UNIT 5 REVIEW

Part 1
(Pages 468469)
1. C
2. D
3. 3, 1, 4, 2
4. B
5. A
6. D
7. C
8. B
9. A
10. D
11. B
12. 4, 9
13. 1, 8
14. 5, 7
15. 2, 6
16. 2, 6
17. 2
18. 5, 7
19. 4

Part 2
(Pages 469473)
20. Organic compounds are classified on the basis of their bonding and types of atoms present.
The first major classification is hydrocarbons (containing only C and H atoms) and
hydrocarbon derivatives (containing C, H, and/or other atoms).
Hydrocarbons
Aliphatics
Aromatics
containing
alkanes, CC
alkenes, C=C
alkynes, C{C
cycloaliphatics

Hydrocarbon Derivatives
organic halide
alcohol
carboxylic acid
ester

RX
(X could be F, Cl, Br, I)
ROH
RCOOH
RCOOR

21. Small samples of each of the unknown chemicals will be tested for their melting points.
Organic compounds tend to have lower melting points compared with inorganic compounds,
whose melting points tend to be very high. Small samples of both types of compounds will be
dissolved in water or tested in their liquid state for conductivity. Molten or aqueous ionic
compounds will conduct electricity; organic compounds will not. Finally, small samples of
both types of compounds will be subjected to a flame test. Organic compounds will usually
melt and burn, whereas ionic compounds will usually not melt and will produce a coloured
flame.
22. Bitumen/Oil sands: used as feedstock to produce all types of hydrocarbons, from
conventional oil and gasoline to heavy lubricants and asphalt.
Heavy oil: used as feedstock to produce all types of hydrocarbons, from conventional oil and
gasoline to heavy lubricants and asphalt.

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Crude oil: primarily used to create gasoline and diesel fuels, and can be cracked or reformed
as needed.
Natural gas and coalbed methane (CBM): the methane primarily used for heating and the
other various components are used as feedstock to produce important petrochemicals such as
ethene and propene.
23. ethylene glycol:
organic
hydrochloric acid:
inorganic
polystyrene:
organic
vinyl chloride monomer: organic
1,2-dichloroethane:
organic
sodium hydroxide:
inorganic
chlorine:
inorganic
ethylene:
organic
polyethylene:
organic
24. l

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25. Chlorine could be added to ethylene:

26. Consumers could find the following in stores:

ethylene glycol: radiator antifreeze
hydrochloric acid: muriatic acid (cement cleaner)
sodium hydroxide: drain cleaner
polyethylene: plastics such as milk jugs
27. (a) octane
(b) 2-methylheptane
(c) 2-methylpentane
28. (a)

(b)
(c)

29. [Be careful in checking answers; some parts in the Student Book are out of order.]
(a) benzene
(b) methylbenzene (or toluene)
(c) 1,2-dimethylbenzene (also called o-xylene)
(d) 1,3-dimethylbenzene (also called m-xylene)
(e) ethylbenzene
(f) 1,4-dimethylbenzene (also called p-xylene)
30. Alkylation (isomerization) is the process where a molecule transforms from one structural
formula, or shape, into another structural formula, or shape, without changing the number or
type of atoms in the molecule.
31. (a) butane o methylpropane
(b) 3-methylhexane o 2,2,3-trimethylbutane
(c)

(d)
32. catalytic reforming
33. (a)

