Chemistry 12: Solutions Manual Part A

Chemistry 12
Solutions Manual Part A
Unit 1 Organic Chemistry 8. a. Wear protective eyewear, apron, thermal gloves;

know location of fire extinguisher, fire blanket, tie
Answers to Unit 1 Preparation Questions back long hair, do not wear loose clothing.
(Student textbook pages 4-5) b. Read label on the cylinder; be aware of reading
on pressure gauge, hold cylinder with both hands,
1. e
pointing the outlet away from your body; open valve
2. e slowly.
3. In addition to the equipment listed, include location of c. Wear protective eyewear, apron, and protective
main gas shut-off valve, fume hood (if equipped), exits gloves.
to hallway, location of lab benches or other work area. d. Wear protective eyewear, apron, and protective
4. Student answer will include gloves. Know the location of eyewash station, tie
• Fire extinguisher type (A, B, C, D, ABC). back long hair, do not wear loose clothing.
• Face the fire with a clear path to an exit available e. Wear protective eyewear, apron, protective gloves,
behind you. tie back long hair, do not wear loose clothing.
• A fire extinguisher lasts for about 30 s. If the fire 9. a. poisonous material causing immediate and serious
cannot be extinguished in this time, leave the area toxic effects
and activate a fire alarm. b. flammable and combustible
• Pull the pin from the top of the extinguisher to c. corrosive
release the tamper seal, activating the extinguisher. d. compressed gas
• Aim the nozzle or nose of the extinguisher toward 10. a. The attraction between two atoms that results from
the base or bottom of the fire. You want to attack the the sharing of electrons.
fire at the source. Remember, this is one time you b. A compound in which the atoms are held together
want to aim low. by covalent bonds.
• Squeeze the handle down toward the extinguisher. c. The electrostatic attraction between a negatively
Depressing the handle releases the extinguishing charged ion and a positively charged ion.
element. d. The temperature at which a pure substance changes
• Sweep across the fire in a side to side motion until the from the solid state to the liquid state.
fire appears to be out. e. The temperature at which a pure substance changes
• Watch the fire closely. If there seem to be any signs of from the liquid state to the gaseous state.
the fire reigniting, repeat the last 4 steps. 11. b
5. Emphasize possibility of spills and splashing of
12. d
chemicals onto hands and clothing. Also the possibility
of losing track of the identity of the contents in a 13. Melting involves separating molecules from their
beaker or flask and the mixing, by mistake, of clear, fixed position in the solid state. Polar molecules
colourless solutions (such as vinegar and solution have a definite shape with areas of fixed negative and
of baking soda) that will produce a gas, causing positive charge. The electrical attraction between
splattering. Also, some common kitchen chemicals these oppositely charged areas on different molecules
such as oven cleaners and drain cleaners are dangerous (dipole-dipole) must be overcome for melting to occur.
and safety gear should be used at home. This takes more energy than that which is needed
to overcome relatively weak attractions (dispersion
6. Mixing of paper waste can cover broken glass which
forces) between non-polar molecules.
presents a danger to the person disposing of this waste,
risking possible cuts and exposure to infection. 14. Cl2, non-polar covalent molecule < CH3OH, polar
covalent molecule < K2O, ionic compound
7. d
Unit 1 Part A • MHR 1

15. Heat and light are given off adopting the symmetrical, tetrahedral arrangement of
16. No. Hazardous (causing injury to health) products its bonds.
come from combustion of a hydrocarbon is CO(g), 5. CH3 CH3
which does not form with excess O2.
H2C CH2 CH2
17. hydrocarbon and oxygen
18. a. Incomplete combustion occurs when there is CH3 CH2 CH2 CH2 CH3
insufficient oxygen to react with all of the reactants 6. There are nine constitutional isomers of heptane.
(such as hydrocarbons). Products other than carbon H H H H H H H H
dioxide and water are carbon (soot) and carbon H C C C C C C C H H C H
monoxide. Less heat is given off, and it is less H H H H
H H H H H H H
efficient than complete combustion. H C C C C C H
H
b. Carbon monoxide is clear, colourless, and odourless. H H H H
H C H
It can accumulate and overcome a person, causing H C H
H H H H H
death. H
H C C C C C C H
H H H H H H H
Chapter 1 Structure and Physical H C H
H
Properties of Organic Compounds H C H
H H H H
H C C C C C H
H H H H H
Answers to Learning Check Questions H C C C C C C H
H H H H
H C H
(Student textbook page 11) H H H H H H
H
1. Up to and including the 1800s, the term organic
H
was used to describe matter that came from living H
H C H
organisms that contained a “vital energy,” and inorganic H H H H H C H
was used to describe matter that came from non-living H C H
H C C C C C H
material. The laboratory synthesis of compounds once H H H H
H H H H
thought to be produced only by living organisms led H C C C C C H
H C H
to the modern definition of an organic compound H H H H H
H
as one in which carbon atoms are bonded to each
other, to hydrogen atoms, and sometimes to a few H H H
specific elements, usually oxygen, nitrogen, sulfur, or H C H H C H H C H

phosphorus. H H H H H H
H C C C C C H H C C C C H
2. The key to carbon’s ability to bond with several atoms
H H H H H H H
is found in its atomic structure. A carbon atom has
H C H H C H
four valence electrons, and a half-filled outer shell of
H H
electrons. It has an intermediate electronegativity and
is much more likely to share electrons than to gain or (Student textbook page 19)
lose enough electrons to form ions. Its four valence
electrons can be shared with up to four other atoms. 7. Examples include methane (CH4) found in natural gas
This leads to the potential for the formation of a wide to heat homes, propane (C3H8) used in barbeques and
variety of molecules. as a heating fuel,c12_techart_c1-lc_ans6
butane (C4H8) found in lighters and
portable burners, octane (C8H18) found in gasoline,
3. Any molecule that contains C–C or C–H are waxes (C20HArt is) too
42 found in candles, and tars (C40H82)
wide to fit in column width.
considered organic, and molecules or ions such as CO2 used in paving.
and CO32– that contain no C–C or C–H bonds are
considered inorganic. 8. In a saturated hydrocarbon, each carbon atom
is bonded to as many other atoms as possible.
4. Atomic systems arrange themselves to minimize their Unsaturated hydrocarbons have at least one multiple
potential energy. For methane, this occurs if the four bond and are therefore not bonded to as many other
bonds are as far apart as possible (because the electron atoms as possible, or they are not completely saturated
pairs repel each other), which the molecule achieves by with hydrogen atoms.
2 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

9. A homologous series is a set of molecules in which 15. a. Alkanes that are liquids at room temperature have
each member differs from the next by an additional between 5 and 16 carbon atoms inclusive.
specific structural unit. The alkane series can be b. Alkanes that are gases at room temperature have
represented by a general formula, CnH2n+2. Ethane, between 1 and 4 carbon atoms inclusive.
C2H6, differs from the next member of the series, 16. CnH2n
propane, C3H8, by –CH2.
17. They are similar in that they have the same number
10. 3 carbon atoms: C3H8; 7 carbon atoms: C7H16; and sequence of carbon atoms as the corresponding
9 carbon atoms: C9H20; 12 carbon atoms: C12H26
alkane. They are different in that there are fewer
11. All reasonable answers should show that an atom or hydrogen atoms in an alkene, there is a double bond in
group of atoms on an alkane has been substituted an alkene, and the shape is different.
in place of a hydrogen atom on the parent chain of 18. H3C CH CH CH3
carbons.
For example
H2C CH CH2 CH3
H H H CH3
H C C C H H3C C CH2
H H H
(Student textbook page 32)
19.
H H H H3C CH CH CH2 CH2 CH3 H2C CH CH2 CH2 CH2 CH3
H C C C H
H H H3C CH2 CH CH CH2 CH3 H3C C CH2 CH2 CH3
H C H CH2
Substituent group
EmpericalHformula H3C C CH CH2 CH3 H3C CH CH CH CH3
12. The root is pent-, the prefix is 2-methyl, and the suffix is CH3 H3C
C4H
-ane. 10
(Student Condensed
textbook structural
page 24)formula H3C CH CH2 CH CH2 H3C C HC CH3
Emperical
13. Empirical formula
formula H3C CH2 CH3
H3C CH2 CH2 CH3
Emperical
C4HC4H
10
formula
10
H3C
Expanded
C4H
molecular formula
Structural
10 formula H3C C C CH3 H3C C CH CH2
CHCondensed
3CH2CH2CH3
structural formula
CH3 CH3 CH3
H Hstructural
Condensed H H formula
Condensed
H3C CH structural
CHformulaCH3

2 2 20. alkenes < alkanes < alkynes
H C C C C H
H3C CH2 CH2 CH3 21. The linear structure of alkynes and the nature of the
H H H H triple bond allow them to attract one another more
Structural
Structural
formula
formula
strongly than corresponding alkanes and alkenes.
Structural
H Hformula H Hformula
Expanded Structural 22. Testosterone and estrogen are two examples of steroid
H C H C H C H C H H hormones containing cyclic hydrocarbons.
CH3CH2CH2CH3
H H C H C H C H C H 23. Straight-chain alkanes have the general formula
CnH2n+2. Cyclic alkanes have the general formula
LineLine
structural
H H formula
structuralHformula
H CnH2n. Alkenes have the general formula CnH2n.
Expanded Structural formula
Alkynes have the general formula CnH2n-2.
Expanded Structural formula
CH3CH2CH2CH3 24. At least three carbon atoms are necessary and the
14. They are insoluble in water but soluble in non-polar
CH3CH2CH2CH3 molecular formula is C3H6.
solvents.
Line structural formula
Line structural formula Unit 1 Part A • MHR 3
(Student textbook page 36) Answers to Section 1.1 Review Questions
25. Cyclic hydrocarbons have higher boiling points and (Student textbook page 14)
melting points than straight-chain hydrocarbons. There 1. An organic compound is one in which carbon atoms
is a greater difference in terms of melting point. are bonded to one another, to hydrogen and a few
26. Aromatic hydrocarbons contain a benzene ring; other non-metal elements (O, N, S P, halogens)
aliphatic hydrocarbons do not contain a benzene ring. 2. The carbon atom is bound only to oxygen atoms.
27. Benzene is more stable than cyclohexene (therefore, There are no C–C or C–H bonds.
less reactive), and it has fewer hydrogen atoms. 3. If the bond angle around carbon atoms was 90o, there
28. All the bonds in benzene are identical and have an would be fewer possible compounds because of greater
intermediate length compared with single and double repulsion between pairs of electrons. Also biological
bonds. compounds would be restricted sheet or cubic shapes.
29. Electrons in the “double bonds” of a benzene ring are
H H
in fact shared by all six carbon atoms. They are not
“localized” to a bond between two carbon atoms. H C H C
30. H H H H
benzene ring
Lewis Structure
4. a. H
Answers to Caption Questions HH H H
H H H
Figure 1.10 (Student textbook page 13): Triple bonds are H C C C C
C C C C
linear and rigid and each carbon atom has only one atom H
H H
attached. H H H H
Figure 1.13 (Student textbook page 15): They all contain
only carbon and hydrogen atoms. All contain only single H H H H
bonds. Except for methane, the carbon atoms are bonded H C C H C H
to other carbon atoms. Each compound has one more CH2 H
H C C H C C C H
unit than the one before.
Figure 1.15 (Student textbook page 22): The compound H H H H H
on the left is unsaturated because the carbon atoms are
not bonded to the maximum number of atoms possible, b. C2H2Cl2
owing to the double bond. The compound on the right
H Cl H H H Cl
is saturated because the carbon atoms are bonded to the C C
C C C C
maximum number of atoms; all of the bonds are single Cl H Cl Cl H Cl
bonds. 5. a. Rotation occurs around a single bond and a trans
Figure 1.16 (Student textbook page 22): These two alkenes “isomer” could easily rotate into a cis “isomer” for
are isomers. The double bond can join an end carbon atom the same molecule
to another carbon atom, or the double bond can join the
H H H Cl
two middle carbon atoms.
Figure 1.25 (Student textbook page 46): Possible response: F C C H H C C H
The CFCs act as catalysts and thus are not used up in the
reactions. The CFCs take a long time to naturally degrade H Cl F H
in the atmosphere. Also, older products, such as old b. Each carbon atom in a triple bond is attached to
refrigerators, may still emit CFCs. only one other atom 180o to each other.
Figure 1.36 (Student textbook page 70): The citric acid
protonates the amines in the fish. That is, the acid adds a Cl C C F
hydrogen ion to the amine, making it a soluble salt which is 6. In the list of words, “trans” means across the nation,
not volatile. continent, or Atlantic respectively. The attached
Figure 1.43 (Student textbook page 80): It is all three. identical atoms or groups in the trans form are across
Glucosamine contains hydroxyl side groups, an amino side the double bond from one another.
group, and a formyl side group.

