1. 1

2. UNIT 1: Organic Chemistry
Chapter 1: Structure and Physical Properties of Organic Compounds
Chapter 2: Reactions of Organic Compounds 2

3. Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Chapter 1: Structure and Physical Properties of Organic Compounds
For thousands of years, scientists and Aboriginal peoples have been isolating organic compounds from natural materials, such as birch bark. The properties of these compounds make them useful in a wide variety of applications.
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4. 1.1 Introducing Organic Compounds
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
1.1 Introducing Organic Compounds
Until the late 1800s, “organic” meant matter from living systems. “Inorganic” meant matter from non-living systems.
Synthesis of urea (organic) from inorganic compounds forced scientists to reconsider their definitions.
Modern Definitions
Modern definitions of “organic” and “inorganic” are based on the presence of carbon and how the carbon atoms are bonded together.
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5. The Special Nature of the Carbon Atom
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
The Special Nature of the Carbon Atom
Important atomic properties of carbon:
It is much more likely to share electrons than gain or lose electrons. Therefore, covalent bonding occurs.
It has four valence electrons. Therefore, it can be bonded to as many as four different atoms.
Carbon has an atomic number of 6. On the periodic table, it is a main group element, in Period 2, Group 14.
Carbon can bond to four different atoms, producing a molecule with a tetrahedron shape.
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6. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
Isomers
Most organic molecules consist of more than one carbon atom bonded together in a chain or ring structure.
Molecules with the same molecular formula but atoms in different arrangements are known as isomers.
Constitutional or structural isomers: molecules with the same molecular formula, but the atoms are bonded in a different sequence.
These molecules are constitutional isomers.
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7. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
Isomers
Stereoisomers: molecules with the same molecular formula and sequence of atoms, but they differ in the three-dimensional orientation of their atoms
diastereomer: stereoisomers based on the presence of a double bond
enantiomer: stereoisomers that are mirror-images of each other.
These molecules are diastereomers.
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8. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
Learning Check
Are the following molecules isomers?
If so, what type of isomers are they?
Tips:
First, determine if the two structures have the same molecular formula.
Second, carefully look at how the atoms are bonded together. If they have the same molecular formula but the atoms are bonded together differently then they are constitutional isomers.
Third, if the atoms are bonded together in the same arrangement and there is a multiple bond, determine if the groups attached to the carbon atoms involved in the double bond are different so that cis and trans forms are possible.
Answer on the next slide
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9. Learning Check UNIT 1 Yes they are isomers.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
Learning Check
Yes they are isomers.
They are stereoisomers, not constitutional isomers.
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10. Section 1.1 Review UNIT 1 Section 1.1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1
Section 1.1 Review
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11. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
1.2 Hydrocarbons
Hydrocarbons are composed of only carbon and hydrogen. The different classes are:
cyclic hydrocarbons
alkanes
alkenes
This slide provides a representative example for each type of hydrocarbon. Important points about the structures, IUPAC rules for naming, and properties of these classes of hydrocarbons will be discussed on the slides that follow.
aromatic hydrocarbons
alkynes
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12. Drawing Hydrocarbons UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Drawing Hydrocarbons
Five ways to represent hydrocarbon molecules are:
empirical molecular formula
condensed structural formula
expanded molecular formula
line structural formula
There are five different types of models that can be used to represent the structures of hydrocarbons. The best one to use will depend on certain factors, such as how much information about the bonding of each atom needs to be shown and how large the molecule is.
1. Emperical molecular formula: indicates the elements and number of atoms of each element in a molecule.
2. Expanded molecular formula: brackets are used to show the locations of side chains. The group within the bracket is attached to the carbon atom the precedes the bracketed group.
3. Structural formula: clearly indicates how the atoms are bonded together and includes all bonds between atoms. But, depending on the size of the molecule, may require a great deal of space and work to draw.
4. Condensed structural formula: indicates how the atoms are bonded together but omits the carbon-hydrogen bonds, making it more clear than a structural formula.
5. Line structural formula: uses lines to represent bonds, but omit carbon-hydrogen bonds. Each end of a line represents a carbon atom and it is assumed that the appropriate number of hydrogen atoms are bonded to each carbon.
structural formula
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13. Alkanes UNIT 1 Contain only single covalent bonds.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Alkanes
Contain only single covalent bonds.
The general formula for straight and branched-chain alkanes: CnH2n+2.
