Transcript Chapter 1: Matter and Measurement

General Chemistry
Principles and Modern Applications
Petrucci • Harwood • Herring
8th Edition
Chapter 27: Organic Chemistry
Philip Dutton
University of Windsor, Canada
N9B 3P4
Prentice-Hall © 2002
Contents
Organic Compounds and Structures: An Overview
Alkanes
Alkenes and Alkynes
Aromatic Hydrocarbons
Alcohols, Phenols, and Ethers
Aldehydes and Ketones
Carboxylic Acids and Their Derivatives
Amines
Heterocyclic Compounds
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Contents
Nomenclature of Stereoisomers in Organic Compounds
An Introduction to Substitution Reactions at
sp3 Hybridized Carbon Atoms
Synthesis of Organic Compounds
Polymerization Reactions
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27-1 Organic Compounds and Structures:
An Overview
• Hydrocarbons – the simplest organic compounds.
• Simplest hydrocarbon is methane.
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Skeletal Isomerism
Same number of atoms (carbons and hydrogens), just different arrangements of atoms.
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Simplified Drawings of Organic Structures
Each “corner” signifies a carbon. We assume that each carbon is saturated (filled up) with
hydrogens (unless otherwise noted).
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Nomenclature
Rules for naming (nomenclature):
• Select the longest continuous carbon chain.
– This determines the base name.
• Consider each branch and name similarly except
change the name from –ane to –yl.
• Number the C atoms so that substituents (attached
stuff) have the lowest possible number.
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Nomenclature
Rules for naming (cont.):
• Name each substituent/attached thing according to
its identity and the number of the C atom to which
it is attached.
– Use di, tri, tetra as appropriate.
• Separate numbers from one another by commas.
• List substituents/attached stuff alphabetically by
name.
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Table 27.1. Some Common Alkyl Groups
Signifies shape
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Nomenclature & Positional Isomerism
Here are naming and drawing examples of C5H11Br
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Functional Groups
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Alkanes
For example: C5H12
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Conformations
(If you were to look at this molecule from an end).
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Ring Structures
Organic chains in a circle get the prefix, cyclo- along with the chain name.
Note that the formulas have changed. Each molecule has 2 less hydrogens
(so the ends of the chain could connect).
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Ring Strain
When you make smaller and smaller
“circles” of atom chains, there is strain
between the atoms (electron
repulsions!!!)
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Cyclohexane Conformations
Once the circles get large enough, they can manipulate themselves into different shapes.
This is the “Boat”
configuration of
cyclohexane,
C6H12.
This is the “Chair”
configuration of
cyclohexane, C6H12.
(Think lounge
chair).
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Combustion Reaction & Octane
C8H18(l) +
Octane
25
2
O2(g) → 8 CO2(g) + 9 H2O(l)
ΔH° = -5.48x103 J
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“Parts” of Hydrocarbons from the Earth
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Alkenes and Alkynes
Naming of Alkenes: Add “–ene” to the base/chain name.
Naming of Alkynes: Add “–yne” to the base/chain name.
These types of bonds are said to be “Unsaturated”.
When you have foods with unsaturated fats, it is indicating that there are double
and even triple bonds within the fat molecules.
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Geometric Isomerism
Tells which way the chain continues. Trans is “across” the double bond
(think about a “Trans-Atlantic” trip. It’s across the Atlantic)
Trans is the SAME that is used in the name “trans fats” identified in food.
It indicates those fats within the food have double bonds and they have
trans configuration.
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Aromatic Hydrocarbons
Aromatic does refer to a property of these compounds. But has then come to mean
molecules containing alternating/associated double bonds.
These
drawings are
Benzene
This drawing is
showing resonance
Naming of Aromatics: mostly come from “old school/historical” naming.
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Characteristics of Aromatic Hydrocarbons
• Planar (flat) cyclic molecules.
• Conjugated п systems (4n + 2)
•P is referring to double bonds.
•Conjugated means they are associated and
alternating.
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Naming Aromatic Hydrocarbons
Remember: start with the “base” chain (or ring) and then count so that the “attached stuff”
have the lowest number(s) possible.
Old School Counting: From the “start” position, the first position (1-) is “Ortho” (o-), the
next (2-) is “meta” (m-), and the last or opposite side (3-) is “Para” (p-).
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Alcohols & Phenols (cyclic alcohols)
Naming of Alcohols: Add “–ol” to the base/chain name.
Primary, secondary, tertiary all refer to
number of carbon groups attached to the
carbon that the functional group is
attached.
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Ethers
Naming of Ethers: Add “ether” after the base/chain name.
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Aldehydes and Ketones
Naming of Aldehydes: Add “–al” to the base/chain name.
Naming of Ketones: Add “–one” to the base/chain name. Also, have some historical
naming.
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Carboxylic Acids
Naming of Carboxilic Acids: Add “–ic acid” to the base/chain name.
Remember: some naming is based off of “Old School” rules and historical names.
For example, Acetic acid is Ethanoic Acid.
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Naming Acids
Old School Counting: Can use “Ortho” (o-), “meta” (m-), “Para” (p-) for aromatics. But
sometimes Greek alphabet letters were used to signify positions too. Alpha (a), Beta
(b), Gamma (g) et al. are used.
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Carboxylic Acid Derivatives
Acetyl naming: Add Acetyl to front the base name.
Esters:
Naming of Esters: Add “–oate” to the base/chain name. Or add the “acetate” to the
base name.
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Carboxylic Acid Derivatives
Amides:
Naming of Amides: Add “amide” to the end of the base/chain name.
Resonance in Amides
The red arrows are showing the movement of pairs of electrons.
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Amines
Naming of Amines: Add “amine” to the base/chain name.
Note: the number of attachments possible for an amine.
Amine are very similar to ammonia in structure.
What do you think about their properties might be?
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Ammonium Salts
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Heterocyclic Compounds
Naming of Heterocyclic compounds: Typically, based off “Old School” naming.
Heterocyclic refers to a cyclic compound that has an atom(s) other than carbon within the ring.
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Nomenclature of Stereoisomers in Organic
Compounds
If a compound has chirality, that is a way to say it is unique and is said to be Chiral.
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