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(b) From lowest to highest boiling points would be: butane, chloroethene, 1-propanol, then
ethanoic acid. Since they have approximately the same number of electrons, London
forces will be approximately the same strength for each. Since butane only has London
forces, it has the weakest forces and therefore the lowest boiling point. Chloroethene has
dipoledipole intermolecular forces due to the chlorine, but no hydrogen bonding as in 1propanol and ethanoic acid, so chloroethene has the second-lowest boiling point. Finally,
ethanoic acid has the highest boiling point because it has an added carbonyl group to
increase its dipoledipole bonding as compared to 1-propanol and this also increases the
number of hydrogen bonds that are possible. This makes the intermolecular forces the
strongest in ethanoic acid and gives it the highest boiling point.
(c) Ethanoic acid and 1-propanol would have high solubility in water because they are both
polar and can form hydrogen bonds with water molecules. Chloroethene may be slightly
soluble in water as it is polar, like water. Butane would have negligible solubility in water
due to the fact that it is non-polar.
34. (a) CH2CHCHCH2 + 2 H2 o C4H10
(b) HCCCH2CH2C6H5 + 2 H2 o C4H9C6H5
(c) C7H14 + H2 o C7H16
35. Problem
Which sample of C6H12(l) is an alkene isomer, and which is a cycloalkane isomer?
Design
The cycloalkane and alkene will each be reacted with a bromine solution in an inert solvent in
separate test tubes. If the colour of the bromine disappears very quickly then the sample
likely contains an alkene. If the colour slowly disappears (in room light) then the sample is
likely a cycloalkane.
Controlled variables: volumes of sample and bromine solution, temperature, light
Manipulated variable: the isomer mixed with the bromine solution
Responding variable: time for a colour change of the bromine

36.

37.

38. (a) Ethanol: Ethene undergoes water addition with an acid catalyst to create ethanol. In
addition, ethanol is created during the fermentation of sugar with yeast.
(b) Propene: Propane is cracked using heat and catalyst to create propene and hydrogen.
(c) Dichlorodifluoromethane: Methane undergoes a series of substitution reactions, two with
fluorine and two with chlorine to create dichlorodifluoromethane, hydrogen fluoride, and
hydrogen chloride.
(d) Teflon polymer: Trifluoroethene monomers undergo addition polymerization to create
Teflon polymer.
(e) Ethyl ethanoate: Ethanol and ethanoic acid undergo an esterification reaction using an
acid catalyst to produce ethyl ethanoate ester.

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39. (a) substitution:

(b) combustion:

(c) addition:

(d) catalytic reforming:

(e) esterification:

(f) elimination:

(g) hydrocracking:

40. (a) 2 C8 H18 (l) + 25 O2 (g) o 16 CO2 (g) + 18 H 2 O(g)

V
1.0 t
114.26 g/mol 44.01 g/mol
0.70 kg/L

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nCO2

1000 k g u

nC8 H18

23 kmol u

mC8 H18

1 mol
44.01 g

23 kmol

2
2.8 kmol
16
114.26 g
325 kg
2.8 k mol u
1 mol
1000 k g CO 2 u

or mC8 H18

2 mol C8 H18
114.26 g C8 H18
1 mol CO 2
u
u
1 mol C8 H18
44.01 g CO 2
16 mol CO 2

= 325 kg
1 L C8 H18
= 0.46 kL
0.70 kg C8 H18
(b) Assuming that a typical car gets 10 L/100 km, a car would be able to travel
100 km
d=
u 4.6 u 102 L = 4.6 u 103 km .
10 L
VC8 H18 = 325 kg C8 H18 u

41. Table 1: Some Important Organic Compounds

IUPAC Name

Condensed structural
formula

ethene

CH2 = CH2

ethane-1,2-diol

HOCH2CH2OH

tetrachloroethene

octane

CH3(CH2)6CH3

ethyl ethanoate

methylbenzene

CH3C6H5

ethanoic acid

ethyne

HC CH

Organic family

Common use

alkene

petrochemical feedstock

alcohol

radiator anti-freeze

organic halide

degreaser for metal

components

alkane

automobile fuel

ester

fingernail polish solvent

aromatic

gasoline component; solvent

carboxylic acid

vinegar

alkyne

welding and cutting torch

42. Problem
What is the percent yield in the initial substitution reaction between methane and chlorine?
Analysis
CH 4 (g) + Cl2 (g) o CH3 Cl(g) + HCl(g)
1.00 kg
m, actual =2.46 kg
16.05 g/mol
50.49 g/mol