7. The wrist, the thumb side, the fingers and flat edge on 12. The boiling point depends upon the intermolecular
the baby finger side. attractions between molecules. This is affected by
8. Venn diagram should show: the surface area of each isomer. The more spherical
the shape of the isomer, the less surface area is in
Diastereomers only:
contact between molecules and less energy is required
• carbon atoms joined by double bond
to separate them. These isomers will have a lower
• non-mirror images, no free rotation about the double boiling point than the more linear shaped isomers.
bond The difference in chemical reactivity may be less
• cis and trans forms have different physical properties notable for hydrocarbons since the bond strengths will
Diastereomers and enantiomers: be much the same regardless of their configuration.
• carbon atoms For constitutional isomers having functional groups
Enantiomers only: attached, there can be a drastic difference in chemical
• mirror images of one another reactivity.
• single bonds 13. +
H
• four different atoms bonded to carbon
–
• same physical properties H N H O C N
9. The physical properties would be similar as their basic H
structure is the same except for the rotation of plane
polarized light. Their chemical properties would also
Answers to Section 1.2 Review Questions
be similar. However, in living systems, the enzymes
that catalyze chemical reactions recognize and bind to (Student textbook page 41)
only one of the two enantiomers. 1. A homologous series is a specific series of compounds
in which each member differs from the next by an
10. Looking at the two carbon atoms in the double bond,
additional specific structural unit. For example, C2H6
the one on the left is bonded to two identical CH3
and C3H8 differ by CH2
groups. The groups must differ in order to form cis or
trans isomers. 2. ethane C2H6
11. a. The ring structure of the pentane causes the carbon H H
atoms to form a rigid plane. Notice that, in the cis
isomer, the two fluorine atoms are above the plane H C C H
of the cyclic carbon atoms and in the trans isomer,
H H
the two fluorine atoms are on opposite sides of the
plane. 3. prefix: 2-methyl; root: hept; suffix: ane
cis- 1, 2 difluoropentane trans- 1, 2 difluoropentane Each name has three parts, the prefix, the root, and

H H H the suffix. The root indicates the number of carbon
H H F H atoms in the longest continuous chain of carbon atoms.
C C
C H C C The prefix indicates the position(s) and name(s) of
H C H H any branches attached to the main chain. The suffix
F
C C C C indicates the series to which the compound belongs.
H H H
F 4. a. CnH2n+2
H H F H
b. CnH2n
b. In the linear structures, a double bond prevents c. CnH2n–2
rotation around the bond, thus preventing the
5. Examples are:
atoms attached to the carbons atoms of the bond. In
• octane, major component of gasoline,
the ring structure, the ring itself prevents rotation
CH3CH2CH2CH2CH2CH2CH2CH3
around the single bonds, preventing an attached
atom from moving from one side of the ring to the • butane, lighter fluid, CH3CH2CH2CH3
other. • nonane, component of camp stove fuel,
CH3CH2CH2CH2CH2CH2CH2CH2CH3
• toluene, used in paint thinner, C6H5(CH3)

6. Both groups are made up of the elements carbon and 12. a. Hormones such as estrogen and testosterone have
hydrogen. Saturated hydrocarbons have single bonds cyclic rings.
between carbon atoms so that each carbon is bonded b. Flavours such as vanilla are aromatics.
to four atoms, the maximum number for carbon. 13 a. There is only one spot for the triple bond which is
Unsaturated hydrocarbons have at least one double between carbons one and two because carbon atoms
bond or triple bond between two carbon atoms. are always numbered so that the double bond is
Comparing the boiling points of alkanes, alkenes and nearest C1.
alkynes with similar number of carbon atoms, the
b. There is only one double bond and multiple bonds
alkenes have the lowest and the alkynes the highest.
in cyclic compounds always begin at the number
7. a. 3-methylheptane one carbon.
b. 2-methylpropene 14. The electrons in the second bond of double bonds are
c. 2,3-dimethylcyclohexene shared equally among all the carbon atoms and are
d. 2-ethyl-1,3-dimethylbenzene termed delocalized. If there were alternating single and
8. a. CH double bonds, the molecule would have unequal bond
C CH CH CH
3 3
lengths. The lengths of all of the bonds in benzene are
CH3 CH3 all the same and between the lengths of typical single
and double bonds.
b. H3CH2C CH3 CH2CH2CH3 CH3
HC C C CH C CH2 CH CH CH2 CH3 Answers to Section 1.3 Review Questions

H3C CH2CH3 CH3 (Student textbook page 82)
1. Alcohols can be used for solvents, antifreezes,
c. CH3 fuels, antiseptics. Only one, ethanol, can be used in
beverages. They can also be used as starting materials
for the synthesis of industrial compounds.
CH3
2. Unlike propane, which would be a gas at room
d. CH3 temperature, propan-1-ol would be a liquid at room
CH2
temperature and would only combust with the oxygen
in the air on the surface of the liquid.
CH3 CH CH2 CH CH2 CH2 CH2 CH3
3. Ethanol is more polar than tetrachloroethene and
would not dissolve non-polar molecules as well.
Ethanol would not evaporate as well and would
therefore take more energy to recover.
9. a. 4. Comparing Aldehydes and Ketones
b. Aldehydes Ketones
Structure formyl group at end of carbonyl group on a non-
carbon chain terminal carbon atom
Naming root: indicates number root: indicates number of

c. of carbon atoms in carbon atoms in longest
longest chain chain
suffix: –al suffix: position number of
carbonyl group, –one
d. Physical • small – soluble in • small
properties water – soluble in water
• polar • polar
• < 15 carbon atoms • < 15 carbon atoms
10. Test their boiling points: – liquid – liquid
hex-1-ene < hexane < hex-1-yne < cyclohexane • > 15 carbon atoms • > 15 carbon atoms
11. CnH2n; The alkenes with one double bond also have – waxy solids – waxy solids
this general formula.

5. Butter, cheese, and vomit may contain partially Answers to Practice Problems
digested fats.
For full solutions to Practice Problems, see Part B
6. The carboxyl group, –COOH, found in carboxylic acids
of this Solutions Manual.
would conduct electric current and turn litmus red.
7. a. Propan-1-ol and ethanoic acid (Student textbook page 19)
b. Ethanol and propan-1-amine 1. 2-methylpropane
8. a. One would expect alcohols, primary and secondary 2. 2,2-dimethylpentane
amines, carboxylic acids, and primary and
3. 5-ethyl-3,4-dimethylnonane
secondary amides to form hydrogen bonds with
identical molecules. 4. 3,3,5-trimethylheptane
b. They would be more soluble in polar solvents such 5. 2,2,5-trimethylhexane
as water and have higher melting and boiling points 6. 2-methylbutane
as compared to similar sized molecules with other
functional groups. 7. dimethylpropane
9. a. Three ethers could have this formula: 8. 2,2,4,4-tetramethylhexane
1-methoxypropane, ethoxyethane, 9. pentane
2-methoxypropane. Ethers have the general formula 10. 2,3-dimethylpentane
R–O–R’.
11. 3,3-dimethylheptane
b. Three alcohols could have this formula: butan-1-ol,
butan-2-ol and 2-methylpropan-1-ol. (Student textbook page 21)
c. The ethers would have lower melting points and 12. CH3
boiling points than the alcohols. The alcohols would
be more soluble in polar solvents such as water. H3C HC CH2 CH3
10 a. hexan–3–ol
13. CH3
b. 3-methylpentane-2,2-diol
c. 1-2-dichloro-1-fluoro-2-methylpropane H3C CH2 C CH2 CH2 CH3
11 a. OH
H2C
CH3
b. OH
14. CH3
HO
c. O CH3 C CH CH2 CH2 CH2 CH2 CH3
CH3 CH2
OH
d. CH2
O
CH3
O
15. (12)
e. NH2
(13)

(14)


16. pentane (Student textbook page 27)
17. 4-ethyloctane 35. H3C CH CH CH2 CH3
18. 3,3-diethyl-4-methylhexane 36. CH2 CH2 CH3

19. H
H3C CH C CH2 CH2 CH2 CH3
HH C HH H
37. CH3
H C C C C H
H3C CH CH C CH2 CH3
H H H H
20. H3C
C
H C H
H H H C H H H H H H H
H C C C C C C C C C H
H H H C HH C H H H H H H
H C HH C H
C C
21. H 38. CH3 CH3

H
H C H H3C CH CH C CH CH2 CH2 CH3
H2C CH3
H C C C C C C C C C C H
39.
H C H
H
H
22. 4-ethyl-4-propylheptane

23. pent-2-ene
c12_techart_c1-pp_ans21
24. 3-methylbut-1-ene 40. hex-2-ene
25. 4,4-dimethylhex-2-ene H3C CH2 CH2 CH CH CH3
26. 2-ethylpent-1-ene
41. 5-ethyloct-2-ene
27. 3,4-diethylhex-2-ene
H3C CH2 HC CH2 CH CH CH3
28. but-1-ene
CH2 CH2 CH3
29. 5,6-dimethylhept-3-ene
30. 4-ethyl-3-methylhex-2-ene 42. 2-methylbut-2- ene
31. 2,5-dimethyloct-3-ene CH3

32. propene H3C CH C
33. 4-methylpent-2-ene
CH3
34. 2-ethyl-3-methylpent-1-ene

43. a. H d.
H H C HH H
C C C C H 51. but-1-yne
H H H 52. but-1-yne
53. 4-methylpent-2-yne
b. H
54. 3-ethyl-5-methyl-3-propylhex-1-yne
H C H
H H HH C HH H (Student textbook page 34)
C C C C C C H 55. cyclopentane
H H 56. 1-ethyl-3-methylcyclobutane
H H C H C HH
H H 57. 4-methylcycloheptene
44. 3-ethyl-3-propyl-4-methylhex-1-ene 58. 3-methyl-5-propylcyclopentene
c12_techart_c1-pp_ans50d
59. 3-cyclopentyloctane
60. CH3
61. CH3
CH3
62.
45. hex-3-yne
46. 4-methylpent-1-yne CH3
47. 5-ethyloct-2-yne 63. CH2 CH3

CH3
48. 4,4,5-trimethylhex-1-yne
H2C CH2
49. a. H3C C C CH3
b. CH3 64. CH3 CH CH2 CH2 CH3
HC C CH2 CH CH CH3
CH3
c. CH3 65. methylbenzene, historically known as toluene
66. 1,2,4-trimethylbenzene
CH3 C C C CH2 CH2 CH3
67. 1-ethyl-3-propylbenzene
CH2 CH3
68. 2,4-diphenyloctane
d. CH3 CH3 CH3 69.
CH2 CH3
H3C HC C C CH CH2 HC CH2 CH3
CH2 CH2 CH3
50. a. H3C
CH2 CH3
b.
70. H3C
CH3
c.

71. H3C CH2 84. OH
CH2 CH3
CH2
CH2 CH3
72. CH3 CH2 CH3
H2C
CH2
85. 2-fluorobutane
CH3
86. 3-bromo-3-methylpentane
H3C
87. 3-chloro-5-methylhexane
CH3
88. 1,3-dichloro-2-fluorobutane
73. CH3
CH3 H2C 89. 1,3-dibromo-2-chlorocyclohexane
90. CH2 CH2 CH3
CH CH2 CH2
CH2 CH
l
H2C
CH2 91. H2C CH2
CH3
F Cl
74. 1-ethyl-4-methylbenzene
92. CH3 Br
CH3
CH3 C CH CH2 CH3
CH3
93. Cl
H2C
CH3 H3C CH HC CH CH2 CH3
Br Br
75. butan-2-ol
94. 1,4-difluoro-2-propylcycloheptane
76. pentane-2,3-diol
F
77. propan-2-ol
78. 3-methylbutane-1,3-diol
79. 6-phenyl-2-propylheptan-1-ol
80. OH F
H2C CH3 5. a. 2-chlorobutane

9
b. 3-bromo-4-chlorohexane
81. OH
c. 1,3-dichlorocyclopentane
H2C CH2 CH3 d. 2-chloro-3,3-dimethylbutane
82. OH (Student textbook page 52)
96. propanal
HO CH2 CH2 HC CH3
97. 2-methylbutanal
83. H3C CH3 OH
98. 3-ethyl-4-methylhexanal
H3C CH2 CH CH HC CH3 99. 2,4-dibromopentanal

100. CH3 110. CH
O 3
O
C CH2 CH CH3 H3C C CH2
H
101. CH3
H 111. O
C O H3C C CH2
H
O
102. CH3 CH3
112. The ketone group lies on a carbon attached to two
H3C HC C O other carbons
H3and
C therefore
C CH2would never have a
numerical assignment of 1. This compound does not
H exist.
103. Cl 113. The correct name
CH3 is pentan-2-one. Numbering of
the longest carbon chain gives the ketone group the
H2C C O H3number.
lowest C C CH2
H 114. The correct name is 5-methyloctane-3,4-dione.

