U N I T

5
Hydrocarbons and Energy

Chapter 13
The Chemistry of Hydrocarbons

Chapter 14
Energy Trapped in Hydrocarbons
 UNIT 5

Hydrocarbons and Energy

Contents
Unit 5 at a Glance . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .507
Suggested Unit 5 Map . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .508
Unit 5 Planning Chart . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .509
Unit 5 Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .511

Chapter 13: The Chemistry of Hydrocarbons . . . . . . . . . . . . . .514

13.1 Introducing Organic Compounds . . . . . . . . . . . . . . . . . . . . . .515

13.2 Representing Hydrocarbon Compounds . . . . . . . . . . . . . . . . .517

Investigation 13-A: Modelling Organic Compounds . . . . . . . . . . . . .519

13.3 Classifying Hydrocarbons . . . . . . . . . . . . . . . . . . . . . . . . . . . .524

Investigation 13-B: Comparing the Reactivity of
Alkanes and Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .525
Investigation 13-C: Structures and Properties of
Aliphatic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .527

13.4 Refining and Using Hydrocarbons . . . . . . . . . . . . . . . . . . . . .531

Chapter 13 Review . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .533

Chapter 14: Energy Trapped in Hydrocarbons . . . . . . . . . . . . . .541

14.1 Formation and Combustion Reactions . . . . . . . . . . . . . . . . . . . . .542

Investigation 14-A: The Formation and Combustion of
Acetylene . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .543

14.2 Thermochemical Equations . . . . . . . . . . . . . . . . . . . . . . . . . . .545

14.3 Measuring Energy Changes . . . . . . . . . . . . . . . . . . . . . . . . . .547

14.4 The Technology of Heat Measurement . . . . . . . . . . . . . . . . . .550

Investigation 14-B: The Heat of Combustion of a Candle . . .554

14.5 The Impact of Petroleum Products . . . . . . . . . . . . . . . . . . . .556

Chapter 14 Review . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .558

Unit 5 Project: Consumer Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . .562

Unit 5 Review . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .562
Course Challenge: Planet Unknown . . . . . . . . . . . . . . . . . . . . . . . . .591

506 MHR • Unit 5 Hydrocarbons and Energy

UNIT 5 AT A GLANCE

Petroleum
Chapter 13 refining distillation
Products
The Chemistry of
Hydrocarbons
Organic properties
petrochemicals
Compounds of carbon

natural/synthetic
fossil fuels Representation
compounds

structural
models isomers
formulas

Nomenclature alkanes alkenes

alkynes cyclics

foods
Chapter 14 Calorimetry Q = mc∆T
and energy
Energy Trapped in
Hydrocarbons
heats of
Impact Risks/Benefits
combustion

environment decision making Bond Energies

thermochemical
exothermic endothermic
equations

Combustion/ balanced complete

Formation equations combustion

incomplete
combustion

Unit 5 Hydrocarbons and Energy • MHR 507

 SUGGESTED UNIT 5 MAP

This map is intended to help you in implementing the new Ontario Science Curriculum. The map outlines the materials in the
student textbook that are:
Essential Unit Content—these parts of the textbook must be taught in order to meet the required curriculum expectations;
Important Background—these sections of the textbook give the students background information related to the essential
expectations;
Enrichment—these sections of the textbook go beyond what is required in the curriculum, and may be assigned as extension or
enrichment to those students who need more challenging material.

Unit 5: Hydrocarbons and Energy

Important Background Essential Unit Content Enrichment

Investigation 13-A: Modelling
Organic Compounds
14.4 The Technology of Heat
Measurement
13.1 Introducing Organic Compounds
13.2 Representing Hydrocarbon Compounds
13.3 Classifying Hydrocarbons
Investigation 13-B: Comparing the Reactivity
of Alkanes and Alkenes
13-C: Structures and Properties of Aliphatic
Compounds
13.4 Refining and Using Hydrocarbons
Careers in Chemistry: Polymer Chemist
14.1 Formation and Combustion Reactions
14.2 Thermochemical Equations
14.3 Measuring Energy Changes
Investigation 14-B: The Heat of Combustion of
a Candle
14.5 The Impact of Petroleum Products
Careers in Chemistry: Oil Spill Advisor
Chemistry Course Challenge: A Planet Unknown
ExpressLab: Making Polymer Putty
Canadians in Chemistry: Dr.
Raymond Lemieux
Chemistry Bulletin: Elastomer
Technology: Useful or Harmful
Chemistry Bulletin: Lamp Oil and the
Petroleum Age
ThoughtLab: Factors in Heat
Transfer
Tools and Techniques: The First Ice
Calorimeter
ExpressLab: The Energy of
Dissolving
ThoughtLab: Energy Content in Fat
and Carbohydrates
ThoughtLab: Heat Combustion of
Propane and Butane

Legend
Investigations
Sections
Activities
Special Features

508 MHR • Unit 5 Hydrocarbons and Energy

UNIT 5 PLANNING CHART
Chapter 13 Chemistry: The Chemistry of Hydrocarbons
ThoughtLab/Express
Lab/Investigation Advance Preparation Time Required Materials Other Considerations

ExpressLab: Make ■ 1 week before: 40-60 min ■ 250 mL beaker (2) Borax is a fine white powder
Polymer Putty, obtain white glue The activity can be ■ 100 mL graduated which is toxic by inhalation
page 535 (try your art dept.) extended if cylinder and ingestion. To remove the
and borax. various ratios of ■ white glue waste neatly, you can have
■ 1 day before: borax : glue are ■ borax students pour their putty into
assemble materials changed. ■ food colouring a large plastic container (2 L
required. ■ warm water pop bottle) that can be sealed
and tossed out.

Investigation 13-A: ■ 1 week before : 50-60 min ■ molecular This activity works best if a
Modelling Organic obtain and examine model kits number of kits are available
Compounds, modelling kits. and students work in small
page 542 groups of two or three. Kits
should be kept in sealed
containers so that parts will
not be lost.

Investigation 13-B: ■ 1 week before: 60-75 min ■ test tubes Students can set up individual
Comparing the obtain fats/oils. (13 × 100 mm) hot baths if hot plates are at a
Reactivity of Alkanes ■ 2/3 days before: ■ test tube rack minimum, ‘melting stations’
and Alkenes, prepare KMnO4 ■ stoppers can be set-up around the
pages 554–555 solution. ■ medicine dropper room using large (1 L) beakers
■ 1 day before: ■ hot plate and hot plates.
assemble all ■ water bath
materials. ■ 5.0 mmol/L KMnO4
■ vegetable oils
(margarine, corn oil,
coconut oil)
■ fat (butter, lard)

Investigation 13-C: ■ 1 week before: 60-75 min ■ molecular None

Structures and obtain reference model kits
Properties of Aliphatic material (CRC
Compounds, handbook of
page 564 Chemistry and
Physics, Merck
Index) and search
the web for suitable
reference sites.

Unit 5 Hydrocarbons and Energy • MHR 509

 UNIT 5 PLANNING CHART
Chapter 14 Chemistry: Energy Trapped in Hydrocarbons
ThoughtLab/Express
Lab/Investigation Advance Preparation Time Required Materials Other Considerations

Investigation 14-A: ■ 2-3 days before: 60 min ■ test tubes (4) It is very important to prepare
The Formation and prepare limewater ■ rubber stoppers (4) the limewater well in advance
Combustion of (add 1.5 g of CaCO3 ■ grease pencil of the lab.
Acetylene, to 1 L of water), ■ ruler Caution must be exercised
pages 585–586 mixture sit overnight, ■ 400 mL beaker when igniting the collected
and decant ■ tweezers gas, and test tubes should be
carefully. ■ phenolphthalein directed downward.
■ 1 day before: ■ limewater
assemble all ■ medicine droppers
materials. ■ distilled water
■ test tube tongs
ThoughtLab: Factors in None. 30-45 min None. None.
Heat Transfer,
page 594

ExpressLab: The ■ 1 day before: 45 min ■ electronic balance NaOH and KOH can burn skin
Energy of Dissolving, pre-weigh out all ■ weight boats or upon contact. These solids
page 608 chemicals and store small beakers should be handled carefully.
in airtight, labelled ■ polystyrene
containers. container
■ 1 day before: ■ thermometer
assemble all ■ stirring rod
materials. ■ distilled water
■ ammonium nitrate
■ potassium hydroxide
■ potassium nitrate
■ sodium hydroxide

ThoughtLab: Energy None. 30-40 min None. None.

