Transcript File

Chapter 14 Lecture
Conceptual
Integrated Science
Second Edition
Organic
Compounds
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This lecture will help you understand:
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Organic Chemistry
Hydrocarbons
Unsaturated Hydrocarbons
Functional Groups
Alcohols, Phenols, and Ethers
Amines and Alkaloids
Carbonyl Compounds
Polymers
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Organic Chemistry
• Organic chemistry is the branch of chemistry
that involves the study of carbon-containing
chemical compounds.
• An organic compound is a carbon-containing
chemical compound. More than 13 million
organic compounds are known.
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Organic Chemistry
• Carbon atoms connect with one another through
strong and stable covalent bonds.
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Organic Chemistry
C
C
347 kJ/mol
C
C
C
N
N
159 kJ/mol
N
N
C
N
O
O
O
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O
N
O
O
138 kJ/mol
S
S
S
S
226
kJ/mol
S
Organic Chemistry
• Carbon atoms also readily form bonds with
many other types of atoms. This provides for a
nearly infinite number of different kinds of
organic compounds.
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Hydrocarbons
• A hydrocarbon is a chemical compound that
contains only hydrogen and carbon.
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Hydrocarbons
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Hydrocarbons
• Structural isomers are molecules that have the
same molecular formula but different
configurations.
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Hydrocarbons
• A configuration is the specific way in which the
atoms of a molecule are connected to one
another.
"configuration" = "connectivity"
• Conformation is the spatial orientation of a
single configuration.
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Formula
Number of
possible
isomers
C5H12
3
C6H14
5
C7H16
9
C8H18
18
C10H22
75
C20H42
366,319
Hydrocarbons
CHECK YOUR NEIGHBOR
What is the chemical formula for the following
structure?
H
H
H
H
A.
B.
C.
D.
C3H8
C4H10
C5H12
C6H14
c
c
H
H
c
H H
c
H
c
H
H
H
Explain your answer to your neighbor.
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Hydrocarbons – Fractional Distillation
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Unsaturated Hydrocarbons
• Carbon always forms four bonds.
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Unsaturated Hydrocarbons
• Some of carbon's four bonds, however, may be
within multiple bonds.
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Unsaturated Hydrocarbons
• An unsaturated hydrocarbon is a hydrocarbon
that contains one or more multiple bonds.
– A special case of an unsaturated hydrocarbon
is the benzene ring.
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Unsaturated Hydrocarbons
CHECK YOUR NEIGHBOR
What is the chemical formula for the following
structure?
H
H
H
A.
B.
C.
D.
C5H10
C5H12
C6H12
C6H14
c
c
H
H
c
H
c
H
c
H
H
H
Explain your answer to your neighbor.
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• Compounds having only single bonds between
carbon atoms are said to be saturated
compounds.
• The ending –ane is used to name saturated
compounds (single bonds)
• For compounds containing a carbon-carbon
double bond, the suffix –ene is used
• For compounds containing a carbon-carbon
triple bond, the suffix -yne is used
• The existence of two or more substance with the
same molecular formula, but different structures,
is called isomerism
• Theses structures are called isomers
• Consider butane with the formula C4H10
• There are 2 structures that can be written for this
formula.
– 1. Butane
– 2. methylpropane
– These are examples of structural isomers or
skeleton isomers, since it is the carbon chain
that is altered
• A second type of isomerism is positional
isomerism.
• This is when 2 compounds that differ only in the
position of something such as a double bond or
an atom other than hydrogen and carbon.
• The first 3 are all named hexene
• We name isomers such as these by
specifying on which carbon atom the double
bond begins
• So you start numbering from the end, giving
the double bond the lowest number
• Name the first 3 compounds above.
• First one is named 1-hexene
• 2nd one is named 2-hexene
• 3rd one is named 3-hexene
Functional Groups
• A heteroatom is any atom other than hydrogen
or carbon in an organic molecule.
• A functional group is a combination of carbon,
hydrogen, and heteroatoms that behave as a
single unit.
– Organic molecules are classified by the
functional groups they contain.
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Functional Groups
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Functional Groups
CHECK YOUR NEIGHBOR
In which of the following structures is carbon
bonded five times?
A.
B.
C.
Explain your answer to your neighbor.
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D.