104. Numbering should begin with giving the ketone
CH2 CH3 H
groups the lowest possible numbers. TheCH 3
longest
H3C CH2 C CH2 CH2 C O continuous chain containing these
H3groups
C C is eight
CH2
carbons long.
H2C CH3 115. Since carbon forms only four bonds and the linkage
105. a. The correct name is ethanal. The aldehyde group between carbons in the benzene ring is considered
should be placed on the number 1 carbon (unless the intermediate of a single and double bond, the
there are other higher priority functional groups carbon atom with the ketone group would not be able
also present such as carboxylic acids). It is not to form a double bond with oxygen. This compound
necessary to include a number in this case as it is does not exist.
assumed the aldehyde is on the first carbon.
b. The correct name is 5-methylheptanal. The longest (Student textbook page 61)
chain would include the ethyl group, and the 116. propanoic acid
methyl group would be a side branch. 117. 4-ethylhexanoic acid
c. Since carbon only forms four bonds, an aldehyde 118.
could not be inside a cyclic hydrocarbon as well O
as having hydrogen and double-bonded oxygen. H3C CH2 CH2 C OH
Therefore, this compound does not exist.
d. Since the terminal carbon would need to have a 119. CH2 CH3
hydrogen and a double-bonded oxygen, and be HO
C CH2 CH2 HC CH2 CH2 CH2 CH3
joined to the hydrocarbon chain, there would be no
room for a fluorine to bond. This compound does O
not exist.
120. CH3
O
C CH2 CH CH CH2 CH3
106. butan-2-one
HO
107. 2-methylpentan-3-one
108. 3-ethyl-4-methyl-hexan-2-one
109. O 121. HO OH
C CH2 CH2 CH2 C
O O

122. The correct name is hexanoic acid. The carboxylic (Student textbook page 69)
acid gets the lowest number on the longest 136. 1-ethoxypropane
hydrocarbon and is assumed to be on carbon 1.
137. 2-ethoxypropane
123. Owing to carbon only being able to form four bonds,
138. ethoxycyclohexane
a carboxylic acid functional group would always be at
the end of a hydrocarbon chain. This compound does 139. H3C O CH2 CH3
not exist.
140. CH3
124. The correct name is 3-ethylheptanoic acid.
Numbering should begin with giving the carboxylic
H3C CH2 CH2 O HC CH2 CH3
acid groups the lowest possible numbers. The longest
continuous chain containing these groups is seven 141. CH2 CH3
carbons long.
125. Since carbon forms only four bonds, a carboxylic acid H3C CH2 O HC CH CH2 CH3
group could never be inside a cyclic hydrocarbon.
CH3
This compound does not exist.
142. CH3
126. methylethanoate O HC CH2 CH2 CH2 CH2 CH3
127. ethylmethanoate
128. butyl 3-chlorobutanoate 143. The correct name is methoxyethane. The root name
should be the longest hydrocarbon chain.
129. O
144. The correct name is 2-propoxybutane. The
H3C CH2 CH2 CH2 O C CH3 numbering of the root name should give the
ether linkage the lowest number possible on its
130. O hydrocarbon chain.
H3C CH2 O C CH2 CH2 CH3 145. The correct name is 2-methoxypentane. The
numbering of the root name should be made to give
131. O the longest possible chain to which the R′ group is
attached.
H3C HC C O CH2 CH3 146. The correct name is ethoxybenzene. It is assumed that
the R′ group is first attached to the number 1 carbon
of the benzene ring and it is not necessary to number
132. it.
O
O (Student textbook page 74)
147. ethanamine
133. 148. pentan-3-amine
O
149. N-ethylbutan-2-amine
O 150. N-methyl-N-propylhexan-2-amine
134. 151. H3C NH2
F O
152.
O
H3C CH2 CH2 CH2 NH CH2 CH2 CH3
135. O
153. H2C CH2 CH2 HC CH2 CH3
O
NH2 NH2

154. Answers to Chapter 1 Review Questions
H3C CH2 CH2 CH2 CH CH2 CH3 (Student textbook pages 87-91)
1. b
H3C N CH2 CH3
2. c
155. NH2 3. a
156. 4. d
NH
5. e
6. d
7. b
157.
8. d
N
9. e
158. 10. e
N 11. a
12. c
13. e
(Student textbook page 79) 14. b
159. methanamide 15. Carbon can form four bonds as it has four unpaired
160. 3-ethylhexanamide electrons. It also has intermediate electronegativity
which prevents it from forming singular ions. This
161. N-propylpentanamide
allows it forms covalent bonds which can continue in
162. N,N-dimethylbutanamide chains.
163. O 16. Isomers are molecules with the same molecular
H 3C C formula but their atoms are in a different arrangement
NH2 17. Stereoisomers have the same molecular formula
and connectivity but different three-dimensional
164. O arrangement of their atoms in space. Constitutional
H3C CH C isomers are molecules that have the same molecular
NH2 formula but have different connections between the
H3C
atoms.
165.
18. Molecules with two different atoms or groups on both
O sides of a double bond can form cis/trans isomers.
H3C CH2 CH2 CH2 CH2 C Cycloalkanes with two side-groups can also form
N CH2 CH3 cis/trans isomers.
H3C CH2 19. Enantiomers have identical structures. Their physical

and chemical properties are essentially the same.
166. However they do affect plane polarized light differently
O and may react with certain other enantiomeric
H3C CH2 CH C molecules differently. As well, enzymes are specific for
one form of the isomer.
N CH2 CH2 CH3
CH3
20. Saturated hydrocarbons have each carbon atom
H2C CH3 bonded to as many other atoms as possible.
167. propanamide Unsaturated hydrocarbons contain at least one double
or one triple bond so each carbon atom has less than
168. N-propyl-2,2-dimethylbutanamide
the maximum atoms bonded to it.
169. N,N-dimethyl-2-propylhexanamide


21. a. CnH2n+2 32. Boiling points could distinguish the two as C2H6 would
b. CnH2n be a gas at room temperature whereas C8H18 would be
c. CnH2n-2 a liquid.
d. CnH2n 33. a. correct name is 3-ethyl-2-methylpentane
22. They are all non-polar and therefore do not dissolve b. correct name is 3-ethylhex-1-ene
well in polar solvents such as water. 34. The formula for hexane is C6H14, cyclohexane is C6H12
23. They are similar in that they are six-carbon rings. The and benzene is C6H6
difference is that the six carbons in cyclohexane are 35. Some examples could be: paradichlorbenzene,
single bonded, whereas the carbons in benzene have C6H5Cl2, used as a moth repellant, phenylacetone,
bonds that are intermediate between single and double. C6H5CH2 –CO–CH3, used to make amphetamines,
The formula for cyclohexane is C6H12 whereas the benzyl alcohol, C6H5CH2OH, used to make perfumes,
formula for benzene is C6H6. paints epoxy resins.
24. Ethanol dissolves in polar solvents; ethane is soluble in 36. There are five constitutional isomers of C4H4 as
polar solvents. Ethanol has higher melting and boiling shown below. Constitutional isomers can have single,
points compared to ethane. At room temperature, double, or triple bonds as long as the number of
ethanol is a liquid and ethane is a gas. atoms present allow for them. The but-2-ene could
25. Both aldehydes and ketones have carbon atoms double have diastereoiosmers but they are not constitutional
bonded to an oxygen atom (carbonyl groups). In isomers.
aldehydes the carbon in the C=O bond is the terminal H2C
carbon of a chain and, therefore, has a formyl group, CH CH3
whereas in ketones the C=O is in the main carbon H2C
chain with a carbon atom bonded to it on each side
H2C CH2
26. An ester is the product of the reaction between
carboxyl, –COOH, and hydroxyl, –OH, functional H2C CH2
groups. CH3 CH CH CH3
27. An amide is the product of a reaction between a CH2 CH CH2 CH3
carboxyl group, –COOH, and an amine, –NH2.
CH3
28. These aromatic compounds were found in naturally
occurring plants and the original names were often CH2 C CH3
taken from those sources.
37. a. Volatile organic compounds are organic compounds
29. a. CH4 — A carbon atom cannot bond to more than that have a vapour pressure high enough to
four atoms. evaporate and produce part per billion levels in the
b. C2H6 — Alkanes must have 2n+2 hydrogen atoms. atmosphere.
c. hexane C6H14, or cyclohexane C6H12 As above. b. There are many beneficial uses: fuels, solvents,
d. CH4 — Pure alkanes do not contain oxygen atoms. refrigerants, anaesthetics, etc. Their drawbacks
include: contributing to global warming, creation of
30. Enantiomers, or optical isomers, are non-
smog, destroying the ozone layer, and they are often
superimposable mirror images of each other. Four
are toxic at elevated levels.
different atoms or functional groups must be bonded
to the central carbon atom to form enantiomers. The c. Examples of naturally occurring VOC’s are natural
mirror images of CH2BrF would be superimposable gas, methane, emitted from decomposition of
animals as well isoprene, 2-methylbuta-1,3-diene
31. CH2Br2 can form cis/trans isomers if the two bromine emitted from forests.
atoms are not on the same carbon atom. The molecule
2-methylbuta-1,3-diene CH2=C(CH3)–CH=CH2
C2H2Br2Cl2 would have single bonds between the
carbon atoms that can rotate freely. The molecule C2HI Examples of anthropogenic sources are
would have a triple bond between the carbons and tetrachlorethane, low molecular weight petroleum
would have a linear arrangement, with the H and I derivatives (eg. hexanes, octanes) and formaldehyde
atoms 180° to one another. (methanal).

38. The molecule can form an enantiomer. There are four c. It should be mainly soluble in non-polar solvents
different groups (methyl, hydroxyl, carboxyl, and due to the long hydrocarbon chain and insoluble in
hydrogen) around the second carbon atom and can water.
therefore form a different mirror image. d. It should form constitutional (structural) as well as
39. Design an experiment to determine the boiling point of cis/trans diastereomers. There is no chiral centre
each compound. Ethane would have low boiling point, (carbon atom bonded to four different atoms or
be a gas at room temperature and be poorly soluble in groups) for enantiomers (optical isomers)
a polar solvent such as water as ethane is non-polar. 4. a. 2-methylbutanoic acid
4
Ethanol would have a higher boiling point, be a liquid b. 7-methyl-7-phenylnonan-3-one
at room temperature at be soluble in water due to the
c. ethylpentanoate
polar alcohol group. Ethanoic acid would be soluble
d. N-methyl-N-propylbutanamine
in water and have an even higher boiling point than
ethanol due to the two very electronegative oxygen 45. a. From lowest to highest boiling points the molecules
atoms in the carboxyl functional group. Ethanoic acid would be: ethane (-89°C), methoxymethane
could also conduct electric current. (-23°C), ethanamine (17°C), ethanoic acid (118oC),
ethanamide (222°C).
40. a. hexane-3,4-diol
b. The molecules of these four compounds are
b. 2-chloro-3,4-dimethylpentane
about the same size and the amount of dispersion
c. 3-ethyl-6-methyldecan-2-one
forces between molecules will be about the same.
d. 3,3-dimethylpentan-2-one All except ethane are polar molecules and will
41. Report should follow the guidelines for report writing, experience dipole-dipole attractions between
using proper grammar, and spelling, and identification molecules. The greatest factor affecting the boiling
of sources of information. Some inorganic greenhouse point would be the amount of hydrogen bonding
gases are CO2, N2O (nitrous oxide), water, and O3 between molecules. Methoxymethane does not form
(ozone). Examples of organic greenhouse gases hydrogen bonds and has the lowest boiling point.
are CH4 (methane), trichlorofluoromethane and Ethanamine can form hydrogen bonds between
dichlorodifluoroethane. Inorganic molecules such as molecules however nitrogen is not as electronegative
carbon dioxide and water are much more abundant in as the oxygen atoms in ethanoic acid so the
the atmosphere and the production of CO2 by humans degree of hydrogen bonding is less in ethanamine.
is much more prevalent. Ethanamine has a lower boiling point than ethanoic
42. a. acid. Ethanamide has both electronegative oxygen
and nitrogen atoms and the highest amount of
Boiling Point vs Number of Carbon Atoms hydrogen bonding would be expected between
200 Decane molecules of this compound.
Nonane c. Ethanoic acid and ethanamide are liquids at room
Octane temperature and the other are gases.
100
Boiling Point (°C)
Hexane Heptane
Pentane
0
Butane
Propane
–100 Ethane
Methane
–200
b. C11H24 about 200°C; C12H26 about 215°C

3. a. Aromatic (phenyl), alkene and alcohol.
4
b. It should have a high boiling point (eg. over 400°C)
due to the long hydrocarbon chain and polar alcohol
groups. It c12_techart_c1-cr_ans42a
would be a liquid due to the unsaturation.