Content in Fat and
Carbohydrates,
page 613

ThoughtLab: Heat of None. 30 min None. None.

Combustion for
Propane and Butane,
page 615

Investigation 14-B: The ■ 2-3 weeks before: 60-75 min ■ electronic balance Soup and juice cans can have
Heat of Combustion of begin to collect ■ calorimeter very sharp edges and should
a Candle, large juice cans and apparatus be handled carefully when
pages 616–617 soup cans. ■ stirring rod assembling the calorimeter
■ 1 week before: ■ matches apparatus.
construct ■ water
calorimeter ■ candle
apparatus as shown
on page 616.
■ 1 day before:
assemble all
materials.

510 MHR • Unit 5 Hydrocarbons and Energy

 UNIT 5

Hydrocarbons and Energy

Student Textbook pages 530–635 observe both exothermic and endothermic energy changes in
Time Required: 25 hours reactions and determine exactly how much energy is
absorbed/released. By the end of the chapter, students will
have acquired a wealth of knowledge of how society makes use
Contents of organic chemicals and, through risk-benefit analysis, will
Chapter 13: The Chemistry of Hydrocarbons have a chance to make their own decisions on the societal
Chapter 14: Energy Trapped in Hydrocarbons benefits and dangers of continued use of hydrocarbons.

Unit 5 Overview
In Unit 5, students will focus on hydrocarbons, energy, and the
impact that they have on our lives. The structure and function
of hydrocarbon molecules and their subsequent use in materials
are explored. Students will examine how society depends on
the use of hydrocarbons for energy and will be encouraged to
make educated decisions on the future use of hydrocarbons and
other alternative sources of energy.

Chapter 13: The Chemistry of Hydrocarbons

This chapter is meant to provide students with insight into the
formation and isolation of hydrocarbon and petroleum prod-
ucts. By this point, students should know how to represent a
variety of inorganic compounds and understand the basic
shapes of ionic and covalently bonded molecules. In this
chapter, students will further their understanding of covalent
bonding and molecular structure by studying carbon and its
ability to form multiple covalent bonds with a variety of differ-
ent atoms. Students will learn to recognize, model, and name a
number of simple organic compounds. Students will gain an
appreciation and understanding of the use of unsaturated and
saturated fats in food products as well as the production of
petroleum.

Chapter 14: Energy Trapped in Hydrocarbons

This chapter examines the relationships between structure and
energy. Many hydrocarbon molecules have originated from
by-products of petroleum (crude oil). The energy found in the
bonds of hydrocarbon molecules is the result of the sun’s ener-
gy absorbed by the plankton, algae, and green plants millions
of years ago, before they were broken down and converted to
fossil fuels. In the process of a chemical reaction, this energy is
released to its surroundings in the form of thermal energy
(heat). In Chapter 14, students will examine the combustion
reaction and the requirements for these reactions to be carried
out to completion. The dangers of incomplete combustion reac-
tions will also be looked at. Using common laboratory tech-
niques (calorimetry), students will have the opportunity to

Unit 5 Hydrocarbons and Energy • MHR 511

 CHAPTER 13 CURRICULUM EXPECTATIONS
Expectations
Overall Inquiry of Expectations
■ [SCH V.05] select and use appropriate numeric, symbolic,
graphical, and linguistic modes of representation to
communicate scientific ideas, plans, and experimental
results (e.g., present a detailed experimental report
according to specified standards)
■ [SCH V.10] identify and describe science-and technology-
based careers related to the subject area under study (e.g.,
describe careers in the area of hydrocarbons and energy,
such as chemical engineering, or careers in transportation
related to the research and development of new fuels
Overall Expectations
■ [HE V.01] demonstrate an understanding of the structure and
properties of hydrocarbons, especially with respect to the
energy changes that occur in their combustion
■ [HE V.02] describe and investigate the properties of
hydrocarbons, and apply calorimetric techniques to the
calculation of energy changes
■ [HE V.03] evaluate the impact of hydrocarbons on our quality
of life and the environment through an examination of some
of their uses
Specific Expectations
Understanding Basic Concepts
■ [HE 1.01] identify the origins and major sources of organic
compounds
■ [HE 1.02] demonstrate an understanding of the particular
characteristics of the carbon atom, especially with respect
to bonding in both aliphatic and cyclic alkanes, including
structural isomers
■ [HE 1.03] describe some of the physical and chemical
properties of hydrocarbons (e.g., solubility in water, density,
melting point, boiling point, and combustibility of the alkanes)
512 MHR • Unit 5 Hydrocarbons and Energy
Text Section/ExpressLab/ThoughtLab/Investigation
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ Investigation 13-B: Comparing the Reactivity of Alkanes and
Alkenes, pages 554–555
■ 13.4 Refining and Using Hydrocarbons, pages 568–572
■ 13.2 Representing Hydrocarbon Compounds, pages 538–543
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ 13.2 Representing Hydrocarbon Compounds, pages 538–543
■ Investigation 13-A: Modelling Organic Compounds, page 542
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ Investigation 13-B: Comparing the Reactivity of Alkanes and
Alkenes, pages 554–555
■ Investigation 13-C: Structures and Properties of Aliphatic
Compounds, page 564
■ 13.1 Introducing Organic Compounds, pages 534–537
■ ExpressLab: Making Polymer Putty, page 535
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ 13.4 Refining and Using Hydrocarbons, pages 568–572
■ 13.1 Introducing Organic Compounds, pages 534–537
■ 13.2 Representing Hydrocarbon Compounds, pages 538–543
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ Investigation 13-B: Comparing the Reactivity of Alkanes and
Alkenes, pages 554–555
■ Investigation 13-C: Structures and Properties of Aliphatic
Compounds, page 564
■ 13.4 Refining and Using Hydrocarbons, pages 568–572
CHAPTER 13 CURRICULUM EXPECTATIONS

Expectations Text Section/ExpressLab/ThoughtLab/Investigation

Developing Skills of Inquiry and Communication ■ 13.3 Classifying Hydrocarbons, pages 544–567
■ [HE 2.02] name, using the IUPAC nomenclature system, and
draw structural representations for, aliphatic and cyclic
hydrocarbons containing no more than ten carbon atoms in
the main chain, with or without sidechains

■ [HE 2.03] use molecular models to demonstrate the ■ 13.2 Representing Hydrocarbon Compounds, pages 538–543
arrangement of atoms in isomers of hydrocarbons (e.g., ■ Investigation 13-A: Modelling Organic Compounds, page 542
structural and cis-trans isomers)

■ [HE 2.04] determine through experimentation some of the
characteristic properties of saturated and unsaturated
hydrocarbons (e.g., compare the products obtained when
bromine is added to cyclohexane and cyclohexene
separately)
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ Investigation 13-B: Comparing the Reactivity of Alkanes and
Alkenes, pages 554–555
■ Investigation 13-C: Structures and Properties of Aliphatic
Compounds, page 564