When naming and drawing alkanes: identify the root, suffix, and prefix.
The International Union of Pure and Applied Chemistry (IUPAC) has a series of rules for naming organic compounds, which apply to alkanes as well as the other hydrocarbons that are discussed in this course. There are three main parts to each name, and it is best to follow a systematic approach to identifying these when naming and drawing hydrocarbons.
1. Determine the root part of the name. This is based on the number of carbon atoms in the longest continuous chain of carbon atoms.
2. Determine the prefix part of the name. Identify any branches from the main chain, called side groups. The name of an alkyl side group is based on the name of the root for the equivalent main chain, but has “–yl” as a suffix instead of “–ane.” The prefix should provide the names of all side groups as well as their positions, according to the numbered carbons on the main chain. The names of the side groups in the prefix are indicated in alphabetical order.
3. Determine the suffix part of the name. This part of the name identifies the type of hydrocarbon that the molecule is. The suffix for alkanes is “-ane.”
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14. Alkenes UNIT 1 Contain one or more double bonds.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Alkenes
Contain one or more double bonds.
The general formula for straight and branched-chain alkenes: CnH2n.
When naming and drawing alkenes: identify the root, suffix and prefix.
For main chains with more than four carbons, the position of the double bond must be indicated.
The same IUPAC rules should be used to identify the root, prefix, and suffix when naming alkenes. However, some additional points need to be considered.
The longest continuous chain that is used for determining the root of the name must contain the double bond.
The main chain is numbered in a manner that gives the carbon atoms involved in the double bond the lowest possible numbers.
The suffix used for alkenes is –ene. If the alkene has more than four carbon atoms in the main chain, the position of the double bond must be indicated in the suffix of the name. The carbon atom that precedes the double bond is used.
This alkene is named 3-ethyl-2,2-dimethylhex-1-ene.
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15. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Learning Check
Name the following hydrocarbon and draw its condensed structural formula.
Answer on the next slide
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16. Learning Check UNIT 1 The name is: pent-2-ene
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Learning Check
The name is: pent-2-ene
The condensed structural formula is:
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17. Alkynes UNIT 1 Contain one or more triple bonds.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Alkynes
Contain one or more triple bonds.
The general formula for straight and branched-chain alkynes: CnH2n-2.
When naming and drawing alkynes: identify the root, suffix, and prefix.
For main chains with more than four carbons, the position of the double bond must be indicated.
The rules for naming alkynes are the same as those for naming alkenes. The only difference is the use of –yne in the suffix.
4-ethylhex-2-yne.
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18. Cyclic Hydrocarbons UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Cyclic Hydrocarbons
Contain carbon-based ring structures. Most are alkanes or alkenes.
The general formula for cyclic alkanes: CnH2n.
When naming and drawing cyclic hydrocarbons: identify the root, suffix, and prefix.
Carbon atoms of a multiple bond are numbered 1 and 2, and side groups are the lowest possible numbers.
3,4-dimethylcyclopentene
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19. Aromatic Hydrocarbons
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Aromatic Hydrocarbons
Hydrocarbons that are derived from benzene, C6H6.
When naming and drawing aromatic hydrocarbons identify the root and prefix.
If a benzene ring is bonded to a hydrocarbon chain that is more than six carbons long, the benzene ring is a phenyl side group.
Benzene is best represented by the resonance hybrid structure. This aromatic hydrocarbon is 1-methyl-4-propylbenzene.
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20. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Learning Check
A student has named a hydrocarbon as
1-ethyl-5-propylbenzene.
Use a drawing of the structure to show why that name is incorrect.
What is the correct name?
Answer on the next slide
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21. Learning Check UNIT 1 The structure is shown below.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Learning Check
The structure is shown below.
Since the side groups should be identified using the lowest possible numbering, the correct name is
1-ethyl-3-propylbenzene
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22. Physical Properties of Hydrocarbons
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Physical Properties of Hydrocarbons
Hydrocarbons are non-polar (not soluble in water).
The shapes and sizes of hydrocarbons affect their boiling points.
Many aromatic compounds have strong odours.
Boiling points increase with length of hydrocarbon chain. The presence of a multiple bond also influences the boiling point. Alkenes have lower boiling points than the corresponding alkanes. However, corresponding alkynes have higher oiling points. This is thought to be due to the linear shape of alkynes due to the presence of the triple bond. This shape allows the molecules to be more attracted to each other and, therefore, requires a higher temperature to break those intermolecular forces.
