Principles of Organic Chemistry

1st Edition - January 27, 2015
Authors: Robert J. Ouellette, J. David Rawn
Language: English
Paperback ISBN:
9 7 8 - 0 - 1 2 - 8 0 2 4 4 4 - 7
eBook ISBN:
9 7 8 - 0 - 1 2 - 8 0 2 6 3 4 - 2

Class-tested and thoughtfully designed for student engagement, Principles of Organic Chemistry provides the tools and foundations needed by students in a short course or one-semes… Read more

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Class-tested and thoughtfully designed for student engagement, Principles of Organic Chemistry provides the tools and foundations needed by students in a short course or one-semester class on the subject. This book does not dilute the material or rely on rote memorization. Rather, it focuses on the underlying principles in order to make accessible the science that underpins so much of our day-to-day lives, as well as present further study and practice in medical and scientific fields. This book provides context and structure for learning the fundamental principles of organic chemistry, enabling the reader to proceed from simple to complex examples in a systematic and logical way.

Utilizing clear and consistently colored figures, Principles of Organic Chemistry begins by exploring the step-by-step processes (or mechanisms) by which reactions occur to create molecular structures. It then describes some of the many ways these reactions make new compounds, examined by functional groups and corresponding common reaction mechanisms. Throughout, this book includes biochemical and pharmaceutical examples with varying degrees of difficulty, with worked answers and without, as well as advanced topics in later chapters for optional coverage.

1: Structure of Organic Compounds

1.1 Organic and Inorganic Compounds
1.2 Atomic Structure
1.3 Types of Bonds
1.4 Formal Charge
1.5 Resonance Structures
1.6 Predicting the Shapes of Simple Molecules
1.7 Orbitals and Molecular Shapes
1.8 Functional Groups
1.9 Structural Formulas
1.10 Isomers
1.11 Nomenclature
Exercises

2: Properties of Organic Compounds

2.1 Structure and Physical Properties
2.2 Chemical Reactions
2.3 Acid–Base Reactions
2.4 Oxidation-Reduction Reactions
2.5 Classification of Organic Reactions
2.6 Chemical Equilibrium and Equilibrium Constants
2.7 Equilibria in Acid-Base Reactions
2.8 Effect of Structure on Acidity
2.9 Introduction to Reaction Mechanisms
2.10 Reaction Rates
Exercises

3: Alkanes and Cycloalkanes

3.1 Classes of Hydrocarbons
3.2 Alkanes
3.3 Nomenclature of Alkanes
3.4 Conformations of Alkanes
3.5 Cycloalkanes
3.6 Conformations of Cycloalkanes
3.7 Physical Properties of Alkanes
3.8 Oxidation of Alkanes and Cycloalkanes
3.9 Halogenation of Saturated Alkanes
3.10 Nomenclature of Haloalkanes
Summary of Reactions
Exercises

4: Alkenes and Alkynes

4.1 Unsaturated Hydrocarbons
4.2 Geometric Isomerism
4.3 E,Z Nomenclature of Geometrical
4.4 Nomenclature of Alkenes and Alkynes
4.5 Acidity of Alkenes and Alkynes
4.6 Hydrogenation of Alkenes and Alkynes
4.7 Oxidation of Alkenes and Alkynes
4.8 Addition Reactions of Alkenes and Alkynes
4.9 Mechanism of Addition Reactions
4.10 Hydration of Alkenes and Alkynes
4.11 Preparation of Alkenes and Alkynes
4.12 Alkadienes (Dienes)
4.13 Terpenes
Summary of Reactions
Exercises

5: Aromatic Compounds

5.1 Aromatic Compounds
5.2 Aromaticity
5.3 Nomenclature of Aromatic Compounds
5.4 Electrophilic Aromatic Substitution
5.5 Structural Effects in Electrophilic Aromatic Substitution
5.6 Interpretation of Rate Effects
5.7 Interpretation of Directing Effects
5.8 Reactions of Side Chains
5.9 Functional Group Modification
5.10 Synthesis of Substituted Aromatic Compounds
Summary of Reactions
Exercises

6: Stereochemistry

6.1 Configuration of Molecules
6.2 Mirror Images and Chirality
6.3 Optical Activity
6.4 Fischer Projection Formulas
6.5 Absolute Configuration
6.6 Molecules with Multiple Stereogenic Centers
6.7 Synthesis of Stereoisomers
6.8 Reactions that Produce Stereogenic Centers
6.9 Reactions that form Diastereomers
Exercises

