Organic Chemistry: A Short Course / Edition 9

Organic Chemistry: A Short Course / Edition 9

by David Hart, Harold Hart, Leslie Craine

ISBN-10: 0395724023

ISBN-13: 9780395724026

Pub. Date: 02/28/1995

Publisher: CENGAGE Learning

Designed specifically for the one-semester short course in organic chemistry, this market leader appeals to a range of non-chemistry science majors through its emphasis on practical, real-life applications of chemistry, coverage of basic concepts, and engaging visual style. In contrast to competitors who offer mainly streamlined versions of full-year texts, this

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Designed specifically for the one-semester short course in organic chemistry, this market leader appeals to a range of non-chemistry science majors through its emphasis on practical, real-life applications of chemistry, coverage of basic concepts, and engaging visual style. In contrast to competitors who offer mainly streamlined versions of full-year texts, this text has always been aimed at the short course and its writing style, approach, and selection of topics best suit the needs of this market. The Twelfth Edition further develops the strengths of the previous editions through an updated, dynamic art program—online, on CD, and in the text—new content to keep students current with developments in the organic chemistry field, and a revised lab manual.

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CENGAGE Learning
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Table of Contents

Note: Each

Chapter concludes with Additional Problems.
1.Bonding and Isomerism
1.1 How Electrons are Arranged in Atoms
1.2 Ionic and Covalent Bonding
1.3 Carbon and the Covalent Bond
1.4 Carbon-Carbon Single Bonds
1.5 Polar Covalent Bonds
1.6 Multiple Covalent Bonds
1.7 Valence
1.8 Isomerism
1.9 Writing Structural Formulas
1.10 Abbreviated Structural Formulas
1.11 Formal Charge
1.12 Resonance
1.13 Arrow Formalism
1.14 The Orbital View of Bonding; the Sigma Bond
1.15 Carbon sp3 Hybrid Orbitals
1.16 Tetrahedral Carbon; the Bonding in Methane
1.17 Classification According to Molecular Framework
1.18 Classification According to Functional Group
2.Alkanes and Cycloalkanes; Conformational and Geometric Isomerism
2.1 The Structures of Alkanes
2.2 Nomenclature of Organic Compounds
2.3 IUPAC Rules for Naming Alkanes
2.4 Alkyl and Halogen Substituents
2.5 Use of the IUPAC Rules A Closer Look at...Natural Gas
2.6 Sources of Alkanes
2.7 Physical Properties of Alkanes and Nonbonding Intermolecular Interactions A Closer Look at...Hydrogen Bonding
2.8 Conformations of Alkanes
2.9 Cycloalkane Nomenclature and Conformation
2.10 Cis-trans Isomerism in Cycloalkanes A Word About: Isomers- Possible and Impossible
2.11 Summary of Isomerism
2.12 Reactions of Alkanes A Word About: Methane, Marsh Gas, and Miller's Experiment
2.13 The Free-Radical Chain Mechanism of Halogenation Reaction Summary Mechanism Summary
3.Alkenes and Alkynes
3.1 Definition and Classification
3.2 Nomenclature
3.3 Some Facts About Double Bonds
3.4 The Orbital Model of a Double Bond; the Pi Bond
3.5Cis-trans Isomerism in Alkenes A Word About: The Chemistry of Vision
3.6 Addition and Substitution Reactions Compared
3.7 Polar Addition Reactions
3.8 Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule
3.9 Mechanism of Electrophilic Addition to Alkenes
3.10 Markovnikov's Rule Explained
3.11 Reaction Equilibrium: What Makes a Reaction Go?
