ^g h + zCO2 ^g h + H2 O ^g h + energy
C ] s g is soot and carbon monoxide ]COg is a toxic gas that can reach dangerous levels in
confined areas.
74
Watch
Carbon dioxide is a product of both complete and incomplete combustion. An excess of carbon
dioxide gas in the atmosphere can cause significant problems.
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “Global
Warming, It’s All About Carbon © NPR”.
What solutions are being proposed to reduce the amount of carbon dioxide in our atmosphere?
75
Lesson 2.2
Addition Reactions
Key Concepts
An addition reaction involves an unsaturated organic

compound and a small molecule reacting together Recall that unsaturated organic
to produce a new compound with an increased level compounds are those containing a double
of saturation. Usually, these reactions occur in the or triple bond.
presence of a catalyst. Study the various types of
addition reactions shown below.
1. An alkene/alkyne is reacted with hydrogen gas to form an alkane.
CH2 CH CH2 CH3 H H CH3 CH2 CH2 CH3
CH C CH3 2H H CH3 CH2 CH3
2. An alkene/alkyne is reacted with a diatomic halogen molecules (such as Cl2, Br2, l2 ) to form a
halogenated hydrocarbon.
H H Cl Cl
C C Cl Cl H C C H
H H H H
H H
H C C H Br Br C C
Br Br
76
3. An unsaturated organic compound is reacted with a hydrogen halide.
Cl Cl F H
C C H F Cl C C Cl
Cl Cl Cl Cl
4. An alkene reacts with water to form an alcohol.
H H H H
H+
C C H2O H C C H
H H H OH
ethene water ethanol
Note that isomers are produced when the hydrocarbon reactant has more than two carbon
atoms in the parent chain.
H2SO4
CH2 CH CH3 H OH CH3 CH CH3 CH3 CH2 CH2
OH OH
propene water propan-2-ol propan-1-ol
To better understand addition reactions, read pages 419 and 420 in the textbook,
Nelson Chemistry.
77
What happens when an alkene reacts with a diatomic halogen molecule? As you watch the Virtual
Investigation, carefully observe any changes that occur to the substances involved.
3. Choose “Double Bonds.” You will find it under Unit A. Answer associated questions in your
Module 2 Summative Assessment.
Learning Tip:
Aqueous bromine is an orange-coloured liquid used to test compounds for their levels of
saturation. If a compound is unsaturated (contains a double or triple bond), the orange colour of
the bromine solution fades quickly.
Complete Practice Questions 8b and 8d on page 423 in the textbook, Nelson Chemistry. Check your
work using the solutions provided in the Appendix.
78
Lesson 2.3
Substitution Reactions
Key Concepts
In a substitution reaction, a carbon-hydrogen bond in an alkane or benzene ring is broken and the
hydrogen atom is replaced with another atom or group of atoms. Light, as a catalyst, is usually
required for a substitution reaction to proceed at any appreciable rate. Other catalysts, such as FeCl3 ,
may be used also.
Consider the following substitution reactions. Note that more than one product is formed.
H H H H
light
H C C H Br Br H C C Br HBr
H H H H
ethane bromine bromoethane hydrogen bromide
Br
light,
FeCl3
Br2 HBr
benzene bromine bromobenzene hydrogen bromide
79
In the third reaction substitution reaction (shown below), note that more than one halogenated
hydrocarbon is produced. Isomers are formed when alkanes longer than two carbon atoms undergo a
substitution reaction.
H H H H H H H H H
light
H C C C H Cl Cl H C C C Cl H C C C H Cl
H H H H H H H Cl H
propane chlorine 1-chloropropane 2-chloropropane hydrogen chloride
To better understand substitution reactions, read pages 421 and 422 in the textbook,
Nelson Chemistry.
Complete Practice Questions 8a, 8c, and 8e on pages 423 of the textbook, Nelson Chemistry. Check
80
Lesson 2.4
Elimination Reactions
Key Concepts
Elimination reactions are organic reactions that involve creation of a double bond through the
elimination of atoms and/or groups of atoms from adjacent carbon atoms.
Elimination reactions are of various types.
I. Dehydrogenation
Dehydrogenation is the removal of two hydrogen atoms. For example, the following reaction
depicts the dehydrogenation of ethane. This reaction, commonly known as ethane cracking,
produces ethene or “ethylene”. Used to synthesize many hydrocarbon derivatives, ethene is
the cornerstone of the Alberta petrochemical industry.
