Fundamentals of organic chemistry
John McMurry
17889454
TABLE DES MATIÈRES
1. Structure and Bonding; Acids and Bases
Atomic Structure
Electron Configuration of Atoms
Development of Chemical Bonding
Theory
The Nature of Chemical Bonds
Forming Covalent Bonds : Valence
Bond Theory
Hybridization : sp3
Orbitals and the Structure of Methane
Hybridization : sp3
Orbitals and the Structure of Ethane
Hybridization : sp3
Orbitals and the Structure of Ethylene
Hybridization : sp Orbitals
and the Structure of Acetylene
Polar Covalent Bonds : Electronegativity
Acids and Bases : The Bronsted-Lowry
Definition
Acids and Bases : The Lewis Definition
INTERLUDE Chemicals, Toxicity, and Risk.
Summary and Key Words
Visualizing Chemistry / Additional
Problems
2. The Nature of Organic Compounds : Alkanes
Functional Group
Alkanes and Alkyl Groups : Isomers
Naming Branched-Chain Alkanes
Properties of Alkanes
Conformations of Ethane
Drawing Chemical Structures
Cycloalkanes
Cis-Trans Isomerism in Cycloalkanes
Conformations of Some Common Cycloalkanes
Axial and Equatorial Bonds in Cyclohexane
Conformational Mobility of Cyclohexane
INTERLUDE Gasoline
Summary and Key Words
Visualizing Chemistry / Additionnal
Problems
3. The Nature of Orbanic Reactions : Alkenes
Naming Alkenes
Electronic Structure of Alkenes
Cis-Trans Isomers of Alkenes
Sequence Rules : The E,Z
Designation
Kinds of Organic Reactions
How Reactions Occur : Mechanisms
The Mechanism of an Organic Reaction
: Addition of HCl to Ethylene
Describing a Reaction : Reaction
Energy Diagrams and Transition States
Describing a Reaction : Intermediates
INTERLUDE Terpenes : Naturally Occurring Alkenes
Summary and Key Words
Visualizing Chemistry / Additional
Problems
4. Reactions of Alkenes and Alkynes
Addition of HX to Alkenes : Hydrohalogenation
Orientation of Alkene Addition Reactions
: Markovnikov's Rule
Carbocation Structure and Stability
Addition of H2O to Alkenes
: Hydration
Addition of X2 to Alkenes
: Halogenation
Addition of H2 to Alkenes
: Hydrogenation
Oxidation of Alkenes : Hydroxylation
and Cleavage
Biological Addition Reactions of
Alkenes
Addition of Radicals to Alkenes
: Polymers
Conjugated Dienes
Stability of Allylic Carbocations
: Resonance
Drawing and Interpreting Resonance
Forms
Alkynes and Their Reactions
INTERLUDE Natural Rubber
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
5. Aromatic Compounds
Structure of Benzene : The Kekulé
Proposal
Structure of Benzene : The Resonance
Proposal
Naming Aromatic Compounds
Electrophilic Aromatic Substitution
Reactions : Bromination
Other Electrophilic Aromatic Substitution
Reactions
The Friedel-Crafts Alkylation and
Acylation Reactions
Substituent Effects in Electrophilic
Aromatic Substitution
An Explanation of Substituent Effects
Oxidation and Reduction of Aromatic
Compounds
Polycyclic Aromatic Hydrocarbons
Organic Synthesis
INTERLUDE Aspirin, NSAID's, and COX-2 Inhibitors
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
6. Stereochemistry
Stereochemistry and the Tetrahedral
Carbon
The Reason for Handedness in Molecules
: Chirality
Optical Activity
Specific Rotation
Pasteur's Discovery of Enantiomers
Sequence Rules for Specifying Configuration
Diastereomers
Meso Compounds
Molecules with More Than Two Stereocenters
Racemic Mixtures and the Resolution
of Enantiomers
Physical Properties of Stereoisomers
A Brief Review of Isomerism
Chirality in Nature
INTERLUDE Chiral Drugs
Summary and Key Words
Additional Problems
7. Alkyl Halides
Naming Alkyl Halides
Preparing Alkyl Halides
Reactions of Alkyl Halides : Grignard
Reagents
Nucleophilic Substitution Reactions
The SN2 Reaction
The SN1 Reaction
Eliminations : The E2 Reaction
Eliminations : The E1 Reaction
A Summary of Reactivity : SN1,
SN2, E1, E2
Substitution Reactions in Living
Organisms
INTERLUDE Naturally Occurring Organohalogen Compounds
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
8. Alcohols, Phenols, and Ethers
Naming Alcohols, Phenols, and Ethers
Properties of Alcohols, Phenols,
and Ethers : Hydrogen Bonding
Properties of Alcohols and Phenols
: Acidity
Synthesis of Alcohols
Reactions of Alcohols
Synthesis and Reactions of Phenols.