Relating Science to Technology, Society, and the Environment ■ 13.4 Refining and Using Hydrocarbons, pages 568–572
■ [HE 3.01] describe the steps involved in refining petroleum to
obtain gasoline and other useful fractions (e.g., butane,
furnace oil, industrial chemicals and solvents)

■ [HE 3.02] demonstrate an understanding of the importance of
hydrocarbons as fuels (e.g., propane for barbecues) and in
other applications, such as the manufacture of polymers, and
identify the risks and benefits of these uses to society and
the environment
■ 13.1 Introducing Organic Compounds, pages 534–537
■ 13.3 Classifying Hydrocarbons, pages 544–567
■ 13.4 Refining and Using Hydrocarbons, pages 568–572

Chapter 13 The Chemistry of Hydrocarbons • MHR 513

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

Key Terms Chapter 13

aliphatic hydrocarbons,
page 544
alkanes, page 544
alkenes, page 552
The Chemistry of
alkynes, page 560
cis-trans isomer, page 558 Hydrocarbons
cracking, page 570
cyclic hydrocarbons, Student Textbook pages 532–575
page 561
expanded molecular formula,
page 539 Contents
fractional distillation,
page 569
13.1 Introducing Organic Compounds . . . . . . . . . . . . . . . . . . . .515
geometric isomer, page 558
ExpressLab: Make Polymer Putty . . . . . . . . . . . . . . . . . . . .516
homologous series, page 544 13.2 Representing Hydrocarbon Compounds . . . . . . . . . . . . . . .517
hydrocarbons, page 533 Investigation 13-A: Modelling Organic Compounds . . . . . .519
isomers, page 539
13.3 Classifying Hydrocarbons . . . . . . . . . . . . . . . . . . . . . . . . . .524
organic compound, page 533
Investigation 13-B: Comparing the Reactivity of
petrochemicals, page 568
Alkanes and Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . .525
petroleum, page 537
Investigation 13-C: Structures and Properties
reforming, page 571
of Aliphatic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . .527
saturated hydrocarbons,
page 544 13.4 Refining and Using Hydrocarbons . . . . . . . . . . . . . . . . . . .531
structural diagram, page 541
structural model, page 540
unsaturated hydrocarbons,
Introduction
page 553 This Chapter provides insight into the structure, formation, and isolation of hydrocarbon
and petroleum products. Students further their understanding of covalent bonding and
molecular structure by studying carbon and its ability to form multiple covalent bonds
with a variety of atoms. Students also learn to recognize, model, and name a number of
simple organic compounds. Along the way, they gain an appreciation and understanding
of the production of petroleum and the use of unsaturated and saturated fats in food
products.

GETTING
STARTED
■ Engage students visually by
demonstrating an everyday
application of an organic
compound, the polymer
sodium polyacrylate.
■ Use three opaque cups: one
containing 1/4 cup (~50 mL)
of sodium polyacrylate and
another 1/8 cup (~25 mL)
distilled water (tap water will
suffice). Note: Do not let
students look into the cups
before the activity begins.
■ As a busker manipulates
three nutshells and a coin,
shuffle the cups around and
ask students to identify
which cup contains the
water. Once it is identified,
invert the cup and pour the
water into the empty cup.
Continue this process. At
one point, pour the water
into the cup that contains
the sodium polyacrylate. The
polymer will absorb the
water and form a gel that
sticks in the cup. When the
cup is eventually inverted,
the water will have “disap-
peared.” Ask students to
guess what happened to it.
Add more water to a cup
and continue the game.
■ Explain that sodium
polyacrylate is a super
absorbent organic
compound that is used in
disposable baby diapers.
Perhaps bring in a diaper to
demonstrate. Ask students
how they think it works.
Explain that polyacrylate can
absorb more than 800 times
its weight of water due to
the difference in sodium
concentration between
polyacrylate and water.
■ Explain that sodium
polyacrylate is just one of
millions of organic
compounds used in our
everyday life. Ask students
to brainstorm more
examples.

514 MHR • Unit 5 Hydrocarbons and Energy

13.1 Introducing Organic Compounds
Student Textbook pages 534–537
This section examines the natural sources of carbon, its common forms, and its applica-
tions. Students gain an understanding of the roots and the scope of organic chemistry
and the importance of carbon compounds to daily life. The ExpressLab demonstrates
how a common organic substance (polymer putty) is produced and explores its uses.

Chemistry Background
■ Simple carbon compounds such as carbonates, carbon oxides, carbides, and cyanides
fall under the heading of inorganic compounds.
■ A polymer is a large molecule created by the combination of small builder molecules
(monomers). Just a few different monomers combine to make thousands of
substances. The monomer ethene (C2H4 ), for example, is a major component of a
variety of polymers called polyethylenes. Small changes made to the atoms found in
monomers produce polymers with varying physical and chemical properties. For
example, the difference between polyethylene and polyvinyl chloride (PVC) is the
substitution of one H in C2H4 by one Cl atom to make the repeating unit C2H3Cl.
■ Hydrocarbons and other organic compounds are components in the carbon cycle, the
continuous exchange of carbon between living and non-living parts of the biosphere.

Teaching Strategies
■ Provide students with several examples of everyday products containing both natural
and synthetic organic compounds, for example, medicines, foods, plastics, compact
discs, and cotton, linen and polyester fabrics. Ask students to add more examples to
the list.
■ Debate/discuss the vital force theory. What made scientists at that time in history
think that way? What knowledge base was available to them (Internet, libraries)?
What evidence would be needed to convince you of the vital force theory? What do
you know now that scientists might not have known then (bonding, periodic table)?
■ When discussing Wohler’s and Berzelius’s work, use models and data on the physical
properties of urea and ammonium cyanate.
■ Use BLM 13-1, The Carbon Cycle/Overhead Master, to discuss how living organisms
have contributed to the storage of hydrocarbons within Earth’s surface, human contri-
butions to the greenhouse effect, organic/inorganic forms of carbon in nature, and Student Textbook page 534
the process of conversion between these two forms. (There is no need to perform a Organic compounds have
detailed explanation of petroleum products. They are dealt with in section 13.4.) carbon-carbon and carbon-
hydrogen covalent bonds.
Common Misconceptions These allow carbon to join
together in rings or chains. In
Some students might have difficulty trying to differentiate between organic material and
the case of sodium
inorganic compounds. To help distinguish one from the other, discuss the ability of car-
bicarbonate, there are no
bon to form four covalent bonds and the fact that, in organic compounds, a carbon atom carbon-carbon or carbon-
is generally either bonded to another carbon atom or to a hydrogen atom. The presence hydrogen covalent bonds.
of hydrogen is very important in distinguishing organic compounds from inorganic
carbon compounds.

Chapter 13 The Chemistry of Hydrocarbons • MHR 515

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

Making Polymer Putty

Student Textbook page 535
Approximate Time Required: 45 min

Safety
Precautions
Store all used chemical
materials in a safe place
where they can be disposed of
in an appropriate manner. Do
not flush them down the drain.
Tips
■ This lab involves cross-linking proteins. You may wish to demonstrate the structural
make up of DNA, amino acids, and proteins. Explain their significance to living
organisms and why they are classified as organic compounds.
■ The cross-linking of casein protein molecules in the glue produces the polymer putty.
Stirring or kneading the glue/borax mixture assists the cross-linking. The resultant
product can be classified as a non-Newtonian fluid because as pressure decreases, the
product becomes more like a fluid, yet behaves as a solid with increased pressure.
Answers to Analysis Questions
1. Borax is a solid and water and glue are liquids. The polymer product behaves like a
solid under high pressure, but like a liquid under low pressure.
2. Practical applications include changing the viscosity of fluids when pressure/force is
applied, or using as a fun toy for kids.

