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Brief Contents
Preface ix
Part I O r g a n ic C hemistry
1 Saturated Hydrocarbons 1
2 Unsaturated Hydrocarbons 42
3 Alcohols, Phenols, and Ethers 81
4 Aldehydes and Ketones 128
5 Carboxylic Acids, Esters, and Other Acid Derivatives 157
6 Amines and Amides 201
Part II b io lo g ic a l C hemistry
7 Carbohydrates 242
8 Lipids 303
9 Proteins 356
10 Enzymes and Vitamins 404
11 Nucleic Acids 449
12 Biochemical Energy Production 503
13 Carbohydrate Metabolism 545
14 Lipid Metabolism 579
15 Protein Metabolism 612
Answers to Selected Exercises A-1

Index/Glossary I-1
iii
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Contents
Preface ix 2 Unsaturated Hydrocarbons 42
2-1 Unsaturated Hydrocarbons 42
Part I O r g a n ic C hemistry 2-2 Characteristics of Alkenes and Cycloalkenes 43
2-3 Nomenclature for Alkenes and Cycloalkenes 45
2-4 Line-Angle Structural Formulas for Alkenes 49
2-5 Constitutional Isomerism in Alkenes 49
2-6 Cis–Trans Isomerism in Alkenes 52
2-7 Naturally Occurring Alkenes 55
2-8 Physical Properties of Alkenes and Cycloalkenes 58
2-9 Preparation of Alkenes 59
2-10 Chemical Reactions of Alkenes 59
2-11 Polymerization of Alkenes: Addition Polymers 65
Chemistry at a glance Chemical Reactions of Alkenes 69
2-12 Alkynes 69
Chemistry at a glance IUPAC Nomenclature for Alkanes,
Alkenes, and Alkynes 71
2-13 Aromatic Hydrocarbons 72
2-14 Nomenclature for Aromatic Hydrocarbons 74
2-15 Properties of and Sources for Aromatic
1 Saturated Hydrocarbons 1 Hydrocarbons 77
1-1 Organic and Inorganic Compounds 1 2-16 Fused-Ring Aromatic Hydrocarbons 79
1-2 Bonding Characteristics of the Carbon Atom 2 CHEMISTRY AT A GLANCE Types of Unsaturated
1-3 Hydrocarbons and Hydrocarbon Derivatives 3 Hydrocarbons 79
1-4 Alkanes: Acyclic Saturated Hydrocarbons 4
Chemical Connections
1-5 Structural Formulas 7
2-A Ethene: A Plant Hormone and High-Volume Industrial
1-6 Alkane Isomerism 8
Chemical 48
1-7 Conformations of Alkanes 10
2-B Cis-Trans Isomerism and Vision 54
1-8 IUPAC Nomenclature for Alkanes 12
1-9 Line-Angle Structural Formulas for Alkanes 19 2-C Carotenoids: A Source of Color 57
Chemistry at a Glance Structural Representations for Alkane
Molecules 20 3 Alcohols, Phenols, and Ethers 81
1-10 Classification of Carbon Atoms 21 3-1 Bonding Characteristics of Oxygen Atoms in Organic
1-11 Branched-Chain Alkyl Groups 23 Compounds 81
1-12 Cycloalkanes 25 3-2 Structural Characteristics of Alcohols 82
1-13 IUPAC Nomenclature for Cycloalkanes 27 3-3 Nomenclature for Alcohols 83
1-14 Isomerism in Cycloalkanes 28 3-4 Isomerism for Alcohols 86
1-15 Sources of Alkanes and Cycloalkanes 30 3-5 Important Commonly Encountered Alcohols 87
1-16 Physical Properties of Alkanes and Cycloalkanes 31 3-6 Physical Properties of Alcohols 92
1-17 Chemical Properties of Alkanes and 3-7 Preparation of Alcohols 94
Cycloalkanes 33 3-8 Classification of Alcohols 95
Chemistry at a Glance Properties of Alkanes and 3-9 Chemical Reactions of Alcohols 97
Cycloalkanes 36 Chemistry at a Glance Summary of Chemical Reactions
1-18 Halogenated Alkanes and Cycloalkanes 37 Involving Alcohols 105
Chemical connections 3-10 Structural Characteristics of Phenols 106
1-A The Occurrence of Methane 6 3-11 Nomenclature for Phenols 106
1-B The Physiological Effects of Alkanes 34 3-12 Physical and Chemical Properties of Phenols 108
1-C Chlorofluorocarbons and the Ozone Layer 40 3-13 Occurrence of and Uses for Phenols 109
iv
Contents v
3-14 Structural Characteristics of Ethers 112 5-11 Preparation of Esters 176

3-15 Nomenclature for Ethers 113 Chemistry at a Glance Summary of the “H Versus R”
3-16 Occurrence of and Uses for Ethers 115 Relationship for Pairs of Hydrocarbon Derivatives 177
3-17 Isomerism for Ethers 116 5-12 Nomenclature for Esters 179
3-18 Physical and Chemical Properties of Ethers 119 5-13 Selected Common Esters 181
3-19 Cyclic Ethers 120 5-14 Isomerism for Carboxylic Acids and Esters 184
3-20 Thiols: Sulfur Analogs of Alcohols 121 5-15 Physical Properties of Esters 185
3-21 Thioethers: Sulfur Analogs of Ethers 124 5-16 Chemical Reactions of Esters 186
Chemistry at a glance Alcohols, Thiols, Ethers, and Chemistry At a glance Summary of Chemical Reactions
Thioethers 126 Involving Carboxylic Acids and Esters 188
Chemical connections 5-17 Sulfur Analogs of Esters 189
3-A Menthol: A Useful Naturally Occurring Terpene 5-18 Polyesters 190
Alcohol 97 5-19 Acid Chlorides and Acid Anhydrides 192
3-B Red Wine and Resveratrol 112 5-20 Esters and Anhydrides of Inorganic Acids 195
3-C Ethers as General Anesthetics 117 Chemical Connections
3-D Garlic and Onions: Odiferous Medicinal Plants 125 5-A Nonprescription Pain Relievers Derived from Propanoic
Acid 167
5-B Carboxylic Acids and Skin Care 168
4 Aldehydes and Ketones 128
5-C Aspirin 183
4-1 The Carbonyl Group 128 5-D Nitroglycerin: An Inorganic Triester 197
4-2 Compounds Containing a Carbonyl Group 129
4-3 The Aldehyde and Ketone Functional Groups 131
4-4 Nomenclature for Aldehydes 132 6 Amines and Amides 201
4-5 Nomenclature for Ketones 134 6-1 Bonding Characteristics of Nitrogen Atoms in Organic
4-6 Isomerism for Aldehydes and Ketones 136 Compounds 201
4-7 Selected Common Aldehydes and Ketones 137 6-2 Structure and Classification of Amines 202
4-8 Physical Properties of Aldehydes and Ketones 141 6-3 Nomenclature for Amines 204
4-9 Preparation of Aldehydes and Ketones 142 6-4 Isomerism for Amines 206
4-10 Oxidation and Reduction of Aldehydes and 6-5 Physical Properties of Amines 207
Ketones 144 6-6 Basicity of Amines 208
4-11 Reaction of Aldehydes and Ketones with 6-7 Reaction of Amines with Acids 210
Alcohols 148 6-8 Alkylation of Ammonia and Amines 213
Chemistry at a glance Summary of Chemical Reactions 6-9 Heterocyclic Amines 214
Involving Aldehydes and Ketones 153 6-10 Selected Biochemically Important Amines 218
4-12 Sulfur-Containing Carbonyl Groups 153 6-11 Alkaloids 221
Chemical Connections 6-12 Structure and Classification of Amides 225
4-A Melanin: A Hair and Skin Pigment 140 6-13 Nomenclature for Amides 227
4-B Diabetes, Aldehyde Oxidation, and Glucose Testing 146 6-14 Selected Amides and Their Uses 229
4-C Lachrymatory Aldehydes and Ketones 155 6-15 Basicity of Amides 231
6-16 Physical Properties of Amides 232
6-17 Preparation of Amides 233
5 Carboxylic Acids, Esters, and Other Acid 6-18 Hydrolysis of Amides 236
Derivatives 157 Chemistry At a glance Summary of Chemical Reactions
5-1 Structure of Carboxylic Acids and Their Derivatives 157 Involving Amines and Amides 237
5-2 IUPAC Nomenclature for Carboxylic Acids 160 6-19 Polyamides and Polyurethanes 238
5-3 Common Names for Carboxylic Acids 163 Chemical connections
5-4 Polyfunctional Carboxylic Acids 166 6-A Caffeine: The Most Widely Used Central Nervous System
5-5 Physical Properties of Carboxylic Acids 169 Stimulant 216
5-6 Preparation of Carboxylic Acids 170 6-B Nicotine Addiction: A Widespread Example of Drug
5-7 Acidity of Carboxylic Acids 171 Dependence 217
5-8 Carboxylic Acid Salts 172 6-C Alkaloids Present in Chocolate 222
5-9 Carboxylic Acid Decarboxylation Reactions 175 6-D Acetaminophen: A Substituted Amide 230
5-10 Structure of Esters 175
vi Contents
Part II b io lo g ic a l C hemistry 8 Lipids 303