H H H H
heat
H C C H C C H H
H H H H
ethane ethene hydrogen
II. Dehydration
Another example of an elimination reaction involves the removal of a water molecule from an
alcohol molecule. This type of elimination reaction is a dehydration.
H H H H
catalyst
H C C H C C H2O
heat
H OH H H
ethanol ethene water
81
III. Dehydrohalogenation
Halogenated hydrocarbons can undergo elimination reactions in the presence of bases.
H H Cl H H H H H H H H H
O
H C C C C H OH¯ H C C C C H H C C C C H Cl¯ H
H
H H H H H H H H
2-chlorobutane hydroxide ion 1-butene 2-butene chloride ion water
To better understand elimination reactions, read pages 431 to 434 in your textbook,
Nelson Chemistry.
Complete Practice Questions 18, 19, 20 on page 433 of the textbook, Nelson Chemistry. Check your
answers using the solutions provided in the Appendix.
82
Lesson 2.5
Esterification Reactions
Key Concepts
Esters can be synthesized in laboratories by reacting an alcohol with a carboxylic acid in the
presence of a catalyst. Because water is formed as a product, this type of reaction is referred to as a
condensation reaction.
Below is the reaction between methanoic acid and ethanol to form ethyl methanoate and water.
O H H O
H
C O C C H H C O
H OH H H
H H O CH2 CH3
Example of esterification
Refer to the bottom of page 438 in the textbook, Nelson Chemistry.
83
3. Choose “Synthesizing an Ester”. You will find it under Unit A. Answer associated questions in
your Module 2 Summative Assessment.
Learning Tip:
If you are provided with the names of the reactants in an esterification reaction, you should be able
to identify the ester that will be formed. Conversely, given an ester’s name, you should be able to
identify the alcohol and the carboxylic acid that were used in its synthesis.
Example 1
When propanoic acid is reacted with ethanol, ethyl propanoate will be synthesized.
Example 2
Methyl ethanoate can be synthesized by the reaction of methanol with ethanoic acid.
Complete Practice Questions 3a, 3b, 3c, and 5 on page 441 of the textbook, Nelson Chemistry. Check
Lesson 2 Assignment
84
Lesson 3
Polymers
Introduction
So far you have learned about various families of hydrocarbon derivatives. You have explored how the
unique functional groups affect the physical and chemical properties of these molecules. One family of
hydrocarbon derivatives not yet discussed is polymers.
Polymers can be either natural or synthetic.
Examples of synthetic polymers include plastic, polyester, teflon, and nylon. Examples of natural
polymers include rubber, cotton, silk, and wool.
85
Lesson 3.1
What is a Polymer?
Key Concepts
Polymers are large molecules composed of many smaller repeating molecules, all linked together.
The small molecules that make up a polymer are called monomers. Various types of monomers have
various functional groups.
The process of joining monomers together is called polymerization.
“Monomers and Polymers”.
86
Learning Tip:
Given a polymer, you need to be able to identify the monomer from which it was produced.
Example: Consider polystyrene, a polymer often used to make cups and containers.
CH 2 CH CH 2 CH CH 2 CH CH 2 CH
polystyrene
In order to identify the monomer, look for the smallest repeating pattern:
CH 2 CH
n
Identifying the monomer in polystyrene
Add a double bond to fulfill all bonding spots. The resulting monomer is shown below.
CH 2
CH
styrene monomer
Polymers are categorized into two major groups – addition polymers and condensation polymers.
87
Lesson 3.2
Addition Polymers
Key Concepts
Addition polymers are produced by the polymerization of monomers that contain a double bond. The
mechanism by which the monomers combine involves an addition reaction in which the double bond
is broken. The resulting free electrons bond the monomer units together. In addition to polymerization,
only one product is formed.
You may recall from Module 1 that ethane is extracted from natural gas. Then hydrogen is removed
from the ethane to produce ethene, also known as ethylene. The ethene monomer is considered
a primary petrochemical because it can be used to make many new compounds, including
polymers.
Consider polyethene as an example of an addition polymer. Polyethene (polyethylene) is used in the