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nCH4

1.00 k g u

1 mol
16.05 g

nCH3Cl

0.0623 kmol u

mCH3Cl

0.0623 k mol u

1
1

0.0623 kmol
0.0623 kmol

50.49 g
1 mol

3.15 kg

1 mol CH 3Cl
50.49 g CH3 Cl
1 mol CH 4
u
u
= 3.15 kg
16.05 g CH 4
1 mol CH 4
1 mol CH 3Cl
m (actual)
2.46 kg
u 100 =
u 100 = 78.2%
% yield =
3.15 kg
m (predicted)
or mCH3Cl

1.00 k g CH 4 u

According to the evidence collected, the percent yield in the initial substitution reaction
between methane and chlorine is 78.2%.
43. (a) The fossil fuels found in natural form in Alberta, from most to least dense, are: coal,
bitumen/oil sands, heavy oil, crude oil, and coalbed methane/natural gas.
(b) Natural gas requires less heat when it is separated in fractionation towers as it easily
vaporizes at lower temperatures, while crude oil requires more heat to vaporize the liquid
mixture during fractionation.
Natural gas contains fewer components than crude oil. Therefore, there is
considerably less physical and chemical processing involved to obtain initial products.
(c) The statement is unacceptable. A more reasonable hypothesis is that during the
combustion process, when the air is drawn into the cylinder to mix with the fuel, nitrogen
oxide is created. The atmosphere contains 78% nitrogen and 21% oxygen, and at high
temperature they combine to form nitrogen monoxide and other nitrogen compounds.
44. (a) Natural sources of methane in the atmosphere, from highest to lowest contribution, are:
wetlands and oceans, termites, and hydrates (methane trapped within water).
Technological sources of methane in the atmosphere include: landfills, natural gas
systems, coal mining, wastewater treatment, and biomass.
(b) Greenhouse gases are chemicals within the atmosphere that trap heat by absorbing
infrared radiation that would normally escape from Earth to outer space.
(c) Other greenhouse gases include: water vapour (part of the hydrological cycle), carbon
dioxide (part of the carbon cycle and produced through respiration and hydrocarbon
combustion), nitrous oxide (industrial and automotive pollution), and ozone (produced in
reactions in the upper atmosphere and in smog).
(d) Actions could include: taking care to avoid spills of gasoline when filling vehicles and
lawn mowers, driving less, and driving more fuel-efficient vehicles.
45. (Dacron is made from two monomers- benzene-1,4-dicarboxylic acid and ethane-1,2-diol.
Alkyd resin is made from benzene-1,3-dicarboxylic acid and propane-1,2,3-triol.)
Table 2: Common Monomers
IUPAC Name
tetrafluoroethene
benzene-1,4-dicarboxylic
acid
ethane-1,2-diol
chloroethene
benzene-1,3-dicarboxylic
acid
propane-1,2,3-triol
phenylethene

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Chemical formula
C2F4
C6H4(COOH)2

Polymer name
Teflon
Dacron

Type of polymer
addition
condensation
(synthetic polyester)

C2H4(OH)2
C2H3Cl
C6H4(COOH)2

PVC
alkyd resin

addition
condensation
(synthetic polyester)

C3H5(OH)3
CH2CHC6H5

styrene

addition

Copyright 2007 Thomson Nelson

amino acids

NH2-R-COOH

proteins

1,1-dichloroethene
glucose

C2H2Cl2
C6H12O6

Saran
starch

propene

C3H6

polypropylene

condensation
(natural polypeptide)
addition
condensation
(natural polysaccharide)
addition

46.

Carbon dioxide: gasoline automobiles, heavy-duty diesel trucks, and light-duty gasoline
trucks.
Methane: light-duty gasoline trucks, gasoline automobiles, heavy-duty diesel trucks.
Nitrous oxide: light-duty gasoline trucks, gasoline automobiles, heavy-duty diesel trucks.
47. The greatest increase in carbon-dioxide-equivalent emissions was for light-duty gasoline
trucks. The greatest decrease in carbon-dioxide-equivalent emissions was for propane and
natural gas vehicles.
48. 1990: CO2

