Download Hewitt/Lyons/Suchocki/Yeh, Conceptual Integrated Science

Chapter 19:
ORGANIC COMPOUNDS
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This lecture will help you
understand:
•
•
•
•
•
•
•
Hydrocarbons
Unsaturated Hydrocarbons
Functional Groups
Alcohols, Phenols, and Ethers
Amines and Alkaloids
Carbonyl Compounds
Polymers
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Organic Chemistry
A branch of chemistry involving the
study of carbon-containing chemical
compounds.
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Organic Chemistry
Organic Compound:
A carbon containing chemical
compound
100,000 new ones each year
natural
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synthetic
Organic Chemistry
Why is carbon so special?
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Organic Chemistry
Why is carbon so special?
• Carbon atoms connect with one another
through strong and stable covalent bonds.
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Organic Chemistry
C
C
C
C
N
C
N
N
C
N
N
N
O
O
O
O
O
S
O
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S
S
S
S
Organic Chemistry
C
C
347 kJ/mol
C
C
C
N
N
N
C
N
N
N
O
O
O
O
O
S
O
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S
S
S
S
Organic Chemistry
C
C
347 kJ/mol
C
C
C
N
N
159 kJ/mol
N
N
C
N
N
O
O
O
O
O
S
O
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S
S
S
S
Organic Chemistry
C
C
347 kJ/mol
C
C
C
N
N
159 kJ/mol
N
N
C
N
N
O
O
O
O
O
O
S
138 kJ/mol
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S
S
S
S
Organic Chemistry
C
C
347 kJ/mol
C
C
C
N
N
159 kJ/mol
N
N
C
N
O
O
O
O
N
O
O
S
138 kJ/mol
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S
S
S
226
kJ/mol
S
Organic Chemistry
S
S
S
S
S
S
S
Sulfur, S8
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S
Organic Chemistry
S
S
S
S
S
S
S
S
Sulfur, S8
More atoms of the same element bound together like this is rare…
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Organic Chemistry
S
S
S
S
S
S
S
S
Sulfur, S8
More atoms of the same element bound together like this is rare…
…for every element except carbon….
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C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
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Organic Chemistry
Why is carbon so special?
• Carbon atoms connect with one another
through strong and stable covalent bonds.
• Carbon atoms also readily form bonds with
many other types of atoms. This provides
for a near infinite number of different kinds
of organic compounds.
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Organic Chemistry
To appreciate organic chemistry,
please minimize memorization…
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Hydrocarbons
Hydrocarbon: A chemical compound
containing only hydrogen and carbon.
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Hydrocarbons
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Hydrocarbons
Structural isomer: Molecules having the same
molecular formula but different structures.
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Hydrocarbons
Structural isomer: Molecules having the same
molecular formula but different structures.
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Hydrocarbons
Structural isomer: Molecules having the same
molecular formula but different structures.
“configurations”
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Hydrocarbons
Structural isomer: Molecules having the same
molecular formula but different configurations.
Configuration: The specific way in which the
atoms of a molecule are connected to one
another.
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Hydrocarbons
Structural isomer: Molecules having the same
molecular formula but different configurations.
Configuration: The specific way in which the
atoms of a molecule are connected to one
another.
“Configuration” = “Connectivity”
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Formula
Number of
possible
isomers
C5H12
3
C6H14
5
C7H16
9
C8H18
18
C10H22
75
C20H42
366,319
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Hydrocarbons
Conformation: The spatial orientation of a
single configuration.
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Hydrocarbons
Conformation: The spatial orientation of a
single configuration.
Rotate this bond
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Hydrocarbons
Conformation: The spatial orientation of a
single configuration.
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Hydrocarbons
Conformation: The spatial orientation of a
single configuration.
Like pivoting your
arm at the elbow
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Hydrocarbons
Conformation: The spatial orientation of a
single configuration.
These are two “conformations” of the same configuration.
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Hydrocarbons
CHECK YOUR NEIGHBOR
What is the chemical formula for the following structure?
A.
B.
C.
D.
C3H8
C4H10
C5H12
C6H14
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Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
A.
B.
C.
D.
C3H8
C4H10
C5H12
C6H14
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Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
c
c
c
c
A.
B.
C.
D.
C3H8
C4H10
C5H12
C6H14
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c
Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
H
H
H
H
c
c
H
H
c
H H
A.
