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Fundamentals of General, Organic, and Biological Chemistryby McMurry, Ballantine, Hoeger, and Peterson provides the background in chemistry and biochemistry essential for allied health students, while ensuring students in other disciplines gain an appreciation of chemistry's significance in everyday life. Unlike many texts on this subject, it is clear and concise, punctuated with practical and familiar examples from students' personal experiences. An exceptional balance of chemical concepts explains the quantitative aspects of chemistry, and provides deeper insight into theoretical chemical principles. It also sets itself apart by requiring students to master concepts before they can move on to the next chapter. The Seventh Editionfocuses on making connections between General, Organic, and Biological Chemistry with a number of new and updated featuresincluding all-new Mastering Reactions boxes, new and updated Chemistry in Action boxes (formerly titled Applications), new and revised chapter problems that strengthen the ties between major concepts in each chapter and practical applications, and much more.
John McMurry, educated at Harvard and Columbia, has taught approximately 17,000 students in general and organic chemistry over a 30-year period. A Professor of Chemistry at Cornell University since 1980, Dr. McMurry previously spent 13 years on the faculty at the University of California at Santa Cruz. He has received numerous awards, including the Alfred P. Sloan Fellowship (1969—71), the National Institute of Health Career Development Award (1975—80), the Alexander von Humboldt Senior Scientist Award (1986—87), and the Max Planck Research Award (1991).
David S. Ballantine received his B.S. in Chemistry in 1977 from the College of William and Mary in Williamsburg, VA, and his Ph.D. in Chemistry in 1983 from the University of Maryland at College Park. After several years as a researcher at the Naval Research Labs in Washington, DC, he joined the faculty in the Department of Chemistry and Biochemistry of Northern Illinois University, where he has been a professor since 1989. He was awarded the Excellence in Undergraduate Teaching Award in 1998 and has been departmental Director of Undergraduate Studies since 2008. In addition, he is the coordinator for the Introductory and General Chemistry programs, and is responsible for supervision of the laboratory teaching assistants.
Carl A. Hoeger received his B.S. in Chemistry from San Diego State University and his Ph.D. in Organic Chemistry from the University of Wisconsin, Madison in 1983. After a postdoctoral stint at the University of California, Riverside, he joined the Peptide Biology Laboratory at the Salk Institute in 1985 where he ran the NIH Peptide Facility while doing basic research in the development of peptide agonists and antagonists. During this time he also taught general, organic, and biochemistry at San Diego City College, Palomar College, and Miramar College. He joined the teaching faculty at University of California, San Diego in 1998. Dr. Hoeger has been teaching chemistry to undergraduates for over 20 years, where he continues to explore the use of technology in the classroom; his current project involves the use of video podcasts as adjuncts to live lectures. In 2004 he won the Paul and Barbara Saltman Distinguished Teaching Award from UCSD. He is deeply involved with the General Chemistry program at UCSD, and also shares partial responsibility for the training and guidance of teaching assistants in the Chemistry and Biochemistry departments.
Virginia E. Peterson received her B.S. in Chemistry in 1967 from the University of Washington in Seattle, and her Ph.D. in Biochemistry in 1980 from the University of Maryland at College Park. Between her undergraduate and graduate years she worked in lipid, diabetes, and heart disease research at Stanford University. Following her Ph.D. she took a position in the Biochemistry Department at the University of Missouri in Columbia and is now Professor Emerita. When she retired in2011 she had been the Director of Undergraduate Advising for the department for 8 years and had taught both senior capstone classes and biochemistry classes for nonscience majors. Although retired Dr. Peterson continues to advise undergraduates and teach classes. Awards include both the college level and the university-wide Excellence in Teaching Award and, in 2006, the University’s Outstanding Advisor Award and the State of Missouri Outstanding University Advisor Award. Dr. Peterson believes in public service and in 2003 received the Silver Beaver Award for service from the Boy Scouts of America.
