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Unit
Organic Chemistry
1
Chapter 1: Organic Compounds
Organic chemistry is the study of carbon-containing compounds and their properties. There are a few carbon compounds, including carbon oxides and carbonates
that we consider to be inorganic. Understanding how carbon atoms bond to each
other and to other atoms helps explain why organic compounds enable life to exist
on Earth.
Alkanes are saturated hydrocarbons in which the atoms of carbon are bonded to
each other by single bonds. Alkenes and alkynes are unsaturated hydrocarbons with
multiple bonds, and they are more reactive than alkanes. They may participate in
addition reactions, including hydrogenation, halogenation, hydrohalogenation, and
hydration.
A naming scheme has been established by the International Union of Pure and
Applied Chemistry (IUPAC) to name the organic compounds. Structural isomers are
compounds that have the same molecular formula but different molecular geometry.
Cis and trans isomers are compounds that are identical except for the position of
groups on either side of a double bond.
Aromatic hydrocarbons are a class of cyclic unsaturated hydrocarbons that have
a ring structure and bonding that causes them to be chemically stable. Other major
classes of organic compounds include alcohols, ethers, aldehydes, ketones, carboxylic
acids, esters, amines, and amides. Their properties and reactions are determined by
their structures and specific functional groups.
Big ideas
• Organic compounds have
predictable chemical and physical
properties determined by their
respective structures.
• Organic chemical reactions and
their applications have significant
implications for society, human
health, and the environment.
Chapter 2: Polymers
Many of the objects that we use today are made of plastic, at least in part. Plastics are
synthetic polymers. Other polymers occur naturally. Silk, spiderwebs, hair, muscle,
cotton, and wood are all composed of polymers made by living organisms.
Polymers are large molecules—natural or synthetic—made up of many monomers
linked together. Homopolymers are polymers made of only a single type of monomer.
Copolymers are polymers made of two or more types of monomers.
Addition polymers form when monomers link during addition reactions.
Condensation polymers are polymers formed when monomers join during condensation reactions. The properties of addition polymers can be varied by selecting
monomers with certain substituent atoms or groups. Polyesters are formed by condensation reactions between carboxylic acids and alcohols that result in ester linkages. Polyamides are formed by condensation reactions between carboxylic acids and
amines that result in amide linkages.
Starch, cellulose, and glycogen are polymers of glucose. Proteins and nucleic acids
are condensation polymers. The shape of a protein molecule depends on intermolecular and intramolecular forces. DNA stores information for amino acid sequences,
enabling the cell to assemble proteins.
Disposal of used plastics has been a serious environmental problem. Many plastics cannot be recycled. The most effective solution is to reduce the quantity of waste
produced.
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Unit 1 • Overview 1
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1.1
Textbook pp. 8–17
Alkanes
Vocabulary
organic compound
cyclic alkane
structural isomer
hydrocarbon
alkyl group
complete combustion
saturated hydrocarbon
substituent group
alkyl halide
alkane
MAIN IDEA: Hydrocarbons contain hydrogen and carbon. In a saturated hydrocarbon,
the atoms of carbon are bonded to each other by single bonds. Structural isomers are compounds that have the same molecular formula but different molecular geometry. Alkanes
may have a straight-chain structure or a ring structure. Substituent groups may be attached
to the parent structure. Alkyl halides are alkanes in which halogen atoms have substituted
for one or more hydrogen atoms.
1. Name two alkanes that are used as fuels to heat homes and solder torches. K/U
Learning Tip
Line Diagrams
In a line diagram, imagine that there
is a carbon atom at the end of every
line and at the intersection of every
line. Each one is surrounded by the
maximum number of hydrogen atoms.
2. Name and describe three common ways of depicting the structures of organic
compounds. K/U
3. Indicate whether each of the following statements is true or false. If you think
a statement is false, rewrite it to make it true. K/U
(a) A substituent group is any atom or group that replaces carbon in an
organic molecule.
(b) A structural isomer is a compound that has the same molecular formula as
another compound, but a different structure.
