Organic Chemistry : A Brief Introduction

by Ouellette, Robert J.

• ISBN13: 9780138419332
• ISBN10: 0138419337
• Edition: 2nd
• Format: Paperback
• Copyright: 1997-08-28
• Publisher: Prentice Hall

Summary

Discussing difficult concepts with exceptional clarity, this book integrates synthetic organic chemistry with medical, pharmaceutical, and biological chemistry, and helps readers clearly define the relationship of organic chemistry to their particular occupation.The book provides numerous problems, exercises, and examples of the physical and chemical properties of bio-organic molecules, and presents complex organic structures on a continual basis throughout, enabling users to focus on relevant functional groups before covering advanced material on chemical reactions. It includes an extensive two-chapter review of general chemistry and offers chapter essays to examine material in greater depth.For nursing, agriculture, and other health and life science professionals.

Table of Contents

Preface	xi
1 Structure of Organic Compounds	1	(35)
1.1 Inorganic and Organic Compounds	1	(1)
1.2 Atomic Structure	2	(1)
1.3 Atomic Properties	3	(2)
1.4 Types of Bonds	5	(3)
1.5 Formal Charge	8	(2)
1.6 Resonance Structures	10	(2)
1.7 Predicting the Shapes of Simple Molecules	12	(2)
1.8 Orbitals and Molecular Shapes	14	(4)
1.9 Functional Groups	18	(3)
1.10 Structural Formulas	21	(5)
1.11 Isomers	26	(3)
1.12 Nomenclature	29	(1)
Explorations with Molecular Models	30	(1)
Exercises	31
Essay Pheromones--Chemical Communications in the Insect World	22
2 Properties of Organic Compounds	36	(33)
2.1 Structure and Physical Properties	36	(5)
2.2 Chemical Reactions	41	(2)
2.3 Acid-Base Reactions	43	(2)
2.4 Oxidation-Reduction Reactions	45	(3)
2.5 Classification of Organic Reactions	48	(2)
2.6 Chemical Equilibrium	50	(1)
2.7 Equilibria in Acid-Base Reactions	51	(3)
2.8 Structure and Acidity	54	(2)
2.9 Reaction Mechanisms	56	(2)
2.10 Reaction Rates	58	(4)
Explorations with Molecular Models	62	(1)
Exercises	63
Essays
Water-Soluble and Fat-Soluble Vitamins	42
Redox Reactions in Biochemistry	47
3 Alkanes and Cycloalkanes	69	(32)
3.1 Classes of Hydrocarbons	69	(1)
3.2 Alkanes	70	(2)
3.3 Nomenclature of Alkanes	72	(4)
3.4 Conformations of Alkanes	76	(3)
3.5 Cycloalkanes	79	(3)
3.6 Conformations of Cycloalkanes	82	(3)
3.7 Physical Properties of Saturated Hydrocarbons	85	(2)
3.8 Oxidation of Alkanes and Cycloalkanes	87	(2)
3.9 Halogenation of Saturated Hydrocarbons	89	(2)
3.10 Nomenclature of Haloalkanes	91	(3)
Summary of Reactions	94	(1)
Explorations with Molecular Models	95	(1)
Exercises	96
Essays
Steroids	86
Freons, Free Radicals, and the Ozone Layer	92
4 Alkenes and Alkynes	101	(37)
4.1 Unsaturated Hydrocarbons	101	(4)
4.2 Geometric Isomerism	105	(2)
4.3 The E,Z Designation of Geometric Isomers	107	(2)
4.4 Nomenclature of Alkenes and Alkynes	109	(3)
4.5 Acidity of Alkenes and Alkynes	112	(1)
4.6 Hydrogenation of Alkenes and Alkynes	113	(3)
4.7 Oxidation of Alkenes and Alkynes	116	(1)
4.8 Addition Reactions of Alkenes and Alkynes	117	(2)
4.9 Mechanism of Addition Reactions	119	(2)
4.10 Hydration of Alkenes and Alkynes	121	(1)
4.11 Polymerization of Alkenes	122	(2)
4.12 Preparation of Alkenes and Alkynes	124	(2)
4.13 Alkadienes	126	(2)
4.14 Terpenes	128	(1)
Summary of Reactions	129	(2)
Explorations with Molecular Models	131	(1)
Exercises	132
Essay Allylic Oxidation in Metabolic Reactions	127
5 Aromatic Compounds	138	(33)
5.1 Substituted Benzene Compounds	138	(1)
5.2 Aromaticity	139	(2)
5.3 Polycyclic and Heterocyclic Aromatic Compounds	141	(4)
5.4 Nomenclature of Benzene Compounds	145	(3)
5.5 Electrophilic Aromatic Substitution	148	(3)
5.6 Structural Effects in Electrophilic Aromatic Substitution	151	(2)
5.7 Interpretation of Rate Effects	153	(2)