Table of Contents
1. Matter and Measurements 1.1 Chemistry: The Central Science 1.2 States of Matter 1.3 Classification of Matter 1.4 Chemical Elements and Symbols 1.5 Elements and the Periodic Table 1.6 Chemical Reaction: An Example of a Chemical Change 1.7 Physical Quantities 1.8 Measuring Mass, Length, and Volume 1.9 Measurement and Significant Figures 1.10 Scientific Notation 1.11 Rounding Off Numbers 1.12 Problem Solving: Unit Conversions and Estimating Answers 1.13 Temperature, Heat, and Energy 1.14 Density and Specific Gravity
2. Atoms and the Periodic Table 2.1 Atomic Theory 2.2 Elements and Atomic Number 2.3 Isotopes and Atomic Weight 2.4 The Periodic Table 2.5 Some Characteristics of Different Groups 2.6 Electronic Structure of Atoms 2.7 Electron Configurations 2.8 Electron Configurations and the Periodic Table 2.9 Electron-Dot Symbols
3. Ionic Compounds 3.1 Ions 3.2 Periodic Properties and Ion Formation 3.3 Ionic Bonds 3.4 Some Properties of Ionic Compounds 3.5 Ions and the Octet Rule 3.6 Ions of Some Common Elements 3.7 Naming Ions 3.8 Polyatomic Ions 3.9 Formulas of Ionic Compounds 3.10 Naming Ionic Compounds 3.11 H _ and OH _ Ions: An Introduction to Acids and Bases
4. Molecular Compounds 4.1 Covalent Bonds 4.2 Covalent Bonds and the Periodic Table 4.3 Multiple Covalent Bonds 4.4 Coordinate Covalent Bonds 4.5 Characteristics of Molecular Compounds 4.6 Molecular Formulas and Lewis Structures 4.7 Drawing Lewis Structures 4.8 The Shapes of Molecules 4.9 Polar Covalent Bonds and Electronegativity 4.10 Polar Molecules 4.11 Naming Binary Molecular Compounds
5. Classification and Balancing of Chemical Reactions 5.1 Chemical Equations 5.2 Balancing Chemical Equations 5.3 Classes of Chemical Reactions 5.4 Precipitation Reactions and Solubility Guidelines 5.5 Acids, Bases, and Neutralization Reactions 5.6 Redox Reactions 5.7 Recognizing Redox Reactions 5.8 Net Ionic Equations
6. Chemical Reactions: Mole and Mass Relationships 6.1 The Mole and Avogadro’s Number 6.2 Gram—Mole Conversions 6.3 Mole Relationships and Chemical Equations 6.4 Mass Relationships and Chemical Equations 6.5 Limiting Reagent and Percent Yield
7. Chemical Reactions: Energy, Rates, and Equilibrium 7.1 Energy and Chemical Bonds 7.2 Heat Changes during Chemical Reactions 7.3 Exothermic and Endothermic Reactions 7.4 Why Do Chemical Reactions Occur? Free Energy 7.5 How Do Chemical Reactions Occur? Reaction Rates 7.6 Effects of Temperature, Concentration, and Catalysts on Reaction Rates 7.7 Reversible Reactions and Chemical Equilibrium 7.8 Equilibrium Equations and Equilibrium Constants 7.9 Le Châtelier’s Principle: The Effect of Changing Conditions on Equilibria
8. Gases, Liquids, and Solids 8.1 States of Matter and Their Changes 8.2 Intermolecular Forces 8.3 Gases and the Kinetic—Molecular Theory 8.4 Pressure 8.5 Boyle’s Law: The Relation between Volume and Pressure 8.6 Charles’s Law: The Relation between Volume and Temperature 8.7 Gay-Lussac’s Law: The Relation between Pressure and Temperature 8.8 The Combined Gas Law 8.9 Avogadro’s Law: The Relation between Volume and Molar Amount 8.10 The Ideal Gas Law 8.11 Partial Pressure and Dalton’s Law 8.12 Liquids 8.13 Water: A Unique Liquid 8.14 Solids 8.15 Changes of State
9. Solutions 9.1 Mixtures and Solutions 9.2 The Solution Process 9.3 Solid Hydrates 9.4 Solubility 9.5 The Effect of Temperature on Solubility 9.6 The Effect of Pressure on Solubility: Henry’s Law 9.7 Units of Concentration 9.8 Dilution 9.9 Ions in Solution: Electrolytes 9.10 Electrolytes in Body Fluids: Equivalents and Milliequivalents 9.11 Properties of Solutions 9.12 Osmosis and Osmotic Pressure 9.13 Dialysis