3.12 Reaction Rates: How Fast Does a Reaction Go?
3.13 Hydroboration of Alkenes
3.14 Addition of Hydrogen
3.15 Additions to Conjugated Systems
3.16 Free-Radical Additions; Polyethylene
3.17 Oxidation of Alkenes A Word About: Ethylene: Raw Material and Plant Hormone
3.18 Some Facts About Triple Bonds
3.19 The Orbital Model of a Triple Bonds
3.20 Additon Reactions of Alkynes A Word About: Petroleum, Gasoline, and Octane Number
3.21 Acidity of Alkynes Reaction Summary Mechanism Summary
4.Aromatic Compounds
4.1 Some Facts About Benzene
4.2 The Kekulé Structure of Benzene
4.3 The Resonance Model for Benzene
4.4 Orbital Model for Benzene
4.5 Symbols for Benzene
4.6 Nomenclature of Aromatic Compounds
4.7 The Resonance Energy of Benzene
4.8 Electrophilic Aromatic Substitution
4.9 The Mechanism of Electrophilic Aromatic Substitution
4.10 Ring-Activating and Ring-Deactivating Substituents
4.11 Ortho, Para-Directing, and Meta-Directing Groups
4.12 The Importance of Directing Effects in Synthesis
4.13 Polycyclic Aromatic Hydrocarbons A Word About: Polycyclic Aromatic Hydrocarbons and Cancer A Closer Look at...Polycyclic Aromatic Hydrocarbons A Word About: C60, an Aromatic Sphere: The Fullerenes Reaction Summary Mechanism Summary
5.1 Chirality and Enantiomers
5.2 Stereogenic Centers; the Stereogenic Carbon Atom
5.3 Configuration and the R-S Convention
5.4 The E-Z Convention for Cis-trans Isomers
5.5 Polarized Light and Optical Activity A Word About: Pasteur's Experiments and the van't Hoff-LeBel Explanation
5.6 Properties of Enantiomers
5.7 Fischer Projection Formulas
5.8 Compounds with More Than One Stereogenic Center; Diastereomers
5.9 Meso Compounds; the Stereoisomers of Tartaric Acid
5.10 Stereochemistry: a Recap of Definitions
5.11 Stereochemistry and Chemical Reactions A Word About: Enantiomers and Biological Activity
5.12 Resolution of a Racemic Mixture A Closer Look at...Thalidomide
6.Organic Halogen Compounds; Substitution and Elimination Reactions
6.1 Nucleophilic Substitution
6.2 Examples of Nucleophilic Substitution
6.3 Nucleophilic Substitution Mechanism
6.4 The SN2 Mechanism
6.5 The SN1 Mechanism
6.6 The SN1 and SN2 Mechanisms Compared A Word About: SN2 Reactions in Nature: Biological Methylations
6.7 Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms
6.8 Substitution and Elimination Competition
6.9 Polyhalogenated Aliphatic Compounds A Word About: CFCs, the Ozone Layer, and Trade-Offs A Word About: Halogenated Organic Compounds from the Sea Reaction Summary Mechanism Summary
7.Alcohols, Phenols, and Thiols
7.1 Nomenclature of Alcohols A Word About: Industrial Alcohols
7.2 Classification of Alcohols
7.3 Nomenclature of Phenols
7.4 Hydrogen Bonding in Alcohols and Phenols
7.5 Acidity and Basicity Reviewed
7.6 The Acidity of Alcohols and Phenols
7.7 The Basicity of Alcohols and Phenols
7.8 Dehydration of Alcohols to Alkenes
7.9 The Reaction of Alcohols with Hydrogen Halides
7.10 Other Ways to Prepare Alkyl Halides from Alcohols
7.11 A Comparison of Alcohols and Phenols
7.12 Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids A Word About: Biologically Important Alcohols and Phenols
7.13 Alcohols with More Than One Hydroxyl Group
7.14 Aromatic Substitution in Phenols A Word About: Quinones and the Bombardier Beetle
7.15 Oxidation of Phenols
7.16 Phenols As Antioxidants
7.17 Thiols, the Sulfur Analogs of Alcohols and Phenols A Word About: Hair—Curly or Straight Reaction Summary
8.Ethers and Epoxides
8.1 Nomenclature of Ethers