5.8 Interpretation of Directing Effects	155	(2)
5.9 Reactions of Side Chains	157	(3)
5.10 Functional Group Modification	160	(2)
5.11 Synthesis of Substituted Aromatic Compounds	162	(2)
Summary of Reactions	164	(2)
Explorations with Molecular Models	166	(1)
Exercises	166
Essay Substituent Effects on Metabolism of Benzene Derivatives	158
6 Stereochemistry	171	(25)
6.1 Configuration of Molecules	171	(1)
6.2 Mirror Images and Chirality	172	(4)
6.3 Optical Activity	176	(2)
6.4 Fischer Projection Formulas	178	(2)
6.5 Absolute Configuration	180	(4)
6.6 Multiple Stereogenic Centers	184	(4)
6.7 Synthesis of Stereoisomers	188	(2)
6.8 Reactions of Chiral Compounds	190	(1)
Explorations with Molecular Models	191	(1)
Exercises	192
Essay
Metabolism May Vary By Species and Within Species	186
Chirality and Your Senses	189
7 Nucleophilic Substitution and Elimination Reactions	196	(21)
7.1 Reaction Mechanisms and Haloalkanes	196	(2)
7.2 Nucleophilic Substitution Reactions	198	(3)
7.3 Nucleophilicity versus Basicity	201	(1)
7.4 Mechanisms of Substitution Reactions	202	(5)
7.5 S(N)2 Versus S(N)1 Reactions	207	(2)
7.6 Mechanisms of Elimination Reactions	209	(1)
7.7 Effect of Structure on Competing Reactions	210	(3)
Summary of Reactions	213	(1)
Explorations with Molecular Models	213	(1)
Exercises	214
Essays
Halogen Compounds in Ocean Organisms	199
Biological Substitution Reactions with Sulfur Compounds	203
8 Alcohols and Phenols	217	(31)
8.1 The Hydroxyl Group	217	(2)
8.2 Classification and Nomenclature of Alcohols	219	(2)
8.3 Physical Properties of Alcohols	221	(2)
8.4 Acid-Base Reactions of Alcohols	223	(2)
8.5 Substitution Reactions of Alcohols	225	(1)
8.6 Dehydration of Alcohols	226	(2)
8.7 Oxidation of Alcohols	228	(1)
8.8 Synthesis of Alcohols	229	(6)
8.9 Phenols	235	(3)
8.10 Sulfur Compounds	238	(2)
Summary of Reactions	240	(2)
Explorations with Molecular Models	242	(1)
Exercises	242
Essays
Toxicity of Alcohols	230
Industrial Synthesis of Alcohols	236
Phenols are Germicides	239
9 Ethers and Epoxides	248	(18)
9.1 Ethers	248	(1)
9.2 Nomenclature of Ethers	249	(2)
9.3 Physical Properties of Ethers	251	(1)
9.4 The Grignard Reagent and Ethers	252	(2)
9.5 Synthesis of Ethers	254	(1)
9.6 Reactions of Ethers	255	(2)
9.7 Synthesis of Epoxides	257	(1)
9.8 Reactions of Epoxides	257	(4)
Summary of Reactions	261	(1)
Explorations with Molecular Models	262	(1)
Exercises	263
Essays
Polyethers in the Laboratory and in Nature	253
Ring Opening of Biological Epoxides	260
10 Aldehydes and Ketones	266	(33)
10.1 The Carbonyl Group	266	(2)
10.2 Nomenclature of Aldehydes and Ketones	268	(4)
10.3 Physical Properties of Aldehydes and Ketones	272	(1)
10.4 Redox Reactions of Carbonyl Compounds	273	(3)
10.5 Addition Reactions of Carbonyl Compounds	276	(2)
10.6 Synthesis of Alcohols from Carbonyl Compounds	278	(2)
10.7 Addition of Oxygen Compounds	280	(3)
10.8 Formation of Acetals and Ketals	283	(2)
10.9 Addition of Nitrogen Compounds	285	(2)
10.10 Reactivity of the ALPHA-Carbon Atom	287	(2)
10.11 The Aldol Condensation	289	(3)
Summary of Reactions	292	(1)
Explorations with Molecular Models	293	(1)
Exercises	294
Essays
Oral Contraceptives	281
Addition Reactions and Vision	286
11 Carbohydrates	299	(31)
11.1 Classification of Carbohydrates	299	(1)
11.2 Chirality of Monosaccharides	300	(6)
11.3 Hemiacetals and Hemiketals	306	(4)
11.4 Conformations of Monosaccharides	310	(2)
11.5 Reduction of Monosaccharides	312	(1)
11.6 Oxidation of Carbohydrates	313	(1)
11.7 Glycosides	314	(2)
11.8 Disaccharides	316	(5)
11.9 Polysaccharides	321	(3)
Summary of Reactions	324	(1)
Explorations with Molecular Models	325	(1)
Exercises	325
Essays
Metabolism of Lactose	320
Human Blood Groups	323
12 Carboxylic Acids and Esters	330	(37)
12.1 The Carboxyl and Acyl Groups	330	(2)