10. Acids and Bases 10.1 Acids and Bases in Aqueous Solution 10.2 Some Common Acids and Bases 10.3 The Brønsted—Lowry Definition of Acids and Bases 10.4 Acid and Base Strength 10.5 Acid Dissociation Constants 10.6 Water as Both an Acid and a Base 10.7 Measuring Acidity in Aqueous Solution: pH 10.8 Working with pH 10.9 Laboratory Determination of Acidity 10.10 Buffer Solutions 10.11 Acid and Base Equivalents 10.12 Some Common Acid—Base Reactions 10.13 Titration 10.14 Acidity and Basicity of Salt Solutions
11. Nuclear Chemistry 11.1 Nuclear Reactions 11.2 The Discovery and Nature of Radioactivity 11.3 Stable and Unstable Isotopes 11.4 Nuclear Decay 11.5 Radioactive Half-Life 11.6 Radioactive Decay Series 11.7 Ionizing Radiation 11.8 Detecting Radiation 11.9 Measuring Radiation 11.10 Artificial Transmutation 11.11 Nuclear Fission and Nuclear Fusion
12. Introduction to Organic Chemistry: Alkanes 12.1 The Nature of Organic Molecules 12.2 Families of Organic Molecules: Functional Groups 12.3 The Structure of Organic Molecules: Alkanes and Their Isomers 12.4 Drawing Organic Structures 12.5 The Shapes of Organic Molecules 12.6 Naming Alkanes 12.7 Properties of Alkanes 12.8 Reactions of Alkanes 12.9 Cycloalkanes 12.10 Drawing and Naming Cycloalkanes
13. Alkenes, Alkynes, and Aromatic Compounds 13.1 Alkenes and Alkynes 13.2 Naming Alkenes and Alkynes 13.3 The Structure of Alkenes: Cis—Trans Isomerism 13.4 Properties of Alkenes and Alkynes 13.5 Types of Organic Reactions 13.6 Reactions of Alkenes and Alkynes 13.7 Alkene Polymers 13.8 Aromatic Compounds and the Structure of Benzene 13.9 Naming Aromatic Compounds 13.10 Reactions of Aromatic Compounds
14. Some Compounds with Oxygen, Sulfur, or a Halogen 14.1. Alcohols, Phenols, and Ethers 14.2. Some Common Alcohols 14.3. Naming Alcohols 14.4. Properties of Alcohols 14.5. Reactions of Alcohols 14.6. Phenols 14.7. Acidity of Alcohols and Phenols 14.8. Ethers 14.9. Thiols and Disulfides 14.10. Halogen-Containing Compounds
15. Amines 15.1. Amines 15.2. Properties of Amines 15.3. Heterocyclic Nitrogen Compounds 15.4. Basicity of Amines 15.5. Amine Salts 15.6. Amines in Plants: Alkaloids
16. Aldehydes and Ketones 16.1. The Carbonyl Group 16.2. Naming Aldehydes and Ketones 16.3. Properties of Aldehydes and Ketones 16.4. Some Common Aldehydes and Ketones 16.5. Oxidation of Aldehydes 16.6. Reduction of Aldehydes and Ketones 16.7. Addition of Alcohols: Hemiacetals and Acetals
17. Carboxylic Acids and their Derivatives 17.1. Carboxylic Acids and Their Derivatives: Properties and Names 17.2. Some Common Carboxylic Acids 17.3. Acidity of Carboxylic Acids 17.4. Reactions of Carboxylic Acids: Ester and Amide Formation 17.5. Aspirin and Other Over-the-Counter Carboxylic Acid 17.6. Hydrolysis of Esters and Amides 17.7. Polyamides and Polyesters 17.8. Phosphoric Acid Derivatives
18. Amino Acids and Proteins 18.1 An Introduction to Biochemistry 18.2 Protein Structure and Function: An Overview 18.3 Amino Acids 18.4 Acid—Base Properties of Amino Acids 18.5 Handedness 18.6 Molecular Handedness and Amino Acids 18.7 Primary Protein Structure 18.8 Shape-Determining Interactions in Proteins 18.9 Secondary Protein Structure 18.10 Tertiary Protein Structure 18.11 Quaternary Protein Structure 18.12 Chemical Properties of Proteins
19. Enzymes and Vitamins 19.1 Catalysis by Enzymes 19.2 Enzyme Cofactors 19.3 Enzyme Classification 19.4 How Enzymes Work 19.5 Effect of Concentration on Enzyme Activity 19.6 Effect of Temperature and pH on Enzyme Activity 19.7 Enzyme Regulation: Feedback and Allosteric Control 19.8 Enzyme Regulation: Inhibition 19.9 Enzyme Regulation: Covalent Modification and Genetic Control 19.10 Vitamins and Minerals