Synthesis and Reactions of Ethers
Cyclic Ethers : Epoxides
Thiols and Sulfides
INTERLUDE Ethanol as Chemical, Drug, and Poison
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
9. Aldehydes and Ketones : Nucleophilic Addition Reactions
The Nature of Carbonyl Compounds
Naming Aldehydes and Ketones
Synthesis of Aldehydes and Ketones
Oxidation of Aldehydes
Nucleophilic Addition Reactions
of Aldehydes and Ketones : Reduction
Nucleophilic Addition of Water :
Hydration
Nucleophilic Addition of Alcohols
: Acetal Formation
Nucleophilic Addition of Amines
: Imine Formation
Nucleophilic Addition of Grignard
Reagents : Alcohol Formation
Conjugate Nucleophilic Addition
Reactions
Some Biological Nucleophilic Addition
Reactions
INTERLUDE Carbonyl Compounds for Insect Control
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
10. Carboxylic Acids and Derivatives
Naming Carboxylic Acids and Derivatives
Occurrence and Properties of Carboxylic
Acids
Synthesis of Carboxylic Acids
Nucleophilic Acyl Substitution Reactions
Reactions of Carboxylic Acids
Chemistry of Acid Halides
Chemistry of Acid Anhydrides
Chemistry of Esters
Chemistry of Amides
Chemistry of Nitriles
Polymers from Carbonyl Compounds
: Nylons and Polyesters
INTERLUDE Vitamin C
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions
Keto-Enol Tautomerism
Reactivity of Enols : The Mechanism
of Alpha-Substitution Reactions
Alpha Halogenation of Aldehydes
and Ketones
Acidity of Alpha Hydrogen Atoms
: Enolate Ion Formation
Reactivity of Enolate Ions
Alkylation of Enolate Ions
Carbonyl Condensation Reactions
Condensations of Aldehydes and Ketones
: The Aldol Reaction
Dehydration of Aldol Products :
Synthesis of Enones
Condensations of Esters : The Claisen
Condensation Reaction
Biological Carbonyl Reactions
INTERLUDE Lactam Antibiotics
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry/ Additional Problems
12. Amines
Naming Amines
Structure and Properties of Amines
Basicity of Amines
Synthesis of Amines
Reactions of Amines
Heterocyclic Amines
Alkaloids : Naturally Occurring Amines
INTERLUDE Opium and Opiates
Summary and Key Words
Summary of Reactions / Visualizing
Chemistry / Additional Problems
13. Structure Determination
Infrared Spectroscopy and The Electromagnetic
Spectrum
Infrared Spectroscopy of Organic Molecules
Ultraviolet Spectroscopy
Interpreting Ultraviolet Spectra :
The Effect of Conjugation
Nuclear Magnetic Resonance Spectroscopy
The Nature of NMR Absorptions
Chemical Shifts
Chemical Shifts in 1H NMR
Spectra
Integration of 1H NMR Spectra
: Proton Counting
Spin-Spin Splitting in 1H
NMR Spectra
Uses of 1H NMR Spectra
13C NMR Spectroscopy
INTERLUDE Magnetic Resonance Imaging (MRI)
Summary and Key Words
Visualizing Chemistry/ Additional Problems
14. Biomolecules : Carbohydrates
Classification of Carbohydrates
Configurations of Monosaccharides :
Fischer Projections
D,L Sugars
Configurations of Aldoses
Cyclic Structures of Monosaccharides
: Hemiacetal Formation
Monosaccharide Anomers : Mutarotation
Reactions of Monosaccharides
Disaccharides
Polysaccharides
Other Important Carbohydrates
Cell-Surface Carbohydrates and Carbohydrate
Vaccines
INTERLUDE Sweetness
Summary and Key Words
Visualizing Chemistry / Additional Problems
15. Biomolecules : Amino Acids, Peptides, and Proteins
Structures of Amino Acids
Isoelectric Points
Peptides and Proteins
Covalent Bonding in Peptides
Peptide Structure Determination : Amino
Acid Analysis
Peptide Sequencing : The Edman Degradation
Peptide Synthesis
Classification of Proteins
Protein Structure
Enzymes
How Do Enzymes Work? Citrate Synthas
INTERLUDE Protein and Nutrition
Summary and Key Words
Visualizing Chemistry / Additional
Problems
16. Biomolecules : Lipids and Nucleic Acids
Lipids
Fats and Oils
Soaps
Phospholipids
Steroids
Nucleic Acids and Nucleotides
Structure of DNA
Base Pairing in DNA : The Watson-Crick
Model
Nucleic Acids and Heredity
Replication of DNA
Structure and Synthesis of RNA : Transcription
RNA and Protein Biosynthesis : Translation
Sequencing DNA
The Polymerase Chain Reaction
INTERLUDE DNA Fingerprinting
Summary and Key Words.
Visualizing Chemistry / Additional
Problems
17. The Organic Chemistry of Metabolic Pathways
An Overview of Metabolism and Biochemical
Energy
Catabolism of Fats : Oxidation Pathway
Catabolism of Carbohydrates : Glycolysis
The Citric Acid Cycle
Catabolism of Proteins : Transamination
The Organic Chemistry of Metabolic
Pathways : A Summary
INTERLUDE Sasal Metabolism
Summary and Key Words
Visualizing Chemistry/ Additional
Problems
29 mars 2004