8-1 Structure and Classification of Lipids 303
8-2 Types of Fatty Acids 305
8-3 Physical Properties of Fatty Acids 309
8-4 Energy-Storage Lipids: Triacylglycerols 311
8-5 Dietary Considerations and Triacylglycerols 315
8-6 Chemical Reactions of Triacylglycerols 319
Chemistry At a glance Classification Schemes for Fatty Acid
Residues Present in Triacylglycerols 327
8-7 Membrane Lipids: Phospholipids 328
8-8 Membrane Lipids: Sphingoglycolipids 333
Chemistry At a glance Terminology for and Structural
Relationships Among Various Types of Fatty-Acid-
Containing Lipids 334
8-9 Membrane Lipids: Cholesterol 335
8-10 Cell Membranes 337
8-11 Emulsification Lipids: Bile Acids 341
8-12 Messenger Lipids: Steroid Hormones 343
7 Carbohydrates 242 8-13 Messenger Lipids: Eicosanoids 347
7-1 Biochemistry—An Overview 243 8-14 Protective-Coating Lipids: Biological Waxes 350
7-2 Occurrence and Functions of Carbohydrates 244 Chemistry At a glance Types of Lipids in Terms of How They
7-3 Classification of Carbohydrates 244 Function 352
7-4 Chirality: Handedness in Molecules 246 8-15 Saponifiable and Nonsaponifiable Lipids 353
7-5 Stereoisomerism: Enantiomers and
Chemical connections
Diastereomers 251
8-A The Fat Content of Tree Nuts and Peanuts 317
7-6 Designating Handedness Using Fischer Projection
8-B Fat Substitutes 320
Formulas 252
8-C The Cleansing Action of Soap and Detergents 323
Chemistry At a glance Constitutional Isomers and
Stereoisomers 257 8-D Trans Fatty Acid Content of Foods 325
7-7 Properties of Enantiomers 258 8-E Anabolic Steroid Use in Competitive Sports 346
7-8 Classification of Monosaccharides 260 8-F The Mode of Action for Anti-Inflammatory Drugs 349
7-9 Biochemically Important Monosaccharides 263
7-10 Cyclic Forms of Monosaccharides 266 9 Proteins 356
7-11 Haworth Projection Formulas 270
9-1 Characteristics of Proteins 356
7-12 Reactions of Monosaccharides 273
9-2 Amino Acids: The Building Blocks for Proteins 357
Chemistry At a glance “Sugar Terminology” Associated with 9-3 Essential Amino Acids 360
Monosaccharides and Their Derivatives 277
9-4 Chirality and Amino Acids 361
7-13 Disaccharides 277
9-5 Acid–Base Properties of Amino Acids 362
7-14 Oligosaccharides 287
9-6 Cysteine: A Chemically Unique Amino Acid 365
7-15 General Characteristics of Polysaccharides 290
9-7 Peptides 365
7-16 Storage Polysaccharides 292
9-8 Biochemically Important Small Peptides 369
7-17 Structural Polysaccharides 294
9-9 General Structural Characteristics of Proteins 371
Chemistry At a glance Types of Glycosidic Linkages for 9-10 Primary Structure of Proteins 372
Common Glucose-Containing Di- and 9-11 Secondary Structure of Proteins 376
Polysaccharides 296
9-12 Tertiary Structure of Proteins 379
7-18 Acidic Polysaccharides 298
9-13 Quaternary Structure of Proteins 383
7-19 Dietary Considerations and Carbohydrates 300
7-20 Glycolipids and Glycoproteins: Cell Recognition 300 Chemistry At a glance Protein Structure 384
9-14 Protein Hydrolysis 385
Chemical connections 9-15 Protein Denaturation 385
7-A Lactose Intolerance or Lactase Persistence 281 9-16 Protein Classification Based on Shape 388
7-B Changing Sugar Patterns: Decreased Sucrose, Increased 9-17 Protein Classification Based on Function 393
Fructose 283 9-18 Glycoproteins 395
7-C Sugar Substitutes 284 9-19 Lipoproteins 398
7-D Blood Types and Oligosaccharides 289 Chemical connections
7-E Edible Fibers and Health 297 9-A “Substitutes” for Human Insulin 374
Contents vii
9-B Denaturation and Human Hair 387 Chemical connections

9-C Protein Structure and the Color of Meat 392 11-A Antimetabolites: Anticancer Drugs That Inhibit DNA
9-D Cyclosporine: An Antirejection Drug 397 Synthesis 467
9-E Colostrum: Immunoglobulins and Much More 399 11-B The Circadian Clock and Clock Genes 476
9-F Lipoproteins and Heart Disease Risk 401 11-C Antibiotic Protein Synthesis Inhibitors 490
11-D Erythropoietin (EPO): Red Blood Cells, Mutations, and
Athletic Performance 494
10 Enzymes and Vitamins 404
10-1 General Characteristics of Enzymes 404
10-2 Enzyme Structure 405 12 Biochemical Energy Production 503
10-3 Nomenclature and Classification of Enzymes 407 12-1 Metabolism 503
10-4 Models of Enzyme Action 412 12-2 Metabolism and Cell Structure 505
10-5 Enzyme Specificity 414 12-3 Important Nucleotide-Containing Compounds in
10-6 Factors That Affect Enzyme Activity 414 Metabolic Pathways 507
Chemistry At a glance Enzyme Activity 418 12-4 Important Carboxylate Ions in Metabolic
10-7 Extremozymes 419 Pathways 515
10-8 Enzyme Inhibition 420 12-5 High-Energy Phosphate Compounds 517
Chemistry at a Glance Enzyme Inhibition 422 12-6 An Overview of Biochemical Energy Production 520
10-9 Regulation of Enzyme Activity 423 Chemistry At a glance Simplified Summary of the Four
10-10 Prescription Drugs That Inhibit Enzyme Activity 426 Stages of Biochemical Energy Production 521
10-11 Medical Uses of Enzymes 430 12-7 The Citric Acid Cycle 522
10-12 General Characteristics of Vitamins 432 Chemistry at a Glance Summary of the Reactions of the
10-13 Water-Soluble Vitamins: Vitamin C 434 Citric Acid Cycle 527
10-14 Water-Soluble Vitamins: The B Vitamins 436 12-8 The Electron Transport Chain 528
10-15 Fat-Soluble Vitamins 443 Chemistry At A Glance Summary of the Flow of Electrons
Chemical connections Through the Four Complexes of the Electron Transport
Chain 533
10-A Enzymatic Browning: Discoloration of Fruits and
Vegetables 411 12-9 Oxidative Phosphorylation 534
10-B H. pylori and Stomach Ulcers 416 Chemistry At A Glance Summary of the Common
Metabolic Pathway 537
10-C Enzymes, Prescription Medications, and the “Grapefruit
12-10 ATP Production for the Common Metabolic
Effect” 431
Pathway 539
12-11 Non-ETC Oxygen-Consuming Reactions 540
11 Nucleic Acids 449 12-12 B Vitamins and the Common Metabolic Pathway 543
11-1 Types of Nucleic Acids 449 Chemical connections
11-2 Nucleotides: Structural Building Blocks For Nucleic 12-A Adenosine Phosphates and Muscle Relaxation/
Acids 450 Contraction 510
11-3 Nucleotide Formation 452 12-B Brown Fat, Newborn Babies, and Hibernating
11-4 Primary Nucleic Acid Structure 455 Animals 537
Chemistry at a Glance Nucleic Acid Structure 458 12-C Cyanide Poisoning 538
11-5 The DNA Double Helix 459 12-D Phytochemicals: Compounds with Color and Antioxidant
11-6 Replication of DNA Molecules 463 Functions 542
Chemistry At A Glance DNA Replication 466
11-7 Overview of Protein Synthesis 468
11-8 Ribonucleic Acids 469
13 Carbohydrate Metabolism 545
11-9 Transcription: RNA Synthesis 471 13-1 Digestion and Absorption of Carbohydrates 545
11-10 The Genetic Code 477 13-2 Glycolysis 548
11-11 Anticodons and tRNA Molecules 480 13-3 Fates of Pyruvate 557
11-12 Translation: Protein Synthesis 484 13-4 ATP Production from the Complete Oxidation
Chemistry at a Glance Protein Synthesis: Transcription of Glucose 563
and Translation 489 13-5 Glycogen Synthesis and Degradation 565
11-13 Mutations 491 13-6 Gluconeogenesis 568
11-14 Nucleic Acids and Viruses 493 13-7 Terminology for Glucose Metabolic Pathways 571
11-15 Recombinant DNA and Genetic Engineering 495 13-8 The Pentose Phosphate Pathway 573
11-16 The Polymerase Chain Reaction 500 Chemistry At A Glance Glucose Metabolism 574
viii Contents
13-9 Hormonal Control of Carbohydrate Metabolism 575 15 Protein Metabolism 612

