Introduction to organic and biochemistry

Front Cover
Title Page
Copyright
Contents in Brief
Contents
Chapter 1 Organic Chemistry
	1.1 What Is Organic Chemistry?
	1.2 Where Do We Obtain Organic Compounds?
	1.3 How Do We Write Structural Formulas of Organic Compounds?
	1.4 What Is a Functional Group?
		Summary of Key Questions
		Problems
		Chemical Connections
		1A Taxol: A Story of Search and Discovery
Chapter 2 Alkanes
	2.1 How Do We Write Structural Formulas of Alkanes?
	2.2 What Are Constitutional Isomers?
	2.3 How Do We Name Alkanes?
	2.4 Where Do We Obtain Alkanes?
	2.5 What Are Cycloalkanes?
	2.6 What Are the Shapes of Alkanes and Cycloalkanes?
	2.7 What Is Cis-Trans Isomerism in Cycloalkanes?
	2.8 What Are the Physical Properties of Alkanes?
	2.9 What Are the Characteristic Reactions of Alkanes
	2.10 What Are Some Important Haloalkanes?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		2A The Poisonous Puffer Fish
		2B Octane Rating: What Those Numbers at the Pump Mean
		2C The Environmental Impact of Freons
Chapter 3 Alkenes and Alkynes
	3.1 What Are Alkenes and Alkynes?
	3.2 What Are the Structures of Alkenes and Alkynes?
	3.3 How Do We Name Alkenes and Alkynes?
	3.4 What Are the Physical Properties of Alkenes and Alkynes?
	3.5 What Are Terpenes?
	3.6 What Are the Characteristic Reactions of Alkenes?
	3.7 What Are the Important Polymerization Reactions of Ethylene and Substituted Ethylenes?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		3A Ethylene: A Plant Growth Regulator
		3B The Case of the Iowa and New York Strains of the European Corn Borer
		3C Cis-Trans Isomerism in Vision
		3D Recycling Plastics
Chapter 4 Benzene and Its Derivatives
	4.1 What Is the Structure of Benzene?
	4.2 How Do We Name Aromatic Compounds?
	4.3 What Are the Characteristic Reactions of Benzene and Its Derivatives?
	4.4 What Are Phenols?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		4A Carcinogenic Polynuclear Aromatics and Smoking
		4B Iodide Ion and Goiter
		4C The Nitro Group in Explosives
		4D FD & C No. 6 (a.k.a. Sunset Yellow)
		4E Capsaicin, for Those Who Like It Hot
Chapter 5 Alcohols, Ethers, and Thiols
	5.1 What Are the Structures, Names, and Physical Properties of Alcohols?
	5.2 What Are the Characteristic Reactions of Alcohols?
	5.3 What Are the Structures, Names, and Properties of Ethers?
	5.4 What Are the Structures, Names, and Properties of Thiols?
	5.5 What Are the Most Commercially Important Alcohols?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		5A Nitroglycerin: An Explosive and a Drug