7: Nucleophilic Substitution and Elimination Reactions

7.1 Reaction Mechanisms and Haloalkanes
7.2 Nucleophilic Substitution Reactions
7.3 Nucleophilicity Versus Basicity
7.4 Mechanisms of Substitution Reactions
7.5 S_N2 Versus S_N1 Reactions
7.6 Mechanisms of Elimination Reactions
7.7 Effect of Structure on Competing Reactions
Summary of Reactions
Exercises

8: Alcohols and Phenols

8.1 The Hydroxyl Group
8.2 Physical Properties of Alcohols
8.3 Acid–Base Reactions of alcohols
8.4 Substitution Reactions of Alcohols
8.5 Dehydration of Alcohols
8.6 Oxidation of Alcohols
8.7 Synthesis of Alcohols
8.8 Phenols
8.9 Sulfur Compounds: Thiols and Thioethers
Summary of Reactions
Exercises

9: Ethers and Epoxides

9.1 Structure of Ethers
9.2 Nomenclature of Ethers
9.3 Physical Properties of Ethers
9.4 The Grignard Reagent and Ethers
9.5 Synthesis of Ethers
9.6 Reactions of Ethers
9.7 Synthesis of Epoxides
9.8 Reactions of Epoxides
Summary of Reactions
Exercises

10: Aldehydes and Ketones

10.1 The Carbonyl Group
10.2 Nomenclature of Aldehydes and Ketones
10.3 Physical Properties of Aldehydes and Ketones
10.4 Oxidation-Reduction Reactions of Carbonyl Compounds
10.5 Addition Reactions of Carbonyl Compounds
10.6 Synthesis of Alcohols from Carbonyl Compounds
10.7 Addition Reactions of Oxygen Compounds
10.8 Formation of Acetals and Ketals
10.9 Addition of Nitrogen Compounds
10.10 Reactivity of the α-Carbon Atom
10.11 The Aldol Condensation
Summary of Reactions
Exercises

11: Carboxylic Acids and Esters

11.1 Carboxylic Acids and Acyl Groups
11.2 Nomenclature of Carboxylic Acids
11.3 Physical Properties of Carboxylic Acids
11.4 Acidity of Carboxylic Acids
11.5 Synthesis of Carboxylic Acids
11.6 Nucleophilic Acyl Substitution
11.7 Reduction of Acyl Derivatives
11.8 Esters and Anhydrides of Phosphoric Acid
11.9 The Claisen Condensation
Summary of Reactions
Exercises

12: Amines and Amides

12.1 Organic Nitrogen Compounds
12.2 Bonding and Structure of Amines
12.3 Structure and Classification of Amines and Amides
12.4 Nomenclature of Amines and Amides
12.5 Physical Properties of Amines
12.6 Basicity of Nitrogen Compounds
12.7 Solubility of Ammonium Salts
12.8 Nucleophilic Reactions of Amines
12.9 Synthesis of Amines
12.10 Hydrolysis of Amides
12.11 Synthesis of Amides
Summary of Reactions
Exercises

13: Carbohydrates

13.1 Classification of Carbohydrates
13.2 Chirality of Carbohydrates
13.3 Hemiacetals and Hemiketals
13.4 Conformations of Monosaccharides
13.5 Reduction of Monosaccharides
13.6 Oxidation of Monosaccharides
13.7 Glycosides
13.8 Disaccharides
13.9 Polysaccharides
Summary of Reactions
Exercises

14: Amino Acids, Peptides, and Proteins

14.1 Proteins and Polypeptides
14.2 Amino Acids
14.3 Acid–Base Properties of α-Amino Acids
14.4 Isoionic Point
14.5 Peptides
14.6 Peptide Synthesis
14.7 Determination of Protein Structure
14.8 Protein Structure
Exercises

15: Synthetic Polymers

15.1 Natural and Synthetic Macromolecules
15.2 Structure and Properties of Polymers
15.3 Classification of Polymers
15.4 Methods of Polymerization
15.5 Addition Polymerization
15.6 Copolymerization of Alkenes
15.7 Cross-Linked Polymers
15.8 Stereochemistry of Addition Polymerization
15.9 Condensation Polymers
15.10 Polyesters
15.11 Polycarbonates
15.12 Polyamides
15.13 Polyurethanes
Exercises

16: Spectroscopy

16.1 Spectroscopic Structure Determination
16.2 Spectroscopic Principles
16.3 Ultraviolet Spectroscopy
16.4 Infrared Spectroscopy
16.5 Nuclear Magnetic Resonance Spectroscopy
16.6 Spin-Spin Splitting
16.7 ¹³C NMR Spectroscopy
Exercises

Solutions to In-Chapter Problems

Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Chapter 14
Chapter 15
Chapter 16

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Robert J. Ouellette

J. David Rawn