13-10 B Vitamins and Carbohydrate Metabolism 577
15-1 Protein Digestion and Absorption 612
Chemical Connections 15-2 Amino Acid Utilization 614
13-A Lactate Accumulation 561 15-3 Transamination and Oxidative Deamination 617
13-B Diabetes Mellitus 576 15-4 The Urea Cycle 623
Chemistry At a glance Metabolic Reactions That Involve
14 Lipid Metabolism 579 Nitrogen-Containing Compounds 629
14-1 Digestion and Absorption of Lipids 579 15-5 Amino Acid Carbon Skeletons 631
14-2 Triacylglycerol Storage and Mobilization 582 15-6 Amino Acid Biosynthesis 633
14-3 Glycerol Metabolism 584 15-7 Hemoglobin Catabolism 635
14-4 Oxidation of Fatty Acids 585 15-8 Proteins and the Element Sulfur 638
14-5 ATP Production from Fatty Acid Oxidation 590 15-9 Interrelationships Among Metabolic Pathways 642
14-6 Ketone Bodies and Ketogenesis 593 Chemistry At a glance Interrelationships Among
14-7 Biosynthesis of Fatty Acids: Lipogenesis 598 Carbohydrate, Lipid, and Protein Metabolism 642
14-8 Relationships Between Lipogenesis and Citric Acid Cycle 15-10 B Vitamins and Protein Metabolism 644
Intermediates 604 Chemical connections
14-9 Fate of Fatty-Acid-Generated Acetyl CoA 606 15-A The Chemical Composition of Urine 628
Chemistry at a Glance Interrelationships Between 15-B Arginine, Citrulline, and the Chemical Messenger Nitric
Carbohydrate and Lipid Metabolism 608 Oxide 630
14-10 Relationships Between Lipid and
Carbohydrate Metabolism 609
14-11 B Vitamins and Lipid Metabolism 610
Answers to Selected Exercises A-1
Chemical Connections Index/Glossary I-1
14-A High-Intensity Versus Low-Intensity Workouts 593
14-B Statins: Drugs That Lower Plasma Levels of
Cholesterol 607
Preface
T he positive responses of instructors and students who used the previous six edi-
tions of this text have been gratifying—and have led to the new seventh edition
that you hold in your hands. This new edition represents a renewed commitment
to the goals I initially set when writing the first edition. These goals have not changed
with the passage of time. My initial and still ongoing goals are to write a text in which:
jj The needs are simultaneously met for the many students in the fields of nursing,
allied health, biological sciences, agricultural sciences, food sciences, and public
health who are required to take such a course.
jj The development of chemical topics always starts out at ground level. The stu-
dents who will use this text often have little or no background in chemistry and
hence approach the course with a good deal of trepidation. This “ground level”
approach addresses this situation.
jj The amount and level of mathematics is purposefully restricted. Clearly, some
chemical principles cannot be divorced entirely from mathematics and, when
this is the case, appropriate mathematical coverage is included.
jj The early chapters focus on fundamental chemical principles, and the later
chapters—built on these principles—develop the concepts and applications cen-
tral to the fields of organic chemistry and biochemistry.
New Features Added to the Seventh Edition

Two new features are present in this seventh edition of the text. They are: (1) Section
Quick Quizzes, and (2) Section Learning Focus Statements.
Section Quick Quizzes: Each section in each chapter of the text now ends with
a “Section Quick Quiz.” Depending on the section length and the number of con-
cepts covered, the quick quiz consists of two to six multiple choice questions which
highlight the key terms and concepts covered in the section that a student should be
aware of after the initial reading of the text section. Answers to the quick quiz ques-
tions are given immediately following the set of questions. The word “quick” in the
phrase “quick quiz” is significant. The questions are designed to generate immedi-
ate answers. In most cases a time of no more than a minute is sufficient to complete
the quiz.
Two important purposes for this new quick quiz feature are: (1) to serve as a
guide to the most important terms and concepts found in the section under study, and
(2) to serve as an important review system for a student when he or she is studying for
an upcoming class exam on the subject matter under study.
Learning Focus Statements: Learning focus statements are now found at the begin-
ning of each section in each chapter of the text. These statements provide the student
with insights into the focus of the section in terms of topics covered and the needed
learning outcomes associated with these topics.
Important Continuing Features in the Seventh Edition

Focus on Biochemistry Most students taking this course have a greater interest in
the biochemistry portion of the course than the preceding two parts. But biochem-
istry, of course, cannot be understood without a knowledge of the fundamentals of
ix
x Preface
organic chemistry, and understanding organic chemistry in turn depends on knowing

the key concepts of general chemistry. Thus, in writing this text, I essentially started
from the back and worked forward. I began by determining what topics would be
considered in the biochemistry chapters and then tailored the organic and then gen-
eral sections to support that presentation. Users of the previous editions confirm that
this approach ensures an efficient but thorough coverage of the principles needed to
understand biochemistry.
Art Program See the story of general, organic, and biological chemistry come alive
on each page! In addition to the narrative, the art and photography program helps tell
a very important story—the story of ourselves and the world around us. Chemistry is
everywhere! An integrated talking label system in the art and photography program
gives key figures a “voice” and helps students learn more effectively.
Emphasis on Visual Support I believe strongly in visual reinforcement of key con-
cepts in a textbook; thus this book uses art and photos wherever possible to teach
key concepts. Artwork is used to make connections and highlight what is important
for the student to know. Reaction equations use color to emphasize the portions of
a molecule that undergo change. Colors are likewise assigned to things like valence
shells and classes of compounds to help students follow trends. Computer-generated,
three-dimensional molecular models accompany many discussions in the organic and
biochemistry sections of the text. Color photographs show applications of chemistry
to help make concepts real and more readily remembered. The following example is
representative of the art program.
C
Carbon
O
C
Nitrogen
C Hydrogen
O
H O
Oxygen
C Side group
N H
O C
N
H O
C
H N
C O
O
N H
H
N
H N
a Arrangement b Backbone c Backbone atomic d Top view of an a

of protein arrangement detail shown, as helix showing that
backbone with with hydrogen- well as hydrogen- amino acid side
no detail shown. bonding bonding chains (R groups)
interactions interactions. point away from
shown. the long axis of
the helix.
Chemistry at a Glance Visual summaries called Chemistry at a Glance pull together