8.2 Physical Properties of Ethers
8.3 Ethers as Solvents
8.4 The Grignard Reagent; an Organometallic Compound
8.5 Preparation of Ethers A Closer Loook at...MTBE
8.6 Cleavage of Ethers A Word About: Ether and Anesthesia
8.7 Epoxides (Oxiranes) A Word About: The Gypsy Moth's Epoxide
8.8 Reactions of Epoxides
8.9 Cyclic Ethers Reaction Summary
9.Aldehydes and Ketones
9.1 Nomenclature of Aldehydes and Ketones
9.2 Some Common Aldehydes and Ketones
9.3 Synthesis of Aldehydes and Ketones
9.4 Aldehydes and Ketones in Nature
9.5 The Carbonyl Group
9.6 Nucleophilic Addition to Carbonyl Groups: An Overview
9.7 Addition of Alcohols: Formation of Hemiacetals and Acetals
9.8 Addition of Water; Hydration of Aldehydes and Ketones
9.9 Addition of Grignard Reagents and Acetylides
9.10 Addition of Hydrogen Cyanide; Cyanohydrins
9.11 Addition of Nitrogen Nucleophiles
9.12 Reduction of Carbonyl Compounds
9.13 Oxidation of Carbonyl Compounds
9.14 Keto-Enol Tautomerism
9.15 Acidity of a-Hydrogens; the Enolate Anion
9.16 Deuterium Exchanges in Carbonyl Compounds
9.17 The Aldol Condensation
9.18 The Mixed Aldol Condensation A Word About: Water Treatment and the Chemistry of Enols/Enolates
9.19 Commercial Synthesis via the Aldol Condensation Reaction Summary Mechanism Summary
10.Carboxylic Acids and their Derivatives
10.1 Nomenclature of Acids
10.2 Physical Properties of Acids
10.3 Acidity and Acidity Constants
10.4 What Makes Carboxylic Acids Acidic?
10.5 Effect of Structure on Acidity; the Inductive Effect Revisited
10.6 Conversion of Acids to Salts
10.7 Preparation of Acids A Word About: Green Chemistry and Ibuprofen: A Case Study A Closer Look at...Green Chemistry
10.8 Carboxylic Acid Derivatives
10.9 Esters
10.10 Preparation of Esters; Fischer Esterification
10.11 The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution
10.12 Lactones
10.13 Saponification of Esters
10.14 Ammonolysis of Esters
10.15 Reaction of Esters with Grignard Reagents
10.16 Reduction of Esters
10.17 The Need for Activated Acyl Compounds
10.18 Acyl Halides
10.19 Acid Anhydrides A Word About: Thioesters, Nature's Acyl-Activating Groups
10.20 Amides
10.21 A Summary of Carboxylic Acid Derivatives
10.22 The a-Hydrogen of Esters; the Claisen Condensation Reaction Summary Mechanism Summary
11.Amines and Related Nitrogen Compounds
11.1 Classification and Structure of Amines
11.2 Nomenclature of Amines
11.3 Physical Properties and Intermolecular Interactions of Amines
11.4 Preparation of Amines; Alkylation of Ammonia and Amines
11.5 Preparation of Amines; Reduction of Nitrogen Compounds
11.6 The Basicity of Amines
11.7 Comparison of the Basicity and Acidity of Amines and Amides
11.8 Reaction of Amines with Strong Acids; Amine Salts A Word About: Alkaloids and the Dart-Poison Frogs
11.9 Chiral Amines as Resolving Agents
11.10 Acylation of Amines with Acid Derivatives
11.11 Quaternary Ammonium Compounds
11.12 Aromatic Diazonium Compounds
11.13 Diazo Coupling; Azo Dyes Reaction Summary Mechanism Summary
12.Spectroscopy and Structure Determination
12.1 Principles of Spectroscopy
12.2 Nuclear Magnetic Resonance Spectroscopy (NMR)
12.3 13C NMR Spectroscopy A Word About: NMR in Biology and Medicine
12.4 Infrared Spectroscopy
12.5 Visible and Ultraviolet Spectroscopy
12.6 Mass Spectrometry A Closer Look at...Mass Spectrometry and Carbon Dating
13.Heterocyclic Compounds
13.1 Pyridine: Bonding and Basicity
13.2 Substitution in Pyridine
13.3 Other Six-Membered Heterocycles