46.
Name Structure Functional Groups Benefits (Pros) Drawbacks (Cons)
Saccharin O ketone, aromatic, 300X sweeter than sucrose bitter; USDA has
amine, (sulfoxyl) removed carcinogen
NH warnings
S
O O
Sucralose OH haloalkane, alcohol, 600x sweeter than sucrose; stable at non-cited

Cl ethers hot and cold temperatures; good for
Cl Cl
O O baking
OH
HO O
OH OH
Mannitol OH OH OH alcohols doesn’t cause tooth decay; does not

affect insulin levels; can be extracted
from plant products; medicinal uses;
OH OH OH not hygroscopic
Aspartame amino group, ester 160 - 220 times sweeter than sucrose; harmful to people
linkage, amide linkage, does not cause tooth decay; does not with rare genetic
carboxyl group affect insulin levels; is metabolized like disease, PKU
other amino acids (phenylketoneurea)
47. a. H H 48. a. NOTE: The name is invalid and should be

H 3,4-dimethylheptane
3, 4-dimethylheptane
H
C C O
H C C C H
H
H H H
H3C CH CH2 b.
CH2 CH OH
OH c.
b. Several constitutional isomers can form by changing

the location of the double bond and the hydroxyl
group. Many more could be formed because it could
form carboxylic acids, ketones, and aldehydes.
The double bond allows for the formation of 49. a. 1,3-dichloro-2-fluoro-2-methylpentane
diasteriomers. b. butanal
c. 3-amino-3-hydroxybutan-2-one
O
50. a. methanal
O O
NH b. methylbenzene
OH NH2 O c. 1,2-dimethylbenzene
d. phenylamine
e. trichloromethane

51. Answers should include the key terms and concepts e.
shown on page 86. Graphic organizer could be a main
Risks Benefits
idea web, a spider map, or a concept map.
Poisonous if taken internally Personal comfort by
52. a. Herbicides are used to kill unwanted plants for preventing painful and
aesthetic purposes and to increase crop yields in distracting parasites from
agriculture. biting
b. The molecule shown is glyophosate or When sold as an aerosol, must Controls insects that carry
N-phosphonomethyl amino acetic acid. Reasons be used with caution and disease
would be that it has no chlorine substituents disposed of in a safe manner.
expected in the name of 2,4-D and the presence Insects can develop immunity
of amino and carboxylic acid groups (as well as a to the compound.
phosphorus atom) present in the IUPAC name for Persists in the environment
glyophosate. affecting non-harmful,
beneficial insects
c. General consensus would be that glyophosates
would be less harmful to the environment due f. Possible alternatives would be: wearing light
shorter persistence and fewer medical side effects to clothing, covering exposed skin, restricting outdoor
this date. activities during peak insect hours, removing
d. Some alternatives around the home are to use environments that breed insects (standing water) or
mulch, plant native plants that would compete attract certain insects (CO2, certain perfumes), using
better with weeds, pull weeds by hand and use less naturally derived insect repellents (e.g., cinnamon),
controversial household chemicals such as acetic 55. Reduce fuel spillage, take public transit, have
acid (vinegar), boiling water, rubbing alcohol or automobiles tuned up and emissions systems in good
corn gluten to remove undesirable plants. Other working order, reduce leaks of heating, cooking and
reasonable alternatives are possible. transportation fuels, reduce unnecessary mechanized
53. a. Putrescine would have the name butan-1,4-diamine travel.
and cadaverine would be pentan-1,5-diamine.
56. a. The difference in boiling point is due to the
b. Rotting flesh smells putrid and another term for an difference in the intermolecular attraction
animal corpse is a cadaver. The suffix “ine” indicates between molecules. The –OH group in methanol
an amino group. is very polar, which allows for the formation of
c. Substances such as citric acid found in citric fruits or hydrogen bonds with neighbouring molecules.
other carboxylic acids would react with the slightly Methanal is slightly polar and can form dipole-
basic amine group and form salts which are non- dipole interactions but has no hydrogen bonding.
volatile. Since there is less attraction between molecules of
4. a. N,N-diethyl-3-methylbenzamide
5 methanal, this compound has a lower boiling point.
b. The common name, DEET, comes from the letters b. Formaldehyde is an aqueous solution of methanal.
“dee” to represent diethyl, and the “t” in toluene. It is 57. a. Saturated fats have higher melting points than
simpler for everyday use. unsaturated and are therefore solids at room
c. It would dissolve in non-polar or slightly polar temperature whereas unsaturated fats are usually
solvents. liquid.
d. WHMIS symbols would poisonous and infectious
causing other toxic effects (if inhaled or long time
exposure); poisonous and infectious with immediate
side effects (if ingested). It is also flammable.

b. Cis fats are unsaturated and have the hydrocarbon Answers to Chapter 1 Self-Assessment Questions
chains on the same side of the double bonds whereas
(Student textbook pages 92-3)
trans unsaturated fats have them on opposite sides.
1. a
cis form
2. c
3. e
4. e
5. d
trans form
6. c
7. a
8. c
c. The unsaturated fats are softer and less likely to form
9. c
a hard layer lining the arteries which leads to strokes
and heart attacks. Also the sites of double bonds in 10. e
unsaturated fats are more reactive than the single 11. The molecules are not constitutional isomers as
bonds between carbons in the saturated fats. they are the same molecule just rotated and drawn
58. a. adrenaline: C9H13NO3; amphetamine: C9H13N differently.
b. Both have a phenyl group, C6H5, and an amine, 12.
NH2 group, adrenaline has –OH groups that are not
c12_techart_c1-cr_ans57 Two pairs are possible
present in amphetamines.
c. Epinephrine (adrenaline) constricts blood vessels
and dilates air passages, which reverses the effects of
an anaphylactic shock.
cis-hex-2-ene trans-hex-2-ene
d. Amphetamines increase alertness and concentration.
59. a.
and
Limonene
cis-hex-3-ene trans-hex-3-ene
CH3
13. a. The root must be the longest continuous chain. The
C
HC CH2 correct name is 2-methylbutane.
H2C CH2 b. Numbering of the carbon atoms in the main chain
C of an alkane must begin at the end that will give the
H chiral/optical centre carbon
side groups the lowest possible numbers. The correct
C
H2C CH3 name is 2,3-dimethylpentane.
c. This molecule is named correctly.
b. One would expect it to be found in citrus fruits. d. The numbering of the carbon atoms in the main
c. The R-(+) limonene smells of oranges and the S-(–) chain of an alkene must begin at the end nearest
limonene smells of lemony turpentine. the double bond. The correct name is 5-ethyl-6-
d. It can be used as an industrial solvent because it is methylhept-3-ene.
less volatile and non-toxic than chlorofluorocarbons 14. a. Solid alkanes could be found in waxes, asphalt and
and methyl ethyl ketone. greases. The molecules would be over 18 carbon
e. As it can be extracted from orange peels and is thus atoms long.
a renewable resource. It is also biodegradable.

b. Liquid alkanes could be found in gasoline, b.
lubricating oils and heating fuels such as kerosene. CH3
The molecules would be between 5–22 carbon atoms
long. CH3 CH2 CH2 CH O CH2 CH3
c. Gaseous alkanes could be found in natural gas, CH3

propane and butane used for heating and cooking.
The molecules would be 1–4 carbon atoms long. c.
O
15. a. Example: 2-methylpentane; C6H14
eg. 2-methylpentane
CH3 C NH CH2 CH2 CH3
19. Both esters and amides have a carbonyl group (C=O)

eg. cyclohexane
but esters have an extra oxygen bonded to this carbon
b. Example: cyclohexane; C6H12 whereas amides have a nitrogen.
They both can be thought of as the product between

a carboxylic acid with another molecule. The other
molecule needed to form an ester is an alcohol whereas
c. Example:eg.3-methylpent-1-yne;
3-methylpent-1-yne C6H10
the other molecule needed to form an amide is an
amine. The alkyl group that was derived from the
carboxylic acid would get the prefix and the alcohol
and amine derivatives would get the suffix. Esters end
in “oate” and amides end in “amide.”
d. cyclohexane
d. Example: cyclohexene; C6H10 Primary and secondary amides will have high melting

and boiling points and will often be solids because
they can hydrogen bond with one another. Esters are
polar but no hydrogen bonding can occur. The melting
e. benzene C H
e. Example: benzene; 6 6 points are therefore lower than the amides of similar
size. At room temperature many are liquids. The longer
chain esters may be waxy solids.
20. a. They IUPAC name would be ethanedioic acid.
16. Benzene is not an alkane because the carbon atoms
b. It would be a solid at room temperature due to its
are bonded to only three other atoms. Each carbon
ability to form multiple hydrogen bonds with other
atom is bonded to only one hydrogen atom. The ring
oxalic acid molecules.
in the centre of the benzene diagram represents the
six-delocalized electrons that are shared equally among c. It would be soluble in polar solvents such as water
atoms. This resonance hybrid has equal bond lengths due to its ability to form hydrogen bonds with the
halfway between a single and double bond. solvent
17. a. 3-methylbutanoic acid 21.

b. N,N-dimethylpropan-2-amine propan-1-ol propan-2-ol methoxyethane
18. a.
HO
O
O
22. No. Cyclopentane has the chemical formula C5H10
CH3 C CH CH2 CH3
while pentane has the chemical formula C5H12.
CH2 23. Use BLM A-32 Presentation Rubric or BLM A-36
CH3 Multimedia Presentation to assess answers.
24. a.
OH
CH3 CH CH3

b. The –OH group in the alcohol can hydrogen bond (Student textbook page 107)
with the water whereas the non-polar propyl group 7. A substitution reaction occurs when the reactants are
can join with the non-polar molecules an alkane with a substituent of a halogen or a hydroxyl
c. Keeping the gas tank as full as possible and having a group, and the other reactant is H−X, or OH−. A
proper gas cap will prevent humid air from entering condensation reaction can occur when the reactants
the tank. are a carboxylic acid and an ammonia or amine. An
25. a. The source for most of the hydrocarbons we use are esterification reaction occurs when the reactants are a
from fossil fuels such as crude oil, natural gas and carboxylic acid and an alcohol.
coal. 8.
b. Some problems associated with the source are oil
spills, acid rain, explosions and the fact that it is condensation reactions
non-renewable, accumulation of CO2 which is a two molecules combine to form one

greenhouse gas associated with global warming. larger molecule and one very small
molecule which is usually water
c. Other sources could be using plants and bacteria to
produce biodiesel and ethanol.
esterification reaction
Chapter 2 Reactions of a special case of a condensation
Organic Compounds reaction in which one reactant is

an alcohol and the other is a
carboxylic acid and the products
are an ester and a water molecule
Answers to Learning Check Questions
1. Both are examples of reactions of organic compounds.
In an addition reaction, atoms are added to an organic 9. They are reactions that form large biomolecules such as
compound at the site of a double or triple bond. proteins, which are essential to living things.
In elimination reactions, atoms are removed from
an organic molecule and a double bond is formed. 10. acetylsalicylic acid, artificial flavours, and artificial
Elimination reactions are the opposite of addition aromas
reactions. 11. Nine esters: Each alcohol will react with each of
2. They act as catalysts. the carboxylic acids. The ester names are methyl
methanoate, methyl ethanoate, methyl propanoate,
3. a. More than one product is possible with an ethyl methanoate, ethyl ethanoate, ethyl propanoate,
asymmetric molecule. propyl methanoate, propyl ethanoate, and propyl
b. The major product occurs when the hydrogen atom propanoate.
is removed from the carbon atom that has the most
2. a. Esterification: The product is an ester.
1
carbon-carbon bonds.
b. condensation: The product is an amide.
4. The hydrogen atoms of the small molecule will attach
to the carbon of a double bond that is already bonded c. substitution: A halogen could replace an hydroxyl
to the most hydrogen atoms. The rule is used when two group on the alcohol.
products can be formed from an addition reaction. (Student textbook page 120)
5. No, if there is a limited amount of X–X, then a 13. A polymer is a large, long-chain molecule with
substituted alkene will be produced. repeating units of small molecules called monomers.
6. Carbons can only have up to four bonds, and alkanes Some uses are plastics, adhesives, and chewing gum.
are already fully saturated. Therefore, the carbons 14.
cannot accept any more bonding partners. Alkenes • Addition polymerization only—Monomers are
and alkynes are unsaturated and can break a double combined by addition reactions. For example, the
or triple bond in order to bond with another element/ monomers could be alkenes. In the polymer, the
compound. former double bonds have become single bonds.