Learning Tip
Memory Aid: Table of Terms
You might find it helpful to create
a 3-column table summarizing the
naming of alkanes with 1 to 10
carbon atoms. List the unbranched
straight-chain alkanes, the
unbranched cycloalkanes, and the
alkyl groups.
2 Unit 1 • Organic Chemistry
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4. An alkyl group consisting of a 3-carbon chain and 7 hydrogen atoms is called
a(n) _________ group. K/U
5. Which of the following is not a saturated hydrocarbon?
(a) 1,3-dichlorobutane
(b) 2,4-dimethylpentane
(c) 2,3,4-trimethyloctane
(d) 1,4-diethylcyclohexane
K/U
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6. Write the name of each of the following compounds.
(a) CH3
CH2
CH
CH2
CH2
CH3
(d) CH3
K/U
T/I
CH3
CH3
CH
CH
CH3
Cl
(b) CH3
CH
CH3
CH2
CH2
CH
(e) CH3
CH3
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(c) CH3
CH2
CH3
CH
CH
CH2
CH2
CH3
(f) CH
CH2
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CH3
CH3
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7. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: Cyclohexane contains 6 carbon atoms with each
carbon atom bonded to 4 atoms, so one molecule of cyclohexane contains a
K/U
total of
atoms.
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8. Which of the following is a property of alkanes? C01-F06-OC12USG.ai
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(a) The combustion reactions are endothermic.
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(b) The molecules are polar and form hydrogen bonding.
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(c) The boiling point decreases with the length of the carbon chain.
Not(d)
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Van der Waal forces are the main intermolecular forces between
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molecules.
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Learning Tip
Molecular Formulas
To obtain the molecular formula, start
with the base formula for straightchain alkanes, CnH2n12, or that for
cycloalkanes, CnH2n. Subtract the
number of hydrogen atoms that have
been replaced by substituent groups
and add the substituent groups. For
example, 1,2-dimethyl cyclobutane
has the base formula C4H8 for
cyclobutane with two H atoms
replaced by two CH3 groups.
Number of H atoms 5 8 2 2 1 6
5 12
Number of C atoms 5 4 1 2 5 6
The molecular formula is C6H12.
9. Draw a structural formula and write the molecular formula for each of the
following compounds. T/I C
(a) 3-ethyl-4-methylhexane
(b) 1-bromo-3-ethylcyclohexane
(c) 4-propan-2-yloctane
10. Draw and name three structural isomers that have the molecular formula
C5H12. T/I C
4 Unit 1 • Organic Chemistry
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1.2
Alkenes and Alkynes
Vocabulary
unsaturated hydrocarbon
stereoisomer
functional group
alkene
cis isomer
addition reaction
alkyne
trans isomer
Markovnikov’s rule
Textbook pp. 18–27
aliphatic hydrocarbon
MAIN IDEA: An alkene is a hydrocarbon that has at least one double bond between two
carbon atoms. The carbon chain is numbered using the lowest number for the double bond. The
root name ends in -ene. An alkyne is a hydrocarbon that has at least one triple bond between
two carbon atoms. Naming alkynes is similar to naming alkenes. The root name ends in -yne.
Cis and trans isomers are compounds that are identical except for the positions of groups on
either side of a double bond. In cis isomers, the groups are located on the same side of the
double bond. In trans isomers, the groups are located on the opposite sides of the double bond.
1. Indicate whether each of the following statements is true or false. If you think
a statement is false, rewrite it to make it true. K/U
(a) Each molecule of a hydrocarbon containing carbon–carbon double or
triple bonds contains fewer than the maximum number of hydrogen
atoms.
(b) Other than the use of cis and trans to describe the positions of the groups
around the double bond, stereoisomers have the same molecular formula
and chemical name.
(c) cis-hex-2-ene and trans-hex-3-ene are stereoisomers.
2. Name the following compounds.
(a) CH2
CH3
CH
CH
C
K/U
T/I
CH3
(c) H3C
CH2
Br
(b) CH
3
CH3
(d) CH2
C
C
C
CH2
CH3
Cl
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1.2 Alkenes and Alkynes 5
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3. Draw the structures of the following compounds.