		5B Breath-Alcohol Screening
		5C Ethylene Oxide: A Chemical Sterilant
		5D Ethers and Anesthesia
Chapter 6 Chirality: The Handedness of Molecules
	6.1 What Is Enantiomerism?
		How To... Draw Enantiomers
	6.2 How Do We Specify the Configuration of a Stereocenter?
	6.3 How Many Stereoisomers Are Possible for Molecules with Two or More Stereocenters?
	6.4 What Is Optical Activity, and How Is Chirality Detected in the Laboratory?
	6.5 What Is the Significance of Chirality in the Biological World?
		Summary of Key Questions
		Problems
		Chemical Connections
		6A Chiral Drugs
Chapter 7 Acids and Bases
	7.1 What Are Acids and Bases?
	7.2 How Do We De. ne the Strength of Acids and Bases?
	7.3 What Are Conjugate Acid-Base Pairs?
		How To... Name Common Acids
	7.4 How Can We Tell the Position of Equilibrium in an Acid-Base Reaction?
	7.5 How Do We Use Acid Ionization Constants?
	7.6 What Are the Properties of Acids and Bases?
	7.7 What Are the Acidic and Basic Properties of Pure Water?
		How To... Use Logs and Antilogs
	7.8 What Are pH and pOH?
	7.9 How Do We Use Titration to Calculate Concentration?
	7.10 What Are Buffers?
	7.11 How Do We Calculate the pH of a Buffer?
	7.12 What Are TRIS, HEPES, and These Buffers with the Strange Names?
		Summary of Key Questions
		Problems
		Chemical Connections
		7A Some Important Acids and Bases
		7B Drugstore Antacids
		7C Respiratory and Metabolic Acidosis
		7D Alkalosis and the Sprinter’s Trick
Chapter 8 Amines
	8.1 What Are Amines?
	8.2 How Do We Name Amines?
	8.3 What Are the Physical Properties of Amines?
	8.4 How Do We Describe the Basicity of Amines?
	8.5 What are the Characteristic Reactions of Amines?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		8A Amphetamines (Pep Pills)
		8B Alkaloids
		8C Tranquilizers
		8D The Solubility of Drugs in Body Fluids
		8E Epinephrine: A Prototype for the Development of New Bronchodilators
Chapter 9 Aldehydes and Ketones
	9.1 What Are Aldehydes and Ketones
	9.2 How Do We Name Aldehydes and Ketones?
	9.3 What Are the Physical Properties of Aldehydes and Ketones?
	9.4 What Are the Characteristic Reactions of Aldehydes and Ketones?
	9.5 What Is Keto-Enol Tautomerism?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		9A Some Naturally Occurring Aldehydes and Ketones
Chapter 10 Carboxylic Acids
	10.1 What Are Carboxylic Acids?
	10.2 How Do We Name Carboxylic Acids?
	10.3 What Are the Physical Properties of Carboxylic Acids?
	10.4 What Are Soaps and Detergents?
	10.5 What Are the Characteristic Reactions of Carboxylic Acids?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		10A Trans Fatty Acid: What Are They and How Do You Avoid Them?
		10B Esters as Flavoring Agents
		10C Ketone Bodies and Diabetes
Chapter 11 Carboxylic Anhydrides, Esters, and Amides
	11.1 What Are Carboxylic Anhydrides, Esters, and Amides?
	11.2 How Do We Prepare Esters?
	11.3 How Do We Prepare Amides?
	11.4 What Are the Characteristic Reactions of Anhydrides, Esters, and Amides?
	11.5 What Are Phosphoric Anhydrides and Phosphoric Esters?
	11.6 What Is Step-Growth Polymerization?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		11A The Pyrethrins; Natural Insecticides of Plant Origins
		11B The Penicillins and Cephalosporins: ß-Lactam Antibiotics
		11C From Willow Bark to Aspirin and Beyond
		11D Ultraviolet Sunscreens and Sunblocks
		11E Barbiturates
		11F Stitches That Dissolve
Chapter 12 Carbohydrates
	12.1 Carbohydrates: What Are Monosaccharides?
	12.2 What Are the Cyclic Structures of Monosaccharides?
	12.3 What Are the Characteristic Reactions of Monosaccharides?
	12.4 What Are Disaccharides and Oligosaccharides?
	12.5 What Are Polysaccharides?
	12.6 What Are Acidic Polysaccharides?
		Summary of Key Questions
		Summary of Key Reactions
		Problems
		Chemical Connections
		12A Galactosemia
		12B L-Ascorbic Acid (Vitamin C)