• Addition and condensation polymerization—In both Answers to Caption Questions
types of reactions, small molecules link to form long Figure 2.3 (Student textbook page 97): The carbon atoms
chains of very large molecules. in the product are bonded to more atoms than the carbon
• Condensation polymerization—Monomers have two atoms in the organic reactant.
functional groups which can undergo condensation Figure 2.14 (Student textbook page 116): Possible
reactions with groups on the other monomers. For responses: train cars linked together to form a long train,
example, the monomers might have both a carboxyl linking building blocks together
group of one end and an alcohol group on the other
end. The carboxyl group of one monomer reacts with
the alcohol group on another monomer to form an
ester linkage. The result is a polyester. (Student textbook page 115)
5. polyurethane
1 1. a. oxidation
b. esterification
16. Addition polymer: There are fewer double bonds in the
polymer than in the monomers. No molecules, other c. elimination NB: First product should be CH2=CH2.
than the polymer, are formed. 2. a. ethylhexanoate + water
Condensation polymer: A small molecule (usually
b. methanoic acid
water) is released with the formation of each c. 2-bromopropane + water
monomer-monomer linkage. d. bromobenzene + hydrobromic acid
17. amino acids e. methanoic acid
18. A polymer containing cross-links is stronger and less 3. Substitution reaction:
flexible than a straight chain polymer. haloalkane + OH− → alcohol + halide ion
(Student textbook page 124) Oxidation reaction:

19. The petroleum is separated into classes of alcohol + [O] → aldehyde

hydrocarbons according to size in a process called Oxidation reaction:

fractional distillation. A variety of organic reactions aldehyde + [O] → carboxylic acid

are used to convert the hydrocarbons into compounds 4. Addition reactions and elimination reactions can
needed as starting materials for the production of result in more than one product if the reactants are
compounds that are useful such as plastics. asymmetric. In addition reactions, the H atom will
20. The petrochemicals are very useful in industry. bond to the carbon with the most H atoms already
21. Ethene is reacted with chlorine to make bonded to it. In elimination reactions, the H atom will
dichloroethane. This is then cracked to produce HCl be removed from the carbon with the most carbon-
and chloroethene. Chloroethene is reacted in an carbon bonds.
addition polymerization reaction to make PVC. 5. a. C3H8(g) + 5O2(g) → 3CO2(g) + 4H2O(ℓ)
22. Advantages: PVC is very useful for industrial products b. 2C4H10(ℓ) + 13O2(g) → 8CO2(g) + 10H2O(ℓ)
such as windows, piping, and doors. c. C13H28(ℓ) + 20O2(g) → 13CO2(g) + 14H2O(ℓ)
Disadvantage: The monomer, vinyl chloride, is a
6. a. CH2=CH2−CH3 + H2O
carcinogen. b. CH3− HC(Cl)−HC(Cl)−CH3
23. Dioxins are chlorinated aromatic hydrocarbons that are c. major product CH3−CH(Br)−CH3
toxic by-products from the production and disposal by minor product CH2(Br) −CH2−CH3
incineration of PVC.
7. It is a hydrolysis reaction.
24. Recycle, Reduce usage, Reuse plastics; purchase
CH3− CH(CH3)−CH2−COOH + HO−CH2−CH3

degradable plastics
8. a. CH3OH
b. CH3−CO−CH3

9. major product: 2-methyl-2-bromooctane, 5. a. polyamide
H3C−C(Br)(CH3)−CH2−(CH2)4−CH3 O O
minor product: 2-methyl-3-bromooctane,
HO C (CH2)4 C OH H2N (CH2)6 NH2
H3C−CH(CH3)−CH2(Br) −(CH2)4−CH3

b. polyamide
10. Carbon monoxide, is an odourless, colourless,
poisonous gas, is a product of incomplete combustion. O O
HO C CH2 C OH H2N CH2 CH NH2

CH2
1. a. Natural polymers are found in living things whereas c. polyester
synthetic polymers are manufactured by chemical O O
processes outside of living things. Both are long HO CH2 CH2 OH HO C CH2 C OH
chains made up of similar or identical monomer
units. 6. a. addition
b. Three examples of naturally occurring polymers are ... CH2 CH2 CH2 CH2 CH2 ...
starch (a polysaccharide), proteins, and DNA. Three
examples of synthetic polymers are polystyrene, b. addition
polyvinylchloride, polyethylene. ... CH2 CH CH2 CH CH2 CH ...
c. The starch monomer is glucose. Protein monomers
are amino acids. DNA monomers are nucleotides,
which consist of a nitrogen base, a five-carbon sugar,
and a phosphate group. The polystyrene monomer is c. condensation
styrene (phenylethene). The monomer of polyvinyl O O O O
chloride is vinyl chloride (chloroethene). The ... C (CH2)3 C NH CH NH C (CH2)3 C NH CH NH ...
monomer of polyethylene is ethylene (ethene).
CH3 CH3
2. Addition and condensation reactions.
d. esterification
3. a. The hydroxyl group (−OH) of an alcohol and the
O O O O
carboxyl group (−COOH) group of a carboxylic
...O C C O CH2 O C C O CH2 ...
acid react to form an ester bond.
b. The carboxyl group (−COOH) of a carboxylic acid
7. Example: crude oil fractional distillation ethane cracking at 800ºC
and an amino group (−NH2) of an amine react to
ethene polymerization polyethylene
form an amide bond.
4. a. (i) During the production of synthetic polymers,
Answers to Practice Problems
harmful by-products are often produced. (ii) Many
synthetic polymers remain in the environment For full solutions to Practice Problems, see Part B
for long periods of time. (iii) The incineration of of this Solutions Manual.
many synthetic polymers produces harmful, toxic
products. (Student textbook pages 99-100)
b. Synthetic polymers are used to mass produce a wide 1. H3C—CH2—CH2—CH3
variety of items that are durable and long lasting
2. a. H3C−CH2 −C(Br)=C(Br)−CH3
and things that could not be made from natural
b. H3C−CH2 −C(Br)2−C(Br)2−CH3
reactants.
c. Possible answer: Yes. Our technological society 3. The product is iodoethane. Only one product is
has become dependent on many of the synthetic possible because if iodine (I) is added to carbon 1 or
polymers for variety of applications. However, we carbon 2, the same product is formed.
need to find ways to minimize risks. 4. CH3−CH(Cl)−CH(Cl)−CH2−CH3

5. most abundant 11.
+ HBr → Br
OH
OH methylcyclohexene + hydrobromic →
CH3 CH CH2 CH CH3 acid
CH3 CH
CH CH2 CH CH3 (Student textbook page 102)

3
CH3
least abundant
OH 12. CH3 C CH2 + H2O
OH CH3
CH3 CH CH2 CH2 CH2
CH3 CH
CH CH2 CH2 CH2 13. H
3
CH3 H C C C H + HOCH2CH3 + NaCl

6. neither is preferred over the other
H H H
Br
14. In addition to the HOCH2CH3 and NaBr which
CH3 CH CH CH2 CH3 will always be products, the original 3-bromo-2-
methylpentane could form three different products.
CH3
These products are 2-methylpent-2-ene, cis-2-
Br methylpent-3-ene, and trans-2-methylpent-3-ene.
CH3 CH CH2 CH CH3 15. Water will always be a product. The reactant,
2-methylpentan-3-ol can be converted to any or the
CH3 three products, 2-methylpent-2-ene, cis-2-methylpent-
7. a. 3-ene, or trans-2-methylpent-3-ene.
Br
16. Sodium bromide and ethanol will always be products.
The reactant, 3-methyl-2-iodibutane can be converted
into 2-methylbut-2-ene or 3-methylbut-1-ene.
b. most abundant

CH3
17. The major product will be 2,4-dimethylcyclohexene.
ICH3 18. The major product will be 1-ethylcyclopentene.
I 19. The possible reactants are butan-1-ol or butan -2-ol.
least abundant
CH3 20. The possible reactants are
CH3 CH3 CH CH CH2 CH2 CH3
I
x CH3
I
or

8. a. OH x
CH3 CH2 C CH2 CH2 CH3
CH3
b. CH2 CH3 X represents one of four possible elements: F, Cl, Br,

Cl or I.
9. a. H2C=CH—CH2—CH3, or 21. The major product would be cyclobutene.
H3C—CH=CH—CH3, or 22. Note: NaOH should be deleted; reactant should be
HC≡C—CH2—CH3, or H3C—C≡C—CH3
+ NaOCH2CH3.
b. CH2=CH—CH2—CH3 The final products would be but-1-yne,

10. HC≡C−CH2CH3, and but-2-yne, H3C−C≡C−CH3.
CH3 CH CH2 CH3
O SO3H

(Student textbook page 104) 40. methanol and salicylic acid
23. This reaction is not specific and, depending on the O OH
amount of chlorine present, a chlorine atom could
replace any or all of the hydrogen atoms. CH3 OH + HO C H
24. There are nine possible products. CH3
25. CH3 CH CH3 + H2O H3C C CH2 acid + propan-1,2-diol

41. 3,3-dimethylheptanoic
CH3 O OH
Cl
CH3 CH2 CH2 CH2 C CH2 C OH + HO CH2 CH CH3
26. bromobenzene + H2O
CH3
27. bromobenzene + HBr
42. butanoic acid + propan-1-ol
28. 2-hydroxypropane + Cl−
CH3 O
29.
CH3 CH2 CH CH3 + Cl− CH3 H23C CHC2
CH CCH2OH + HO CH2 CH2 CH3
OH
A base such as NaOCH2CH3 would give an elimination

43. oxidation
reaction but a hydroxide ion results in a substitution
reaction. 44. reduction
30. Note: FeBr2 should be FeBr3 45. reduction
46. oxidation
47. addition and reduction
31. CH3CH2CH3 + Br2 48. esterification and condensation
32. 49. CH4 + 2OCH

2 → CO2 + 2H2O + energy
3
50. C4H8 + 6O2 → 4CO2 + 4H2O + energy
CH3 CH CH2Cl + OH− H3C C CH2
51. C3H8 + 5O2 → 3CO2 + 4H2O + energy
CH3 52. C6H12O6 + 6O2 →6CO2 + 6H2O + energy
(Student textbook page 108-9) (Student textbook page 121)

33. condensation reaction 53. addition
34. esterification reaction 54. addition
35. esterification reaction 55. condensation
36. esterification reaction 56. polyamide
37. condensation reaction
H2N CH2 CH2 NH2
38. ethanoic acid and octanol
O O CH3 O
CH3 C OH + HO CH2 (CH2)6 CH3 HO C H3(CH

C 2)C6 CH2 OH
C
39. butanoic acid and methanol 57. polyester

O HO CH2 CH2 CH2 CH3
OH
CH3 CH2 CH2 C OH + HO CH3 O O H3C C CH2
HO C CH2 C OH

58. polyester 13. e
14. a
HO OH
15. a. Y Z
O O C C + Y Z C C
HO C CH2 C OH
The carbon atoms in the products are bonded to
59. First, treat the 1-bromoethane with NaOCH2CH3 to more atoms than the carbon atoms in the reactants.
eliminate the bromine atom and a hydrogen atom b. Y Z
resulting in ethene.
CH2BrCH3 + NaOCH2CH3 →
C C C C + Y Z
NaBr + HOCH2CH3 + CH2=CH2
The carbon atoms in the organic product are bonded
Then
carry out addition polymerization on the ethene.
to fewer atoms than were the carbon atoms in the
n CH2=CH2 → - - - —CH2—CH2—CH2—CH2— - - - organic reactant.
60. c.
O O O CO Y + A Z → C Z + A Y
C C O CH2 CH2 O C C O CH2 CH2 O

Two compounds react to form two different
compounds and the carbon atoms are bonded to the
O O
same number of atoms in the product and reactant.
CH2 O C C O CH2 CH2 O d.
O O
61.
R C OH + H N R C N + HOH
... CH2 CH CH2 CH CH2 CH ...
CN CN CN carboxylic acid ammonia amide water

or amine
62. Look for an amide and water molecule as products.
O O O e.
... O CH2 C O CH2 C O CH2 C ... O O
H2SO4
R C OH + HO R C O + HOH
Answers to Chapter 2 Review Questions carboxylic acid alcohol ester water
(Student textbook pages 137-41)

Look for an ester and water molecule as products.
1. c
f.
2. d OH O
3. a C H + [O] C
4. d
alcohol oxidizing agent aldehyde or ketone
5. d
6. a O O
7. c
C + [O] C
8. b H OH
9. b aldehyde oxidizing agent carboxylic acid
10. b Look for carbon having more bonds to oxygen or fewer

CHEM12_2.052A
11. a bonds to hydrogen.
12. d

g. O OH 3. a. substitution
2
b. elimination
C + [H] C H c. addition
d. substitution
aldehyde or ketone reducing agent alcohol
e. addition
H H
f. elimination
4. a. oxidation,
2
C C + [H] C C
b. reduction,
c. oxidation
alkene reducing agent alkane
5. a. esterification,
2
Look for carbon having fewer bonds to oxygen or b. condensation,
more bonds to hydrogen. c. hydrolysis
h. hydrocarbon + O2 → CO2 + water + energy.
26. polyvinylacetate
Look for a hydrocarbon chain reacting with oxygen
to form carbon dioxide and water. 27. polyesters – polymers in which the monomers are
connected by ester bonds. Typically, one reactant
16. Addition and elimination reactions are the opposite
monomer has an alcohol group on both ends and the
of each other. In addition reaction a double or triple
other reactant monomer has a carboxyl group on both
bond between carbon atoms is lost and two new
ends.
single carbon bonds with new atoms are formed.
With elimination reactions two single bonds are lost polyesters and polyamides – Both are made through
and a double or triple bond between carbon atoms
CHEM12_2.069A condensation polymerization reactions using two
are formed while two atoms are eliminated from the different monomers. Both use a carboxylic acid
reactant. monomer as a reactant. Both reactions also produce
a small molecule such as H2O. Both are durable
17. During an addition reaction use Markovnikov’s
products.
rule and add the hydrogen atom to the carbon atom
already bonded to the most hydrogen atoms. During polyamides – polymers in which the monomers are

an elimination reaction remove the hydrogen from the connected by amide linkages. One of the reactant
carbon with the most bonds to other carbon atoms. monomers has an amine group on both ends and the
other has a carboxyl group of both ends.
18. The reactions result in a large mixture of products.
There are other ways to obtain the desired product. 8. a. addition,
2
19. Both reactions involve two large molecules coming b. condensation,
together to form a large molecule and a small molecule c. addition
(water). The difference is that esterification reactions 9. a. elimination,
2
always occur between an alcohol and a carboxylic acid. b. addition,
An esterification reaction is a special case of a more
c. combustion,
general condensation reaction.
d. substitution
20. A molecule is broken apart by adding the hydroxyl
0. a. butan-2-ol
3
group from a water molecule to one side of a bond and
the hydrogen atom of the water molecule to the other b. major product: 2-bromo-2-methylbutane
side of the bond. minor product: 2-bromo-3-methylbutane
21. When naming polymers add poly in front of the name c. propene
of the monomer unit. In this case the monomer is d. major product: 3-methylpent-2-ene
called propylene (propene). minor product: 3-methylpent-1-ene
22. Polymers are long-chain molecules made with 1. a. propan-1-ol
3
repeating units of small molecules and these natural b. N-ethylpropanamide
molecules contain repeating units of small molecules.
For example, proteins have repeating units of amino
acids

