John E. McMurry • Robert C. Fay
C H E M I S T R Y
Fifth Edition
Chapter 23
Organic Chemistry
Lecture Notes
Alan D. Earhart
Southeast Community College • Lincoln, NE
Copyright © 2008 Pearson Prentice Hall, Inc.
The Nature of Organic
Molecules
Organic Chemistry: The study of carbon compounds.
•
Carbon is tetravalent. It has four outer-shell
electrons (1s22s22p2) and forms four bonds.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/2
The Nature of Organic
Molecules
•
Organic molecules have covalent bonds. In ethane,
for instance, all bonds result from the sharing of two
electrons.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/3
The Nature of Organic
Molecules
•
Organic molecules have polar covalent bonds when
carbon bonds to an element on the right or left side
of the periodic table.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/4
The Nature of Organic
Molecules
•
Carbon can form multiple covalent bonds by sharing
more than two electrons with a neighboring atom.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/5
The Nature of Organic
Molecules
•
Organic molecules have specific three-dimensional
shapes, which can be predicted by the VSEPR
model.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/6
The Nature of Organic
Molecules
•
Organic molecules have specific three-dimensional
shapes, which can be predicted by the VSEPR
model.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/7
The Nature of Organic
Molecules
•
Carbon uses hybrid atomic orbitals for bonding.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/8
Alkanes and Their Isomers
Hydrocarbons: Molecules that contain only carbon
and hydrogen.
Alkanes: Hydrocarbons that contain only single
bonds.
Space-filling models:
Structural formulas:
Molecular formulas:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/9
Alkanes and Their Isomers
Isomers: Compounds with the same molecular
formula but different chemical structures.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/11
Drawing Organic Structures
Structural
Formula
Condensed
Formula
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/12
The Shapes of Organic
Molecules
Naming Alkanes
IUPAC Rules
Alkane
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/14
Naming Alkanes
1. Name the main chain. Find the longest continuous
chain of carbons in the molecule, and use the name
of that chain as the parent name:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/15
Naming Alkanes
2. Number the carbon atoms in the main chain.
Beginning at the end nearer the first branch point,
number each carbon atom in the parent chain:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/16
Naming Alkanes
3. Identify and number the branching substituent.
Assign a number to each branching substituent group
on the parent chain according to its point of attachment:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/17
Naming Alkanes
3. Identify and number the branching substituent.
Assign a number to each branching substituent group
on the parent chain according to its point of attachment:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/18
Naming Alkanes
•
Write the name as a single word. Use hyphens to
separate the different prefixes, and use commas to
separate numbers when there are more than one. If two
or more different substituent groups are present, list
them in alphabetical order. If two or more identical
substituent groups are present, use one of the Greek
prefixes:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/19
Naming Alkanes
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/20
Naming Alkanes
Cycloalkanes
Cycloalkane: One or more rings of carbon atoms.
3C
4C
5C
Copyright © 2008 Pearson Prentice Hall, Inc.
6C
Chapter 23/22
Cycloalkanes
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/23
Cycloalkanes
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/24
Reactions of Alkanes
Combustion:
CH4(g) + 2O2(g)
Halogens (Cl2 or Br2):
CO2(g) + 2H2O(l)
DH° = -890 kJ
Families of Organic Molecules:
Functional Groups
Functional Group: An atom or group of atoms within a
molecule that has a characteristic chemical behavior
and that undergoes the same kinds of reactions in
every molecule where it occurs.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/26
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/27
Alkenes and Alkynes
Alkene: A hydrocarbon that contains a carbon-carbon
double bond.
Alkyne: A hydrocarbon that contains a carbon-carbon
triple bond.
Unsaturated: A hydrocarbon that contains fewer
hydrogens per carbon than the related alkane.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/30
Alkenes and Alkynes
Alkenes
-ene suffix since they are alkenes.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/31
Alkenes and Alkynes
Alkenes and Isomers
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/32
Alkenes and Alkynes
Alkenes and Isomers
Alkenes and Alkynes
Alkenes and Isomers
Why are they isomers?
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/34
Alkenes and Alkynes
Alkenes and Isomers
Alkenes and Alkynes
Alkynes
-yne suffix since they are alkynes.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/36
Reactions of Alkenes
•
Addition of Hydrogen:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/37
Reactions of Alkenes
•
Addition of Hydrogen:
Reactions of Alkenes
•
Addition of Cl2 and Br2:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/39
Reactions of Alkenes
•
Addition of Water:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/40
Aromatic Compounds and
Their Reactions
Aromatic: A class of compounds that contain a sixmembered ring with three double bonds.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/41
Aromatic Compounds and
Their Reactions
The stability of benzene comes from its six pi-bond
electrons which are spread equally around the entire
ring:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/42
Aromatic Compounds and
Their Reactions
•
Nitration (Substitution of a Nitro Group):
Aromatic Compounds and
Their Reactions
•
Halogenation (Substitution of a Bromine or
Chlorine):
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/44
Alcohols, Ethers, and Amines
Alcohols: A class of compounds that contain a hydroxyl
group (-OH).
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/45
Alcohols, Ethers, and Amines
Alcohols
Simple alcohols are often soluble in water because of
hydrogen bonding:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/46
Alcohols, Ethers, and Amines
Alcohols
-ol suffix since they are alcohols.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/47
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/49
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
Alcohols, Ethers, and Amines
Ethers
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/51
Alcohols, Ethers, and Amines
Amines
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/52
Alcohols, Ethers, and Amines
Amines
Base
Acid
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/53
Aldehydes and Ketones
All have carbonyl groups
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/54
Aldehydes and Ketones
-al suffix since they are
aldehydes.
-one suffix since they
are ketones.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/55
Aldehydes and Ketones
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/56
Aldehydes and Ketones
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/57
Carboxylic Acids, Esters, and
Amides
These are bonded to a strongly
electronegative atom (O or N).
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/58
Carboxylic Acids, Esters, and
Amides
All three undergo carbonyl-substitution reactions:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/59
Carboxylic Acids, Esters, and
Amides
Carboxylic Acids
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/60
Carboxylic Acids, Esters, and
Amides
Carboxylic Acids
They are weaker than their strong inorganic counterparts.
For acetic acid, Ka = 1.75 x 10-5
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/61
Carboxylic Acids, Esters, and
Amides
Carboxylic Acids
A common industrial
solvent.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/62
Carboxylic Acids, Esters, and
Amides
Esters
Gives bananas their odor.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/63
Carboxylic Acids, Esters, and
Amides
Esters
Hydrolysis:
Saponification (“soap”) is the base catalyzed
hydrolysis of naturally occurring esters in animal fat.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/64
Carboxylic Acids, Esters, and
Amides
Amides
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/65
Carboxylic Acids, Esters, and
Amides
Amides
Hydrolysis:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/66
Synthetic Polymers
Polymers: Large molecules formed by the repetitive
bonding of many smaller molecules, called monomers.
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/67
Synthetic Polymers
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/68
Synthetic Polymers
Polymerization:
Initiator
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/69
Synthetic Polymers
Polymerization:
Copyright © 2008 Pearson Prentice Hall, Inc.
Chapter 23/70