chapter 19: organic compounds
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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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100,000 new ones each year
Organic Chemistry
Organic Compound:
A carbon containing chemical compound
naturalnatural syntheticsynthetic Over 13 m
illion known!
Over 13 m
illion known!
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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
C
C
N N NN
N
N
O O OO
O
O
S SS
S S
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Organic Chemistry
C C C
C
C
C
N N NN
N
N
O O OO
O
O
S SS
S S
347 kJ/mol
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Organic Chemistry
C C C
C
C
C
N N NN
N
N
O O OO
O
O
S SS
S S
347 kJ/mol 159 kJ/mol
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Organic Chemistry
C C C
C
C
C
N N NN
N
N
O O OO
O
O
S SS
S S
347 kJ/mol 159 kJ/mol
138 kJ/mol
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Organic Chemistry
C C C
C
C
C
N N NN
N
N
O O OO
O
O
S SS
S S
347 kJ/mol 159 kJ/mol
138 kJ/mol
226kJ/mol
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Organic Chemistry
S SS
S S
S
SS
Sulfur, S8
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Organic Chemistry
S SS
S S
S
SS
Sulfur, S8More atoms of the same element bound together like this is rare…
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Organic Chemistry
S SS
S S
S
SS
Sulfur, S8More 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
Diamond
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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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C7H16
C8H18
C10H22
C20H42
C6H14
C5H12
9
18
75
366,319
5
3
Formula
Number of possible isomers
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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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What is the chemical formula for the following structure?
A. C3H8
B. C4H10
C. C5H12
D. C6H14
HydrocarbonsCHECK YOUR NEIGHBOR
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What is the chemical formula for the following structure?
A. C3H8
B. C4H10
C. C5H12
D. C6H14
HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C3H8
B. C4H10
C. C5H12
D. C6H14
cc
cc
c
HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C3H8
B. C4H10
C. C5H12
D. C6H14
cc
cc
c
H
HH
HH
HH
H
H
HH
H
HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C3H8
B. C4H10
C. C5H12
D. C6H14
cc
cc
c
H
HH
HH
HH
H
H
HH
H
HydrocarbonsCHECK YOUR ANSWER
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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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What is the chemical formula for the following structure?
A. C5H10
B. C5H12
C. C6H12
D. C6H14
Unsaturated HydrocarbonsCHECK YOUR NEIGHBOR
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What is the chemical formula for the following structure?
A. C5H10
B. C5H12
C. C6H12
D. C6H14
Unsaturated HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C5H10
B. C5H12
C. C6H12
D. C6H14
cc
cc
c
Unsaturated HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C5H10
B. C5H12
C. C6H12
D. C6H14
cc
cc
c
H
HH
HH
H
H
HH
H
Unsaturated HydrocarbonsCHECK YOUR ANSWER
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What is the chemical formula for the following structure?
A. C5H10
B. C5H12
C. C6H12
D. C6H14
cc
cc
c
H
HH
HH
H
H
HH
H
Unsaturated HydrocarbonsCHECK YOUR ANSWER
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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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In which of the following structures is carbon bonded five times?
A. B. C. D.
Functional GroupsCHECK YOUR NEIGHBOR
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A. B. C. D.
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…
In which of the following structures is carbon bonded five times?
Functional GroupsCHECK YOUR ANSWER
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A. B. C. D.
In which of the following structures is carbon bonded five times?
Functional GroupsCHECK YOUR NEIGHBOR
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A. B. C. D.
Explanation:
Carbon can never be bonded five times! Structure C, therefore, is NOT a plausible structure for any existing organic compound.
In which of the following structures is carbon bonded five times?
Functional GroupsCHECK YOUR ANSWER
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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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Caffeine
Phosphoric acid
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Phosphoric acid
Caffeinesalt
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Phosphoric acid
Caffeinesalt
Water soluble
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Which of the following compounds should have a higher boiling point?
A. Structure A.
B. Structure B.
C. Both the same.
D. No way to tell.
N
H
O
Structure A Structure B
Amines and AlkaloidsCHECK YOUR NEIGHBOR
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Which of the following compounds should have a higher boiling point?
A. Structure A
B. Structure B
C. Both the same
D. No way to tell
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.
N
H
O
Structure A Structure B
Amines and AlkaloidsCHECK YOUR ANSWER
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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
Aldehyde Group
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Acetone
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Acetone Acetaldehyde
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FormaldehydeAcetone
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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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Acetylsalicylic acid
Aspirin
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Ester group
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Salicylic acid
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Salicylic acid
H2SO4
CH3OH
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Methyl salicylate
(Wintergreen)
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Penicillin
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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.
Lysine
Carbonyl CompoundsCHECK YOUR NEIGHBOR
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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.
Lysine
Carbonyl CompoundsCHECK YOUR ANSWER
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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
Polymer: A very long organic molecule made by the joining together of smaller organic molecule units known as monomers.
MonomerMonomer MonomerMonomer MonomerMonomer MonomerMonomer
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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
Ethylene
C CH
HH
HC C
H
HH
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
Ethylene
C CH
HH
HC C
H
HH
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
Ethylene
C CH
HH
HC C
H
HH
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
Ethylene Ethylene
H
C C
H
H
H
C C
H
HH
H
Addition Polymer:
A polymer whose mass is equal to the sum of the masses of the monomer units.
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Polymers
Ethylene Ethylene
H
C C
H
H
H
C C
H
HH
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
C C
H
H
C C
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
C C
H
H
C CH
H H
H H
H
C C
H
H H
H
C C
H
H H
C
H
H
H
CH
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 C
H
H
C CH
H H
H H
H
C C
H
H H
H
C C
H
H H
C
H
H
H
CH
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 C
H
H
C C
H
H H
H H
H
C C
H
H H
H
C C
H
H H
C
H
H
H
C
H
Ethylene Ethylene Ethylene Ethylene EthyleneEthylene
Polyethylene
C
H
H
C
H
H
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Polymers
Propylene
C CCH3
HH
HC C
CH3
HH
H
Propylene
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Polymers
Polypropylene
C
H
C C
H
H
C C
H H
H
H
C C
H
H CH3
C C
H H
H
C
H H
HCH3 CH3 CH3 CH3
Propylene Propylene Propylene Propylene Propylene Propylene
H
C
H
C
H
CH3
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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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PolymersCONSIDER 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)Citral
Polymers
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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)Citral
Polymers
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Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units within the structure shown below.
Isoprene
(2-methyl-1,3-butadiene)
Beta-carotene
Polymers
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Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units within the structure shown below.
Isoprene
(2-methyl-1,3-butadiene)
Beta-carotene
Polymers
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