UNIT 1: Organic Chemistry
Chapter 1: Structure and Physical
Properties of Organic Compounds
Chapter 2: Reactions 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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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
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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 can bond to four
different atoms,
producing a molecule
with a tetrahedron shape.
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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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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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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?
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Answer on
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
LEARNING CHECK
Yes they are isomers.
They are stereoisomers, not
constitutional isomers.
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Section 1.1
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.1 Review
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Section 1.1
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
• alkynes
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• aromatic 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
• structural formula
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UNIT 1
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.
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UNIT 1
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.
This alkene is named 3-ethyl2,2-dimethylhex-1-ene.
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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.
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Answer on
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UNIT 1
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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UNIT 1
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.
4-ethylhex-2-yne.
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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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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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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?
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Answer on
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
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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Section 1.2
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.
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.2 Review
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Section 1.2
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.
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Hydrocarbon Derivatives
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Section 1.3
UNIT 1
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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UNIT 1
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)
1,3-dichloro-3-fluoro-2methylbutane
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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.
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Answer on
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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.
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
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)
3,4-dimethylpentanal
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Section 1.3
UNIT 1
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)
Butanone
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UNIT 1
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)
2-ethylhexanoic acid
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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?
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Answer on
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
LEARNING CHECK
The carbonyl group
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Section 1.3
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 )
•
•
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prefix (alkyl group on oxygen and on the main chain)
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)
An ether is composed of an
alkoxy group and parent
alkane chain that are connected
by an oxygen.
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UNIT 1
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)
•
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prefix (indicate alkyl groups on N)
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
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 )
•
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prefix (alkyl groups on N, then on main chain)
Section 1.3
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:
a. Methylethanoate
b. 1-ethoxypropane
c. N-ethylpentamide
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Answer on
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UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
LEARNING CHECK
a.
b.
c.
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Section 1.3
UNIT 1
Chapter 1: Structure and Physical Properties of Organic Compounds
Section 1.3 Review
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Section 1.3