Assessment and Evaluation

ThoughtLab/
ExpressLab/ Curriculum Assessment Achievement
Investigation Expectations Tools/Techniques Chart Category Learning Skills

ExpressLab: Making Overall Expectations ■ Assessment ■ Inquiry ■ Teamwork

Polymer Putty, ■ [HE V.03] evaluate the impact of hydrocarbons Checklist 5: ■ Work Habits
page 535 on our quality of life and the environment Learning Skills
through an examination of some of their uses (see
Understanding Basic Concepts “Assessment
■ [HE 1.03] describe some of the physical and
and Evaluation”
chemical properties of hydrocarbons (e.g., in the front
solubility in water, density, melting point, boiling matter of
point, and combustibility of the alkanes) Teacher’s
Resource
CD-ROM)

Section Review Answers

Student Textbook page 537
1. (a) some organic compounds: gasoline, medication, nylon, oils, perfumes, plastic,
polystyrene, rubber, solvents, food (sugar, protein, fibre, fats), cotton, linen, wool
(b) some inorganic compounds: water, aluminum chloride (deodorant), calcium
chloride (road salt), carbon dioxide, carbon monoxide, potassium chloride
(fertilizer), sodium chloride (table salt), sodium fluoride (toothpaste), zinc
chloride (solder paste)
(c) Students may suggest that CO, CO2 , H2O, or any other compound containing
only non-metals with two or more of the atoms being C or O can be classified
as organic.

516 MHR • Unit 5 Hydrocarbons and Energy

 2. Hydrocarbons originate deep below Earth's surface and are the result of the decom-
position of once-living organisms. Most organic compounds originated when ancient
plants used energy from the Sun to convert inorganic carbon dioxide and water into
organic sugars.
3. Sources of hydrocarbons and other organic compounds include wood and fossil fuels
such as coal, oil, and natural gas.
4. compound

organic compound inorganic compound

hydrocarbon

fossil fuels

petroleum natural gas

5. (a) CH4 methane organic

(b) CH3OH methanol organic
(c) CO2 carbon dioxide inorganic
(d) HCN hydrogen cyanide inorganic
(e) C6H6 benzene organic
(f) NH4SCN ammonium thiocyanate inorganic
(g) CH3COOH acetic acid organic
(h) CaCO3 calcium carbonate inorganic

13.2 Representing Hydrocarbon Compounds

Student Textbook pages 538–543
This section begins to look at the ability of carbon to bond to itself, and the wide variety
of structures that result. Students learn how to represent hydrocarbon molecules using
various structural formats. In the investigation, they use molecular models to visualize the
isomers of organic compounds. Previous knowledge of the chemical and physical proper-
ties of substances is extended to include a comparison between structural formulas and
melting and boiling points.
Gifted Students: BLM 13-2,
Molecular Structure and
Chemistry Background Physical Properties/Skill
■ Covalent bonding occurs when pairs of electrons are shared, more or less equally, Builder, can be used to further
between two atoms. In a single covalent bond, one pair of electrons is shared between explore the relationship
two atoms. Two pairs of electrons are shared in a double covalent bond, while three between structure and physi-
cal properties. Specifically,
pairs of electrons are shared in a triple covalent bond.
BLM 13-2 compares the boiling
■ A Lewis structure uses the symbol of an element to represent the nucleus and dots
points of the first ten alkanes
placed around the element symbol to represent the electrons in the valence shell. This to the number of carbon atoms
notation is a powerful tool for predicting and explaining the formation of organic in the main chain.
compounds.

Chapter 13 The Chemistry of Hydrocarbons • MHR 517

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

Figure 13.3 Teaching Strategies

Student Textbook page 538
Carbon is a “chemical
chameleon” because it can
bond to itself and a variety of
different elements in a wide
array of geometrical structures.
Student Textbook page 539
The bond energy of a triple
bond is greater than a double
bond, which, in turn, is greater
than a single bond. Carbon-
carbon bonds have greater
energy than silicon bonds
because the electrons of the
covalent bond are closer to the
nucleus in a carbon atom,
creating a more stable bond.
There are more carbon-based
compounds than silicon-based
compounds due to the greater
■ Have three-dimensional models available to show how twisting (around the bonds)
and rotating does not produce a different structure.
■ Show Lewis structures for some simple alkanes and, together with the students, try to
develop the structural diagrams commonly used in organic chemistry.
■ When going over the three types of two-dimensional structural diagrams, discuss the
merits of each type and the possibility of errors. Which representation do students
think is the easiest to work with? Which one could easily incorporate elements other
than C and H?
■ Students should memorize the list of prefixes meth- through dec-. Emphasize that the
IUPAC naming system is just as important to organic chemistry as taxonomy is to
the classification and organization of organisms.
Common Misconceptions
Students may have difficulty differentiating intermolecular forces. In most organic com-
pounds, the attractive forces between molecules are primarily London (dispersion) forces.
The fewer the number of carbon atoms in a molecule, the weaker the London (disper-
sion) forces are between molecules. Therefore, the melting point is lower.
1000
900
800
Bond Energy (kJ/mol)

stability in the bonds of carbon 700

atoms.
600

500
Figure 13.6
Student Textbook page 540 400
Ball-and-stick models 300
represent a given molecule in
three dimensions, while an 200
expanded molecular formula
shows the molecular structure 100
in only two dimensions. Since
one isomer differs from the 0
H

H
Si

Si
C

rest by the spatial location of

the carbon atoms, it is much
Si
C

Si

Si
C

easier to distinguish between

Bond Type
two isomers using
ball-and-stick models.

518 MHR • Unit 5 Hydrocarbons and Energy

 Investigation 13-A
Modelling Organic Compounds
Student Textbook page 542
Approximate Time Required: 50–60 min

Tips
■ This is a great activity for visual and tactile learners, and also for ESL students and
those that may have difficulty understanding the concepts in this section.
■ If suitable kits are not available, bulk candy and toothpicks are a convenient
alternative, but never allow students to eat anything in the lab.
■ Review the electronic configuration of nitrogen prior to the lab. (N can from only
three covalent bonds.)
■ For isomers of C5H12 , make only five carbon and 12 hydrogen atoms available to
students. This avoids the unwanted addition or deletion of hydrogen atoms.

Answers to Procedure Questions

1. Isomers of C5H12
H H H H H

H C C C C C H

H H H H H
H

H C H
H H

H C C C H

H H
H C H

H
H H H H

H C C C C H

H H H
H C H
Only 3 isomers exist as
H these two are the same

H H H H

H C C C C H

H H H
H C H

Chapter 13 The Chemistry of Hydrocarbons • MHR 519

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

2. Isomers of C3H9N

H H
N
H H

H C C C H

H H H

H H H H

H C N C C H

H H H

H H

H C N C H

H H
H C H

H H H
H
H C C C N
H
H H H

Answers to Analysis Questions

1. Answers should mention the difference between two-dimensional and three-dimen-
sional models and the fact that four isomers initially can be sketched for C5H12 , but
models reveal that two of the four are identical.
2. Rotation and manipulation of the main chain demonstrates that the carbon backbone
is not necessarily a straight line.

Answer to Conclusion Question

3. The real-life structural arrangements of C5H12 and C3H9N do not look like ball-and-
stick models. Space-filling models more accurately represent them.