material from several sections of a chapter to help students see the larger picture.
Representative of such features are those entitled
jj Properties of Alkanes and Cycloalkanes (Section 1-17)
jj Types of Glycosidic Linkages for Disaccharides and Polysaccharides
(Section 7-17)
jj Types of Lipids in Terms of How They Function (Section 8-14)
jj Summary of the Reactions of the Citric Acid Cycle (Section 12-7)
Preface xi
Given the popularity of the Chemistry at a Glance summaries in the previous editions,
several new ones have been added and several existing ones have been revised. New
and revised Chemistry at a Glance topics include:
jj Types of Unsaturated Hydrocarbon (Section 2-16)
jj Summary of Chemical Reactions Involving Alcohols (Section 3-9)
jj Summary of Chemical Reactions Involving Carboxylic Acids (Section 5-7)
jj Constitution Isomers and Stereoisomers (Section 7-6)
jj Interrelationships Among Carbohydrate, Lipid, and Protein Metabolism
(Section 15-8)
Chemical Connections In every chapter Chemical Connection boxes emphasize
the relevancy of chemical topics under consideration. They focus on issues relevant
to a student’s own life in terms of health issues, societal issues, and environmental
issues. Representative of issues selected for Chemical Connection coverage are the
following:
jj Chlorofluorocarbons and the Ozone Layer (Section 1-18)
jj Red Wine and Resveratrol (Section 3-14)
jj Alkaloids Present in Chocolate (Section 6-11)
jj The Fatty Content of Tree Nuts and Peanuts (Section 8-4)
New topics selected for Chemical Connection emphasis in this edition are:
jj Edible Fiber and Health (Section 7-17)
jj The Circadian Clock: Clock Genes (Section 11-9)
jj EPO: Red Blood Cells, Mutations, and Athletic Performance (Section 11-13)
jj Adenosine Phosphates and Muscle Relaxation/Contraction (Section 12-3)
jj Phytochemicals: Compounds with Color and Antioxidant Properties
(Section 12-11)
Updated Chemical Connection boxes include
jj Caffeine: A Widely Used Central Nervous System Stimulant (Section 6-9)
jj Lactose Intolerance or Lactase Persistence (Section 7-13)
jj Trans Fatty Acid Content of Foods (Section 8-6)
jj Enzymes, Prescription Medications and the “Grapefruit Effect”
(Section 10-11)
Commitment to Student Learning In addition to the study help Chemistry at a
Glance offers, the text is built on a strong foundation of learning aids designed to help
students master the course material.
jj Problem-solving pedagogy. Because problem solving is often difficult for stu-
dents in this course to master, I have taken special care to provide support to
help students build their skills. Within the chapters, worked-out Examples fol-
low the explanation of many concepts. These examples walk students through
the thought processes involved in problem solving, carefully outlining all of the
steps involved.
Diversity of Worked-out Examples Worked-out examples are a standard feature
in the general chemistry portion of all textbooks for this market. This relates pri-
marily to the mathematical nature of many general chemistry topics. In most texts,
fewer worked-out examples appear in the organic chemistry chapters, and still fewer
(almost none) are found in the biochemistry portion due to decreased dependence of
the topical matter on mathematical concepts. Such is not the case in this textbook.
All chapters in the latter portions of the text contain numerous worked-out examples.
Several additional worked-out examples have been added to this new edition. Topics
for worked out examples include the following:
jj Classifying Alcohols as Primary, Secondary, or Tertiary (Section 3-8)
jj Generating Structural Formulas for Carboxylic Acids From Their Names
(Section 5-3)
xii Preface
jj Changing a Fischer Projection Formula to a Haworth Projection Formula

(Section 7-11)
jj Identifying Components of a Nucleotide (Section 11-1)
jj Identifying Weak and Strong Bonds Present in Adenosine Phosphates
(Section 12-5)
jj Margin notes. Liberally distributed throughout the text, margin notes provide
tips for remembering and distinguishing between concepts, highlight links
across chapters, and describe interesting historical background information.
jj Defined terms. All definitions are highlighted in the text when they are first pre-
sented, using boldface and italic type. Each defined term appears as a complete
sentence; students are never forced to deduce a definition from context. In addi-
tion, the definitions of all terms appear in the combined Index/Glossary found
at the end of the text. A major emphasis in this new edition has been “refine-
ments” of the defined terms. All defined terms were reexamined to see if they
could be stated with greater clarity. The result was a “rewording” of many de-
fined terms.
jj Concepts to Remember review. A concise review of key concepts presented in
each chapter appears at the end of the chapter, placed just before the end-of-
chapter problems. This is a helpful aid for students as they prepare for exams.
jj End-of-chapter problems. An extensive set of end-of-chapter problems comple-
ments the worked-out examples within the chapters. These end-of-chapter prob-
lems are organized by topic and paired, with each pair testing similar material.
The answer to the odd-numbered member of the pair is given at the back of the
book are two problem-set features:
Problems denoted with a ▲ involve concepts found not only in the section un-
der consideration but also concepts found in one or more earlier sections of
the chapter.
Content Changes Coverage of a number of topics has been expanded in this edi-
tion. The two driving forces in expanded coverage considerations were (1) the requests
of users and reviewers of the previous editions and (2) my desire to incorporate new
research findings, particularly in the area of biochemistry, into the text. Topics with
expanded coverage include:
jj Preparation of Alkenes (Section 2-9)
jj Functional Group Isomerism (Section 3-7)
jj Alcohol Condensation Reactions (Section 3-9)
jj Carboxylic Acid Decarboxylation Reactions (Section 5-9)
jj OxyContin Formulations (Section 6-12)
jj Medical Uses of Enzymes (Section 10-11)
jj Fat-Soluble Vitamins (Section 10-15)
jj The Human Transcriptome (Section 11-9)
jj Mutations (Section 11-13)
jj Transamination Reactions (Section 15-3)
jj Proteins and the Element Sulfur (Section 15-8)
Supporting Materials
Please visit http://www.cengage.com/chemistry/stoker/gob7E for information about
the student and instructor resources for this text.
Preface xiii
Acknowledgments
The publication of a book such as this requires the efforts of many more people than
merely the author. Special thanks to the Editorial and Production Team at Cengage:
Alyssa White, my Content Developer; Maureen Rosener, my Product Manager, Te-
resa Trego, my Senior Content Product Manager; I would also like to thank Katy
Gabel, my Senior Project Manager at Lumina Datamatics, Inc., and my Photo Re-
searcher, Abbey Stebing at Lumina Datamatics, Inc.
I also appreciate the time and expertise of my reviewers, who read my manuscript
and provided many helpful comments.
Special thanks to my accuracy reviewers:
David Shinn, United States Merchant Marine Academy
Jordan Fantini; Denison University
Reviewers of the 7th edition:

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Meredith Ward, Elmira College

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Michael Myers, California State University—Long Beach
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Shashi Rishi, Greenville Technical College
Steven M. Socol, McHenry County College
Saturated Hydrocarbons
Chapter Outline
1
1-1 Organic and Inorganic
Compounds 1
1-2 Bonding Characteristics of the
Carbon Atom 2
1-3 Hydrocarbons and Hydrocarbon
Derivatives 3
1-4 Alkanes: Acyclic Saturated
Hydrocarbons 4
1-5 Structural Formulas 7
1-6 Alkane Isomerism 8
1-7 Conformations of Alkanes 10
1-8 IUPAC Nomenclature for
Alkanes 12
1-9 Line-Angle Structural Formulas for
Alkanes 19
Bill Ross/Corbis
1-10 Classification of Carbon
Atoms 21
1-11 Branched-Chain Alkyl Groups 23
1-12 Cycloalkanes 25
Crude oil (petroleum) constitutes the largest and most important natural source for saturated
1-13 IUPAC Nomenclature for
hydrocarbons, the simplest type of organic compound. Here is shown a pump and towers
Cycloalkanes 27
associated with obtaining crude oil from underground deposits.
1-14 Isomerism in Cycloalkanes 28
T
1-15 Sources of Alkanes and
his chapter is the first of six that deal with the subject of organic chem- Cycloalkanes 30
istry and organic compounds. Organic compounds are the chemical
1-16 Physical Properties of Alkanes and
basis for life itself, as well as an important component of the current
Cycloalkanes 31
high standard of living enjoyed by people in many countries. Proteins, carbo-
hydrates, enzymes, and hormones are organic molecules. Organic compounds 1-17 Chemical Properties of Alkanes
also include natural gas, petroleum, coal, gasoline, and many synthetic mate- and Cycloalkanes 33
rials such as dyes, plastics, and clothing fibers. 1-18 Halogenated Alkanes and
Cycloalkanes 37
1-1 Organic and Inorganic Compounds