production of many plastics.
It is produced by an addition reaction that links ethene (ethylene) monomers together in a long chain.
H H H H H H H H H H H H
C C C C C C … C C C C C C
H H H H H H H H H H H H
ethene (ethylene) polyethene (polyethylene)
“Polymerising ethene”.
88
Polypropene is also a commonly used

polymer. For example, some ropes and Propane is extracted from natural gas and
certain carpets are made from polypropene. converted into propene (propylene). The
This polymer is produced by an addition propene monomer is also considered a primary
reaction that links propene monomers. petrochemical.
CH3 H CH3 H CH3 H CH3 H CH3 H
C C C C C C C C or C C
H H H H H H H H H H n
propene (propylene) polypropene (polypropylene)
You probably have heard of the material known as “PVC”. PVC is a polymer that is used to insulate
electrical wires and coat upholstery fabrics. This polymer is produced by an addition reaction that links
vinyl chloride monomers.
Cl H Cl H Cl H
C C C C C C
H H H H H H
vinyl chloride
Cl H Cl H Cl H
C C C C C C
H H H H H H
polyvinylchloride (PVC)
Read pages 445 to 458 in the textbook, Nelson Chemistry.
89
Watch
Although addition polymers are very useful, their widespread use had taken a heavy toll on our
environment.
Watch the following videos to learn more about this problem and its possible solutions.
Log in to your Chemistry 30 course in Moodle and click on Instructional Videos. Choose “It’s a Plastic
World” and “Google Science Fair 2013”.
Complete Practice Questions 1 (a, b) and 2 to 6 on page 448 of the textbook, Nelson Chemistry.
Check your work using the solutions provided in the Appendix.
90
Lesson 3.3
Condensation Polymers
Key Concepts
Condensation polymers and condensation polymerization reactions are very common in industry and
in biological systems.
polyester cellulose nylon
Condensation polymerization reactions are characterized by two monomers reacting to produce a

polymer and another small molecule, usually water.
Condensation polymers can be synthetic or natural.
I. Synthetic Condensation Polymers
Polyester is an example of a synthetic polymer that is formed through the process of

condensation polymerization. In this particular reaction, a carboxylic acid reacts with an alcohol
group to from an ester linkage. Because both the alcohol and the carboxylic reactants have
two functional groups, this reaction can be repeated to create a long chain that consists of
many esters joined together.
nHOCH2CH2OH nHOOC COOH CO COOCH2CH20 nH2O
ethylene glycol terephthalic acid polyethylene terephthalate
91
II. Natural Condensation Polymers
Proteins are an example of a natural polymer that is formed through the process of
condensation polymerization.
Two amino acids can link together form a dipeptide.
H O H O
H R H R
C O N C H C N C H O
H H
H C O O
N C H N C C H H
R H
H O H O R H
amino acid 1 amino acid 2 dipeptide
A polymer known as a polypeptide forms when amino acids (monomers) link together in long
chains, as shown below:
H H O H H O H O H O
N C C O N C C OH N C C N C C H O
H R´ H H R´´ H R´ H R´´ H
amino acid 1 amino acid 2 polypeptide segment
Starch is another example of a natural polymer that is formed through the process of
condensation polymerization. Starch is formed when many glucose monomers link together.
To view an animation illustrating condensation polymerization, log in to your Moodle

course and click on Animations. Under Unit A, choose “Forming Starch”.
92
3. Choose “Polymerization”. You will find it under Unit A. Answer associated questions in your
Module 2 Summative Assessment.
Read pages 449 to 454 in the textbook, Nelson Chemistry.
Complete Practice Questions 12 and 13 on page 452 of the textbook, Nelson Chemistry. Check your
work using the solutions provided in the Appendix.
93
Lesson 3 Assignment
Module 2 Summative Assessment