(a) 3-methylhexa-1,3-diene
T/I
C
(b) 5-ethyl-2-methylhept-3-yne
(c) 1-ethylcyclobut-1-ene
4. Match the condensed formula on the left with the possible alkene or alkyne on
the right. K/U T/I
(a) CH3CH2CCCH2CH3
(b) CH3CH2CH2CH2CCH
(c) CH3CHCHCHCHCH3
(d) CH3CH2CHCHCH2CH3
6 Unit 1 • Organic Chemistry
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(i) hex-3-ene
(ii) hex-2,4-diene
(iii) hex-1-yne
(iv) hex-3-yne
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5. An aliphatic hydrocarbon has molecular formula C5H10. T/I C
(a) Draw all possible non-cyclic structural isomers of the compound. Write
the name of each structure.
Learning Tip
Remembering Cis and Trans
To use cis and trans correctly, you
could think of cis as being like
sisters: side by side. And trans means
“across,” as in transatlantic.
Learning Tip
(b) Identify if any of the structures in part (a) have stereoisomers. Draw and
name the cis and trans isomers of the compound.
6. Draw the cis and trans isomers of the following compounds.
(a) 3-chlorohex-3-ene
K/U
Stereoisomers vs. Structural
Isomers
Structural isomers have the same
molecular formula—the same
numbers and types of atoms, but
with the atoms bonded in different
ways. Stereoisomers are identical
in their structural formulas, but the
arrangement of the atoms or groups
in space around two carbon atoms
do not allow these atoms or groups
to be rotated to change from one
isomer to the other. Cis/trans isomers
are common for alkenes, as their
molecules cannot rotate around the
double bond.
C
(b) 1,2-dimethylcyclobut-1-ene
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1.2 Alkenes and Alkynes 7
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MAIN IDEA: Hydrocarbons with multiple bonds are more reactive than alkanes and
participate in addition reactions in which atoms from one molecule are added to another
molecule. Addition reactions include hydrogenation, halogenation, hydrohalogenation, and
hydration. Markovnikov’s rule states that, when two non-identical entities are added at a
double bond, the major product will be formed by the hydrogen atom bonding to the carbon
atom with more hydrogen atoms attached.
7. A __________________ group is a specific group of atoms within a molecule
that affects the properties of the compound such as the chemical reactivity
with other elements or compounds. K/U
8. Which of the following is not true for the addition reactions of alkenes or
alkynes with water? T/I
(a) The double-bonded or triple-bonded carbon atoms take part in the
reaction.
(b) The alkene or alkyne gains atoms but does not lose any atoms.
(c) There is only one product resulting from the reaction.
(d) Two molecules react to form one molecule.
9. Draw the structure of the product of each of the following reactions. Write
the IUPAC names of the reactant and the product, and identify the type of
addition reaction. Apply Markovnikov’s rule if needed. T/I C
(a)
CH3
CH3
C
CH
CH3
H2
CH3 Br2
(b)
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CH3
(c)
CH3
C
CH
CH
CH3 HCI
CH3
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CH2
(d)
CH3
CH2
C
CH2
CH3 H2O
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1.3
Aromatic Hydrocarbons
Vocabulary
aromatic hydrocarbon
Textbook pp. 28–31
phenyl group
MAIN IDEA: Aromatic hydrocarbons are a class of cyclic unsaturated hydrocarbons that
have a ring structure and bonding that causes them to be chemically stable. Measurements
show that the bonds in a benzene ring are all equal in length.
1. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: The commercial use of benzene has discontinued
because benzene contains caffeine. K/U
2. The structural diagram of benzene shows that a benzene molecule has three
double bonds and three single bonds. K/U C
(a) Experiments indicate that all six bonds are equal in length. Explain how
this can occur.
(b) Draw a common representation of benzene.
3. (a) Name a commercial solvent that has replaced benzene as a solvent used in C01-F15-OC12USG.ai
industrial processes and for dry-cleaning clothes.
(b) Draw the structure of the compound and write its IUPAC name.