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23. Section 1.2 Review UNIT 1 Section 1.2
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2
Section 1.2 Review
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24. 1.3 Hydrocarbon Derivatives
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
1.3 Hydrocarbon Derivatives
Hydrocarbon derivatives have one or more functional groups.
A summary of the different hydrocarbon derivatives that are discussed in this course are summarized on this slide. Each is described in more detail on the slides that follow.
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25. Hydrocarbon Derivatives
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Hydrocarbon Derivatives
A summary of the different hydrocarbon derivatives that are discussed in this course are summarized on this slide. Each is described in more detail on the slides that follow.
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26. Alcohols UNIT 1 Contain a hydroxyl functional group, -OH
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Alcohols
Contain a hydroxyl functional group, -OH
When naming and drawing alcohols, identify the
root (longest chain with the –OH group)
suffix (add –ol to the end of the parent alkane name)
prefix (name and number the alkyl side groups)
The addition of an –OH group to a hydrocarbon increases the polarity of the molecule.
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27. Haloalkanes UNIT 1 Contain one or more halogen atoms (F, Cl, Br, I).
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Haloalkanes
Contain one or more halogen atoms (F, Cl, Br, I).
When naming and drawing haloalkanes, identify the
root (longest chain with the halogen)
suffix (use the alkane name)
prefix (name and number the alkyl side groups and halogens)
Haloalkanes are artificial molecules that have been synthesized by chemists in the laboratory.
Image source: MHR, Chemistry 12 © ISBN ; page 47
1,3-dichloro-3-fluoro-2methylbutane
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28. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check
Draw the structural formula for fluoroethane.
Explain why numbers are not required in the prefix of the name.
Answer on the next slide
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29. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check
Because there are only two carbon atoms, the number 1 is not used in the prefix to designate the position of the halogen.
Image source: MHR, Chemistry 12 © ISBN ; page 87
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30. Aldehydes UNIT 1 Contain a formyl group.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Aldehydes
Contain a formyl group.
When naming and drawing aldehydes, identify the
root (longest chain with the formyl group)
suffix (ends in –al)
prefix (name and number the alkyl side groups)
For naming and drawing aldehydes:
When numbering the carbon atoms in the longest continuous chain, carbon 1 is always the one with the formyl group bonded to it.
The formyl group consists of the carbonyl group with a hydrogen bond singly bonded to the carbon.
The root of the name is the name of the parent alkane without the –e on the end.
Image source: MHR, Chemistry 12 © ISBN ; page 50
3,4-dimethylpentanal
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31. Ketones UNIT 1 Contain a carbonyl group bonded to two carbons.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Ketones
Contain a carbonyl group bonded to two carbons.
When naming and drawing ketones, identify the
root (longest chain with the carbonyl group)
suffix (position of the carbonyl carbon is indicated and ends in -one)
prefix (name and number the alkyl side groups)
For naming and drawing ketones:
The longest continuous chain must contain the carbonyl group.
The root of the name is the name of the parent alkane without the –e on the end.
Image source: MHR, Chemistry 12 © ISBN ; page 53
Butanone
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32. Carboxylic Acids UNIT 1 Contain a carboxyl group.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Carboxylic Acids
Contain a carboxyl group.
When naming and drawing carboxylic acids, identify the
root (longest chain with the carboxyl group)
suffix (ends in –oic acid )
prefix (name and number the alkyl side groups)
For naming and drawing carboxylic acids:
The longest continuous chain must contain the carboxyl group. When numbering the carbon atoms in the longest continuous chain, carbon 1 is always part of the carboxyl group.
The root of the name is the name of the parent alkane without the –e on the end.
Image source: MHR, Chemistry 12 © ISBN ; page 59
2-ethylhexanoic acid
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33. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check
What functional group do aldehydes, ketones, and carboxylic acids have in common?
Answer on the next slide
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34. Learning Check UNIT 1 The carbonyl group Section 1.3
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check
The carbonyl group
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35. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Esters
Contain a carbonyl group with another oxygen singly bonded to the carbon.
When naming and drawing esters, identify the
root (the “acid part”)
suffix (ends in –oate )
prefix (alkyl group on oxygen and on the main chain)
The general formula for an ester is RCOOR’. The symbol R represents a hydrocarbon or hydrogen atom. The symbol R’ represents a hydrocarbon and must contain at least one carbon atom. Note that if R’ represented a hydrogen atom this hydrocarbon derivative would not longer be a an ester and instead be a carboxylic acid.