Answers to Applications Questions

4. Isomers with fewer branches have higher boiling points. Pentane has the highest boil-
ing point. This makes sense, since it has the least number of branches. The boiling
points for the isomers of pentane are:
■ Pentane, 36.1˚C

■ 2,2-dimethylpropane, 9.5˚C

■ 2-methylbutane, 27.8˚C

Among the isomers of C3H9N, n-propylamine has the least number of branches and,
hence, the highest boiling point. Note that students will not yet be able to name the
following isomers:

520 MHR • Unit 5 Hydrocarbons and Energy

 ■ n-propylamine (1-amino propane) CH3CH2CH2NH2 , 47.8˚C
■ methylethylamine CH3NHCH2CH3 , 36.7˚C

■ isopropylamine (2-amino propane) (CH3)2CHNH2 , 32.4˚C

■ trimethylamine (CH3)3N, 2.9˚C

5. There are nine isomers of heptane.

heptane CH3 CH2 CH2 CH2 CH2 CH2 CH3

CH3

2-methylhexane CH3 CH CH2 CH2 CH2 CH3

CH3

3-methylhexane CH3 CH2 CH CH2 CH2 CH3

CH3

2,2-dimethylpentane CH3 C CH2 CH2 CH3

CH3

CH3 CH3

2,3-dimethylpentane CH3 CH CH CH2 CH3

CH3 CH3

2,4-dimethylpentane CH3 CH CH2 CH CH3

CH3

3,3-dimethylpentane CH3 CH2 C CH2 CH3

CH3

CH3

CH2

3-ethylpentane CH3 CH2 CH CH2 CH3

CH3 CH3

2,2,3-trimethylbutane CH3 C CH CH3

CH3

Chapter 13 The Chemistry of Hydrocarbons • MHR 521

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

Assessment and Evaluation

ThoughtLab/
ExpressLab/ Curriculum Assessment Achievement
Investigation Expectations Tools/Techniques Chart Category Learning Skills

Investigation 13-A: Overall Expectations ■ Rubric for ■ Knowledge/ ■ Teamwork

Modelling Organic ■ [HE V.02] describe and investigate the properties Investigation Understanding ■ Work Habits
Compounds, of hydrocarbons, and apply calorimetric 13-A: Modelling ■ Inquiry
page 542 techniques to the calculation of energy changes Organic ■ Communication
Compounds
Specific Expectations (see
Developing Skills of Inquiry and Communication “Assessment
■ [HE 2.03] use molecular models to demonstrate and Evaluation”
the arrangement of atoms in isomers of in the front
hydrocarbons matter of
Teacher’s
Resource
CD-ROM)

Section Review Answers

Student Textbook page 543
1. 1) Carbon has four bonding electrons, which allow the formation of four strong
covalent bonds to a variety of different elements.
2) Carbon can form single/double/triple covalent bonds and stable chains.
3) Carbon-based molecules can assume various geometric shapes.
2. Students should represent their hydrocarbon molecule using a complete structural
diagram, a condensed structural diagram, a line structural diagram, and (if time and
material exist) a ball-and-stick model.
3. Isomers of C6H14

H H H H H H

H C C C C C C H CH3 CH2 CH2 CH2 CH2 CH3

H H H H H H
hexane
H

H C H
H H H H CH3

H C C C C C H CH3 CH CH2 CH2 CH3

H H H H H
2-methylpentane
H

H C H
H H H H CH3

H C C C C C H CH3 CH2 CH CH2 CH3

H H H H H
3-methylpentane

522 MHR • Unit 5 Hydrocarbons and Energy

 H

H C H
H H H CH3

H C C C C H CH3 CH CH CH3

H H H CH3
H C H

H
2,3-dimethylbutane
H

H C H
CH3
H H H
CH3 C CH2 CH3
H C C C C H
CH3
H H H
H C H

H 2,2-dimethylbutane

4. Isomers of C5H12

H H H H H

H C C C C C H CH3 CH2 CH2 CH2 CH3

H H H H H

H pentane

H C H
H H H CH3

H C C C C H CH3 CH CH2 CH3

H H H H
2-methylbutane
H

H C H
H H CH3

H C C C H CH3 C CH3

H H CH3
H C H

H 2,2-dimethylpropane

5. The condensed structural diagram for ethanol is CH3CH2OH . A line structural

diagram for ethanol cannot be drawn because the lines and points only represent car-
bon atoms. This type of diagram can be used only for hydrocarbons such as alkanes,
alkenes, and alkynes and cannot be used for organic compounds containing atoms
other than C and H.
H H

H C C O H

H H Chapter 13 The Chemistry of Hydrocarbons • MHR 523

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS
Gifted Students: Have students
prepare poster presentations
on topics that involve health
issues and organic chemicals,
such as the one listed in the
Biology Link on page 556.
Other topics can include: cis-
trans isomerism and vision,
and carcinogens (cancer-
causing organic compounds
such as chloroform).
Students Who Need Extra
Help: Use Lewis structures and
molecular models to demon-
strate that each carbon atom
in an alkane, alkene or alkyne
molecule requires a total of
four covalent bonds.
Student Textbook page 545
Methane contains only one
carbon atom and four
hydrogen atoms. Carbon has
four valence electrons and can
pick up a maximum of four
more electrons through
covalent bonding. The simplest
manner in which this can
occur is the bonding of four
hydrogen atoms, making four
equal covalent bonds around
the carbon centre.
Student Textbook page 546
Under STP conditions,
methane is a highly volatile
gas that must be stored in a
cool, dry, well-ventilated area.
For large-scale applications,
methane is either stored in
large pressurized cylinders or
tanks. These must be located
in a spark-proof environment
where temperatures must not
exceed 40 °C.
524 MHR • Unit 5 Hydrocarbons and Energy
13.3 Classifying Hydrocarbons
Student Textbook pages 544–567
This section continues chemical nomenclature, delving into the world of organic
designations. Students learn the IUPAC system for naming aliphatic hydrocarbons and
apply this system through both practice and investigation. Investigation 13-B compares
the reactivity of alkanes and alkenes. Investigation 13-C examines the structures and
properties of aliphatic hydrocarbon molecules. The idea of unsaturated and saturated
hydrocarbons is introduced and related to our dietary input of fats and oils.
Chemistry Background
■ IUPAC formulas do not necessarily indicate the 3-D structure of a molecule.
■ The degree of saturation affects the firmness and stability of fats. In general,
unsaturated fats are liquids (e.g., vegetable oils) while saturated fats are harder (e.g.,
animal fats).
■ Some chemical properties of alkenes:
– They react with oxygen at high temperatures to produce CO2 and H2O.
– Oxidizing agents, such as KMnO4 and K2Cr2O7 , attack at the site of the double
bond. This reaction is usually accompanied by a change in colour of the
oxidizing agent.
– Alkenes are more reactive than alkanes and will undergo addition reactions at the
site of the double bond.
■ C2H4 is also known as ethylene and is one of the only alkenes which is referred to
using a non-IUPAC name.
■ The compact arrangement of carbon atoms in cyclic compounds gives them higher
boiling points than straight chain hydrocarbons have.
■ Cyclic alkenes tend to have a higher reactivity than linear alkenes due to ring strain.
Teaching Strategies
■ Provide students with practice drawing and naming aliphatic hydrocarbons according
to the IUPAC system by using the following: BLM 13-3, Working with Alkanes,
Alkenes, Alkynes and Isomers/Reinforcement; and BLM 13-4, Working with Cyclic
Aliphatics/Reinforcement.
■ Use models to demonstrate the rigidity of the carbon backbones containing double
and triple bonds. Point out that the backbone is linear around a triple bond and that
there can be up to 360˚ of rotation around a C–C bond but there can be no rotation
around a double or triple bond.
■ Have students try to determine a general formula for the number of carbon and
hydrogen atoms in a cyclic compound. The general formula for a cyclic alkane is
CnH2n . The general formula for a cyclic alkene is CnH2n−2 .
■ Use BLM 13-5, Organic Nomenclature Quiz/Assessment, to assess student under-
standing upon completion of this section.
Common Misconceptions
■ Students might have difficulty relating common products to IUPAC names. We refer
to many organic compounds by common names they were given long before the
IUPAC system was universally accepted.
■ Many students begin numbering atoms at the end most convenient to them.
Emphasize that the numbering of carbon atoms in alkenes must begin at the end
closest to the double bond.
Figure 13.11
Student Textbook page 545 Student Textbook page 547
All four molecules are saturated hydrocarbons called alkanes. Each molecule has one The number of hydrogen
more carbon atom than the previous molecule and follows the general rule (2n + 2) for atoms in an alkane equals
the number of hydrogen atoms in the molecule. 2(n) + 2, where n is the num-
ber of carbon atoms. In the
case of heptane, n = 7 , so
Figure 13.12 there should be 2(7) + 2 = 16
Student Textbook page 545 hydrogen atoms in the
molecule.
Both ethane and propane are alkanes. Propane differs from ethane due to an additional
CH2 unit found within the main chain.