B.
C.
D.
c
H
c
H
C3H8
C4H10
C5H12
C6H14
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H
H
Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
H
H
H
H
c
c
H
H
c
H H
A.
B.
C.
D.
c
H
c
H
C3H8
C4H10
C5H12
C6H14
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H
H
Hydrocarbons
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Unsaturated Hydrocarbons
Carbon always forms four bonds.
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Unsaturated Hydrocarbons
Carbon always forms four bonds.
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Unsaturated Hydrocarbons
Carbon always forms four bonds.
Some of these bonds, however, may be within
multiple bonds.
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Unsaturated Hydrocarbons
Carbon always forms four bonds.
Some of these bonds, however, may be within
multiple bonds.
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Unsaturated Hydrocarbons
Unsaturated Hydrocarbon: A hydrocarbon containing
one or more multiple bonds.
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Unsaturated Hydrocarbons
Unsaturated Hydrocarbon: A hydrocarbon containing
one or more multiple bonds.
A special case of an unsaturated hydrocarbon is the benzene ring.
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Unsaturated Hydrocarbons
Unsaturated Hydrocarbon: A hydrocarbon containing
one or more multiple bonds.
A special case of an unsaturated hydrocarbon is the benzene ring.
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Unsaturated Hydrocarbons
Unsaturated Hydrocarbon: A hydrocarbon containing
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?
A.
B.
C.
D.
C5H10
C5H12
C6H12
C6H14
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Unsaturated Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
A.
B.
C.
D.
C5H10
C5H12
C6H12
C6H14
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Unsaturated Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
c
c
A.
B.
C.
D.
c
c
c
C5H10
C5H12
C6H12
C6H14
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Unsaturated Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
H
H
H
c
c
H
H
c
H
A.
B.
C.
D.
c
H
c
H
C5H10
C5H12
C6H12
C6H14
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H
H
Unsaturated Hydrocarbons
CHECK YOUR ANSWER
What is the chemical formula for the following structure?
H
H
H
c
c
H
H
c
H
A.
B.
C.
D.
c
H
c
H
C5H10
C5H12
C6H12
C6H14
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H
H
Functional Groups
Heteroatom:
Any atom other than hydrogen or
carbon in an organic molecule.
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Functional Groups
Heteroatom:
Any atom other than hydrogen or
carbon in an organic molecule.
Functional Group:
A combination of carbon,
hydrogen, and heteroatoms that
behave as a single unit.
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Functional Groups
Heteroatom:
Any atom other than hydrogen or
carbon in an organic molecule.
Functional Group:
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
Heteroatom:
Any atom other than hydrogen or
carbon in an organic molecule.
Functional Group:
A combination of carbon,
hydrogen, and heteroatoms that
behave as a single unit.
Organic molecules are classified
by the functional groups they
contain.
For example…
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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.
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C.
D.
Functional Groups
CHECK YOUR ANSWER
In which of the following structures is carbon bonded five times?
A.
B.
C.
Explanation:
Carbon can never be bonded five times! In none of
the above structures is carbon indicated to be
bonded five times. Sorry for the trick question…
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D.
Functional Groups
CHECK YOUR NEIGHBOR
In which of the following structures is carbon bonded five times?
A.
B.
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C.
D.
Functional Groups
CHECK YOUR ANSWER
In which of the following structures is carbon bonded five times?
A.
B.
C.
Explanation:
Carbon can never be bonded five times! Structure
C, therefore, is NOT a plausible structure for any
existing organic compound.
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D.
Alcohols, Phenols, and Ethers
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Alcohols Contain the
Hydroxyl Group
Hydroxyl Group
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Methanol
(bp 65°C)
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Ethanol
(bp 78°C)
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2-Propanol
(bp 97°C)
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Phenols Contain the
Phenol Group
Phenol
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
H+
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Phenols are acidic
H+
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Phenols are acidic
H+
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
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Phenols are acidic
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4-n-Hexylresorcinol
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Thymol
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Ethers contain an oxygen
bonded to two carbons
Ether Group
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Dimethyl ether (bp −25°C)
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Dimethyl ether (bp −25°C)
Ethanol
bp 78°C
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Diethyl ether
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Amines and Alkaloids
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Amines form alkaline
solutions
Amine Group
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Ethyl amine
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Hydroxide
ion
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Phosphoric
acid
Caffeine
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Caffeine
salt
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Phosphoric
acid
Caffeine
salt
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Phosphoric
Water soluble
acid
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 A.