When considering the structures of esters, it is common to think of them as a combination of a carboxylic acid and an alcohol.
For naming and drawing esters:
Determine the longest continuous chain that contains the “acid part” of the ester. The root of the name for an ester is the root of the name for the parent carboxylic acid.
Ester names end in –oate. The carbon of the carbonyl group is always carbon 1.
The prefixes in esters must indicate two separate groups:
the hydrocarbon group bonded to the oxygen that is singly bonded to the carbonyl group (or, the alcohol part of the ester)
any alkyl side groups bonded to the main chain of the “acid” part of the ester
Image source: MHR, Chemistry 12 © ISBN ; page 62
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36. UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Ethers
Contain an oxygen atom singly bonded to two carbon atoms (R-O-R′)
When naming and drawing ethers, identify the
root (longest chain, or R group)
suffix (ends according to the main chain)
prefix (indicate the alkoxy group then side groups)
The general formula for all ethers is R-O-R’; whereby both R groups are alkyl groups. However, the longer-chain alkyl group is always designated as the R group and the shorter-chain alkyl group is part of the alkoxy group.
For naming and drawing ethers:
Determine the longest continuous chain that is bonded to the oxygen. The root is the name of this parent alkane. The chain is numbered so that the carbon bonded to the oxygen is the lowest possible number.
The suffix of the parent alkane name is used for names of ethers.
The prefixes in ether must indicate two separate groups:
the first part indicates the identity and position of the alkoxy group. The name of the alkoxy group is based on the root of the parent alkane with –oxy added to the end.
any alkyl side groups bonded to the main chain of the R group
Image source: MHR, Chemistry 12 © ISBN ; page 67
An ether is composed of an alkoxy group and parent alkane chain that are connected by an oxygen.
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37. Amines UNIT 1 Primary (R-NH2), secondary (R2-NH), or tertiary (R3-N)
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Amines
Primary (R-NH2), secondary (R2-NH), or tertiary (R3-N)
When naming and drawing amines, identify the
root (longest chain bonded to the nitrogen)
suffix (ends in –amine and indicate position of the N)
prefix (indicate alkyl groups on N)
Amines are classified according to how many alkyl groups are bonded to the nitrogen atom.
Primary amines have one alkyl group and two hydrogens bonded to the nitrogen.
Secondary amines have two alkyl groups and one hydrogen bonded to the nitrogen.
Tertiary amines have three alkyl groups and no hydrogens bonded to the nitrogen.
For naming and drawing amines:
Determine the longest continuous chain that is bonded to the nitrogen. The root is the name of this parent alkane without the –e on the end.
The suffix always ends in -amine. When the main chain is three carbons or longer, the position of the nitrogen atom is included just before the –amine suffix.
The prefix used depends on the type of amine:
primary amines: no prefix is used
secondary amines: N- and then the name of the alkyl group
tertiray amines: N- in front of each alkyl group name
Image source: MHR, Chemistry 12 © ISBN ; page 72
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38. Amides UNIT 1 Contain a carbonyl group bonded to a nitrogen
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Amides
Contain a carbonyl group bonded to a nitrogen
When naming and drawing amides, identify the
root (longest chain with the carbonyl)
suffix (ends in -amide )
prefix (alkyl groups on N, then on main chain)
For naming and drawing esters:
Determine the longest continuous chain that contains the carbonyl group.
Amide names end in –amide. The carbon of the carbonyl group is always carbon 1.
The prefix includes
the identity of any alkyl groups on the nitrogen. The prefixes to indicate alkyl groups on the nitrogen follows the same rules for naming amines (use N- and then the alkyl name).
the identity and position of alkyl groups on the main chain.
Image source: MHR, Chemistry 12 © ISBN ; page 77
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39. Answer on the next slide
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check
Draw the condensed structural formula for each of the following:
Methylethanoate
b. 1-ethoxypropane
c. N-ethylpentamide
Answer on the next slide
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40. Learning Check UNIT 1 b. c. Section 1.3
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Learning Check b. c.
Image source: MHR, Chemistry 12 © ISBN ; pages 65, 69, 77
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41. Section 1.3 Review UNIT 1 Section 1.3
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3
Section 1.3 Review
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