L e a r n i n g F oc u s
Understand the historical and modern definitions for the terms organic chemistry and
inorganic chemistry.
During the latter part of the eighteenth century and the early part of the
nineteenth century, chemists began to categorize compounds into two types:
organic and inorganic. Compounds obtained from living organisms were
called organic compounds, and compounds obtained from mineral constitu-
ents of Earth were called inorganic compounds.
During this early period, chemists believed that a special “vital force”
supplied by a living organism was necessary for the formation of an organic
1
2 Chapter 1 Saturated Hydrocarbons
Inorganic compound. This concept was proved incorrect in 1828 by the German chemist
compounds Friedrich Wöhler. Wöhler heated an aqueous solution of two inorganic compounds,
(~1.7 million) ammonium chloride and silver cyanate, and obtained urea (a component of urine).
NH4Cl + AgNCO h (NH2)2CO + AgCl
Urea
Soon other chemists had successfully synthesized organic compounds from inorganic
starting materials. As a result, the vital-force theory was completely abandoned.
The terms organic and inorganic continue to be used in classifying compounds,
Organic compounds but the definitions of these terms no longer reflect their historical origins. Organic
(~10 million)
chemistry is the study of hydrocarbons (compounds of carbon and hydrogen) and
their derivatives. Nearly all compounds found in living organisms are still classified
as organic compounds, as are many compounds that have been synthesized in the
Figure 1-1 Sheer numbers is one laboratory and have never been found in a living organism. Inorganic chemistry is the
reason why organic chemistry is study of all substances other than hydrocarbons and their derivatives.
a separate field of chemical study. In essence, organic chemistry is the study of the compounds of one element
Approximately 10 million organic (carbon), and inorganic chemistry is the study of the compounds of the other
compounds are known, compared 117 elements. This unequal partitioning occurs because there are approximately
to “just” 1.7 million inorganic 10 million organic compounds and only an estimated 1.7 million inorganic com-
compounds. pounds (Figure 1-1). This is an approximately 6:1 ratio between organic and inor-
ganic compounds. ◀
▶ The prefixes un-, dis-, and in-
are all used to convey the meaning
“not” or “the opposite of.” Thus Section 1-1 Quick Quiz
the word inorganic is literally
interpreted as not organic. A few 1. Which of the following statements concerning organic compounds is correct?
other “in” prefix words where a. Organic compounds are found only in living organisms.
“in” means “not” are incorrect, b. Organic compounds always contain the element carbon.
invisible, inanimate, inadequate, c. Organic compounds cannot be prepared in the laboratory.
and incapable. d. no correct response
2. Which of the following statements concerning the number of known organic and
inorganic compounds is correct?
a. Organic compounds greatly outnumber inorganic compounds.
b. Inorganic compounds greatly outnumber organic compounds.
c. Organic and inorganic compound numbers are about the same.
d. no correct response
Answers: 1. b; 2. a
1-2 Bonding Characteristics of the Carbon Atom

Describe the various ways carbon atoms can meet the requirement of forming four
covalent bonds.
▶ Some textbooks define organic Why does the element carbon form six times as many compounds as all the other ele-
chemistry as the study of carbon- ments combined? The answer is that carbon atoms have the ability to bond to each
containing compounds. Almost other in a wide variety of ways that involve long chains of carbon atoms or cyclic
all carbon-containing compounds arrangements (rings) of carbon atoms. Sometimes both chains and rings of carbon
qualify as organic compounds.
However, the oxides of carbon, atoms are present in the same molecule. ◀
carbonates, cyanides, and metal- The variety of covalent bonding “behaviors” possible for carbon atoms is related
lic carbides are classified as to carbon’s electron configuration. Carbon is a member of Group IVA of the peri-
inorganic rather than organic odic table, so carbon atoms possess four valence electrons. In compound formation,
compounds. Inorganic carbon four additional valence electrons are needed to give carbon atoms an octet of valence
compounds generally contain a
single carbon atom and no hydro- electrons. These additional electrons are obtained by electron sharing (covalent bond
gen atoms (CO, CO2, NaCN, formation). The sharing of four valence electrons requires the formation of four cova-
Na2CO3, MgCO3, and so on). lent bonds.
1-3 Hydrocarbons and Hydrocarbon Derivatives 3
Carbon can meet this four-bond requirement in three different ways:
1. By bonding to four other atoms. This situation requires the presence of four single
bonds.
A
OC O
A
Four single bonds
2. By bonding to three other atoms. This situation requires the presence of two
single bonds and one double bond.
A
OC P
Two single bonds and
one double bond
3. By bonding to two other atoms. This situation requires the presence of either two
double bonds or a triple bond and a single bond.
P CP OC
Two double bonds One triple bond and
one single bond
Section 1-2 Quick Quiz

1. Which of the following statements about the covalent bonding capabilities of carbon
atoms is incorrect?
a. Single bond formation to another atom is possible.
b. Double bond formation to another atom is possible.
c. Triple bond formation to another atom is possible.
2. Which of the following “bonding behaviors” is not possible for a carbon atom?
a. formation of four single bonds
b. formation of two double bonds
c. formation of two triple bonds
Answers: 1. d; 2. c
1-3 Hydrocarbons and Hydrocarbon Derivatives

Define the terms hydrocarbon and hydrocarbon derivative; know the characteristic that differenti-
ates saturated hydrocarbons from unsaturated hydrocarbons.
The field of organic chemistry encompasses the study of hydrocarbons and hydrocar-
bon derivatives (Section 1-1). A hydrocarbon is a compound that contains only carbon
atoms and hydrogen atoms. Thousands of hydrocarbons are known. A hydrocarbon
derivative is a compound that contains carbon and hydrogen and one or more additional ▶ The term saturated has the
elements. Additional elements commonly found in hydrocarbon derivatives include O, general meaning that there is no
N, S, P, F, Cl, and Br. Millions of hydrocarbon derivatives are known. more room for something. Its use
Hydrocarbons may be divided into two large classes: saturated and unsaturated. with hydrocarbons comes from
early studies in which chemists
A saturated hydrocarbon is a hydrocarbon in which all carbon–carbon bonds are single tried to add hydrogen atoms to
bonds. Saturated hydrocarbons are the simplest type of organic compound. An various hydrocarbon molecules.
unsaturated hydrocarbon is a hydrocarbon in which one or more carbon–carbon multi- Compounds to which no more
ple bonds (double bonds, triple bonds, or both) are present. In general, saturated and hydrogen atoms could be added
unsaturated hydrocarbons undergo distinctly different chemical reactions. ◀ (because they already contained
the maximum number) were
Saturated hydrocarbons are the subject of this chapter. Unsaturated hydrocarbons called saturated, and those to
are considered in the next chapter. Figure 1-2 summarizes the terminology presented in which hydrogen could be added
this section. were called unsaturated.
Figure 1-2 A summary of

classification terms for organic ORGANIC
compounds. COMPOUNDS
Hydrocarbons and their

derivatives
HYDROCARBON
HYDROCARBONS
DERIVATIVES (Chapters 3–6)
Compounds containing Compounds containing carbon,

only carbon and hydrogen hydrogen, and one or more other
elements
SATURATED UNSATURATED
HYDROCARBONS HYDROCARBONS (Chapter 2)
Hydrocarbons in which Hydrocarbons containing one or

all carbon-to-carbon more carbon-to-carbon multiple bonds
bonds are single bonds
Two categories of saturated hydrocarbons exist, those with acyclic carbon

atom arrangements and those with cyclic carbon atom arrangements. The term acy-
clic means “not cyclic.” The following notations contrast simple acyclic and cyclic
arrangements of six-carbon atoms.
C
C C
C C
COCOCOCOCOC C
Acyclic Cyclic
Sections 1-4 through 1-11 of this chapter treat the subject of saturated hydrocarbons
▶ The prefix a- in acyclic means with acyclic carbon atom arrangements. ◀ A discussion of saturated hydrocarbons
“not,” so an acyclic hydrocarbon with cyclic carbon atom arrangements follows in Sections 1-12 through 1-14.
has an arrangement of carbon
atoms within its structure that is
not cyclic. Section 1-3 Quick Quiz
1. Which of the following characterizations is not possible for a hydrocarbon derivative?
a. contains C and H
b. contains C, H, and O
c. contains C, H, and N
2. The distinction between a saturated hydrocarbon and an unsaturated hydrocarbon relates to
a. flammability
b. number of carbon atoms present
c. types of carbon–carbon bonds present
Answers: 1. a; 2. c
1-4 Alkanes: Acyclic Saturated Hydrocarbons