2001: CO2

103 000 kt CO 2
107 000 kt CO 2 equivalent
127 000 kt CO 2
134 000 kt CO 2 equivalent

u 100 = 96.3%
u 100 = 94.8%

49. From least to most problematic as GHGs are: CO2, (1 CO2 equivalent), CH4 (21 CO2
equivalent), and N2O (310 CO2 equivalent). (Note that the huge relative mass of CO2 emitted
compared with other GHGs more than compensates for the higher global warming
potentials.)
50. From a social perspective, all the people of Alberta could own the fossil fuels equally,
with profits from the sale distributed evenly.
From an economic perspective, companies have a financial incentive to develop costly
technologies to recover hard-to-refine fossil fuels, such as bitumen, when oil can be sold
as a commodity. Alternatively, the fossil fuel industry could argue that they are as
environmentally conscious as they can be and that they pay taxes so some of this money
goes to repair any damage they have done.
From a legal perspective, treaty rights may or should provide traditional views of their
land for Aboriginal peoples.
51. (a) CH 3 (CH 2 )8SH(l) + 15 O 2 (g) o 9 CO2 (g) + 10 H 2 O(g) + SO2 (g)
(b) Sulfur within gasoline causes environmental problems, as it is released as sulfur dioxide
during the combustion process. Sulfur dioxide is a toxic pollutant that increases the
acidity of rain because it reacts with moisture in the atmosphere to produce sulfurous acid
(as well as sulfuric acid).
(c) Yes, acid rain is a global problem that crosses provincial and international borders. We
should all do our part to help reduce this problem.
52. (a) Since the molecules in bitumen and water are of different polarity, they cannot mix with
water. Consequently, bitumen rises and floats on the water layer, where it can be
skimmed off.
Because water and the molecules in bitumen are of different polarity, the thin
water layer prevents bitumen from adhering to the sand. However, if the water layer
evaporates, bitumen adheres to the sand grains, making it very difficult to extract
economically.
Naphtha is a useful solvent to dilute the bitumen for transport because its
molecules are similar in polarity to those in bitumen.
(b) (i)

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(ii)
(iii)

(c) (i)

(ii)
53. [The solution for Chapter 9s Exploration Issue is on page 332]
Issue
Should we be saving more of this resource for petrochemical use in the future?
Resolution
We should be saving more fossil fuels for future use as petrochemicals.
Design
Information will be collected from a variety of sources on the pros and cons of the resolution.
This information will form the evidence that will be used for an analysis of the resolution and
an evaluation.
Evidence
Perspective
scientific

technological

404

Pro statements
Scientific research is producing a better
understanding of molecular structure and
properties that will eventually lead to new
synthetic materials with better properties.
Research shows that alcohols are good
solvents in organic reactions because they
are effective for both polar and nonpolar
compounds.
Many organic halides are important
chemicals for use in various industries or
serve a useful purpose such as pest control.
Increasingly, one of the most important
technological applications of alcohols is as a
gasoline additive.
Plastic bags are one of the most efficient and
innovative means to transport items from
store to home, being strong and lightweight.
We need a continuing supply of
petrochemicals to ensure enough feedstock
for the ongoing development of new
polymers.
Natural polymers do not have the range of
properties to replace synthetic polymers in
many technological products and processes.

Unit 5 Solutions Manual

Con statements
Research may provide alternatives
to fossil fuels as sources of
petrochemicals.

Technological developments for

vehicles (hybrid cars, fuel cells,
etc.) will greatly reduce fossil fuel
requirements for transportation.
Society will still have the benefit of
petrochemicals without giving up
use of fossil fuels. In other words,
cutting fossil fuel use is not a
problem.
Alcohols can be efficiently
produced from plant materials with
existing technologies.