Alcohols, Phenols, and Ethers
• Alcohols contain the hydroxyl group.
Hydroxyl group
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Alcohols, Phenols, and Ethers
Methanol
(bp 65°C)
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Ethanol
(bp 78°C)
2-Propanol
(bp 97°C)
Alcohols, Phenols, and Ethers
• Phenols contain the phenol group.
Phenol group
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Alcohols, Phenols, and Ethers
• Phenols are acidic
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Alcohols, Phenols, and Ethers
4-n-Hexylresorcinol
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Thymol
Alcohols, Phenols, and Ethers
• Ethers contain the ether group, an oxygen atom
bonded to two carbon atoms.
Ether group
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Alcohols, Phenols, and Ethers
Dimethyl ether
(bp −25°C)
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Diethyl ether
Amines and Alkaloids
• Amines form alkaline solutions.
Amine group
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Alcohols, Phenols, and Ethers
Ethyl amine
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Hydroxide
ion
Alcohols, Phenols, and Ethers
Caffeine
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Phosphoric
acid
Caffeine
salt
Water
soluble
Amines and Alkaloids
CHECK YOUR NEIGHBOR
Which of the following compounds should have a
higher boiling point?
O
N
H
Structure A
A.
B.
C.
D.
Structure B
Structure A
Structure B
Both should have the same boiling point.
There is no way to tell.
Explain your answer to your neighbor.
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Carbonyl Compounds
• A carbonyl is a carbon atom double bonded to
an oxygen atom.
Carbonyl
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Carbonyl Compounds
Ketone
group
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Aldehyde
group
Carbonyl Compounds
Acetone
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Acetaldehyde
Carbonyl Compounds
Cinnamonaldehyde
Vanillin
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Benzaldehyde
Carbonyl Compounds
Amide
group
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Carbonyl Compounds
N,N-Diethyl-m-toluamide
DEET
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Carbonyl Compounds
Carboxyl
group
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Carbonyl Compounds
Aspirin
Salicylic acid
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Acetylsalicylic acid
Carbonyl Compounds
Ester
group
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Carbonyl Compounds
CH3OH
H2SO4
Salicylic acid
Methyl salicylate
(wintergreen)
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Carbonyl Compounds
Penicillin
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Carbonyl Compounds
CHECK YOUR NEIGHBOR
The amino acid lysine is shown below. What functional group must be
removed in order to produce the very smelly amine cadaverine, which
is 1,5-pentanediamine?
A.
B.
C.
D.
The hydrogen (shown) must be removed and
and replaced with an amino (NH2) group.
Lysine is 1,5-pentanediamine. Nothing
has to be removed.
The carboxyl group must be removed
and replaced with a hydrogen.
One amino group must be removed and
replaced with a hydrogen.
Explain your answer to your neighbor.
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Polymers
• A polymer is a very long organic molecule made
by the joining together of smaller organic
molecule units known as monomers.
Monomer
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Monomer
Monomer
Monomer
Polymers
• An addition polymer is a polymer whose mass is
equal to the sum of the masses of the monomer
units.
H
H
H
H
H
H
H
H
H
H
C C C C C C C C C C
H
H
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H
H
H
H
H
H
H
H
Polymers
H
H
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
Ethylene
Ethylene
Ethylene
Ethylene
Polyethylene
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Ethylene
Ethylene
Polymers – tough plastic
H
H
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
C
C
C
C
C
C
H
CH3
H
CH3
H
CH3
H
CH3
H
CH3
H
CH3
Propylene
Propylene
Propylene
Propylene
Propylene
Polypropylene
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Propylene
Polymers - PVC
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Polymers
• A condensation polymer is a polymer formed
when the joining of monomer units is
accompanied by the loss of a small molecule,
such as water.
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Polymers
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Polymers
• Many of the natural product
molecules synthesized by plants are
formed by the joining together of
isoprene monomers via an addition
polymerization. A good example is
the flavoring molecule citral, which is
made of two isoprene units. Find
and circle these units in the structure
shown to the right.
Isoprene
(2-methyl-1,3-butadiene)
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Citral
Polymers
• Beta-carotene is a natural addition polymer
made of eight isoprene units. Find and circle
these units in the structure shown below.
Beta-carotene
Isoprene
(2-methyl-1,3-butadiene)
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