32. a. Both of the compounds have an amine group and b. Br2(aq) WHMIS: Corrosive. Harmful if inhaled.
a carboxyl group. Any two molecules could react Causes respiratory tract irritation and possible
to form an amide bond. Therefore, although they burns. Causes eye and skin irritation and possible
are shown to alternate in the figure below, the two burns. Wear gloves when making the bromine water.
compounds will not necessarily alternate in the Work in a fume hood.
polymer. c. addition
O
O d. H3C–CH(Br)−CH(Br)−CH3
N ...
N ... 37.
N
N
H • heat an alcohol in the presence of H2SO4
N. H O O
. .N . O O • react a haloalkane with a strong base such as sodium
..
ethoxide NaOCH2CH3
O
b. N ... 38. a. hex-3-ene + HCl

N F F F F F F
N
H
O O
F F F F F F b. 3-methylbutanoic acid + propan-2-ol
...
... C C C C C C . . .
... C C C C C C ... c. 2-methylpropan-2-ol + HCl
F F F F F F
FC F F F F F d. 2,5,-dimethylhex-2,4-diene
... ...
C C C C C F F F F F F e. methane + chlorine
F F F F F F
c. f. 2,3-dimethybutan-2-ol → 2,3-dimethylbutanal
O O O O
O O O
39. O
O O O O
... C
.C. . NH CCH2 CH2 NH C C NH CH 2 CH NH ...
2 • monomer CH3−CH=CH−CH3 ...
... C NH CH2 CH2 NH C C NH CH2 CH2 NH ...
C C NH CH2 CH2 NH C • polybutene −[−CH(CH
C NH CH 3
CH
)−CH(CH
2 2 3
NH
)−]n −
3. a.
3 O
• solvent alkylethers, tertiary alcohols
HO C CH2 CH OH • acid catalyst
WHMIS: 2-butene is a gas at room temperature, highly
CH3
flammable, explosive with air mixture, inhalation can
b. CH2 CH cause dizziness and unconsciousness, evaporation from
skin can lead to frostbite, used face shield
CH2 CH3 40. Major product: 2-bromopropane, CH3—CHBr—CH3
c. Minor product: 1-bromopropane, CH2Br—CH2—CH3

O O 41. The product, 1-bromopropane, gives the impression
NH2 CH2 CH NH2 + HO C CH2 C OH that the reaction is a substitution reaction because a
bromine atom is seen in place of a hydrogen atom.
CH However, if it was a properly written equation, there
would have to be an HBr in the products. Also, this
34. A polyamide because the functional groups that react
method of substitution with alkanes is nonspecific and
to form proteins are a carboxyl group and an amino
there would also be many other products.
group which form amide linkages.
42. 2 glucose → maltose + water
5. a. 2C2H6 + 7O2 → 4CO2 + 6H2O
3
3. a. 2 -phenylacetic acid + ethanol
4
b. 2C2H5OH + 6O2 →4CO2 + 6H2O
b. butyric acid + ethanol
36. a. • use 2 fats and 2 oils
c. ethanoic acid + ethanol
• add equal portions of each fat and oil to separate
test tubes 44. Without the alcohol present, the esterification reaction
• added a measured volume of bromine water to shown will slow down and the reverse hydrolysis
each test tube reaction will be favoured.
• shake gently or warm in a water bath while 45. Degradable plastics are good because they break down
looking for a decrease in the intensity of the over time when exposed to environmental conditions.
reddish colour of bromine water. It may be difficult to use across the world due to cost of
manufacturing

46. Hex-1-ene + HBr → proteins – monomers are amino acids joined through
2-bromohexane + 1-bromohexane Brcondensation
Br reactions with amide linkages between
the amino acids; include various functions of proteins
CHCH
2 2 CH
CH CHCH
2 2 CH 2 2 CH2 2 CH 3 +HBr
HBr→ →CHCH3 3 CH
CH CH 3 +
CH CH
in theCH 2 2 CH
CH
human 2 2 CH
CH
body 2 2 CH
CH
such CH
3 3
as building of muscle tissue,
Br
Br Br Br forming enzymes, hormones. DNA—monomers are

nucleotides, forms through condensation reactions
CH2 2 CH
CH CH3 3 ++ HBr
HBr → CH3 3 CH
→ CH CH CH2 2 CH
CH CH2 2 CH
CH2 2 CH
CH CH 2 2 CH 2 CH 2 2 CH 2 CH CHCH
+ 3+
3 CH CH CH CH CH
of
2 the nucleotides,
2 found2 in
2 cell 3nuclei,
3 codes for
Br → 3-bromohexane
hex-3-ene +Br
HBr amino acid sequence to make a protein, controls cell
development.
Br Br
++CHCH2 2 CHCH2 2 CH
CH2 2 CHCH2 2 CHCH2 2 CHCH3 3
51. The wax candle is made up of very large alkanes.
CHCH 3 3 CH 2 2 CH
CH CH CHCH CHCH 2 2 CH 3 +
CH 3 +HBrHBr→ →CHCH3 3 CH 2 2 CH
CH CH CHCH 2 2 CHCH2 2 CH CH
3 3
Incomplete combustion of these alkanes results in
Br
Br the formation of the black soot. The black residue on
CH2 2
CH CH3 3 ++ HBr
CH HBr → CH3 3 CH
→ CH CH2 2 CH
CH CH CH2 2 CH CH2 2 CH
CH3 3 the watch glass is soot which consists of incompletely
burned hydrocarbons.
When HBr is added to hex-1-ene the Br can be added
52.
to either carbon 1 or 2. Carbon 2 is preferred because it
• PET is polyethylene terephthalate, a thermoplastic,
is bonded to the most carbon atoms.
polyester
When HBr is added to hex-3-ene the Br can be added • monomer is ethylene terephthalate made from an
to either carbon 3 or 4. However, because the molecule esterification reaction between ethylene glycol and
is symmetrical, and carbon atoms are always numbered terephthalic acid
such that the substituent has the lowest number,
• repeating unit in the polymer is C10H8O4
adding to either carbon 3 or 4 results in the same
product, 3-bromohexane. • modification of product is accomplished through
a copolymerization reaction e.g. if cyclohexane
47. Some reactions can be categorized as two different dimethanol replaces ethylene glycol or if isophthalic
reaction names because they fit both descriptions. For acid replaces terephthalatic acid, a softer product is
example, the reduction of an alkene to an alkane can obtained
also be thought of as an addition reaction (hydrogen
53. a. One estimate is 400 years.
adding across the double bond)
b. Plastic bags are not part of curbside recycling
48. The concept map should include the following types programs likely because of expense to get rid them.
of reactions, with an example of each: addition, Individuals are reusing more and more.
elimination, substitution, condensation, esterification,
c. Much less plastic waste goes into landfill. It is also
hydrolysis, oxidation, reduction, combustion (complete
more economical.
and incomplete), as well as addition and condensation
polymerization. The students should create categories d. Cleanliness and contamination can be a problem

such as “opposites” with examples of hydrolysis and especially if the bag is used for carrying food.
condensation, or oxidation and reduction. They could 54. Answers can include: recycling of plastic bottles and
group reactions with respect to the functional groups other plastics in cafeteria; use of dishes rather than
involved. use plastics plates when possible; reuse plastic garbage
49. Answer can focus on such information as: plastics are bags; refrigerate left overs in reusable containers rather
made up of long chains so they are flexible so they can than covering with plastic wrap, use refillable bottle for
be molded into a variety of shapes but may also be hard water; …and more
and rigid and have uses where durability is important. 55. Students should consult Appendix A, pages 712-14
They are used for many everyday products such as if they are unsure of which organizer to choose.
water bottles and plastic shopping bags, piping, conduit Alternatively, they could prepare a short audio report,
and their low density and high durability leads to many animation, or other type of electronic presentation that
industrial and construction uses. covers the topics outlined on page 136 of the student
50. Refer to Appendix A page 712 SE format for Spider textbook.
Organizer. The central concept should be the fact
that both are polymers found in living systems.
Other ideas from brainstorming would include:

56. 61.
CH3 O • React the 2-methylprop-1-ene-1,3-diol with HBr
n HO OH + n to produce 2-bromo-2-methylpropan-1,2-diol, as
2n HCl
CH3 Cl Cl shown below. There will also be some 1-bromo-
O 2-methylpropan-1,2-diol which will have to be
CH3 removed.
O O • React carbonic acid with the 2-bromo-2-
CH3 n methylpropan-1,2-diol to get the final product, also
shown below. The second reaction is shown with the
BPA mimics human hormones and can have negative

compounds shaped so it is clear that the two OH
neurological effects especially if ingested at a young
groups on the carbonic acid will react with the two
age. BPA is useful because it makes Polycarbonate
alcohol groups on the 2-bromo-2-methylpropan-1,2-
plastic, which is clear and nearly shatter-proof.
diol.
57. Note: Assume that the starting material is
bromomethane and the product is methyl octanoate. HO CH C CH2 OH + HBr →
Convert bromomethane to methanol through a

CH3
substitution reaction. Oxidize octan-1-ol to an CH3
aldehyde then to the carboxylic acid, octanoic acid.
Esterification reaction between methanol and octanoic HO CH2 C CH2 OH
acid will produce methyl octanoate
Br
CH3−Br + OH− → CH3OH + Br−

C8H17OH + [O] → C7H15CH=O → + [O] →
O O
C7H15COOH
C C
C7H15CH=O + [O] → C7H15COOH
HO OH O O
+ → 2H2O + +
CH3OH + C7H15COOH →
HO OH
CH2 CH2
H2O + CH3-O–CO−C7H15 CH2 CH2 C
58. There is cross linking between strands specifically the C CH3 Br
formation of hydrogen bonds between N−H and O=C CH3 Br
As well there is strength from the aromatic stacking 62. You can use the alcohol of the carboxylic acid you
interactions. need with the same R group and then oxidize it with
59. an oxidizing agent. You could also find an alkene
• Carry out an elimination reaction by treating with a C1–C2 double bond and perform an addition
bromoethane with NaOCH2CH3 to produce ethene. reaction to make it into an alcohol which you can then
• Carry out a reduction reaction on propan-2-one to oxidize
produce propan-2-ol. 63. For example:
• Carry out an elimination reaction by treating alanine phenylalanine serine
propan-2-ol with with sulfuric acid to produce O O O
propene.
H N CH C N CH C N CH C OH
• Carry out an addition polymerization with the ethene
and propene. H CH3 H CH2 H CH2
60. a. As the particles become small enough, animals
OH
including fish and birds can ingest the plastic. This
cannot be digested and can interfere with normal
functions in their bodies. Death can result from 64. • O xidize the original oct-6-ene-1-ol to oct-6-eneoic
this or from blockage of airways. Also, further acid
degradation can release harmful chemicals. • Carry out an addition reaction with water to convert
b. Reduce, Reuse, Recycle. the oct-6-eneoicacid to 6-hydroxyoctanoic acid.


• Carry out a condensation polymerization reaction to 11. Amino acids would be found in muscle-building
product the poly-6-hydroxyoctanoic acid. supplements because they are the monomers of
OH O proteins which help athletes build muscle. (In reality,
+ [O] →
only exercise can build muscle.)
OH
12. a. 2-methylpropan-2-yl 2,2-dimethylbutanoate +
O O
water,
+ H2O
OH OH b. N-propyl-3-chlorobutanamide + water
OH
O 13. cycloheptene + H2O → cycloheptanol + [O] →
cycloheptanone
n OH → nH2O +
4. a. addition polymer
1
OH
O CH2=CH—C≡N
... O
O O b. condensation polymer
O O
O ...
O OH HO
HO
65. Use different coloured paper clips. For example HO
nylon 6,6. The monomers are adipyl chloride and
hexamethylene diamine can be represented by different 15. Both cellulose and starch are polymers with glucose as
colours or sizes of paper clips. the monomer. However they differ in how the glucose
66. a. H H H H H H H H monomers are linked together. Cellulose has beta
linkages and starch has alpha linkages. Because of the
H C C C C C C C C H beta linkages humans cannot digest cellulose; we do
not have the enzymes that recognize beta linkages.
H H H H H H H H
Cellulose fibers are used to compose wood, paper,
b. 2C8H18(ℓ) + 25O2(g) → 16CO2(g) + 18H2O(ℓ) cotton and flax. Starch is used as an energy storage unit
c. CO2, a major greenhouse gas that is linked to for plants.
global warming and acid precipitation, is constantly 16. • reduce the carboxylic acid to an aldehyde
added to the environment. Combustion is usually • reduce the aldehyde to an alcohol
incomplete, thus adding soot and carbon monoxide • an elimination reaction of the alcohol to make an
to the atmosphere. Also, the octane has additives alkene
that can further pollute the air. • add the alkene to itself to perform an addition
polymerization reaction
Answers to Chapter 2 Self-Assessment Questions
17. a. 2-chloroheptane and 3-chloroheptane; In the
(Student textbook pages 142-3) reactant, the two carbon atoms involved in the
1. d double bond are bonded to an equal number of H
2. c atoms and an equal number of C atoms. Therefore,
3. b neither product will be preferred.
b. 2-methylhept-3-ene and 6-methylhept-3-ene
4. d
Carbon atoms 3 and 5 are bonded to the same
5. a number of other carbon atoms as well as the same
6. e number of hydrogen atoms. Therefore, neither
7. b product is preferred.
8. d 18. Essay can focus on common uses such as furniture,
cooking utensils, car parts, fabrics, toys, footwear,
9. b
bags, phones, or computers. If we depended on natural
10. c materials for these uses, many applications would
not be possible. Also there would not be enough
natural products to make items to support the world
population.