Structure B.
Both the same.
No way to tell.
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Structure B
Amines and Alkaloids
CHECK YOUR ANSWER
Which of the following compounds should have a higher
boiling point?
O
N
H
Structure A
A.
B.
C.
D.
Structure A
Structure B
Both the same
No way to tell
Structure B
Explanation:
Structure B has a hydrogen attached to a strongly
electronegative atom, nitrogen. This makes for a
polar N—H bond that participates in hydrogen
bonding.
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Carbonyl Compounds
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Carbonyl
A carbon atom
double bonded
to an oxygen
atom
Carbonyl
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Ketone
Group
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Ketone
Group
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Aldehyde
Group
Acetone
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Acetone
Acetaldehyde
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Acetone
Formaldehyde
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Citral
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Cinnamonaldehyde
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Benzaldehyde
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Vanillin
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Amide
Group
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N,N-Diethyl-m-toluamide
DEET
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Carboxyl
group
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Salicylic acid
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Aspirin
Acetylsalicylic acid
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Ester
group
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Salicylic acid
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CH3OH
H2SO4
Salicylic acid
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Methyl salicylate
(Wintergreen)
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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.
The hydrogen (shown) must be
removed and replaced with an amino
(NH2) group.
B.
Lysine is 1,5-pentanediamine. Nothing
has to be removed.
C.
The carboxyl group must be removed
and replaced with a hydrogen.
D.
One amino group must be removed and
replaced with a hydrogen.
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Lysine
Carbonyl Compounds
CHECK YOUR ANSWER
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.
The hydrogen (shown) must be
removed and replaced with an amino
(NH2) group.
B.
Lysine is 1,5-pentanediamine. Nothing
has to be removed.
C.
The carboxyl group must be removed
and replaced with a hydrogen.
D.
One amino group must be removed and
replaced with a hydrogen.
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Lysine
Polymers
Polymer: A very long organic molecule made by
the joining together of smaller organic
molecule units known as monomers.
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Polymers
Monomer
Monomer
Monomer
Monomer
Polymer: A very long organic molecule made by
the joining together of smaller organic
molecule units known as monomers.
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Polymers
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
C
C
H
H
H
H
C
C
H
Ethylene
H
Ethylene
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
C
C
H
H
H
H
C
C
H
Ethylene
H
Ethylene
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
C
C
H
H
H
H
C
C
H
Ethylene
H
Ethylene
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
C
H
H
H
C
C
H
H
Ethylene
C
H
Ethylene
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
C
H
H
H
C
H
Ethylene
H
C
H
C
H
Ethylene
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
H
H
C
C
C
C
H
H
H
H
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
H
H
H
H
C C C C C
C C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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Polymers
H
H
H
H
H
H
C C C C C
C C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Addition Polymer:
A polymer whose mass is equal to the sum
of the masses of the monomer units.
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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
H
H
C
C
H
CH3
Propylene
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H
H
H
C
C
CH3
Propylene
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
CH3
H
CH3
H
CH3
H
CH3
H
CH3
H
CH3
Propylene
Propylene
Propylene
Propylene
Propylene
Polypropylene
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Propylene
Polymers
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Polymers
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Polymers
Condensation Polymer:
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
CONSIDER THIS…
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 within the
structure shown to the right.
Isoprene
(2-methyl-1,3-butadiene)
Copyright © 2008 Pearson Education, Inc., publishing as Pearson Addison-Wesley
Citral
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 within the
structure shown to the right.
Isoprene
(2-methyl-1,3-butadiene)
Copyright © 2008 Pearson Education, Inc., publishing as Pearson Addison-Wesley
Citral
Polymers
Beta-carotene is a natural addition polymer made of eight isoprene units.
Find and circle these units within the structure shown below.
Beta-carotene
Isoprene
(2-methyl-1,3-butadiene)
Copyright © 2008 Pearson Education, Inc., publishing as Pearson Addison-Wesley
Polymers
Beta-carotene is a natural addition polymer made of eight isoprene units.
Find and circle these units within the structure shown below.
Beta-carotene
Isoprene
(2-methyl-1,3-butadiene)
Copyright © 2008 Pearson Education, Inc., publishing as Pearson Addison-Wesley