Solutions for Practice Problems

Student Textbook page 545
Student Textbook page 549–550
Student Textbook page 551–552
Student Textbook page 557–558
Student Textbook page 558
Student Textbook page 560
Safety
Student Textbook page 563 Precautions
Ensure that students have read
See Solutions Manual for solutions to Practice Problems.
“Safety in Your Chemistry
Laboratory” on pages x-xiii of
the student
Investigation 13-B textbook. Also ensure that they
follow all safety precautions
Comparing the Reactivity of Alkanes and Alkenes outlined for this investigation in
the student textbook. Store all
Student Textbook pages 554–555 used chemical materials in a
Approximate Time Required: 60–75 min safe place where they can be
disposed of in an appropriate
Tips manner. Do not flush them
down the drain.
■ One week before the lab, obtain fats and oils.
■ Two or three days before the lab, prepare KMnO4 solution (5 mmol/L); dissolve 0.08
g of KMnO4 in 100 mL of water.
■ One day before the lab, assemble all materials.
Student Textbook page 547
Answer to Procedure Question Meaning of the roots for the
1. Students should generate a table similar to the one shown below. first 10 prefixes used in organ-
ic chemistry nomenclature:
Observations (after addition meth- methyl (coined by
Sample in Test Tube Prediction of potassium permanganate)
chemist Jons Jakob
Berzelius)
eth- ether (means upper,
purer air)
prop- first
but- butylium (from butter)
pent- five
Answers to Analysis Questions
hex- six
1. In order for students to make accurate predictions, they should complete the Biology hept- seven
Link on page 556 of the student textbook. This will provide students with a better oct- eight
knowledge base for the investigation. non- nine
dec- ten

Chapter 13 The Chemistry of Hydrocarbons • MHR 525

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

2. This answer will differ based on the students’ preconceptions of the products used
and their contents.

Answer to Conclusion Question

3. A connection should be made between unsaturated compounds and a change in
colour of the permanganate ion.

Answer to Application Question

4. Students are asked to find the structures of those fatty acids examined in the lab that
are unsaturated and underwent a reaction with KMnO4, and the structures of those
that are saturated and had no reaction.
Fatty Acid Composition of Some Fats and Oils
Saturated Fatty Acids (%) Unsaturated Fatty Acids (%)

Source Lauric Acid Myristic Acid Palmitic Acid Stearic Acid Oleic Acid Linoleic Acid
Lard (fat) - 1 25 15 50 6
Butter (fat) 2 10 25 10 25 5
Coconut Oil 50 18 8 2 6 1
Olive Oil - 1 5 5 80 7
Peanut Oil - - 7 5 60 20

Biology Link O H H

Student Textbook page 556 CH3 (CH2)14 C C C

The following Internet sites OH (CH2)7 (CH2)7
provide information about palmitic Acid
saturated and unsaturated fats CH3 C O
and their effects on human OH
health: O oleic Acid
http://www.womensmedia.
CH3 (CH2)10 C
com/health-fat.html and
http://www.heartinfo.com/ OH
nutrition/fatdefin4798.htm lauric Acid

Figure 13.25 O
Student Textbook page 561 CH3 (CH2)12 C
Steroids are compounds with
OH
a basic structure of three
hexagonal and one pentagonal myristic Acid H H O OH
carbon rings. These rings may
be saturated or unsaturated. C C C
Different functional groups O (CH2)4 CH2 (CH2)7
attached to these rings give
rise to the chemical properties CH3 (CH2)16 C CH3 C C
of the steroid. OH H H
stearic Acid linoleic Acid

526 MHR • Unit 5 Hydrocarbons and Energy

Assessment and Evaluation
ThoughtLab/
ExpressLab/ Curriculum Assessment Achievement
Investigation Expectations Tools/Techniques Chart Category Learning Skills

Investigation 13-B: Overall Inquiry Expectations ■ Rubric for ■ Knowledge/ ■ Works

Comparing the ■ [SCH V.05] select and use appropriate numeric, Investigation Understanding Independently
Reactivity of symbolic, graphical, and linguistic modes of 13-B: Comparing ■ Inquiry ■ Organization
Alkanes and representation to communicate scientific ideas, the Reactivity of ■ Communication
Alkenes, plans, and experimental results Alkanes and
pages 554–555 Overall Expectations Alkenes (see
■ [HE V.02] describe and investigate the properties “Assessment
of hydrocarbons, and apply calorimetric and Evaluation”
techniques to the calculation of energy changes in the front
matter of
Specific Expectations Teacher’s
Understanding Basic Concepts Resource
■ [HE 1.03] describe some of the physical and CD-ROM)
chemical properties of hydrocarbons
Developing Skills of Inquiry and Communication
■ [HE 2.04] determine through experimentation
some of the characteristic properties of
saturated and unsaturated hydrocarbons

Investigation 13-C
Structures and Properties of Aliphatic Compounds
Student Textbook page 564
Approximate Time Required: 60-75 min

Tips
■ One week before, obtain and inspect model kits for the required molecules.
■ Try to have reference books (CRC Handbook of Chemistry and Physics, Merck Index)
available so students can research the boiling points of various compounds.

Answers to Procedure Questions

2. H H H H H H

H C C C C H H C C C C H

H H H H H H
butane 2-butyne

H
H H
H C H
H C C H
H C C H
H H C C H
C
H H H H
trans-2-butene cyclobutane

Chapter 13 The Chemistry of Hydrocarbons • MHR 527

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

3. The three-dimensional appearance of the molecule changes slightly but the

arrangement of atoms does not change. The carbon atoms in cyclobutane are unable
to rotate, and are fixed in a strained position.
4.
30

Boiling Point (˚C)

20

10

–10

butane

trans-2-butene

2-butyne

cyclobutene
5. H 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
pentane 2-pentyne

H H H H
H C H C H
H C H C C
C C H
H H
H C C H C C H
H
H H H
trans-2-pentene cyclopentane
6. Prediction based on question 5 should be as follows (from highest boiling point to
lowest boiling point): 2-pentyne > cyclopentane > trans-2-pentene > pentane
Actual boiling points: cyclopentane 49.2˚C; 2-pentyne 56˚C; trans-2-pentene
36.3˚C; pentane 36.1˚C

Answers to Analysis Questions

1. Multiple-bond compounds are more rigid and have fewer bonds available for rotation
than the alkanes.
2. Alkyne and cyclic compounds both have high boiling points, while straight chain
alkanes have the lowest boiling points.

Answer to Conclusion Question

3. Alkynes and cyclic compounds have a more structured arrangement in the solid state
compared to other carbon compounds. A more ordered “crystalline” configuration
requires more heat to break the intermolecular forces necessary for a compound to go
from a liquid state to a gaseous state.