Log in to your Chemistry 30 course in Moodle and click on Module Summative
Assessments. Download and complete the Module 2 Summative Assessment. You
may complete electronically or by hand. Submit your work electronically using the
“Add submission” button (scroll down to see this button). Once your assessment has
been marked, you may see your graded work, view feedback and access the module
test password by scrolling down on this same page until you see an area entitled
“Feedback.”
Module 2 Test
Log in to your Chemistry 30 course in Moodle and click on Module Tests. Complete
the Module 2 Test online, using the password provided in your Module 2 Summative
Assessment feedback.
94
Appendix
ADLC | Chemistry 30 Unit A – Appendix
Solutions to Self-Check Questions
Unit A – Introduction
Page 361, Section 9.1, Question 1
a. inorganic
b. organic
c. inorganic
d. organic
e. organic
f. inorganic
g. inorganic
h. organic
Module 1 – Lesson 1.2

Page 371, Practice Question 9
a. 2-methylheptane
b. 3,7-dimethylnonane
c. 2,4,6-trimethylheptane
d. 3-ethyl-6-methyloctane
You may have found (b) and (d) tricky because of the way the molecules were displayed. Not all
carbons in the longest chain were in a horizontal line.
a. This is incorrect. A number is required for each branch. The correct name is
2,2-dimethylhexane.
b. This is incorrect. A “di” prefix should be used when two of the same branch are present. The
correct name is 3,3-diethylpentane.
c. This is correct.
d. This is incorrect. There are four carbons in the longest chain, not three. The correct name is
2,2-dimethylbutane.
e. This is incorrect. There are six carbons in the longest chain, not five. The correct name is
3-ethylhexane.
f. This is incorrect. The longest chain has four carbons, not three. The correct name is
methylbutane.
a. ethylpentane
b. trimethylbutane
c. 4-ethyl-2,4-dimethylhexane
d. 3-methyl-5-propyloctane
Although the numbers are unnecessary, it is acceptable to name (a) as 3-ethylpentane and (b) as
2,3,3-trimethylbutane.
97
Unit A – Appendix ADLC | Chemistry 30

a. b.
c. d.
e. f.
g.
a. b.
98
c. d.
a.
b.
c.
8 5
d.
e.
99

a. propane + pentane  octane + hydrogen
b. hexane  2,2-dimethylbutane
c.
The names are 2,3-dimethylbutane and 2-methylpentane. You may also have used
3-methylpentane as one isomer.

a. alkene or cycloalkane ]C n H2ng
b. alkane ]C n H2n + 2g
c. alkyne or cycloalkene ]C n H2n - 2g
d. alkene or cycloalkane ]C n H2ng

Using a number in the name to indicate the position of a multiple bond is not necessary because,
with a three-carbon chain, the multiple bond can only be on an end carbon. These numbers are
unnecessary, but strictly speaking, not incorrect.
100
a. 3,3-dimethylpent-1-ene
b. 3,3-dimethylpent-1-ene
c. 5-ethyl-4-methylhept-2-yne
Although (a) and (b) are drawn differently, they are the same compound. They are not isomers!

a. b.
c. d.
a. b.
c. d.
101

There are more possible isomers for an alkene because the position of its double bond can vary.
Five aliphatic structural isomers of C5 H10 are:
Cyclical structural isomers are also acceptable.

Benzene, C 6 H 6 , is the simplest aromatic compound. Its carbon-carbon bond lengths are all the same,
but they are neither single nor double bonds. Each pair of carbons shares one electron pair. The six
remaining valence electrons are shared around the ring.
102
a. aliphatic
b. aromatic
c. aliphatic
d. aliphatic
e. aromatic
f. aromatic
a. unsaturated
b. saturated
c. unclassified*
d. unsaturated
e. unsaturated
f. unclassified*
* Recall that aromatics are classified neither as saturated nor unsaturated.
Cyclohex-1,3,5-triene is misleading and incorrect because the physical and chemical properties of
benzene suggest it has no double bonds as such.