Learning Focus
Know the general molecular formula for alkanes and the structural characteristic common to all
alkanes.
An alkane is a saturated hydrocarbon in which the carbon atom arrangement is acy-

clic. Thus an alkane is a hydrocarbon that contains only carbon–carbon single bonds
(saturated) and has no rings of carbon atoms (acyclic).
1-4 Alkanes: Acyclic Saturated Hydrocarbons 5
Methane Ethane Propane
H H
H H H H
H H
Dash-wedge-line 109.5 C
structures H C C C 109.5
C C 109.5
H H
H H H
H H H H
Ball-and-stick
models
Space-filling
models
Figure 1-3 Three different three-dimensional ways of representing the structures of methane,
ethane, and propane: dash-wedge-line structure, ball-and-stick model, and space-filling model.
The molecular formulas of all alkanes fit the general formula CnH2n+2, where n is
the number of carbon atoms present. The number of hydrogen atoms present in an
alkane is always twice the number of carbon atoms plus two more, as in C4H10, C5H12,
and C8H18.
The three simplest alkanes are methane (CH 4), ethane (C 2H6), and propane
(C3H8). Three different methods for showing the three-dimensional structures of these
simplest of all alkanes are given in Figure 1-3. They are dash-wedge-line structures,
ball-and-stick models, and space-filling models. Note how each carbon atom in each
of the models participates in four bonds (Section 1-2). Note also that the geometri-
cal arrangement of atoms about each carbon atom is tetrahedral, an arrangement
consistent with the principles of VSEPR theory. The tetrahedral arrangement of the
atoms bonded to alkane carbon atoms is fundamental to understanding the structural
aspects of organic chemistry.
The natural environmental presence of methane, the simplest alkane, is consid-
ered in the focus on relevancy feature Chemical Connections 1-A—The Occurrence
of Methane. The air we breathe contains a small amount of methane (2 parts per
million by volume). The major component of natural gas used in residential home
heating is methane.
Section 1-4 Quick Quiz

1. What is the general molecular formula for an alkane?
a. CnH2n
b. CnH2n−2
c. CnH2n+2
2. How many hydrogen atoms are present in an alkane that contains seven atoms?
a. 16
b. 14
c. 12
(continued)
3. The four hydrogen atoms bonded to the central carbon atom in methane, CH4, lie at the
corners of a
a. rectangle
b. square
c. tetrahedron
Answers: 1. c; 2. a; 3. c
C h e m ic a l co n n e c t io n s 1 -A
The Occurrence of Methane

Methane (CH 4), the simplest of all hydrocarbons, is a It should be noted that some greenhouse gas presence in
major component of the atmospheres of Jupiter, Saturn, the atmosphere is not only desirable but necessary. The
U ranus, and Neptune but only a minor component of average surface temperature of Earth is about 15°C. In the
Earth’s atmosphere (see the accompanying table). Earth’s absence of “normal amounts” of greenhouse gases, Earth’s
gravitational field, being weaker than that of the large average surface temperature would drop to about −18°C,
outer planets, cannot retain enough hydrogen (H2) in its which would not be a good situation for humans. Of con-
atmosphere to permit the formation of large amounts of cern are the ever increasing amounts of greenhouse gases
methane; H2 molecules (the smallest and fastest-moving of entering the atmosphere as the result of human activities
all molecules) escape from it into outer space. and the associated increase, still small, in Earth’s average
The small amount of methane present in Earth’s atmos- surface temperature.
phere comes from terrestrial sources. The decomposi- Methane gas is also found associated with coal and
tion of animal and plant matter in an oxygen-deficient petroleum deposits. Methane associated with coal mines
environment—swamps, marshes, bogs, and the sediments is considered a hazard. If left to accumulate, it can form
of lakes—produces methane. A common name for meth- pockets where air is not present, and asphyxiation of min-
ane, marsh gas, refers to the production of methane in this ers can occur. When mixed with air in certain ratios, it can
manner. also present an explosion hazard. Methane associated with
petroleum deposits is most often recovered, processed, and
marketed as natural gas. The processed natural gas used in
Composition of Earth’s Atmosphere the heating of homes is 85% to 95% methane by volume.
(in parts per million by volume) Because methane is odorless, an odorant (smelly compound)
must be added to the processed natural gas used in home
Major Components Minor Components heating. Otherwise, natural gas leaks could not be detected.
nitrogen 780,800 argon 9340
oxygen 209,500 carbon 314
dioxide
neon 18
helium 5
methane 2
krypton 1
Bacteria that live in termites and in the digestive tracts

of plant-eating animals have the ability to produce methane
from plant materials (cellulose). The methane output of a
Doug Martin / Science Source
large cow (via belching and flatulence) can reach 20 liters

per day. Livestock are the source of about 20% of methane
emissions to the atmosphere each day.
Methane entering the atmosphere from terrestrial
sources presents an environmental problem. Methane,
like carbon dioxide, is a “greenhouse gas” that contrib-
utes to global warming. Methane is 15 to 30 times more
efficient than carbon dioxide in trapping re-radiated heat
from Earth. Fortunately, atmospheric levels of methane Decomposition of plant and animal
(2.0 ppm by volume) are much lower than those of carbon matter in marshes is a source of
dioxide (314 ppm by volume). methane gas.
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Wherefore to stroy vs hee did all hee might.[971]
7.
His cursed sonne ensued his cruell path,

And kept my giltlesse cosin strayt in duraunce:
For whome my father hard entreated hath:
But liuing hopelesse of his line’s assuraunce,
Hee thought it best by pollitike procuraunce,
To priue[972] the king, and so restore his frend:
Which brought him selfe to an infamous end.[973]
8.
For whan king Henry,[974] of that name the fifte,

Had tane my father in his[975] conspiracy,[976]
Hee, from sir Edmund all the blame to shifte,
Was fayne to say the[977] French kinge’s ally[978]
Had hyred him this trayterous act to trye,
For which condemned shortly hee was slaine,
In helping right this was my father’s gaine.[979]
9.
Thus whan the linage of the Mortimers

Was made away by his[980] vsurping line,
Some hang’d, some slaine, some pined prisoners,
Because the crowne by right of lawe was mine,
They gan as fast against mee to repine,
In feare alwayes, least I should stur them to[981] strife,
For guylty hearts haue neuer quiet life.[982]
10.
Yet at the last, in Henrye’s dayes the sixt,

I was restored to my father’s landes,
Made duke of Yorke: where through my minde I fixt
To get the crowne and kingdome in my handes,
For ayde wherein I knit assured handes
With Neuil’s stocke, whose daughter was my make,
Who for no woe would euer mee forsake.[983]
11.
O Lord, what hap had I through mariage,

Fower goodly boyes in youth my wife shee bore
Right valiaunt[984] men and prudent for their age,
Such brethren[985] shee had and nephues [still] in store
As none had erst, nor any shall haue more:[986]
The earle of Salisbury, and his sonne of Warwicke,
Were matchlesse men[987] from Barbary to Barwicke.
12.
Through helpe of whome and fortune’s louely looke,

I vndertooke to claime my lawfull right,
And to abash such as against mee tooke,[988]
I raysed power at all poyntes prest to fight:
Of whome the chiefe, that chiefly bare mee spight,
Was Somerset the duke, whome to annoy
I alway sought, through spite, spite to destroy.[989]
13.
And maugre him, so choyse, lo, was my chaunce,

Yea though the quene, that all rulde, tooke his part,[990]
I twise bare rule[991] in Normandy and Fraunce,
And last lieuetenaunt in Ireland, where my hart
Found remedy for euery kinde of smart:
For through[992] the loue my doinges there did breede,
I had their helpe at all times in my neede.
14.
This spitefull duke, his seely king[993] and queene,

With armed hoastes I thrise met in the fielde,
The first vnfought through treaty made betweene:
The second ioynde, wherein the king did yeelde,
The duke was slaine, the queene enforst to shyelde
Her selfe by flight: the third the queene did fight,
Where I was slaine being ouer matcht by might.[994]
15.
Before this last were other battayles three,

The first the earle of Salisbury led[995] alone,
And[996] fought on Bloreheath, and got[997] victory:
In the next was I and my kinsfolke[998] euery one:
But seeing our souldiers stale vnto our foen,
Wee warely brake our company on a night,
Dissolued our hoast, and tooke our selues to flight.[999]
16.
This boy and I, in Ireland did vs saue,

Mine eldest sonne, with Warwicke and his father,
To Calais got, whence, by the reade I gaue,
They came agayne to London, and did gather
An other hoast whereof I spake not[1000] rather:
And met our foes, slewe many a lord and knight,
And tooke the king, and draue the queene to flight.
17.
This done I came[1001] to England all in haste,