13.4 Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene
13.5 Electrophilic Substitution in Furan, Pyrrole, and Thiophene
13.6 Other Five-Membered Heterocycles: Azoles A Word About: Porphyrins: What Makes Blood Red and Grass Green?
13.7 Fused-Ring, Five-Membered Heterocycles: Indoles and Purines A Word About: Morphine and Other Nitrogen-Containing Drugs Reaction Summary Mechanism Summary
14.Synthetic Polymers
14.1 Classification of Polymers
14.2 Free-Radical Chain-Growth Polymerization
14.3 Cationic Chain-Growth Polymerization
14.4 Anionic Chain-Growth Polymerization
14.5 Stereoregular Polymers; Ziegler-Natta Polymerization A Word About: Polyacetylene and Conducting Polymers
14.6 Diene Polymers: Natural and Synthetic Rubber
14.7 Copolymers
14.8 Step-Growth Polymerization: Dacron and Nylon A Word About: Degradable Polymers A Word About: Aramids, the Latest in Polyamides A Closer Look at...Nylon
14.9 Polyurethanes and Other Step-Growth Polymers Reaction Summary Mechanism Summary
15.Lipids and Detergents
15.1 Fats and Oils; Triesters of Glycerol
15.2 Hydrogenation of Vegetable Oils
15.3 Saponification of Fats and Oils; Soap
15.4 How Do Soaps Work?
15.5 Synthetic Detergents (Syndets) A Word About: Commercial Detergents
15.6 Phospholipids
15.7 Prostaglandins, Leukotrienes, and Lipoxins A Word About: Prostaglandins, Aspirin, and Pain
15.8 Waxes
15.9 Terpenes and Steroids Reaction Summary
16.1 Definitions and Classification
16.2 Monosaccharides
16.3 Chirality in Monosaccharides; Fischer Projection Formulas and D,L-Sugars
16.4 The Cyclic Hemiacetal Structures of Monosaccharides
16.5 Anomeric Carbons; Mutarotation
16.6 Pyranose and Furanose Structures
16.7 Conformations of Pyranoses
16.8 Esters and Ethers from Monosaccharides
16.9 Reduction of Monosaccharides
16.10 Oxidation of Monosaccharides
16.11 Formation of Glycosides from Monosaccharides
16.12 Disaccharides A Word About: Sweetness and Sweeteners
16.13 Polysaccharides A Word About: Fat Substitutes from Carbohydrates
16.14 Sugar Phosphates
16.15 Deoxy Sugars
16.16 Amino Sugars
16.17 Ascorbic Acid (Vitamin C) Reaction Summary
17.Amino Acids, Peptides, and Proteins
17.1 Naturally Occurring Amino Acids
17.2 The Acid-Base Properties of Amino Acids
17.3 The Acid-Base Properties of Amino Acids with More Than One Acidic or Basic Group
17.4 Electrophoresis
17.5 Reactions of Amino Acids
17.6 The Ninhydrin Reaction
17.7 Peptides A Word About: Some Naturally Occurring Peptides
17.8 The Disulfide Bond
17.9 Proteins
17.10 The Primary Structure of Proteins
17.11 The Logic of Sequence Determination A Word About: Protein Sequencing and Evolution
17.12 Peptide Synthesis
17.13 Secondary Structure of Proteins
17.14 Tertiary Structure: Fibrous and Globular Proteins
17.15 Quaternary Protein Structure A Closer Look at...Nobel Laureates and Protein Chemistry Reaction Summary
18.Nucleotides and Nucleic Acids
18.1 The General Structure of Nucleic Acids
18.2 Components of Deoxyribonucleic Acid (DNA)
18.3 Nucleosides
18.4 Nucleotides
18.5 The Primary Structure of DNA
18.6 Sequencing Nucleic Acids A Word About: DNA and Crime
18.7 Laboratory Synthesis of Nucleic Acids
18.8 Secondary DNA Structure; the Double Helix
18.9 DNA Replication
18.10 Ribonucleic Acids; RNA
18.11 The Genetic Code and Protein Biosynthesis A Word About: The Human Genome A Word About: Nucleic Acids and Viruses
18.12 Other Biologically Important Nucleotides Reaction Summary

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