a. 1-ethyl-3-methylbenzene
b. 1-methyl-4-propylbenzene
c. 3-methyl-2-phenylpentane
d. 3-menthyl-4-phenylhexane
e. 2-phenylhept-3-ene
f. 4-phenylpent-1-yne
103

a. b.
c. d.
a.
b. ethylbenzene  1,2-dimethylbenzene
c. benzene + ethene  ethylbenzene
104

Methane, ethane, propane, butane, pentanes, and hexanes typically are present in natural gas before
it is refined. Natural gas for home heating is almost pure methane because the other components have
been removed.
Sour natural gas contains hydrogen sulfide; sweet natural gas does not. Hydrogen sulfide is a deadly
toxin and poses a major safety problem if it is not removed safely.
To remove alkanes (other than methane) from natural gas, the natural gas is cooled under high
pressure so that the alkanes with more than one carbon atom condense to a liquid.
a. Two consumer uses for the energy obtained from natural gas are
1. residential heating
2. fueling barbeques and camp stoves
Two commercial uses for the energy obtained from natural gas are
1. fueling some taxicabs
2. heating office buildings
Two industrial uses for the energy obtained from natural gas are
1. fueling some power plants that produce electricity
2. separating bitumen from oil sand
b. Production of plastic objects, wooden objects, building materials, and paper products require
energy from natural gas.
105
Page 373, Section 9.2, Question 10(a)
The boiling point is directly proportional to the number of carbon atoms in the alkane. The relationship
is almost linear. This is because the London forces become stronger with the increasing number of
electrons, and the number of electrons increases by eight with each successive alkane.

a. Crude oil is heated in the absence of air in the fractionation tower because, at such a high
temperature, the oxygen in the air would cause the crude oil to burn.
b. C5 H12 ] l g + heat " C5 H12 ^g h
C8 H18 ] l g + heat " C8 H18 ^g h
c. C5 H12 ^g h " C5 H12 ] l g + heat
C8 H18 ^g h " C8 H18 ] l g + heat
d. Octane has a higher boiling point than pentane does because its London forces are stronger,
mainly because of its greater number of electrons ]66 e versus 42 e g .
- -
e. Pentane rises higher in the tower than octane does.
Approximately 95% of petroleum is used as fuel. The major fuel produced is gasoline.
106
a. The hydrocarbons are all similar non-polar molecules so are mutually soluble.
b. Water molecules are very unlike hydrocarbons in that water is a highly polar hydrogen-bonded
substance. There is little tendency for the crude oil solution to dissolve any water.
If only physical means were used to refine oil, an excess of the heavier fractions would be produced
and the supply of products such as gas, oil, and greases would exceed the demand. In addition,
straight-run gasoline is of lower quality than gasoline containing compounds produced by reforming
and alkylation.
a. CH3- ]CH2g16- CH3 " CH3- ]CH2g6- CH3 + CH3- ]CH2g7- CH3 + C
b. CH3- ]CH2g8- CH3 " CH3- ]CH2g3- CH3 + CH3- ]CH2g2- CH3 + C
c. CH3- ]CH2g14- CH3 " CH3- ]CH2g7- CH3 + CH3- ]CH2g4- CH3 + C
Alkylation increases the amount of branching within the molecules. Catalytic reforming increases the
number of aromatic molecules in the gasoline.
a. CH3- ]CH2g4- CH3 + H2 " CH3- CH3 + CH3- CH2 - CH2 - CH3
b. CH3- CH ]CH3g - CH2 - CH2 - CH3 + H2 " CH3- CH2 - CH3 + CH3 - CH2 - CH3
c. CH3- C ]CH3g2 - CH2 - CH3 + H2 " CH3- CH3 + CH3 - CH ]CH3g - CH3