To make a[1002] claime vnto the realme and crowne:
And in the house while parliament did last,
I in the kinge’s seat boldly[1003] sate mee downe,
And claymed it, whereat[1004] the lordes did frowne,
But what for that? I did so well proceede,
That all at last confest it mine indeede.[1005]
18.
But sith the king had raigned now so long,[1006]

They would hee should continue till hee dyed,
And to the end, that than none did mee wrong,[1007]
Protector and heyre apparant they mee[1008] cryed:
But sith the queene and others this denyed,
I sped mee towardes the north, where then shee lay,
In minde by force to cause her to obay.[1009]
19.
Whereof shee warnd preparde a mighty powre,

And ere that mine were altogether ready,
Came swift to Sandale[1010] and besieged my bowre:
Where like a beast I was so rash and heady,
That out I would, there could be no remedy,
With scant fiue thousand souldiers, to assayle
Fowre times so many, encampt to most auayle.[1011]
20.
And so was slaine at first: and while my childe

Scarse twelue yeare old, sought secretly to parte,
That cruell Clifford, lord, nay lorell wylde,
While the infant[1012] wept, and prayed him rue his smart,
Knowing what hee was, with dagger cloue his heart:[1013]
This done, he came to th’camp where I lay dead,
Despoylde my corps and cut away my head.
21.
And when he had put a paper crowne thereon,
As a gawring stocke he sent it to the queene:[1014]
And shee for spite commaunded it anon
To be had to Yorke: where that it mought[1015] bee
seene,
They placed it where other traytors beene:
This mischiefe fortune did mee after death:
Such was my life, and such my losse of breath.[1016]
22.
Wherefore see, Baldwine, that thou set it forth,

To th’end the fraude of fortune may bee knowen,
That eke all princes well[1017] may way the worth
Of thinges, for which the seedes[1018] of warre be sowen:
No state so sure but soone is ouerthrowen:[1019]
No worldly good can counterpeyze the prise
Of halfe the paynes that may thereof arise.
23.
Far[1020] better it were to lose a piece of right,

Than lymmes and life in sousing[1021] for the same:
It is not force of friendship, nor of might,
But God that causeth thinges to fro or frame,[1022]
Not wit but lucke[1023] doth wield the winner’s game:
Wherefore if wee our follyes would refrayne,
Time would redresse all wronges, wee voyde of payne.
24.
Wherefore warne princes not to wade[1024] in war

For any cause, except the realme’s defence:[1025]
Theyr troublous titles are vnworthy far
The bloud, the life, the spoyle of innocence:
Of friendes, of foes,[1026] behold my foule[1027] expence,
And neuer the neare: best therefore tary time,
So right shall raigne, and quyet calme ech crime.[1028]
[With that[1029] maister Ferrers shooke mee by the sleue, saying:
“Why how now man, do you forget your selfe? belike you minde our
matters very much.” “So I doe indeede,” sayd I,[1030] “for I dreame of
them.” And whan I had rehersed my dreame, wee had long talke
concerning the nature of dreames, which to stint, and to bring vs to
our matter agayne, thus sayd one of them: “I am glad it was your
chaunce to dreame of duke Richard, for it had bene pity to haue
ouerpassed him. And as concerning this lord Clyfford which so
cruely killed his sonne, I purpose to gieue you notes: who (as hee
well deserued) came shortly after to a sodayne death, and yet too
good for so cruell a tyrant. [For on Palmesonday next following,
being the xxix day[1031] of March, in the yeare of Christ a thousand
four hundreth threescore and one, this lord Clyfford with Henry Percy
the thirde earle of Northumberland, the earle of Westmerland, the
lord Dacres, the lord Welles, and other were slayn at Towton in
Yorkeshyre.][1032] Wherefore as you thought you saw and hearde
the headles duke speake through his necke, so now[1033] suppose
you see this lord Clyfford, all armed saue his head, with his brest
plate all gore bloud running from his throate wherein an headlesse
arrow sticketh through which wound hee sayth thus.”[1034]]
How the Lorde Clyfford for his
straunge and abhominable cruelty
came to as straunge and sodayne a
death,[1035] Anno 1461.[1036]
1.
Open confession axeth open pennaunce,

And wisdome would a man his shame to hyde:[1037]
Yet sith forgieuenes commeth through repentaunce,
I thinke it best that men theyr crimes ascride,
For nought so secret but at length is spyed:
For couer fire, and it will neuer lynne
Till it breake forth, in like case shame and sinne.[1038]
2.
As for my selfe my faultes be out so playne,

And published [so] abroade[1039] in euery place,
That though I would I cannot hide a grayne.[1040]
All care is bootelesse in a curelesse case,
To learne by other’s griefe,[1041] some haue the grace:
And therefore, Baldwine, write my[1042] wretched fall,
The briefe whereof I briefly vtter shall.
3.
I am the same that[1043] slue duke Richard’s childe,

The louely babe that begged[1044] life with teares,
Whereby mine honour[1045] fouly I defilde:
Poore sely lambes the lion neuer teares,
The feeble mouse may ly among the beares,
But wrath of man, his rancour to requite,
Forgets all reason, ruth, and vertue[1046] quite.
4.
I meane by rancour the parentall[1047] wreke

Surnamde a vertue, as the vicious[1048] say,
But litle knowe the wicked[1049] what they speake,
In boldening vs[1050] our enmyes kin to slay:
To punish sinne is good, it is no nay:
They wreke not sinne, but merit wreke for sinne,
That wreke the father’s fault vpon[1051] his kinne.
5.
Because my father lord Iohn Clyfford, dyed,

Slayne at S. Albane’s, in his prince’s ayde,
Agaynst the duke my heart for malice fryed,
So that I could from wreck no way bee stayed,
But to auenge my father’s death, assayde
All meanes I might the duke of Yorke t’annoy,[1052]
And all his kin and friendes to kill and stroy.[1053]
6.
This made mee with my bloudy[1054] dagger wound

His guiltlesse sonne, that neuer agaynst mee storde:
His father’s body lying dead on ground
To pearce with speare, eke with my cruell sworde,
To part his necke, and with his head to bourd
Enuested with a royall paper[1055] crowne,
From place to place to beare it vp and downe.[1056]
7.
But cruelty[1057] can neuer scape the scourge
Of shame, of horror, or of sodayne death:[1058]
Repentaunce selfe, that other sinnes may pourge,
Doth fly from this, so sore the soule it slayeth:
Despayre dissolues the tyraunt’s bitter[1059] breath:
For sodayn vengeaunce sodaynly alightes
On cruell deedes,[1060] to quite theyr cruell spights.
[1061]
8.
This finde I true, for as I lay in stale,

To fight with[1062] duke Richard’s eldest son,
I was destroyde not far[1063] from Dintingdale,
For as I would my gorget haue vndon
To euent[1064] the heat that had mee nigh vndone,
An headles arrow strake mee through the throte,
Where through my soule forsooke his fylthy cote.[1065]
9.
Was this a chaunce? no sure, God’s iust awarde,

Wherein due[1066] iustice playnly doth appeare:
An headlesse arrow payde mee my rewarde:[1067]
For heading Richard lying on his[1068] bere,
And as I would his childe in no wise heare,
So sodayne death bereft my tongue the power
To aske for pardon at my dying[1069] hower.
10.
Wherefore, good Baldwine, warne the[1070] bloudy sort,