		12C Testing for Glucose
		12D A, B, AB, and O Blood Types
		12E Life-Saving Carbohydrate Bandages
Chapter 13 Lipids
	13.1 What Are Lipids?
	13.2 What Are the Structures of Triglycerides?
	13.3 What Are Some Properties of Triglycerides?
	13.4 What Are the Structures of Complex Lipids?
	13.5 What Role Do Lipids Play in the Structure of Membranes?
	13.6 What Are Glycerophospholipids?
	13.7 What Are Sphingolipids?
	13.8 What Are Glycolipids?
	13.9 What Are Steroids?
	13.10 What Are Some of the Physiological Roles of Steroid Hormones?
	13.11 What Are Bile Salts?
	13.12 What Are Prostaglandins, Thromboxanes, and Leukotrienes?
		Summary of Key Questions
		Problems
		Chemical Connections
		13A Rancidity
		13B Waxes
		13C Transport Across Cell Membranes
		13D The Myelin Sheath and Multiple Sclerosis
		13E Lipid Storage Diseases
		13F Anabolic Steroids
		13G Oral Contraception
		13H Action of Anti-in. ammatory Drugs
Chapter 14 Proteins
	14.1 What Are the Many Functions of Proteins?
	14.2 What Are Amino Acids?
	14.3 What Are Zwitterions?
	14.4 What Determines the Characteristics of Amino Acids?
	14.5 What Are Uncommon Amino Acids?
	14.6 How Do Amino Acids Combine to Form Proteins?
	14.7 What Are the Properties of Proteins?
	14.8 What Is the Primary Structure of a Protein?
	14.9 What Is the Secondary Structure of a Protein?
	14.10 What Is the Tertiary Structure of a Protein?
	14.11 What Is the Quaternary Structure of a Protein?
	14.12 How Are Proteins Denatured?
		Summary of Key Questions
		Problems
		Chemical Connections
		14A Aspartame, the Sweet Peptide
		14B AGE and Aging
		14C The Use of Human Insulin
		14D Sickle Cell Anemia
		14E Protein /Peptide Conformation-Dependent Diseases
		14F Proteomics, Ahoy!
		14G Quaternary Structure and Allosteric Proteins
		14H Laser Surgery and Protein Denaturation
Chapter 15 Enzymes
	15.1 What Are Enzymes?
	15.2 How Are Enzymes Named and Classi. ed?
	15.3 What Is the Terminology Used with Enzymes?
	15.4 What Factors In. uence Enzyme Activity?
	15.5 What Are the Mechanisms of Enzyme Action?
	15.6 How Are Enzymes Regulated?
	15.7 How Are Enzymes Used in Medicine?
	15.8 What Are Transition-State Analogs and Designer Enzymes?
		Summary of Key Questions
		Problems
		15A Muscle Relaxants and Enzyme Speci. city
		15B Enzymes and Memory
		15C Active Sites
		15D Medical Uses of Inhibitors
		15E Glycogen Phosphorylase: A Model of Enzyme Regulation
		15F One Enzyme, Two Functions
		15G Catalytic Antibodies Against Cocaine
Chapter 16 Chemical Communications: Neurotransmitters and Hormones
	16.1 What Molecules Are Involved in Chemical Communications?
	16.2 How Are Chemical Messengers Classified as Neurotransmitters and Hormones?
	16.3 How Does Acetylcholine Act as a Messenger?
	16.4 What Amino Acids Act as Neurotransmitters?
	16.5 What Are Adrenergic Messengers?
	16.6 What Is the Role of Peptides in Chemical Communication?
	16.7 How Do Steroid Hormones Act as Messengers?
		Summary of Key Questions
		Problems
		Chemical Connections
		16A Calcium as a Signaling Agent (Secondary Messenger)
		16B Botulism and Acetylcholine Release
		16C Alzheimer’s Disease and Chemical Communication
		16D Parkinson’s Disease: Depletion of Dopamine
		16E Nitric Oxide as a Secondary Messenger
		16F Diabetes
		16G Hormones and Biological Pollutants
Chapter 17 Nucleotides, Nucleic Acids, and Heredity
	17.1 What Are the Molecules of Heredity?
	17.2 What Are Nucleic Acids Made Of?
	17.3 What Is the Structure of DNA and RNA?
	17.4 What Are the Different Classes of RNA?
	17.5 What Are Genes?
	17.6 How Is DNA Replicated?
	17.7 How Is DNA Repaired?
	17.8 How Do We Amplify DNA?
		Summary of Key Questions
		Problems
		Chemical Connections
		17A Anticancer Drugs
		17B Telomeres, Telomerase, and Immortality
		17C DNA Fingerprinting
		17D The Human Genome Project: Treasure or Pandora’s Box?