528 MHR • Unit 5 Hydrocarbons and Energy

Answer to Application Question
4. highest boiling point to lowest boiling point: cyclohexane (80.7˚C), cyclopentane
(49.2˚C), cyclobutane (12˚C), cyclopropane (-32.7˚C)

Assessment and Evaluation

ThoughtLab/
ExpressLab/ Curriculum Assessment Achievement
Investigation Expectations Tools/Techniques Chart Category Learning Skills

Investigation 13-C: Overall Expectations ■ Rubric for ■ Knowledge/ ■ Teamwork

Structures and ■ [HE V.02] describe and investigate the properties Investigation Understanding ■ Work Habits
Properties of of hydrocarbons, and apply calorimetric 13-C: Structures ■ Inquiry
Aliphatic techniques to the calculation of energy changes and Properties of ■ Communication
Compounds, Understanding Basic Concepts Aliphatic
page 564 ■ [HE 1.03] describe some of the physical and
Compounds
chemical properties of hydrocarbons (see
“Assessment
Developing Skills of Inquiry and Communication and Evaluation”
■ [HE 2.04] determine through experimentation in the front
some of the characteristic properties of matter of
saturated and unsaturated hydrocarbons Teacher’s
Resource
CD-ROM)

Section Review Answers

Student Textbook pages 566–567
1. (a) alkanes, alkenes, and alkynes
(b) Alkanes are saturated, non-polar compounds with relatively low boiling points
and low solubility in water. Alkenes and alkynes are unsaturated compounds.
Alkenes are non-polar and usually have a lower boiling point than similar-sized
alkanes, although there are exceptions, as seen in Investigation 13-C. Alkenes and
alkynes are much more reactive that alkanes, as observed in Investigation 13-B.
Alkenes and alkynes react with potassium permanganate, but alkanes do not.
2. meth – 1 carbon atom; eth – 2; prop – 3; but – 4; pent – 5; hex – 6; hept – 7;
oct – 8; non – 9; dec – 10.
3. Octane is a non-polar molecule that does not dissolve in water, which is polar.
4. (a) 3-ethyl-2,4-dimethylhexane
(b) 2,4,4-trimethyl-1-pentene
(c) 4-ethyl-3-propyl-1-hexyne
(d) 2-ethyl-3,4,5,6-tetramethyl-1-cycloheptene
5. (a) 2,4-dimethyl-3-hexene
CH3 CH3

CH3 CH CH C CH2 CH3

Chapter 13 The Chemistry of Hydrocarbons • MHR 529

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

(b) 5-ethyl-4-propyl-2-heptyne
CH3

CH2

CH3 C C CH CH CH2 CH3

CH2

CH2

CH3
(c) 3,5-diethyl-2,4,7,8-tetramethyl-5-propyldecane
CH3 CH3

CH2 CH2

CH3 CH CH CH C CH2 CH CH CH2 CH3

CH3 CH3 CH2 CH3 CH3

CH2

CH3
(d) trans-4-methyl-3-heptene
H CH2 CH2 CH3
C C
CH2 CH3 CH3
6. (a) CH C CH3
propyne

CH2

CH CH
cyclopropene

H2C C CH2
propadiene
(b) CH3 CH2 CH2 CH2 CH3
pentane

CH3

CH3 CH CH2 CH3

2-methylbutane

CH3

CH3 C CH3

CH3
2,2-dimethylpropane

530 MHR • Unit 5 Hydrocarbons and Energy

 (c) CH3

CH2 CH CH2 CH2 CH3 H2C C CH2 CH3

1-pentene 2-methyl-1-butene

H H
C C
CH3 CH2 CH3
cyclopentane cis-2-pentene

CH3 H CH3 CH3

C C C C
H CH2 CH3 CH3 H
trans-2-pentene 2-methyl-2-butene

7. (a) There should be a double bond on carbon 2 rather than a triple bond. Also, the
compound should be numbered starting from the right. The correct name would
be 2-methyl-2-butene.
(b) This cyclic alkene is numbered improperly. It should be 3-ethyl-5,
6-dimethyl-1-cyclohexene.
8. (a) propadiene
CH2 C CH2
(b) 2-methyl-1,3-butadiene
CH3

CH2 C CH CH2
(c) 1,3,5-cycloheptatriene
CH CH2
CH
CH
C
C CH
(d) cyclopentylcyclohexane
CH2 CH2 CH2 CH2
CH2 CH CH
CH2 CH2 CH2 CH2

13.4 Refining and Using Hydrocarbons

Student Textbook pages 568–572
This section stresses the importance of hydrocarbons in everyday activities. It looks at
the isolation of petrochemical products from crude sources and the many uses of
these products.

Chapter 13 The Chemistry of Hydrocarbons • MHR 531

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS
Student Textbook page 571
A catalyst is a substance that
speeds up a chemical reaction
without being changed or used
up itself.
Unit Project Prep
Student Textbook page 572
Ethene is used to produce
most plastics, and thus almost
all products’ packaging.
532 MHR • Unit 5 Hydrocarbons and Energy
Chemistry Background
Solubility can be explained in terms of intermolecular forces. Ionic compounds easily
dissolve in water due to the hydration of positive and negative ions by polar water
molecules. This dipole-ion attraction is great enough to overcome the interionic
attraction within an ionic solid. Organic molecules do not have a strong dipole moment,
making them generally insoluble in water. This, plus a lower density than water, allows
organic compounds to float on water.
Teaching Strategies
■ Distillation of an acetone/water mixture or and ethanol/water mixture helps students
understand the process of distillation. BLM 13-6, Demo of Fractional
Distillation/Inquiry Assessment, can be used as a guide to performing the demo or, if
enough equipment is available, as a lab worksheet for students. This BLM also is use-
ful when performing Part 3 of the Course Challenge. Note that an ethanol/water
mixture is recommended if this lab is used as a student investigation.
■ Students can use BLM 13-7, Fractional Distillation Tower/Information Handout, as a
starting point to summarize the information presented in this section. It provides
space to record typical boiling points of petroleum products and the common uses of
these products.
■ Students who have a keen interest in oil production and the consumption of
non-renewable resources can do questions 24 and 25 in the Chapter 13 Review as
additional activities.
Careers in Chemistry
Polymer Chemist
Student Textbook page 572
Make Career Connections
Popular polymer manufacturers that can be found on the Internet are:
■ DuPont: www.dupont.ca
■ Polymer Plastics Corporation: www.polymerplastics.com
■ Polychem Corporation: www.polychem.com
■ Plastix Universe: www.plasticx.com
Section Review Answers
Student Textbook page 572
1. (a) the boiling point
(b) fractional distillation. Each hydrocarbon component has a unique range of boiling
points. A large furnace vaporizes these liquid components. Several plates inside a
tower collect condensates from the rising vaporized fractions at levels where the
temperature is just below their boiling points. Larger hydrocarbons have higher
boiling points, so they condense first. Smaller hydrocarbons rise higher up
before condensing.
2. The cracking process uses heat to break larger hydrocarbon molecules into smaller
gasoline molecules. The reforming process uses heat, pressure, and catalysts to convert
small hydrocarbons into larger hydrocarbon compounds or aromatic compounds.
 3. methanol, ethylene, propylene, styrene, butadiene, butylenes, toluene, and xylene
How each has affected students’ lives depends on individual experience, circumstance,
and opinion.