K/U
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1.3 Aromatic Hydrocarbons 9
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4. Name the following compounds.
(a)
CH3
K/U
(c)
CH3
CH2CH
CH2
Br
(b)
Cl
H3C
Learning Tip
Traditional Names for Aromatic
Hydrocarbons
An older naming convention for
substituted aromatic compounds
used the Greek prefixes ortho–,
meta–, and para– to indicate the
positions of substituents. Ortho
substituents are on adjacent carbon
atoms in 1,2 positions. Meta
substituents are separated by 1
carbon atom in 1,3 positions. Para
substituents are located on opposite
sides of the 6-carbon ring in 1,4
positions.
CH2CH3
5. Draw a structural formula to represent each of
the following compounds.
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metadiethylbenzene
K/U
C
(b) 5-chloro-7-phenyloct-1-yne
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MAIN IDEA: Benzene is less reactive than alkenes but more reactive than alkanes. Since
it participates in substitution reactions, benzene behaves more like an alkane.
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Learning Tip
6.
Which
of
the
following
compound is the least reactive? T/I
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Reactivity of Hydrocarbons
(a) benzene
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In general, saturated
hydrocarbons
(b) hex-1-yne 1st pass
Technicalare more stable than unsaturated
Pass
(c) hex-1-ene
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hydrocarbons. Compared
to
Approved
(d) hexane
unsaturated hydrocarbons, each
Approved
Not Approved
bond in benzene is identical and
7. Draw the chemical equation for the following reactions. Include the names of
Not Approved
these
bonds
are
much
more
stable
the organic reactant and product. T/I C
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than a carbon–carbon double bond.
(a) hydrogenation of benzene
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Figure
muchNumber
less reactive thanC01-F17-OC12USG.ai
alkenes but
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more reactive than alkanes.
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(b) substitution reaction of benzene using hydrochloric acid, HCl(aq)
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1.4
Alcohols, Ethers, and Thiols
Vocabulary
Textbook pp. 32–39
alcohol
tertiary alcohol
ether
primary alcohol
hydrogen bonding
condensation reaction
secondary alcohol
dehydration reaction
thiol
MAIN IDEA: Alcohols contain a hydroxyl group, –OH. The hydroxyl group allows alcohols
to form hydrogen bonds. Alcohols can be further classified as primary, secondary, and
tertiary.
1. What are two reactions that can be used for the commercial preparation of
ethanol? K/U
2. Since the electronegativity difference between carbon and hydrogen is
_______________ than that between carbon and oxygen, the C—H bond is
_______________ polar than the C—O bond. Also, the bond between carbon
and _______________ is polar, so alcohol molecules are polar. K/U
3. Match each alcohol on the left with the description and use on the right.
(a) ethanol
(b) propan-1-ol
(c) propan-2-ol
(d) ethane-1,2-diol
(e) propane-1,2,3-triol
K/U
(i)polyalcohol with three –OH groups used in
pharmaceutical preparations to help dissolve
less polar compounds
(ii)primary alcohol used as a solvent for lacquers
and waxes, and as brake fluid
(iii)polyalcohol with two –OH groups used as
antifreeze in automobile engines
(iv)secondary alcohol used as an antiseptic to
clean the skin before injections
(v) primary alcohol used in alcoholic beverages
4. Indicate whether each of the following statements is true or false. If you think
a statement is false, rewrite it to make it true. K/U
(a) The simplest aromatic alcohol has one hydroxyl group bonded to
cyclohexane.
Learning Tip
Classifying Alcohols
Alcohols are classified according to
the number of other carbon atoms
that are directly bonded to the carbon
atom attached to the hydroxyl group,
–OH. A primary alcohol has the –OH
group attached to the carbon atom
at the end of the carbon chain, which
has only 1 carbon atom attached to
it. A secondary alcohol has the –OH
group bonded to a carbon atom that
is attached to 2 other carbon atoms.
A tertiary alcohol has the –OH group
bonded to a carbon atom that is
attached to 3 other carbon atoms.
(b) As the size of the carbon chain of a simple alcohol grows, the alcohol
becomes less soluble in water because the hydrocarbon region of an
alcohol molecule is non-polar.