12.2 Nomenclature of Carboxylic Acid Derivatives	332	(4)
12.3 Physical Properties of Carboxylic Acids and Esters	336	(4)
12.4 Acidity of Carboxylic Acids	340	(2)
12.5 Synthesis of Carboxylic Acids	342	(2)
12.6 Nucleophilic Acyl Substitution	344	(4)
12.7 Reduction of Acyl Derivatives	348	(3)
12.8 Synthesis of Esters	351	(1)
12.9 Hydrolysis of Esters	352	(4)
12.10 The Claisen Condensation	356	(2)
Summary of Reactions	358	(1)
Explorations with Molecular Models	359	(1)
Exercises	360
Essays
Industrial Synthesis of Acetic Acid	337
Thioesters Are Nature's Active Acyl Compounds	348
Polyesters	352
Esters and Anhydrides of Phosphoric Acid	354
13 Lipids	367	(22)
13.1 Classification of Lipids	367	(1)
13.2 Waxes	368	(1)
13.3 Fatty Acids	369	(2)
13.4 Triacylglycerols	371	(2)
13.5 Hydrogenation of Vegetable Oils	373	(1)
13.6 Saponification of Triacylglycerols	374	(2)
13.7 Glycerophospholipids	376	(2)
13.8 Sphingophospholipids	378	(1)
13.9 Glycosphingolipids	379	(1)
13.10 Biological Membranes	380	(3)
13.11 Transport Across Membranes	383	(2)
Summary of Reactions	385	(1)
Explorations with Molecular Models	385	(1)
Exercises	386
Essays
Prostaglandins	372
Sleep Disorders and Brain Lipids	384
14 Amines and Amides	389	(30)
14.1 Organic Nitrogen Compounds	389	(2)
14.2 Structure and Classification of Amines and Amides	391	(2)
14.3 Nomenclature of Amines and Amides	393	(3)
14.4 Physical Properties of Amines and Amides	396	(2)
14.5 Basicity of Nitrogen Compounds	398	(5)
14.6 Solubility of Ammonium Salts	403	(1)
14.7 Nucleophilic Reactions of Amines	404	(2)
14.8 Synthesis of Amines	406	(2)
14.9 Hydrolysis of Amides	408	(1)
14.10 Synthesis of Amides	409	(2)
Summary of Reactions	411	(1)
Explorations with Molecular Models	412	(1)
Exercises	413
Essays
Amphetamines	399
Polyamides	410
15 Amino Acids, Peptides, and Proteins	419	(28)
15.1 Proteins and Polypeptides	419	(1)
15.2 Amino Acids	420	(1)
15.3 Acid-Base Properties of Amino Acids	421	(3)
15.4 Isoionic Point	424	(3)
15.5 Peptides	427	(3)
15.6 Synthesis of Peptides	430	(2)
15.7 Structure Determination of Proteins	432	(4)
15.8 Structure of Proteins	436	(7)
Explorations with Molecular Models	443	(1)
Exercises	444
Essays
Essential Amino Acids and Dietary Protein	426
Cholesterol and Lipoproteins	442
16 Nucleic Acids	447	(24)
16.1 The Control of Life Processes	447	(1)
16.2 Nucleic Acids Are Polymers	448	(3)
16.3 Polynucleotides	451	(3)
16.4 The Double Helix of DNA	454	(1)
16.5 DNA Replicates Itself	455	(2)
16.6 The Flow of Genetic Information	457	(1)
16.7 DNA Produces Several Types of RNA	458	(3)
16.8 The Genetic Code	461	(1)
16.9 Protein Synthesis and Translation	462	(6)
Explorations with Molecular Models	468	(1)
Exercises	469
Essay Chemistry and Medicine	464
17 Synthetic Polymers	471	(24)
17.1 Natural and Synthetic Macromolecules	471	(1)
17.2 Structure and Properties of Polymers	472	(3)
17.3 Classification of Polymers	475	(1)
17.4 Methods of Polymerization	476	(3)
17.5 Addition Polymerization	479	(2)
17.6 Copolymerization of Alkenes	481	(1)
17.7 Cross-linked Polymers	482	(1)
17.8 Stereochemistry of Addition Polymerization	483	(2)
17.9 Condensation Polymers	485	(1)
17.10 Polyesters	486	(1)
17.11 Polycarbonates	487	(1)
17.12 Polyamides	488	(2)
17.13 Polyurethanes	490	(1)
Explorations with Molecular Models	491	(1)
Exercises	491
Essay Polyurethanes in Treatment of Cancer	490
18 Spectroscopy	495	(31)
18.1 Structure Determination	495	(1)
18.2 Spectroscopy	496	(2)
18.3 Ultraviolet Spectroscopy	498	(2)
18.4 Infrared Spectroscopy	500	(7)
18.5 Nuclear Magnetic Resonance Spectroscopy	507	(4)
18.6 Spin-Spin Splitting	511	(3)
18.7 (13)C NMR Spectroscopy	514	(6)
Explorations with Molecular Models	520	(1)
Exercises	521
Essay Magnetic Resonance Imaging	515
Answers to Problems	526	(4)
Answers to Odd-Numbered Exercises	530	(17)
Index	547