The chemical processes used to upgrade bitumen are coking, hydrotreating, and hydrocracking.
Page 397 Section 9.5 Question 7
a. There is a higher proportion of aromatic compounds in bitumen, as compared to crude oil.
b. A chemical difference between synthetic and conventional crude oil is that synthetic oil is
produced using chemical reactions involving the upgrading of bitumen.
107

a. Chloroethene has a higher boiling point than ethene because it has stronger intermolecular
forces. Firstly, because it is polar, it exhibits dipole-dipole forces. Secondly, it has more
electrons - therefore its London forces are stronger.
b. Chloroethene is more soluble than ethene because it is polar (recall that water is a polar
solvent).
Both molecules have the same number of electrons and both exhibit dipole-dipole forces because of
their polarity. In this case, molecular shape is the determining factor. The 2-bromopropane molecule is
more compact and does not make as much surface contact with neighbouring molecules compared to
the more “stretched out” 1-bromopropane molecules.

a. triiodomethane
b. 3-chloromethylpropene
c. dichloromethane
d. 1,2,3-tribromopropane
e. chlorobenzene
f. phenylethene
You might have used names that contain redundancies; these are still correct. For example,
3-chloro-2-methylprop-1-ene is acceptable for question (b) above.

a. c.
b. d.
108
a. c.
b. d.
a. c.
b. d.

Methanol ( CH3 OH , 18 electrons) exhibits London forces, dipole-dipole forces, and hydrogen bonding.
Methane ( CH4 , 10 electrons) has weaker London forces than methanol and exhibits no dipole-dipole
forces or hydrogen bonding.
The order is ethane ( C2 H 6 , 18 electrons), fluoromethane ( CH3 F , 18 electrons), methanol ( CH3 OH ,

18 electrons). Each compound has similar London forces, but fluoromethane has dipole-dipole forces,
and methanol has dipole-dipole forces and hydrogen bonding.
The order is pentane ( C5 H12 , 42 electrons), 1-chlorobutane ( C4 H 9 Cl , 50 electrons), butan-1-ol

( C4 H 9 OH , 42 electrons). Pentane has only London forces. The other two have London forces and
dipole-dipole forces. Although the London forces in 1-chlorobutane are slightly stronger than those
of butan-1-ol, this is more than offset by the fact that butan-1-ol is the only compound exhibiting
hydrogen bonding.
With its three - OH bonds, glycerol forms strong hydrogen bonds with water molecules. This makes
it more difficult for water molecules to come together in the correct arrangement to form crystals.
Therefore, a lower temperature is needed to cause freezing.
109
Ethane ( C2 H 6 , 18 electrons) has the lowest boiling point because it exhibits only London forces.
Chloroethane ( C2 H5 Cl , 34 electrons) has a boiling point between that of ethane and ethanol because
it has stronger London forces than ethane, plus it has dipole-dipole forces. Ethanol
( C2 H5 OH , 26 electrons) has the highest boiling point because, although it has weaker London forces
than chloroethane, it exhibits hydrogen bonding.
Ethanol has the greatest solubility. Like the solvent water, it is a small, polar, hydrogen-bonded
substance. Chloroethane has slight solubility because it is a small polar molecule. Ethane is the least
soluble because it has no polarity or hydrogen bonding.

a. butan-2-ol
b. pentan-2-ol
c. cyclohexane-1,3-diol

a. c.
b. d.
a. c.
(butan-2-ol) (pentan-2-ol)
b. d.
(pentan-1-ol)
(pentan-3-ol)
110

a. methanoic acid (You may hear the common name “formic acid”.)
b. pentanoic aid (You may hear the common name “valeric acid”.)
c. hexanoic acid (You may hear the common name “caproic acid”.)

a.
b.
c.

a. ethyl propanoate (from propanoic acid and ethanol)
b. methyl butanoate (from butanoic acid and methanol)
c. butyl methanoate (from methanoic acid and buan-1-ol)
d. propyl ethanoate (from ethanoic acid and propan-1-ol)
If you had the two fragments backwards when you named the esters in this question, try writing the
full structural formula for each – it will help you get the name right!
111
a.
b.
c. H H H O
H C C C C H
H H H O C H

There are several other possibilities, such as the following:
112

Page 423, Practice Questions 8b and 8d
b.
This is an addition reaction.
d.
This is an addition reaction.