Copyright 2007 Thomson Nelson

Perspective
economic

ecological

political

ethical

social

Pro statements
The future value of fossil fuels will increase
over time, as they are nonrenewable
resources. Saving fossil fuels now will
guarantee a larger supply in the future at
higher prices.
Saving more fossil fuels for use as
petrochemicals will create more secondary
and tertiary industries, that in turn create
more jobs and wealth for governments and
citizens. For example, for every 11 jobs
involved in the manufacture of ethylene,
6000 jobs are created in the manufacture of
polyvinyl chloride products such as pipes and
tiles. This does not include all of the other
final products from ethylene.
Farmers have saved considerable amounts
of money by using organic halide pesticides.
Plastic items are inexpensive.

Con statements
The large resource revenue
generated within Alberta would be
restricted and would slow down the
economy of the province as a
result.
Since 95% of Albertas fossil fuel
production is used for energy
production, including heating
homes and automobile
transportation, a reduction in fossil
fuel use will have to be
compensated for by using more
costly technologies.
The economic benefits of an
increased petrochemical industry
are mostly lost if we simply export
most of the raw materials,
feedstocks, and primary
petrochemicals.
The reduction in fossil fuel usage, with 95%
Many organic halides are toxic and
being burned for heating, electricity, and
many are also carcinogenic. Some
transportation, would greatly decrease the
organic halides have caused and
quantity of harmful pollutants and
continue to cause the depletion of
greenhouse gases sent into the atmosphere
the ozone layer.
in Alberta.
It is better for the environment to
Paper bags can be made from renewable
produce alcohols from renewable
resources and are easier to recycle. Plastic
plant materials than from
bags are made from nonrenewable fossil
nonrenewable fossil fuels.
fuels.
Plastic bags and other items often
end up in the environment, are
non-biodegradable, and have been
known to harm fish.
There are health concerns about
the use of plastics in microwaves,
food wraps and other plastic items.
We should make more use of
natural polymers from renewable
resources that do less harm to the
environment in their production
and disposal.
Provincial legislation to include 10% ethanol
Any talk of reduction of petroleum
in gasoline, and tax incentives, will accelerate
usage would be met with great
the expansion of the ethanol industry.
resistance by industry lobby
groups and the general public that
depends on this industry.
Politicians who support any
reduction would probably never be
(re-)elected.
Unless governments enact more
legislation, and provide regulations
and enforcement, recycling will
continue to be haphazard.
The use of organic halide pesticides has
It is not right to deny third-world
resulted in increased crop production, thus
countries the opportunity to
feeding more people.
develop their industries using fossil
fuels as we have done.
Society has become very dependent on the
We do not need all of the gadgets
many products that are made using a variety
and disposable items that keep
of polymers from petrochemical feedstock.
being produced.

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Perspective
militaristic

Pro statements
Petrochemicals and final synthetic products
are very important in modern-day warfare.

Con statements
If we did not have the
sophisticated equipment with
which to wage conflict, maybe
some countries would be less
likely to go to war.

Analysis
According to the evidence collected, some alternative solutions are:
1. Immediately cut fossil fuel production to only essential energy uses to reserve these fuels for
future petrochemical use.
2. Continue to research and develop alternate non-fossil fuel and more efficient fossil fuel
energy sources without specifically cutting back on fossil fuel production for no reason other
than to save these resources for future use.
3. Ignore all calls to reduce fossil fuel use because there is no problem.
Evaluation
To evaluate each of the alternative solutions, a scale of 15 was used to rank the value of the
particular solution from each perspective.
Perspectives
scientific
technological
economic
ecological
political
ethical
social
militaristic
Total

Perceived value of each solution (scale: 1 5)

Alternative 1
Alternative 2
Alternative 3
2
4
1
1
3
2
1
3
4
4
2
1
1
2
3
1
2
3
1
3
2
2
3
1
13
22
17