20. The Generation of Biochemical Energy 20.1. Energy and Life 20.2. Energy and Biochemical Reactions 20.3. Cells and Their Structure 20.4. An Overview of Metabolism and Energy Production 20.5. Strategies of Metabolism: ATP and Energy Transfer 20.6. Strategies of Metabolism: Metabolic Pathways and Coupled Reactions 20.7. Strategies of Metabolism: Oxidized and Reduced Coenzymes 20.8. The Citric Acid Cycle 20.9. The Electron-Transport Chain and ATP Production 20.10. Harmful Oxygen By-Products and Antioxidant Vitamins
21. Carbohydrates 21.1 An Introduction to Carbohydrates 21.2. Handedness of Carbohydrates 21.3. The D and L Families of Sugars: Drawing Sugar Molecules 21.4. Structure of Glucose and Other Monosaccharides 21.5. Some Important Monosaccharides 21.6. Reactions of Monosaccharides 21.7. Disaccharides 21.8. Variations on the Carbohydrate Theme 21.9. Some Important Polysaccharides
22. Carbohydrate Metabolism 22.1. Digestion of Carbohydrates 22.2. Glucose Metabolism: An Overview 22.3. Glycolysis 22.4. Entry of Other Sugars into Glycolysis 22.5. The Fate of Pyruvate 22.6. Energy Output in Complete Catabolism of Glucose 22.7. Regulation of Glucose Metabolism and Energy Production 22.8. Metabolism in Fasting and Starvation 22.9. Metabolism in Diabetes Mellitus 22.10. Glycogen Metabolism: Glycogenesis and Glycogenolysis 22.11. Gluconeogenesis: Glucose from Noncarbohydrates
23. Lipids 23.1. Structure and Classification of Lipids 23.2. Fatty Acids and Their Esters 23.3. Properties of Fats and Oils 23.4. Chemical Reactions of Triacylglycerols 23.5. Phospholipids and Glycolipids 23.6. Sterols 23.7. Structure of Cell Membranes 23.8. Transport Across Cell Membranes 23.9. Eicosanoids: Prostaglandins and Leukotrienes
24. Lipid Metabolism 24.1 Digestion of Triacylglycerols 24.2. Lipoproteins for Lipid Transport 24.3. Triacylglycerol Metabolism: An Overview 24.4. Storage and Mobilization of Triacylglycerols 24.5. Oxidation of Fatty Acids 24.6. Energy from Fatty Acid Oxidation 24.7. Ketone Bodies and Ketoacidosis 24.8. Biosynthesis of Fatty Acids
25. Nucleic Acids and Protein Synthesis 25.1. DNA, Chromosomes, and Genes 25.2. Composition of Nucleic Acids 25.3. The Structure of Nucleic Acid Chains 25.4. Base Pairing in DNA: The Watson—Crick Model 25.5. Nucleic Acids and Heredity 25.6. Replication of DNA 25.7. Structure and Function of RNA 25.8. Transcription: RNA Synthesis 25.9. The Genetic Code 25.10. Translation: Transfer RNA and Protein Synthesis
26. Genomics 26.1. Mapping the Human Genome 26.2. A Trip Along a Chromosome 26.3. Mutations and Polymorphisms 26.4. Recombinant DNA 26.5. Genomics: Using What We Know
27. Protein and Amino Acid Metabolism 27.1. Digestion of Proteins 27.2. Amino Acid Metabolism: An Overview 27.3. Amino Acid Catabolism: The Amino Group 27.4. The Urea Cycle 27.5. Amino Acid Catabolism: The Carbon Atoms 27.6. Biosynthesis of Nonessential Amino Acids
28. Chemical Messengers: Hormones, Neurotransmitters, and Drugs 28.1. Messenger Molecules 28.2. Hormones and the Endocrine System 28.3. How Hormones Work: Epinephrine and Fight-or-Flight 28.4. Amino Acid Derivatives and Polypeptides as Hormones 28.5. Steroid Hormones 28.6. Neurotransmitters 28.7. How Neurotransmitters Work: Acetylcholine, Its Agonists and Antagonists 28.8. Histamine and Antihistamines 28.9. Serotonin, Norepinephrine, and Dopamine 28.10. Neuropeptides and Pain Relief 28.11. Drug Discovery and Drug Design
29. Body Fluids 29.1 Body Water and Its Solutes 29.2. Fluid Balance 29.3. Blood 29.4. Plasma Proteins, White Blood Cells, and Immunity 29.5. Blood Clotting 29.6. Red Blood Cells and Blood Gases 29.7. The Kidney and Urine Formation 29.8. Urine Composition and Function