		17E Pharmacogenomics: Tailoring Medicine to an Individual’s Predispositions
Chapter 18 Gene Expression and Protein Synthesis
	18.1 How Does DNA Lead to RNA and Protein?
	18.2 How Is DNA Transcribed into RNA?
	18.3 What Is the Role of RNA in Translation?
	18.4 What Is the Genetic Code?
	18.5 How Is Protein Synthesized?
	18.6 How Are Genes Regulated?
	18.7 What Are Mutations?
	18.8 How and Why Do We Manipulate DNA?
	18.9 What Is Gene Therapy?
		Summary of Key Questions
		Problems
		Chemical Connections
		18A Breaking the Dogma: The Twenty-First Amino Acid
		18B Viruses
		18C Mutations and Biochemical Evolution
		18D Silent Mutations
		18E p53: A Central Tumor Suppressor Protein
		18F Human Diversity and Transcription Factors
Chapter 19 Bioenergetics: How the Body Converts Food to Energy
	19.1 What Is Metabolism?
	19.2 What Are Mitochondria, and What Role Do They Play in Metabolism?
	19.3 What Are the Principal Compounds of the Common Metabolic Pathway?
	19.4 What Role Does the Citric Acid Cycle Play in Metabolism?
	19.5 How Do Electron and H+ Transport Take Place?
	19.6 What Is the Role of the Chemiosmotic Pump in ATP Production?
	19.7 What Is the Energy Yield Resulting from Electron and H+ Transport?
	19.8 How Is Chemical Energy Converted to Other Forms of Energy?
		Summary of Key Questions
		Problems
		Chemical Connections
		19A Uncoupling and Obesity
Chapter 20 Speci. c Catabolic Pathways: Carbohydrate, Lipid, and Protein Metabolism
	20.1 What Is the General Outline of Catabolic Pathways?
	20.2 What Are the Reactions of Glycolysis?
	20.3 What Is the Energy Yield From Glucose Catabolism?
	20.4 How Does Glycerol Catabolism Take Place?
	20.5 What Are the Reactions of b-Oxidation of Fatty Acids?
	20.6 What Is the Energy Yield from Stearic Acid Catabolism?
	20.7 What Are Ketone Bodies?
	20.8 How Is the Nitrogen of Amino Acids Processed in Carabolism?
	20.9 How Are the Carbon Skeletons of Amino Acids Processed in Catabolism?
	20.10 What Are the Reactions of Catabolism of Heme?
		Summary of Key Questions
		Problems
		Chemical Connections
		20A Lactate Accumulation
		20B Effects of Signal Transduction on Metabolism
		20C Ketoacidosis in Diabetes
		20D Hereditary Defects in Amino Acid Catabolism: PKU
Chapter 21 Biosynthetic Pathways
	21.1 What Is the General Outline of Biosynthetic Pathways?
	21.2 How Does the Biosynthesis of Carbohydrates Take Place?
	21.3 How Does the Biosynthesis of Fatty Acids Take Place?
	21.4 How Does the Biosynthesis of Membrane Lipids Take Place?
	21.5 How Does the Biosynthesis of Amino Acids Take Place?
		Summary of Key Questions
		Problems
		Chemical Connections
		21A Photosynthesis
		21B The Biological Basis of Obesity
		21C Essential Amino Acids
Chapter 22 Nutrition
	22.1 How Do We Measure Nutrition?
	22.2 Why Do We Count Calories?
	22.3 How Does the Body Process Dietary Carbohydrates?
	22.4 How Does the Body Process Dietary Fats?
	22.5 How Does the Body Process Dietary Protein?
	22.6 What Is the Importance of Vitamins, Minerals, and Water?
		Summary of Key Questions
		Problems
		Chemical Connections
		22A The New Food Guide Pyramid
		22B Why Is It So Hard To Lose Weight?
		22C Dieting and Arti. cial Sweeteners
		22D Iron: An Example of a Mineral Requirement
		22E Food for Performance Enhancement
		22F Organic Food—Hope or Hype?
Chapter 23 Immunochemistry
	23.1 How Does the Body Defend Itself from Invasion?
	23.2 What Organs and Cells Make Up the Immune System?
	23.3 How Do the Antigens Stimulate the Immune System?
	23.4 What Are Immunoglobulins?
	23.5 What Are T Cells and T-Cell Receptors?
	23.6 How Is the Immune Response Controlled?
	23.7 How Does the Body Distinguish “Self” from Nonself”?
	23.8 How Does the Human Immunodeficiency Virus Cause AIDS?
		Summary of Key Questions
		Problems
		Chemical Connections
		23A The Mayapple and Chemotherapy Agents
		23B Monoclonal Antibodies Wage War on Breast Cancer
		23C Immunization
		23D Antibiotics: A Double-Edged Sword
		23E Why Are Stem Cells Special?
Body Fluids
Appendix 1 Exponential Notation
Appendix 2 Signi. cant Figures
Answers to In-Text and Odd-Numbered End-of-Chapter Problems
Glossary
Index