This relatively simplistic evaluation clearly shows that alternative 2 is the best choice. More
evidence in terms of different perspectives would help to clarify the decision-making process and
more clearly indicate where trade-offs occur.
54. Many common organic compounds can be classified as being either aliphatic or aromatic.
Aliphatic compounds are based on single, double, or triple bonded carbons in an open
chain or ring structure. Aromatic compounds are based on the benzene ring. The IUPAC
naming system has been developed as a systematic way to name organic chemicals based
on their structures. The naming of aliphatic compounds involves numbering the parent
carbon chain and identifying the position of branches. Aromatics are named on the basis
of the numbered position of branches on the benzene ring.
Other common organic compounds include organic halides, alcohols, organic acids, and
esters. These compounds are identified and named according to their characteristic
functional group.
There are numerous applications for the reactions of organic compounds. Combustion
reactions, for example, are used to fuel industrial, commercial, and domestic processes
such as heating our homes. Polymerization reactions are used to make numerous
synthetic polymers like nylon and polyester. Other organic reactions are used to
manufacture important consumer products such as medications, cosmetics, and cleaning
agents.
There are numerous environmental risks associated with the extraction and processing of
fossil fuels, which are the raw material used to make most organic chemicals.
Responsible handling and use of fossil fuels ensures that these chemicals do not pose an
unnecessary risk to current ecosystems. Reducing the consumption of fossil fuels will
also ensure that they will be available for future generations of consumers.

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55. Extension
Fruit/vegetables
apple (non-chilled)
broccoli
cherry (sweet)
mango
peas
potato (table)
banana

Ethylene
production
very high
very low
very low
medium
very low
very low
medium

Ethylene
sensitivity
high
high (yellowing)
low (softening)
high
medium
medium
high

56. The four main segments of Albertas chemical industry are: petrochemicals, fertilizers,
inorganic chemicals, and specialty or fine chemicals. The petrochemical industry is the
largest of the four, and benefits from the abundant and competitively priced hydrocarbon
feedstock. The main basis of the petrochemical segment is ethane, which is converted, by
cracking, into ethene (ethylene). The ethylene is used to make plastics, antifreeze, film,
fibers, and other products. There are many employment opportunities for engineers,
researchers, technologists, operators, tradesmen, and support personnel.
57. Linear alpha olefins are alkenes (CnH2n) with the double bond always on the first carbon
(alpha position).
Examples:

Typically, the smaller linear alpha olefins (C4-C8) are used in the production of
polyethylene. Medium (C10-C16) LAOs are used in a variety of ways, from synthetic
lubricants to surfactants to detergents. Large LAOs (C20-C30+) have a low production
volume as they are used as feedstock for low-molecular-weight polymers, used to enhance
waxes.
58. E10 fuel: a 10% ethanol/90% gasoline blend that most gasoline engines can use. It provides a
cleaner-burning fuel because of the oxygen within the ethanol. It provides gas line antifreeze
as the ethanol can bond to and help dissolve moisture within the fuel system. It produces
approximately 38% lower GHG emissions than standard fuel.
E85 fuel: a 85% ethanol/15% gasoline blend that only modified gasoline engines can use.
It provides gas line anti-freeze as the ethanol can bond to and help dissolve moisture
within the fuel system. It produces approximately 75% lower GHG emissions than
standard fuel.
Oxydiesel: 80-84% low-sulfur diesel/15% ethanol/2% additives that all diesel engines
can run on. It provides gas line antifreeze naturally, as the ethanol can bond to and help
dissolve moisture within the fuel system.
P-series fuel: P-Series fuel is a unique blend of natural gas liquids (pentanes plus),
ethanol, and the biomass-derived co-solvent methyltetrahydrofuran. P-Series fuels are
clear, colorless, 89-93 octane, liquid blends that are formulated to be used in flexible fuel
vehicles.
59. The main advantages of the hydrocarbon gas injection process are that it has the potential to
significantly lower greenhouse gas emissions and reduce the amount of water used in bitumen
recovery. It can also be used in situations where the bitumen layer is too thin for conventional
recovery methods involving heat.

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60. Methylbenzene is a useful solvent to dissolve hydrocarbon oil because both substances
contain nonpolar molecules. Methyl ethyl ketone can dissolve ester-wax because both
substances contain polar molecules. Methyl ethyl ketone is polar due to the bent or angular
shape of the molecule about the central oxygen atom.

methyl ethyl ketone

The presence of the oxygen atoms in the ester linkage in ester-wax makes the molecules in
this substance polar.

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