Chapter 1: Structure and Physical Properties of Organic Compounds
Chapter 2: Reactions of Organic Compounds
UNIT 1: Organic Chemistry
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 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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1.1 Introducing Organic Compounds
UNIT 1 Section 1.1
• 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
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Chapter 1: Structure and Physical Properties of Organic Compounds
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.
UNIT 1 Section 1.1
The Special Nature of the Carbon Atom
Carbon can bond to four different atoms, producing a molecule with a tetrahedron shape.
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Chapter 1: Structure and Physical Properties of Organic Compounds
• Constitutional or structural isomers: molecules with the same molecular formula, but the atoms are bonded in a different sequence.
UNIT 1 Section 1.1
Isomers
These molecules are constitutional isomers.
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• 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.
Chapter 1: Structure and Physical Properties of Organic Compounds
Stereoisomers: molecules with the same molecular formula and sequence of atoms, but they differ in the three-dimensional orientation of their atoms
UNIT 1 Section 1.1
These molecules are diastereomers.
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• diastereomer: stereoisomers based on the presence of a double bond
• enantiomer: stereoisomers that are mirror-images of each other.
Chapter 1: Structure and Physical Properties of Organic Compounds
Isomers
Are the following molecules isomers?If so, what type of isomers are they?
UNIT 1 Section 1.1
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
Yes they are isomers.
They are stereoisomers, not constitutional isomers.
Section 1.1UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
Section 1.1 Review
UNIT 1 Section 1.1Chapter 1: Structure and Physical Properties of Organic Compounds
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1.2 Hydrocarbons
UNIT 1 Section 1.2
• aromatic hydrocarbons
Hydrocarbons are composed of only carbon and hydrogen. The different classes are:
• alkanes
• alkenes
• cyclic hydrocarbons
• alkynes
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Chapter 1: Structure and Physical Properties of Organic Compounds
Drawing Hydrocarbons
UNIT 1 Section 1.2
• line structural formula
Five ways to represent hydrocarbon molecules are:
• empirical molecular formula
• expanded molecular formula
• condensed structural formula
• structural formula
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Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.2
Alkanes
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• 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.
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.2
Alkenes
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• 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.
This alkene is named 3-ethyl-2,2-dimethylhex-1-ene.
Chapter 1: Structure and Physical Properties of Organic Compounds
Name the following hydrocarbon and draw its condensed structural formula.
UNIT 1 Section 1.2
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
The name is: pent-2-ene
The condensed structural formula is:
Section 1.2UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
UNIT 1 Section 1.2
Alkynes
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• 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.
4-ethylhex-2-yne.
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.2
Cyclic Hydrocarbons
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• 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
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.2
Aromatic Hydrocarbons
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• 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.
Chapter 1: Structure and Physical Properties of Organic Compounds
A student has named a hydrocarbon as1-ethyl-5-propylbenzene.
Use a drawing of the structure to show why that name is incorrect.
What is the correct name?
UNIT 1 Section 1.2
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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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
Section 1.2UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
UNIT 1 Section 1.2
Physical Properties of Hydrocarbons
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• Hydrocarbons are non-polar (not soluble in water).
• The shapes and sizes of hydrocarbons affect their boiling points.
• Many aromatic compounds have strong odours.
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2 Review
UNIT 1 Section 1.2Chapter 1: Structure and Physical Properties of Organic Compounds
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1.3 Hydrocarbon Derivatives
UNIT 1 Section 1.3
Hydrocarbon derivatives have one or more functional groups.
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Chapter 1: Structure and Physical Properties of Organic Compounds
Hydrocarbon Derivatives
UNIT 1 Section 1.3
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Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Alcohols
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• 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.
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Haloalkanes
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• 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)
1,3-dichloro-3-fluoro-2methylbutane
Chapter 1: Structure and Physical Properties of Organic Compounds
Draw the structural formula for fluoroethane.
Explain why numbers are not required in the prefix of the name.
UNIT 1 Section 1.3
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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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.
UNIT 1 Section 1.3Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
UNIT 1 Section 1.3
Aldehydes
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• Contain a formyl group.
3,4-dimethylpentanal
• 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)
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Ketones
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• 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)
Butanone
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Carboxylic Acids
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• Contain a carboxyl group.
2-ethylhexanoic acid
• 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)
Chapter 1: Structure and Physical Properties of Organic Compounds
What functional group do aldehydes, ketones, and carboxylic acids have in common?
Section 1.3UNIT 1
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
The carbonyl group
Section 1.3UNIT 1
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Chapter 1: Structure and Physical Properties of Organic Compounds
LEARNING CHECK
UNIT 1 Section 1.3
Esters
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• 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)
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Ethers
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• Contain an oxygen atom singly bonded to two carbon atoms (R-O-R′)
An ether is composed of an alkoxy group and parent alkane chain that are connected by an oxygen.
• 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)
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Amines
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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)
Chapter 1: Structure and Physical Properties of Organic Compounds
UNIT 1 Section 1.3
Amides
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• 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)
Chapter 1: Structure and Physical Properties of Organic Compounds
Draw the condensed structural formula for each of the following:
a.Methylethanoate
b. 1-ethoxypropane
c. N-ethylpentamide
UNIT 1 Section 1.3
Answer on the next slide
Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
a.
b.
c.
Section 1.3UNIT 1 Chapter 1: Structure and Physical Properties of Organic Compounds
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LEARNING CHECK
Section 1.3 Review
UNIT 1 Section 1.3Chapter 1: Structure and Physical Properties of Organic Compounds
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