5. Which of the following compound is a tertiary alcohol? T/I
(a) 2,4-dimethylpentan-3-ol
(c) 4-methylheptan-3-ol
(b) 3-ethylhexan-3-ol
(d) 3,5-diethyloctan-4-ol
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1.4 Alcohols, Ethers, and Thiols 11
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6. Write the name of each of the following compounds.
CH3
(a)
H2C
CH
CH2
CH2
CH
CH2
CH2
CH3
CH2
K/U
(c) CH3
OH
CH2
CH3
CH2
CH2
OH
(d) H3C
(b)
OH
OH
CH
CH
CH
OH
OH
OH
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7. Draw a structural
formula for each of the following compounds. K/U C
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(a) 3-methylpentane-2,4-diol
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(b) 5-bromo-3-ethylhexan-2-ol
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(c) 3-chloro-2-methylcyclohexanol
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MAIN IDEA: Alcohols can be produced by hydration reactions of alkenes. Dehydration
reactions use a catalyst and acid to change the alcohol back to an alkene and water. In a
combustion reaction an alcohol reacts with oxygen, producing carbon dioxide and water.
9. Write a chemical equation for each of the following reactions. Classify the
reaction type. K/U T/I C
(a) butan-2-ol from but-2-ene
(b) but-1-ene from butan-1-ol
(c) water and carbon dioxide from ethanol
(d) methoxybutane from butan-1-ol and methanol
MAIN IDEA: Ethers can be produced from the condensation reaction of alcohols. Ethers
are widely used as solvents because of their ability to dissolve both polar and non-polar
substances. Thiols contain the sulfhydryl functional group, –SH. They typically have strong
odours and react similarly to alcohols.
10. Ethoxyethane is an effective anesthetic that has been used successfully for
decades. Why is it being replaced? What is the current major use of this
compound? K/U
11. Which of the following is not true of thiols? K/U
(a) Thiols generally have strong odours.
(b) Gas delivery companies add thiols to natural gas to detect leaks.
(c) Hydrogen peroxide reacts with thiols to form disulfide compounds with a
strong odour.
(d) The reaction of thiol is similar to that of alcohols as the sulfhydryl group,
–SH, is similar to the hydroxy group, –OH.
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1.5
Textbook pp. 40–46
Aldehydes and Ketones
Vocabulary
carbonyl group
aldehyde
ketone
MAIN IDEA: If a carbonyl group (C w O) is attached to at least 1 hydrogen atom, the
molecule is an aldehyde. It is named using the suffix –al. If a carbonyl group is attached to
2 carbon atoms, the molecule is a ketone. It is named using the suffix –one. The carbonyl
group makes organic molecules polar, giving them higher boiling points and greater water
solubility than the corresponding alkanes.
1. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: In an aldehyde other than methanal, the carbonyl
group is bonded to only one hydrogen atom. K/U
Study Tip
Naming Aldehydes and Ketones
When numbering the atoms in an
aldehyde or a ketone, the carbonyl
(C w O) functional group takes
precedence over other substituents,
such as alky groups, halogen atoms,
and a hydroxyl groups.
2. Name each of the following aldehydes and ketones.
(a) (c) CH3
CH3
CH2
CH
CH3
(b) C
O
CH2
CH
CH
CH3
Br
(d) CH3
CH3
K/U
C
O
OH
O
H
(e) CHC01-F23-OC12USG.ai
3CH2CH(CH3)CH2CHO
O
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(f) CH3C(Cl)2CH2COCH3
3. Draw a structural formula for each of the following compounds.
(a) 2,2-dimethylpropanal
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K/U
C
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(b) 1-hydroxyhexan-3-one
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14 Number
Unit 1 • Organic
Chemistry Figure Number
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4. Draw a line diagram for 2-ethylpentanal.
K/U
C
5. Which of the following is a property of aldehydes and ketones? K/U
(a) Their boiling points are higher than similar alcohols.
(b) The molecules are polar and form hydrogen bonds with one another.