Chapter 13 Review Answers

Student Textbook pages 573–575

Answers to Knowledge/Understanding Questions

1. (a) decomposition of once-living organisms deep below Earth’s surface
(b) three of the following: wood, coal, oil, or natural gas
(c) petroleum (crude oil)
2. heat, pressure, and time
3. Carbon has four bonding electrons, which allow it to form strong covalent bonds
with a variety of different elements (primarily H, N, P, and S). Carbon can form
single, double, and triple bonds. It can also form long, stable chains. Carbon
compounds can have different structural shapes, such as chains and rings.
4. Fractional distillation is a process used to separate petroleum into its hydrocarbon
components. Petrochemicals are basic hydrocarbons that are converted into plastics
and other synthetic materials.
5. Isomers are compounds having the same formula but different structural arrange-
ments. One example of a set of isomers is:
CH2 CH CH2 CH2 CH3 CH3 CH CH CH2 CH3
pentene 2-pentene

cyclopentane

CH3 H H H
C C C C
H CH2 CH3 CH3 CH2 CH3
cis-1-methylbutene trans-1-methylbutene

6. Aliphatic compounds are non-polar molecules. The only intermolecular forces exhib-
ited by such molecules are London (dispersion) forces. Therefore, the boiling point of
an aliphatic compound such as an alkane increases as the chain length increases.
7. alkanes alkenes alkynes
polarity non-polar non-polar non-polar
boiling point lower than similar- usually slightly higher higher than similar-
sized alkenes and than similar-sized sized alkanes and
alkynes alkanes but lower than alkenes
similar-sized alkynes
degree of saturation saturated unsaturated unsaturated
reactivity less reactive than more reactive than more reactive than
alkenes and alkynes alkanes but less alkanes and alkenes
reactive than alkynes

Chapter 13 The Chemistry of Hydrocarbons • MHR 533

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

8. Structural isomers have the same formula but different structural arrangements.
Cis-trans isomers have different groups of atoms arranged around a double bond. The
formula and basic structural arrangement (i.e., which atoms are bonded to each
other) is the same for a cis isomer and a trans isomer; however, the spatial arrange-
ment of atoms is different for each isomer.
9. (a) butane (b) ethane
(c) 2,3,4-trimethylpentane (d) 3-ethyl-4-methylhexane
10. (a) 2-methyl-1-propene (alkene) (b) 1-ethyl-2-methylcyclohexane
(cycloalkane)
(c) 3-methyl-1-pentyne (alkyne) (d) trans-3-methyl-2-pentene (alkane)
(e) 3-ethyl-3,4-dimethylhexane
11. trans-2-heptene
cis-2-heptene
12. (a) D; (b) none;
(c) C; (d) A;
(e) none; (f) B
13. No, the numbering must begin at the double bond.
or

CH3 CH3
3-methyl-1-cyclobutene 1-methyl-1-cyclobutene
14. Oil molecules are non-polar; they do not dissolve in water molecules, which are polar.
Oil floats on the surface of water.
15. The “1” position at the end of an alkane chain is always a methyl group that is part
of the main chain.
16. True isomers of C6H14 are diagrams (a), (b), and (e). Diagrams (a), (c) and (b), (d)
represent the same isomer.

Answers to Inquiry Questions

17. Add potassium permanganate to each beaker. A change in colour will occur in the
beaker that contains the alkene.
18. First, determine the possible structural formulae for the isomers of C6H12 . Only
structural diagrams of cycloalkanes and alkenes fit the criteria. Next, determine the
boiling points of the two compounds and compare them to the literature value.
Another test is the addition of KMnO4, which turns brown in the presence of
an alkene.
19. (a) Springs were required to accommodate the orientation of the carbon atoms
in this configuration. Carbon allows covalent bonds to occur in a tetrahedral
arrangement around its nucleus but does not allow a perfect cube to form from
four carbon atoms. For this reason, a straight connection cannot be made in a
model and springs must be used.
(b) Cyclobutane is a relatively unstable molecule.

534 MHR • Unit 5 Hydrocarbons and Energy

Answers to Communication Questions
20. (a) 3-ethylhexane (b) 1-butene
H H H H H H H H H H

H C C C C C C H C C C C H

H H H H H H H H
H C H

H C H

H
(c) 2,3-dimethlylpentane
H

H C H
H H H H

H C C C C C H

H H H H
H C H

H
21. (a) methylpropane
CH3

CH3 CH CH3
(b) 1-ethyl-3-propylcyclopentane
CH2 CH3

CH
CH2 CH2

CH2 CH CH2 CH2 CH3

(c) cis-3-methyl-3-heptene
CH3 CH2 CH2 CH2 CH3
C C
CH3 H
(d) 3-butyl-4-methyl-1-octyne
CH2 CH2 CH2 CH3

HC C CH CH CH2 CH2 CH2 CH3

CH3
(e) 4-ethyl-1-cyclooctene
CH2 CH2
CH2 CH2

CH2 CH2
CH C
CH2 CH3

Chapter 13 The Chemistry of Hydrocarbons • MHR 535

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

22. (a) CH3 CH2 CH2 CH2 CH3

CH3

CH3 CH CH2 CH3

CH3

CH3 C CH3

CH3
There are only three isomers of C5H12 .
(b) CH3 CH2 CH2 CH2 CH2 CH3
C C
H H
CH3 CH2 CH2 CH2 CH2 CH3
C C
H H
H CH2 CH2 CH2 CH3
C C
CH2 CH2 H
H CH2 CH2 CH3
C C
CH3 CH2 CH2 H
23. (a) Each hydrocarbon component has its own range of boiling points. Hydrocarbons
with lower boiling points vaporize first and rise to the top of the tower.
Hydrocarbons with higher boiling points remain in the solid state and stay at the
bottom of the tower.
(b) A chain that is 15 carbon atoms in length would most likely be removed from the
“gas oil” section of the fractionation tower, which is close to the base. As the num-
ber of carbon atoms in a chain increases, so does the compound’s boiling point, so
this particular compound would fractionate out close to the bottom of the tower.

536 MHR • Unit 5 Hydrocarbons and Energy

24. crude oil fractionation tower

gas oil kerosene straight-run gasoline

hydro-cracking catalytic reforming

gas recovery and separation

further processing

gasoline

25. crude oil

fractional distillation

condensate

polymerization further processing

synthetic rubber

26. The cracking process must be employed.

27. Alkanes containing the fewest carbon atoms in the main chain have the lowest
boiling point.
CH3 CH2 CH3 lowest BP
propane

CH3 CH2 CH2 CH3

butane

CH3 CH2 CH2 CH2 CH3

pentane

CH3

CH3 CH CH3
2-methylpropane
highest BP

Chapter 13 The Chemistry of Hydrocarbons • MHR 537

UNIT 5 Chapter 13 THE CHEMISTRY OF HYDROCARBONS

28. H H

H C H H C H
H H H

H C C C C C H

H H H H
H C H

H
complete structural diagram

CH3 CH3

CH3 CH CH CH CH3

CH3
condensed structural diagram

line structural diagram

Complete structural diagrams provide a strong visual representation of the

arrangement of atoms in a molecule but are difficult to produce for large
hydrocarbon molecules. Condensed structural diagrams are easy to produce and can
be used to represent virtually any organic compound. Line structural diagrams are
very easy to draw but some confusion can exist when trying to determine the number
of carbon and hydrogen atoms found within a particular molecule.

Answers to Making Connections Questions

29. Ethene is used to increase the ripening of fruit and to manufacture plastics.
30. Two Internet sites containing information on oil drilling are:
- http://www.hibernia.ca/index.html (information about the Hibernia oil drilling
platform off the coast of Newfoundland)
- http://www.capp.ca/(official site of the Canadian Association of
Petroleum Producers)
31. Responses will vary based on students’ opinions on the use of natural resources. It
appears there are plenty of resources for the current generation but what might not be
realized is that it took billions of years to build up these resources and, at the current
rate of use, we will run out of petroleum resources before more can be created.

538 MHR • Unit 5 Hydrocarbons and Energy