Page 423, Practice Questions 8a, 8c, and 8e
a.
This is a substitution reaction.
c.
e.
113

a.
b.
c.
114

a. O H H H O
C O C C H H C O
H OH H H
H H O CH2 CH3
b. O H H H O
C O C C H C O
OH O H H
H H
c. H H H O H H H H O
H C C C C OH C H H C C C C H O
H H
H H H O H H H H H O C H
a. As shown in Table 2 on page 439 of the textbook, the ester is pentyl butanoate. The acid
required is butanoic acid and the alcohol needed is pentan-1-ol.
b. As shown in the same table, the ester is octyl ethanoate. The acid required is ethanoic acid and
the alcohol needed is octan-1-ol.

a. b.
c. F F F F F F
C C C C C C
Cl F Cl F Cl F
115
a. but-2-ene
b. 1-chloro-1,2-difluoropropene
If you are having difficulty determining the monomer from the polymer structure, write the formula for
ethane. Then, replace the H atoms with the groups that are dangling off the polymer chain.
The monomer should be an alkene or alkyne.
monomers:
polymer:
a. Typical properties of a plastic are insolubility in water, good insulators of heat and electricity,
flexibility, and high melting point for a molecular material.
b. Within a polymer molecule, there are very strong covalent intramolecular bonds. Between the
polymer molecules, there are always intermolecular London forces. Depending on the structure
of the polymer, there may be dipole-dipole forces and hydrogen bonding.
c. Plastics are flexible because the intermolecular bonds holding the polymer chains together are
easily deformed. Plastics are good insulators because they are molecular, so they do not have
freely moving ions or electrons. The intermolecular forces for such large molecules help explain
the insolubility and high melting point of plastics.
116

Carboxylic acid ]- COOHg and alcohol ]- OHg functional groups must be present to form a polyester.
117
Glossary
ADLC | Chemistry 30 Unit A – Glossary
addition polymerization: a reaction in which many unsaturated monomer units are added together to
create a long chained polymer
addition reaction: a type of organic reaction involving an unsaturated hydrocarbon and a small
molecule, usually hydrogen or a halogen, which increases the saturation of the hydrocarbon
alcohol: an organic compound containing one or more hydroxyl groups as the functional group
aliphatic: a broad class of hydrocarbons including straight or branched chains or rings of alkanes,
alkenes, and alkynes.
alkane: a class of hydrocarbon containing only single bonds
alkyl branch: a group of atoms, consisting of only singly bonded carbon and hydrogen, that is not
part of the main structure of the molecule
amide functional group: a group of atoms composed by connecting a carboxyl group to an amine
group
carbohydrate: a carbon compound that contains many hydroxyl groups and has the general chemical
formula CnH2 nOn (such as glucose, C 6 H12 O 6 )
carboxylic acids: a family of organic compounds characterized by the carboxyl group ]- COOHg
condensation polymerization: a reaction that involves removal of a small molecule from the
functional groups of two different monomer molecules to form a condensation polymer
cycloalkane: a cyclic hydrocarbon in which all carbon bonds are single bonds
elimination reaction: the removal of two adjacent atoms or groups of atoms, creating a double bond
ester: a family of organic compounds characterized by the ester functional group ]- COO -g
esterification reaction: a chemical reaction in which a carboxylic acid and an alcohol combine to
produce an ester and water
functional group: a characteristic arrangement of atoms or bonds within a molecule that determines
the most important chemical and physical properties of a class of compounds
halogenated hydrocarbon: an organic compound in which one or more hydrogen atoms have been
replaced by halogen atoms
121
Unit A – Glossary ADLC | Chemistry 30
homologous series: a progression of organic compounds that differs only in the number of repeating
units
hydrocarbon: a compound containing only carbon and hydrogen atoms
hydrocarbon derivative: a molecular compound of carbon and, usually, hydrogen plus at least one
other element
hydrocarbon molecule: a chemical compound containing only hydrogen and carbon atoms
monomer: a small molecule that links with many other similar molecules in an addition or condensation
reaction to create a polymer
nylon: a synthetic condensation polymer
organic compound: a compound containing carbon, except for oxides (such as CO ^g h and
CO2 ^g h) and ionic compounds of carbon such as those that contain carbonate, cyanide, and
carbide ions
petrochemical: a chemical made or extracted from petroleum
petroleum: a mixture of hydrocarbons obtained from oil or natural gas
polymer: a large molecule made by linking many smaller molecules called monomers
polymerization: the process of forming polymers from monomers through addition or condensation
reactions
proteins: natural polymers of amino acids forming the basic material of living things
saturated hydrocarbon: a hydrocarbon with the maximum amount of hydrogen atoms bonded
because all carbon-carbon bonds are single
structural isomer: a compound with the same molecular formula but a different structure
substitution reaction: a type of organic reaction involving breaking a carbon-hydrogen bond and
replacing the hydrogen atom with another atom or group of atoms
122