(c) The molecules are more soluble in water than similar-sized alcohol
molecules.
(d) The solubility in water decreases as additional carbons are added to
the chain.
MAIN IDEA: The controlled oxidation of a primary alcohol produces an aldehyde. The
controlled oxidation of a secondary alcohol produces a ketone. Tertiary alcohols do not
readily undergo controlled oxidation. The hydrogenation of an aldehyde produces a primary
alcohol. The hydrogenation of a ketone produces a secondary alcohol.
6. Complete the chemical equation for each of the following controlled
oxidations of alcohol. Draw the structure of the product and write the IUPAC
names of the reactant and product. T/I C
(a)
H
CH3
CH
CH2
CH3
C
OH (O)
H
Reactant:
Product:
(b)
OH
CH3
CH
C
CH3 (O)
CH3 H
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Reactant:
Product:
(c)
OH H
CH3
C
CH
CH3
(O)
CH3
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Reactant:
Product:
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7. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: When a primary alcohol is hydrogenated, the
carbonyl group forms on the terminal carbon atom, resulting in an aldehyde.
K/U
8. Which of the following is a condensed formula for 4-methylhexan-2-one? K/U
(a) CH3CH2CH(CH3)CH2COCH3
(b) CH3CH(CH3)CH2COCH2CH3
(c) CH3COCH2CH2CH(CH3)CH3
(d) HCOCH2CH2CH(CH3)CH2CH3
9. Complete Table 1 for the hydrogenation reactions of aldehydes and ketones.
K/U
C
Table 1 Hydrogenation of Aldehydes and Ketones
Reactant
Product
18 or 28 alcohol
(a) Name:
Name:
(b) O
Name:
Name:
(c) OH
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O
Name:
Name:
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1.6
Carboxylic Acid, Esters, and Fats
Vocabulary
carboxylic acid
esterification
fatty acid
carboxyl group
hydrolysis
triglyceride
ester
lipid
saponification
Textbook pp. 47–55
MAIN IDEA: A carboxyl group is a combination of a carbonyl group, C w O, and a
hydroxyl group, –OH. Carboxylic acids are named by replacing the –e ending of the alkane
with –oic acid. Carboxylic acids are formed by the controlled oxidation of aldehydes.
1. Write two common uses of each carboxylic acid. K/U
(a) methanoic acid
(b) ethanoic acid
2. Name each of the following carboxylic acids. K/U
(a)
O
CH3
HO
C
CH2
CH2
CH2
CH
CI
(b) HOOCCH2CH2COOH
(c)
OH
O
Learning Tip
IUPAC and Common Names
You have probably realized that many
compounds have both common
names and systematic IUPAC names.
The textbook mostly uses the
systematic names as they help with
visualizing the molecular structure
of the compound. However, some
common names are so familiar that
they are also recognized by IUPAC.
Acetic acid and formic acid are two
such names. You should be familiar
with the common names as well
as the systematic names of these
compounds.
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3. Draw a structural
formula for each of the following carboxylic acids. K/U C
(a) 2,2-dimethylpropanoic acid
(c) 2-ethyl-3-methylbutanoic acid
(b) 3-methylbenzoic
acid
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4. Which of the following compound has the highest melting point? K/U
(a) butane
(b) propane
(c) butanoic acid
(d) propanoic acid
5. Use condensed formulas to write a chemical equation for the controlled
oxidation of 2-methylpropanal to produce a carboxylic acid. Also write the
IUPAC name of the product. K/U C
MAIN IDEA: An ester’s name is derived from the name of the alkyl group of alcohol followed
by the name of the alkyl group of the carboxylic acid with the ending –oate. Esterification is
the formation of an ester from a carboxylic acid and an alcohol. Hydrolysis of esters is the
breaking down of the ester by a strong base to form the carboxylic acid and alcohol.
6. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: The functional group of an ester is similar to a carboxyl
group except that the carbonyl group is replaced with an alkyl group. K/U
7. Name each of the following esters. K/U
O
(a)
CH3 CH2 CH2 C
O CH2
CH3
(b)
O
O
8. The IUPAC name of this ester is ethyl 2-methylpropanoate.
O
CH3 CH C
O CH2 CH3
CH3
K/U
C
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(a) Write a condensed formula for the ester.