19. (CH3)2 CHCH=CHCH3 + 9O2 → 6CO2 + 6H2O carbons long, whereas the second has the longest
20. Polyamide. The −COOH of one amino acid reacts with chain containing the double bond is only four
NH2 of another amino acid to form amide linkages. carbons long.
21. The number of C−O bonds decrease or the number of 17. Both types of stereoisomers have their atoms bonded
C−H bonds increase in the same sequence on the carbon chain. Cis/trans
(Z/E) diastereomers (geometric isomers) have two
22. a. CH3CH2C(Cl)=CH(Cl)
unique atoms or groups arranged on the same side
and CH3CH2C(Cl)2–CH(Cl)2,
(cis/Z) or on opposite sides (trans/E) of the double
b. cyclopentene + water bonds. They have different physical but similar
c. HO-CH2CH2CH3 + Cl- chemical properties. Enantiomers (optical isomers)
23. butanone + [H] → butan-2-ol are non-superimposable mirror images of each other
butan-2-ol + HCl → 2-chlorobutane + water and don’t require a double bond. They have essentially
24. a. hexyl propanoate + water, the same physical and chemical properties except how
b. cyclobutanol the rotate plane-polarized light and react with other
enantiomers and with enzymes.
25. HOOC−CH2−CH2−CH2−CH2−OH with H2SO4 as
a catalyst 18 a. substitution
b. addition
The −OH group on one end of the molecule will react

with the −COOH group on the other end to form the c. condensation
cyclic compound. d. hydrolysis
e. elimination
Answers to Unit 1 Review Questions f. combustion
(Student textbook pages 147-53) 19. A polymer is a long-chained molecule made up of
1. c repeating units. A monomer is the unit which repeats
in a polymer. Glucose is a monomer and starch is one
2. c
of its polymers.
3. b
20. Primary amides would be expected to be more soluble
4. b in water as they have the greatest number of N–H
5. a bonds that allows for hydrogen bonding with H2O.
6. d 21. They are both made through condensation
polymerization reactions. Polyamides contain amide
7. b
linkages, –CO–NH– while polyesters contain ester
8. c linkages, –CO–O–.
9. b 22. The reactant in an addition reaction is an alkene which
10. e must contain a double bond between two carbon
11. a atoms. When a small molecule such as HX is added to
an asymmetric alkene, two products can form because
12. e the X could be added to either of the carbon atoms
13. a involved in the double bond. Markovnikov’s rule is
14. c used to predict which product is more abundant. Also,
two different products can form when each double
5. a. alkene
1
bond has two different atoms or groups of atoms
b. alkane single bonded to it. The products will be cis and trans
c. alkene or cycloalkane isomers.
d. alkyne 23. Petrochemicals are products derived from petroleum.
16 a. These are not constitutional (structural) isomers but Basic hydrocarbons, such as ethene and propene, are
the same molecule rotated 180 degrees. converted into plastics and other synthetic materials.
b. These are constitutional (structural) isomers, as the 24. a. chloroprene,
longest chain containing the double bond is five b. methyl methacrylate

25. condensation polymerization low solubility in water. Propan-1-ol would both be
26. a. addition soluble in water because both can enter into hydrogen
bonding. The –COOH group in propanoic acid makes
b. condensation
this molecule more polar than the corresponding
c. combustion
alcohol and it will have the higher boiling point will
27. a. oxidation be higher than the alcohol. Propanoic acid will turn
b. reduction litmus red.
28. a. hydrolysis 33. Esterification (cyclic) and polymerization
b. esterification and condensation O
29. a. N-butylethanamide C
b. cyclopentylbutanoate O O CH2
H2SO4
30. a. The longest carbon chain is five carbon atoms long. OH CH2 CH2
+ H2O
The correct name is pentane. HO
CH2 CH2
b. Numbering of the side groups should give the lowest
places on the longest chain for alkanes. The correct O
n H2SO4
name would be 2,3-dimethylpentane. OH n H2O +
c. Side groups on an alkane should be placed in HO
alphabetic order excluding multiplying prefixes. The
correct name would be 3-ethyl-2,2-dimethylnonane. O
d. The benzene group has the greatest number of ... O C CH2 CH2 CH2 CH2 CH2 O
carbon atoms and therefore would receive the root O
name. The correct name would be 1-pentylbenzene.
C CH2 CH2 CH2 CH2 CH2 ...
31. a. Aldehydes are always at the end of a carbon chain.
The molecule would be a ketone and have the name 34.
propanone. • Convert ethane to ethene by cracking.
b. Numbering of a cycloalkane would place the CH3—CH3 800PtºC CH2=CH2 + H2
halogens in alphabetic order giving the first in the
• Convert ethene into ethanol by addition of H2O.
alphabet the lowest number. The correct name
CH2=CH2 + H2O → CH3—CH2OH
would be 1-bromo-2-chlorocyclobutane.
• Convert ethanol to ethoxy ethane by dehydration.
c. The alcohol group would receive the lowest number
This reaction requires strong sulfuric acid as a
in the longest chain. The longest carbon chain that
catalyst and high temperatures.
does not contain multiple bonds is nine carbons H SO
long. The correct name would be 7-methylnonan-3- 2CH3—CH2OH heat CH3—CH2—O—CH2—CH3
2 4
ol. + H2O
d. The longest carbon chain in an ether gets the root 35. a. propan-1-ol + ethanol
name. The correct name would be ethoxybutane. b. 3-chloro-2,2-dimethylpentane
e. The longest unsaturated chain receives the root c. N-methyl-N-(2-methylpropyl)ethanamide
name. Numbering gives the multiple bond the 36. a. A is ethane; C is ethanol; B is ethyl ethanoate ; D is
lowest number. The correct name is 2-ethylpent-1- ethanoic acid
ene.
b. ethane CH3—CH3; ethanol CH3—CH2—OH; ethyl
f. The longest carbon chain in the root name is five ethanoate CH3—CH2—CO—O—CH2—CH3;
carbons long. The correct name would be methyl-3-
ethanoic acid CH3— COOH
methylpentanoate
37. a. Both molecules have aromatic (benzene) rings and
32. Use difference in their boiling points, solubility in
halogens.
water and reaction to litmus to distinguish between
b. Both names contain the name phenyl which is
these molecules. Propyne would have the weakest
benzene ring, the prefix bi- which indicates that
intermolecular forces (dispersion forces) between
there are two benzene rings, and the name of a
molecules and therefore the lowest boiling point and
halogen.
be a gas at room temperature. The gas would have a

c. The molecules would be expected to be liquids or 45. a. poly-1,1-dichloroethene;
solids due to the large number of carbon atoms and ... CH2 CCl2 CH2 CCl2 CH2 CCl2 CH2 CCl2 ...
highly electronegative halogen atoms there would be
significant dispersion forces between molecules. b. trade name is Dacron
O O O O
d. These molecules would not be soluble in water ...
... O C C O CH2 CH2 O C C O CH2 CH2
but be soluble in non-polar substances such as
hydrocarbons (oils & fats for example). 46. a.
e. They would be expected to have other similar • use 2 fats and 2 oils
physical properties such as melting point boiling • a dd equal portions of each fat and oil to separate
point density. They may have similar physiological test tubes
effects since they can dissolve and accumulate in fat
• a dded a measured volume of bromine water to each
tissue
test tube
38. an ether • s hake gently or warm in a water bath while looking
39. Carry out a substitution reaction of benzene with for a decrease in the intensity of the reddish colour
bromine. of bromine water.
benzene + 2Br2 →1,3-dibromobenzene + HBr b. Br2(aq) WHMIS: Corrosive. Harmful if inhaled.
40. a. 7-methylocta-2,6-dien-1-ol Causes respiratory tract irritation and possible
burns. Causes eye and skin irritation and possible
b. It would be a volatile liquid at room temperature. It
burns. Wear gloves when making the bromine water.
would be slightly soluble in polar solvents and very
Work in a fume hood.
soluble in non-polar solvents.
c. addition
c. Ethanol would be a suitable solvent as it would
evaporate quickly allowing the geraniol to slowly d. H3C—CH(Br)—CH(Br)—CH3
volatilize. 47. Ethanol is the only one of the three that will mix with
41 a. Amino acids have both amino, –NH2, and carboxyl, water. Adding water to each will indicate which one
–COOH, functional groups. is ethanol. Hex-2-ene can be separated from benzene
by the addition of Br2(aq). The bromine water will
b. Glycine would be named 2-aminoethanoic acid and
discolour as it reacts with the hex-2-ene but will not
alanine would be 2-amino-propanoic acid.
react with benzene.
c. Glycine would be more soluble in water than alanine
as it has fewer alkyl groups. 48. a. 3-hydroxypropanoic acid
b. 4-aminobutanal
42. a. O
49. butane; 3-methylpentane; 2-chloropentane;
b. It should be a gas at room temperature, be soluble in 2-iodopentane; 1-bromohexane
non-polar solvents and of low solubility in water. 50.
c. Its extreme flammability would be one of the reasons • Oxidize the ethanol all the way to ethanoic acid.
for not being used in operating rooms. • Carry out an addition reaction using HCl with the
43. non-1-en-5-amine to form 2-chloronon-5-amine.
• monomer CH3—CH=CH—CH3 • Carry out a condensation reaction between the
• polybutene –[—CH(CH3)—CH(CH3)—]n – ethanoic acid with the 2-chloronon-5-amine in the
presence of an acid catalyst to form the amide bond.
• solvent alkylethers, tertiary alcohols
51. The teacher might suggest to the students that they
• acid catalyst
start this question early and carry a list of the classes of
WHMIS: 2-butene is a gas at room temperature, highly
compounds for several days or a week. As they are in
flammable, explosive with air mixture, inhalation can
different locations, they can look for examples. It would
cause dizziness and unconsciousness, evaporation from
be interesting for them to look for a certain category of
skin can lead to frostbite, use face shield
used (e.g. foods, medications, cleaning solutions) that a
4. a. butanal, butanoic acid
4 particular hydrocarbon or derivative fits into.
b. 4-methylhexan-3-ol


‑ 52. H 58. Students have 58 terms to consider and link;
organization will most likely reflect the section
C Cl organization of the two chapters. Answers should
H
include additional explanatory words to show
H meaningful relationships between the words and
The chlorine atom is above the plane of the paper, one
clusters of words.
hydrogen atom is below and two hydrogen atoms are in 59. Some ideas to expand on: The disposal of items and
the plane of the paper. products made of plastic leads to very large amounts
53. The simplest hydrocarbon that can form cis and trans of waste that is harmful to the environment. Since they
isomers is 2-butene. take a very long time to degrade, they take up space
in land disposal sites. No one wants garbage sites near
H H H CH3 where they live so there are not many places to put this
C C C C waste. There is a large mass of garbage in the ocean
HH
3C HCH3 H3H
C H3
CH
which is mostly made up of plastics. This interferes
C
cis-2-buteneC C -2-butene
trans C with marine life and can cause the death of animal
H3C Cl CH3 H3C Cl H
54. life in the ocean. Reuse and recycling are part of the
Br ClC F F ClC Br solution to this problem.
60. All aspects of our everyday life have uses of organic
Br CCH3F F CCH3Br compounds. The answer should cover a wide variety of
uses and abuses of e.g. pharmaceuticals, plastics, food
CH3 CH3
additives, fuels.
The diagrams show that 1-bromo-1-chloro-1-

61. One possible flowchart is:
fluoroethane can form non-superimposable mirror
images of each other. Therefore, there can be Organic compounds
Organic compounds
enantiomers of 1-bromo-1-chloro-1-fluoroethane. are defined by the
55. Sample answer: Cotton requires large amounts of water funtional group(s)
that they contain.
to grow and a large amount of pesticides are used on Addition Functional groups
Elimination
the plant. Polyester uses 10 times more energy than Reactions between organic
Substitution
cotton during production and produces 4 times more Esterification compounds and the resulting
carbon dioxide products are controlled by the
types of functional groups present.
56. Reactions of Polymerization
• complete combustion – excess of O2(g) available; organic compounds
reactions(addition
products of complete combustion of hydrocarbons and condensation)
are only carbon dioxide and water. produce very large
molecules
• complete and incomplete combustion - starting
Synthetic polymers Natural polymers
material is a hydrocarbon; CO2 and H2O are always
produced
• incomplete combustion – insufficient O2(g) available; Biological molecules
Petrochemicals
less heat given off; in addition to CO2 and H2O, CO and their functions
and C are also products.
Incomplete combustion is dangerous because CO
is poisonous, colourless, odourless, gas that is
undetectable to our senses.
57. Life in the 1800s would centre around providing
necessities rather than conveniences. Discuss
availability of choices in modes of travel, clothing,
furniture, type of work.