Chem 30 Unit A PDF

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Chem 30 Unit A PDF

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Chemistry 30

Student Module Book

Module 1 : Structure and Properties of Hydrocarbons

Unit A: Organic Chemistry

Module 1: Structure and Properties of Hydrocarbons.............................................................................. 1

Module 2: Organic Reactions of Hydrocarbons and Hydrocarbon Derivatives...................................... 43

pumpjack organic molecule plastics

Unit A consists of two modules:

Organic molecules are carbon-containing compounds.

Other organic compounds contain atoms in addition to

 oxides, such as CO ^g h and CO2 ^g h

Check Your Understanding

1. Log in to your Chemistry 30 course in Moodle.

2. Click on Virtual Investigations.

natural gas mothballs gasoline

Module 1 contains three lessons:

Lesson 1 Aliphatic Hydrocarbons

Saturated Hydrocarbons Unsaturated Hydrocarbons

Alkanes Alkenes and Alkynes

Study the following table displaying the first ten alkanes.

IUPAC Name Molecular Formula

hexane C6 H14 ] l g The prefixes indicating one to ten carbon

Read pages 366 to 367 in your textbook, Nelson Chemistry.

I. Naming Unbranched Alkanes and/or Cycloalkanes

1. Count the number of carbons in the chain or ring.

3. Add the suffix “ane”.

II. Naming Branched Alkanes and/or Cycloalkanes

To name branched alkanes, follow the steps below:

5. When naming a branched cycloalkane, keep the following in mind:

Examples of Branched Alkanes and Cycloalkanes

Diagram of Molecule IUPAC Name

CH3 CH2 CH2 CH CH3 2,2-dimethylbutane

CH3 CH2 C C CH2 CH3 3,4-diethyl-3-methyl-4-propylheptane

Check Your Understanding

Drawing branched alkanes can be more difficult.

To draw a branched alkane, follow these steps:

2. Number the carbons from left to right.

4. Add hydrogen atoms to give each carbon four single bonds.

Check Your Understanding

Go to your textbook, Nelson Chemistry, and complete Practice Questions 7 (a to g) and 10 on

Perhaps you would draw this:

Check Your Understanding

For example, consider ethene, the simplest alkene.

For example, consider ethyne ]C2 H2g, the simplest alkyne.

Check Your Understanding

To name alkenes and alkynes:

C1 C2 C3 C4 C5 H When naming branched

5. Now, write the IUPAC name using this format:

(Branch location) – (branch name)(prefix) – (multiple bond location) – ene/yne

Examples of Organic Compounds Containing Multiple Bonds

Diagram of Molecule IUPAC Name

CH3 CH2 CH3

Check Your Understanding

To draw alkenes and alkynes:

3. Add the branches listed in the name of the molecule.

4. Add hydrogen atoms to give each carbon atom four bonds.

Check Your Understanding

pent-2-ene, C5 H10 pent-1-ene, C5 H10

Check Your Understanding

aspirin TNT vanillin

Check Your Understanding

To name aromatic hydrocarbons:

Examples of Aromatic Compounds

oxides, such as CO ^g h and CO2 ^g h

Primary alcohols – The hydroxyl group is attached to a terminal carbon.