(b) Draw a line diagram for the ester.
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9. Use structural formulas to write a chemical equation for the preparation
of ethyl pentanoate from an acid and an alcohol. Name the reactants and
products, and state the type of reaction. T/I C
10. What are the products from the hydrolysis of methyl propanoate?
K/U
MAIN IDEA: Fats and oils are triglycerides. They are esters made from long chains of fatty
acids. Saponification is the process by which a fatty acid reacts with a strong base to form
a salt of the fatty acid: soap. Saponification is a type of esterification.
11. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: Fats and oils are large ester molecules known as
lipids. Fats and oils have the same general structure, with fats referring to
solids and oils referring to liquids at room temperature. K/U
12. Soap is a sodium salt of a ______________________. It is formed together
with glycerol when an ester called ______________________ is heated
with the strong base sodium hydroxide in a type of reaction classified as
______________________. K/U
13. Which of the following is not true for trans fats? K/U
(a) They have unsaturated hydrocarbon chains containing double bonds that
cannot be rotated.
(b) Their melting points are lower than the corresponding cis forms, since
their molecules are more tightly packed together.
(c) Eating foods containing them could lead to health problems as they are
not easily digested as saturated fats.
(d) They are not water soluble because of the non-polar nature of the long
hydrocarbon chains in their molecules.
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1.6 Carboxylic Acid, Esters, and Fats 19
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1.7
Amines and Amides
Vocabulary
Textbook pp. 56–62
amine
amide
MAIN IDEA: Amines can be viewed as alkyl groups bonded to a nitrogen atom or an
amino group bonded to an alkane. Primary amines have one alkyl group attached to the
nitrogen atom; secondary amines have two; tertiary amines have three. Amines are named
by adding the suffix –amine to the root of the name of the longest alkyl group attached to the
nitrogen atom. The prefix N- indicates that a second (or third) alkyl group is also attached
to the nitrogen atom.
1. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: The IUPAC name for an aromatic amine consisting
of an amine group attached to a benzene ring is benzamine. K/U
Study Tip
Structures of Amines
To draw the structure of an amine,
remember that an amine is a
derivative of ammonia in which one
or more of the hydrogen atoms are
replaced with alkyl groups.
2. Name each of the following amines.
(a)
H
CH3CH2CH N
CH2Cl
CH3
K/U
(b)
CH3
N
CH3
3. Draw the structural formulas for all primary amines with the molecular
formula C4H11N. Write the names of the isomers. K/U C
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4. Name each of the following isomers of an amine with molecular formula
C4H11N. Classify the amine as secondary or tertiary. K/U
(a)
CH CH CH
3
2
2
(b)
CH3CH2
N
N
H
CH3
H
CH2CH3
(c) CH3
CH3CH2 N
CH3
(d) C01-F40-OC12USG.ai
H
CH3CH N
CH3
CH3
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5. Draw the structure of a tertiary amine with molecular formula C5H13N that
has only one methyl group attached to the nitrogen atom. Write the name of
this amine. T/I C
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6. Is the following statement true or false? If you think the statement is false,
rewrite it to make it true: The boiling points of amines of similar size increases
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1.7 Amines and Amides 21
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7. An amine can generally be synthesized from the reaction of
_________________ and ammonia. The reaction gives a mixture of primary,
secondary, and tertiary amines, which are separated using the process of
_________________ since they all have different boiling points. K/U
MAIN IDEA: Amides are formed from the reaction of carboxylic acid and amines. Amides
can be hydrolyzed to reform the amine and carboxylic acid. Amides are named with the root
of the name of the carboxylic acid first, followed by the root of the name of the amine, and
ending with –amide.
8. Write the IUPAC name of each of the following amides. K/U
(a)
O
CH3
CH3
CH2
(b)
CH3
CH2
CH2
C
O
CH3
C
N
NH
CH2
CH
CH3
CH3
9. Which of the following is true for amides? K/U
(a) The solubility in water increases with the length of the carbon chain.