62. One possible flowchart is illustrated below: c. Stinging insects such as bees and beetles will secrete
formic acid.
Crude Oil
d. It is a defense mechanism to ward off predators.
65. a. Teflon has a very low coefficient of friction and the
Fractional distillation Teflon polymer is non-reactive to compounds found
in foods.
b. At high temperatures, above 240oC, it is known that
Teflon breaks down and gives off toxic particles and
Cracking
and reforming gases.
c. A safety note should be included cautioning users
to not heat this pan above normal temperatures
Ethene (ethylene) Xylene
used for cooking. Do not place in an oven or on a
oxidation by oxidation by barbeque.
addition of addition of
oxygen gas with potassium
66. a. Any molecule that has a large hydrocarbon chain
a silver catalyst permanganate with polar groups such as alcohols or carboxylic
acids on the end would suffice.
Ethylene oxide Terephthalic acid b. Emulsifiers make heterogeneous mixtures such
with oil and water appear to be homogeneous. For
example lecithin in egg yolks helps to prevent the
separation of oil and vinegar mixtures in certain
Polymerization reactions
(addition and condensation)
salad dressings.
produce very large molecules 67. Some examples would be pharmacist, medical doctor,
researchers in the cosmetics, pesticides and polymer
condensation
Ethylene glycol
polymerization industries, food and drug analyst, petrochemical
engineers, hazardous waste handlers as well as a
Terephthalic acid myriad of others. Training for most of these programs
would involve a four year undergraduate degree as well
63. With respect to solubility, the statement is too general as possible post graduate degrees. To become a medical
to agree with. The general statement that matches doctor would require at least six years. Only certain
this is that “like dissolves like” Non-polar solvents schools would offer pharmacy and medical programs
dissolve non-polar compounds and polar solvents 68. CH2 CH2 CH2 OH
dissolve polar compounds. Water is a polar solvent. H3C CH2 O CH2
Hydrocarbons are non-polar and have low solubility
in water while organic compounds with a polar part b. One would expect them to be considered flammable
on the molecule will dissolve in water. The ability to and possibly toxic in large doses.
conduct an electric current depends on the presence c. The sorbitan molecule contains alcohol, ether, ester
of ions. Few organic compounds will form ions in and large alkyl functional groups. This combination
solution; even carboxylic acids ionize only slightly. The would make one end of the molecule soluble in
statement is generally true regarding conductivity. water and the other end soluble in the oil.
64. a. Formic acid is the simplest of the carboxylic acids, d. Skimmers recapture the oil which could be reused
HCOOH. The IUPAC name is methanoic acid. but require much energy and effort. Burning
b. Human use is to use formic acid as an antibacterial removes it from the ecosystem but creates
agent and preservative with animal feed; it can be greenhouse gases and harms organisms on the
reduced to formaldehyde, a preservative for animal surface. The dispersants reduce the concentration of
specimens, it can act as a reducing agent to reduce the oil but just spread it and when used underwater
metals from their solutions; it is used in the tanning may damage the ecosystem deeper than just on
industry; it is used to synthesize esters. the surface. Other benefits and repercussions are
possible.

e. Reduce one’s use of fossil fuels such as using public 77. a. With so many organic compounds widely used,
transit, recycling plastics, encouraging governments solvents have become specific for various classes
companies to have safeguards in place are just some of compounds. The advantage is that there are no
of the many answers students could give. organic compounds for which a solvent cannot
69. The chains of this polymer have –NH2 and –C=O be found so that any compound can be cleaned of
groups attached, which allows hydrogen bonding to a surface. The disadvantage is that many organic
occur. This increases the strength. solvents are volatile and are hazardous to our health
if inhaled. Disposal of solvents is another problem
70. The greater the intermolecular attractions between
since they can persist in the environment for long
molecules the greater the boiling point. The boiling
periods of time.
points of benzene and cyclohexane are higher than for
b. Research should focus on absorption of solvents
hexane because the structure of these two compounds
through the skin and inhalation.
gives a greater surface area. This results in greater
intermolecular attractions between their molecules. c. Results can be organized, for example, with respect
type of health effect, seriousness of health effect,
71. (1) It is similar to a condensation reaction
type of solvent
(2) reduction,
d. Greater care could be taken to avoid using more
(3) polymerization
of the solvent than necessary. Research the type of
72. The tar-like substance is most likely a long chain solvent that will dissolve a particular compound and
carbon compound that is non-polar. Vegetable oil use the one that has the least effect on health and the
would likely be the best since it has fairly long carbon environment.
chains and the esters that make it up are only slightly
polar. Answers to Unit 1 Self-Assessment Questions
73. This is oxidation because a carbon atom in the product (Student textbook pages 154-5)
is bonded to fewer hydrogen atoms. 1. b
74 a. Ethanol or grain alcohol, C2H5OH, is the alcohol 2. e
present in wine, spirits and beer. 3. b
b. Due to their ability to form hydrogen bonds, 4. b
alcohols would be liquids or solids at room
5. e
temperature.
c. Due to the toxic and combustible nature one 6. b
would expect the WHMIS symbols for poison and 7. d
flammable to be on containers used in the workplace 8. b
75. Rusting is an oxidation of a metal. The oxidation 9. b
and reduction discussed in this chapter have organic
10. a
compounds as reactants.
76. Student answers will likely include some of the
following points. The public often believes that
“natural” is safer and better than “synthetic,” even if
the compounds are identical. This is evident in natural
and artificial flavourings, and with natural and artificial
sweeteners. The public is prepared to pay a premium
for “organic” or “natural” products, without knowing or
understanding the differences between them. In order
for consumers to make informed product choices, they
have to thoroughly research the differences between
the products. Many manufactured products have strict
guidelines around labelling, while there are few if any
guidelines around “natural” products.

11. There are five structural isomers, one of which has two 13. Some benefits would be better medicines, dyes, foods,
diasteroisomers. cosmetics, transportation, and agricultural yields.
Some drawbacks would be increased reliance on
H H H H
hydrocarbons with the resulting environmental effects
H C C C C H such as oil spills and emission of VOCs and ozone
destroying CFCs. The release of toxins such as dioxins
H H as well as drugs and pesticides that have had negative
H H H H side effects on humans and the environment could also
cis
be mentioned
or
trans H C C C C H
14. a. Vitamin C could form enantiomers as it has two
H H carbon atoms that are bonded to four different
atoms or groups. These two carbon atoms are circled
H H
in the figure below.
H C C H
HO
H C C H H
HO O O
H H H
H HO OH
H C H b. Due to the large number of hydroxyl groups and
oxygen atoms, which could hydrogen bond with
H C C C H other molecules, it would have a high melting point
H H H and be a solid at room temperature. Due to the large
number of polar hydroxyl groups it would be soluble
H H in water.
H C c. Yes as fats are non-polar and vitamin C molecules
polar, the vitamin C would not dissolve in the fats.
H C C C H It is water soluble and would be quickly eliminated
H H H from the body.
15 a. 3-ethyl-2,2-dimethyloctane
12. a. CH CH CH2 CH2 CH3 b. 1-ethyl-2-fluorobenzene
2
c. butan-2-ol
CH CH
d. 3-phenylnonane
b. O CH3 6. a. fuels
1
b. beverages, antiseptics
c. c. pharmaceuticals
O
d. sour tasting foods such as vinegar
CH3 CH2 CH2 CH CH2 C OH e. artificial and natural flavourings
CH2 These are just some examples of the many places
students may find these substances
CH2
17. alkane to haloalkane: substitution
CH3 haloalkane to alcohol: substitution

d. H alcohol to carboxylic acid: oxidation

O O
H C H
CH3 C C CH3
e. H C C C H
O
H H H
CH3 C O CH2 CH2 CH2 CH2 CH3
H H
H C Unit 1 Part A • MHR 37
H C C C H
18. Molecules must have double bonds to undergo 23.
addition polymerization or they must have two • Oxidize the ethanol first to ethanal and then to
functional groups which can react to combine and ethanoic acid.
release a small molecule to undergo condensation • Carry out an addition reaction to add water to the
polymerization. double bond of the but-3-en-2-amine producing
19. The first polymer is an addition polymer and the 3-aminobutan-2-ol.
second is a condensation polymer (polyamide). The • Combine the ethanoic acid and the 3-aminobutan-
polyamide would be stronger because its chains can 2-ol and use sulfuric acid as a catalyst to carry out
hydrogen bond to each other. condensation reactions. The carboxyl group of one
20. Recycle bags, have a no plastic bag rule, buy degradable molecule of ethanoic acid will react with the amino
garbage bags. Have recycle containers available for soft group of the 3-aminobutan-2-ol, and the carboxyl
drink and water bottles. group of a second molecule of ethanoic acid will
react with the alcohol group on the other end of the
1. a. 3-methylpentan-2-ol + HCl
2
3-aminobutan-2-ol to form the desired compound.
b. 3-methylpentan-3-ol and H2SO4 as a catalyst
24. a. major product: 3-bromo-3-methylpentane
22. minor product: 2-bromo-3-methylpentane
O O
b. 3-methylbutanoic acid and ethanol
HO OH c. 2-methylpentan-3-one
25. Small carbon chains ignite too early and explode
instead of burn, causing incomplete combustion. This
HO CH2 CH2 OH
is also damaging to the engine. Carbon chains with
more than 12 carbon atoms would not vaporize well
enough and would therefore not undergo complete
combustion. Soot would build up in the engine and
cause damage.

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Chemistry 12: Solutions Manual Part A

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Chemistry 12

Solutions Manual Part A

Unit 1 Organic Chemistry 8. a. Wear protective eyewear, apron, thermal gloves;

Unit 1 Part A • MHR 1

specific elements, usually oxygen, nitrogen, sulfur, or H C H H C H H C H

2 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

H H H3C CH2 CH CH CH2 CH3 H3C C CH2 CH2 CH3

4 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

Unit 1 Part A • MHR 5

HC C C CH C CH2 CH CH CH2 CH3 Answers to Section 1.3 Review Questions

Naming root: indicates number root: indicates number of

6 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

Unit 1 Part A • MHR 7

18. 3,3-diethyl-4-methylhexane 36. CH2 CH2 CH3

21. H 38. CH3 CH3

(Student textbook page 26)

31. 2,5-dimethyloct-3-ene CH3

8 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

47. 5-ethyloct-2-yne 63. CH2 CH3

Unit 1 Part A • MHR 9

H2C CH3 5. a. 2-chlorobutane

10 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

H 114. The correct name is 5-methyloctane-3,4-dione.

Unit 1 Part A • MHR 11

12 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

H3C CH2 19. Enantiomers have identical structures. Their physical

Unit 1 Part A • MHR 13

14 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

b. C11H24 about 200°C; C12H26 about 215°C

Unit 1 Part A • MHR 15

Sucralose OH haloalkane, alcohol, 600x sweeter than sucrose; stable at non-cited

Mannitol OH OH OH alcohols doesn’t cause tooth decay; does not

47. a. H H 48. a. NOTE: The name is invalid and should be

b. Several constitutional isomers can form by changing

16 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

Unit 1 Part A • MHR 17

18 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

c. Gaseous alkanes could be found in natural gas, CH3

19. Both esters and amides have a carbonyl group (C=O)

17. a. 3-methylbutanoic acid 21.

Unit 1 Part A • MHR 19

non-renewable, accumulation of CO2 which is a two molecules combine to form one

Chapter 2 Reactions of a special case of a condensation

Organic Compounds reaction in which one reactant is

20 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

(Student textbook page 124) Oxidation reaction:

Unit 1 Part A • MHR 21

HO C CH2 C OH H2N CH2 CH NH2

22 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4

CH3 H C C C H + HOCH2CH3 + NaCl

CH3 CH2 C CH2 CH2 CH3

Unit 1 Part A • MHR 23

25. CH3 CH CH3 + H2O H3C C CH2 acid + propan-1,2-diol

31. CH3CH2CH3 + Br2 48. esterification and condensation

32. 49. CH4 + 2OCH

(Student textbook page 108-9) (Student textbook page 121)

CH3 C OH + HO CH2 (CH2)6 CH3 HO C H3(CH

39. butanoic acid and methanol 57. polyester

24 MHR • Chemistry 12 Solutions Manual 978-0-07-106042-4