(b) Amides are structurally similar to esters, so they generally have a pleasant
odour.
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(c) Primary amides have higher melting points and boiling points than similar
amides.
(d) Amides can be prepared by the hydrolysis reaction of a carboxylic acid
with ammonia or an amine.
10. Name a carboxylic acid and an amine that can be used to prepare N,Ndimethyl-3-methylbutanamide.
Write a chemical equation to show the
C01-F44-OC12USG.ai
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C
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CHAPTER
1 Summary
Organic Compounds
Organic chemistry is defined as the study of carbon-containing compounds and their
properties. There are a few carbon compounds, including carbon oxides and carbonates, that we consider to be inorganic. Organic molecules may contain one carbon
atom or tens of thousands of carbon atoms. The following graphic organizer summarizes some of the main ideas from Chapter 1. Add to it to create your own study notes.
Organic compounds
classes of
compound
structures
•
naming of
compounds
functional
groups
•
properties
C
• polarity of molecules
•
based on:
alkanes
• structural formulas
C
•
•
•
alkenes
reactions
•
•
alkynes
alcohols
• addition
-
substituent
groups:
• alkyl
-
•
-
•
-
•
•
•
aldehydes
•
impacts on society
and environment
•
•
ketones
•
uses
carboxylic
acids
amines
hazards
•
•
•
•
•
•
•
•
•
amides
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•
Chapter 1 Summary 23
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CHAPTER
K/U
T/I
C
A
1 Questions
(a) Cl
H3C
CH
CH2
CH
CH3
O
(b)
CH3
CH2
C
O
CH
O
H3C
(c)
OH
HO
(f) CH3CH2COCH2OH
(g) HCCCH2CHBrCH2CH(CH3)CH3
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(h) H2NCH2CH2CHNH2CH3
N
(d) C
CH3
Br
K/U
(e) CH3
CH3
O
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2. Draw a structure for each of the following compounds. (1.4, 1.6)
(a) line diagram for 3,5-diethyloctan-4-ol
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(b) condensed formula for 3-chloro-2-methylbutanoic acid
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1. Name each of the following compounds. (1.1, 1.2, 1.3, 1.5, 1.6, 1.7)
Knowledge/Understanding
Thinking/Investigation
Communication
Application
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3. Which of the following compounds does not form hydrogen bonds with
water? (1.4, 1.5, 1.6, 1.7) K/U
(a) ketone
(b) primary amine
(c) carboxylic acid
(d) primary alcohol
4. Which of the following compounds is an ether? (1.4, 1.6, 1.7) K/U
(a) aniline
(b) ethanamide
(c) methoxyethane
(d) methyl ethanoate
5. Indicate whether each of the following statements is true or false. If you think
a statement is false, rewrite it to make it true. (1.1, 1.2, 1.3, 1.7) K/U
(a) Bonds between carbon and hydrogen in saturated hydrocarbons are
almost non-polar, so these compounds have lower melting points and
boiling points than compounds of similar sizes.
(b) The melting points of trans isomers are lower than the corresponding cis
forms because their molecules are more tightly packed together.
(c) An aromatic hydrocarbon is an unsaturated hydrocarbon that has a ring
structure and a bonding arrangement that causes it to be chemically stable.
(d) Since nitrogen is more electronegative than either carbon or oxygen, the
N–C bonds and any N–H bonds in amines are polar.
6. Complete Table 1 for simple organic compounds and their reactions. (1.1–1.7)
K/U
T/I
Table 1 Organic Compounds and Their Reactions
Reaction
Reactants
Products
methane 1 oxygen
carbon dioxide 1 water
ethene 1 hydrogen
substitution
dehydration
chlorobenzene
propanol
methanol 1 ethanol
methoxyethane 1 water
ethanol 1 oxygen
ethanal 1 water
esterification
methyl propanoate 1 water
methyl ethanoate 1 water
condensation
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ethanoic acid 1 methanol
ethanoic acid 1 ammonia
Chapter 1 Questions 25
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