To leaue theyr wrath, theyr[1071] rigour to refrayne:
Tell cruell judges horror is the port
Through which they sayle to shame[1072] and sodayn
payne:[1073]
Hell haleth[1074] tyrauntes downe to death amayne:
Was neuer yet, nor shal be cruell deede,
Left vnrewarded with as[1075] cruell meede.
[Whan this tragedy was ended: “O Lord,” sayd[1076] another,
“how horrible a thing is diuision in a realme, to how many mischiefes
is it the mother, what vice is not therby kindled, what vertue left
vnquenched? for what was the cause of the duke of Yorke’s death,
and of the cruelty of this Clyfford, saue[1077] the variaunce betwene
king Henry and the house of Yorke? which at length, besides millions
of the commons, brought to destruction all the[1078] nobility. For
Edward the duke’s eldest son immediately after his[1079] father was
slayn, through help of the Neuills, gaue the king a battayle, whereat,
besides this Clyfford, and xxxvi thousand other souldiers, were slain
theyr captaynes, the earles[1080] of Northumberland and
Westmerland, with the lordes Dacres and Welles: the[1081] winning
of which fielde brought Edward to the crowne, and the losse draue
king Henry and his wife into Scotland. But as few raignes begin
without bloud, so king Edward to keepe order,[1082] caused Thomas
Courtney earle of Deuonshyre, and Iohn Veer earle of Oxeforde, and
Aubrey Veer eldest sonne to the sayd earle, with diuers[1083] other
his enemies,[1084] to bee attaynted and put to death. And shortly
after he[1085] did execution vpon the duke of Somerset, and the
lordes Hungerford and Rosse, whom he toke prisoners at Exham
fielde. For thither they came with[1086] king Henry out of Scotland,
with an army of Scottes, and fought a battayle, which was lost, and
the most[1087] part of them slayn.[1088] And because these are all
noble men, I will leaue them to Baldwine’s discretion. But seyng the
earle of Worcester was the chiefe instrument whom king Edward
vsed as well in these men’s matters as in like bloudy affayres,
because he should not be forgotten, yee shall here what I haue
noted concerning his tragedy.”[1089]]
The infamovs end of the Lord Tiptoft
Earle of Worcester, for cruelly
executing his Prince’s butcherly
commaundementes, An. 1470.[1090]
1.
The glorious man is not so loth to lurke,

As the infamous glad to lye vnknowen:
Which makes mee, Baldwine, disalow thy worke,
Where prince’s faultes so openly be blowen:
I speake not this alonly for mine owne,
Which were my prince’s (if that they were any)
But for my peeres, in nombre very many.
2.
Or might report vprightly vse her tong,

It would lesse greue vs to augment the matter,
But suer I am thou shalt be forst among,
To frayne the truth the liuing for to flatter,
And otherwhiles in poyntes vnknowen to smatter:
For time neuer was, nor neuer[1091] I thinke shalbe
That truth vnshent should speake in all thinges free.
3.
This doth appeare (I dare say) by my story,

Which diuers writers diuersly declare:
But story writers ought for neyther glory,
Feare, nor fauour, truth of thinges to spare?
But still it fares as alway it did fare,
Affections, feare, or doubts that dayly brue,
Doe cause that stories neuer can be true.[1092]
4.
Unfruitfull Fabian followed the face

Of tyme and dedes, but let the causes slip:
Which Hall hath added, but with double grace,[1093]
For feare I thinke lest trouble might him trip:
“For this or that,” sayeth he, “he felt the whip:”
Thus[1094] story wryters leaue the causes out,
Or so rehearse them as they were in dout.[1095]
5.
But seing causes are the chiefest thinges

That should be noted of the story wryters,
That men may learne what endes all causes bringes,
They be vnworthy the[1096] name of chroniclers
That leaue them cleane out of theyr registers,
Or doubtfully report them: for the fruite
Of reading storyes standeth in the suite.
6.
And therefore, Baldwine, eyther speake vpright[1097]

Of our affayres, or touch them not at all:
As for my selfe I way all thinges so light,
That nought I passe how men report my fall:
The truth whereof yet playnly shew I shall,
That thou mayst write and others thereby rede,
What thinges I did whereof they should take heede.
7.
Thou hast heard of[1098] Tiptoft’s earles of Worcester,

I am that lord that liu’d in Edwarde’s days
The fourth, and was his friend and counsaylour,
And butcher to, as common rumor sayes:
But people’s voyce is neyther shame nor prayse,
For whom they would aliue deuoure to day,
To morow dead they will[1099] worship what they may.
8.
But though the people’s verdit go by chaunce,

Yet was there cause to call mee as they did:
For I, enforst by meane of gouernaunce,
Did execute what euer[1100] my king did bid,
From blame herein my selfe I cannot rid:
But fye vpon the wretched state, that must
Defame it selfe, to serue the prince’s lust.
9.
The cheifest crime wherewith men doe me charge,

Is death of th’[1101] earle of Desmund’s noble sonnes,
Of which the kinge’s charge doth me clere discharge,
By strayt commaundement and iniunctions:
Th’effect whereof so rigorously runnes,
That eyther I must procure to see them dead,
Or for contempt as a traytour loose my head.[1102]
10.
What would mine enemies[1103] doe in such a case,

Obay the king or proper death procure?
They may well say theyr fancy for a face,
But life is sweete, and loue hard to recure:
They would haue done as I did, I am sure,
For seldom will a welthy man at ease
For other’s cause his prince in ought displease.
11.
How much lesse I, which was lieuetenaunt than

In th’[1104] Irish isle, preferred by the king:
But who for loue or dread of any man,
Consents t’[1105] accomplish any wicked thing,
Although chiefe fault thereof from other spring,
Shall not escape God’s vengeance for his deede,
Who scuseth none that dare doe ill for drede.
12.
This in my king and mee may well appeare,

Which for our faultes did not escape the scourge:
For whan wee thought our state most sure and clere,
The wynd of Warwicke blew vp such a sourge,
As from the realme and crowne the king did pourge,
And mee both from mine office,[1106] friendes, and
wife,
From good report, from honest death and life.
13.
For the earle of Warwicke, through a cancarde

grudge[1107]
Which to king Edward causelesse hee did beare,
Out of his realme by force did make him trudge,
And set king Henry agayne vpon his chaire:
And then all such as Edwarde’s louers were,
As traytours tane were greuously opprest,
But chiefly I, because I lou’d him best.
14.
And, for[1108] my goods and liuinges were not small,

The gapers for them bare[1109] the world in hand
For ten yeares space, that I was cause of all
The executions done[1110] within the land:
For this did such as did not vnderstand
Mine enmies drift, thinke all reportes were true:
And so did[1111] hate mee worse then any Jewe.
15.
For seldom shall a ruler lose his life,

Before false rumors openly be spred:
Wherby this prouerbe is as true as rife,
That ruler’s rumors hunt about a head,
Frowne fortune once, all good report is fled:
For present shew doth make the mayny blind,
And such as see dare not disclose their minde.
16.
Through this was I king Edward’s butcher named,

And bare the shame of all his cruell deedes:
I cleare me not, I worthely was blamed,
Though force was such I must obay him needes:
With hiest rulers seldome well it speedes,
For they be euer nerest to the nyp,
And fault who shall, for all feele they the whip.
17.
For whan I was by parliament attaynted,

King Edward’s euils all were counted mine:
No truth auayled, so lies were faste and painted,
Which made the people at my life, repine,
Crying, “Crucifige, kill that butcher’s lyne:”
That when I should haue gone to Blockham feast,
I could not passe, so sore they one me preast.
18.
And had not bene the officers so strong,

I thinke they would haue eaten[1112] me aliue,
Howbeit, hardly haled from the throng,
I was in the flete fast shrouded by the shriue:
Thus one daye’s life theyr malice did mee gieue,
Which whan they knew, for spite the next day after
They kept them calme, so suffered I the slaughter.
19.
Now tell mee, Baldwine, what fault dost thou finde

In mee, that iustly should such death deserue?
None sure except desire of honour blinde,
Which made mee seeke in offices to serue:
What minde so good that honours make not swerue?
So mayst thou see it only was my state
That caus’d my death, and brought mee so in hate.
20.
Warne therfore all men wisely to beware,

What offices they enterprise to beare:
The hiest alway most maligned are,
Of people’s grudge, and prince’s hate in feare.
For prince’s faults his faultors all men teare:
Which to auoyde, let none such office take,
Saue he that can for right his prince forsake.
[This earle’s[1113] tragedy was not so soone finished, but one of
the company had prouided for another of a notable person, lord
Tiptoft’s chiefe enemy: concerning whom hee sayd: “Lord God what
trust is there in worldly chaunces? what stay in any prosperity? for
see the earle of Warwicke which caused the earle of Worcester to be
apprehended, attainted, and put to deth, triumphing with his old
imprisoned and new vnprisoned prince, king Henry, was by and by
after, and his brother with him, slayn at Barnet field by king Edward,
whom hee had before time damaged diuers wayes. As first by his
friendes at Banbury fielde, where to reuenge the death of his cosin
Henry[1114] Neuill, syr Iohn Coniers, and Iohn Clappam, his
seruauntes, slue fiue thousand Welshmen, and beheaded theyr
captaynes, the earle of Pembroke and syr Richard Harbert his
brother, after they were yeelded prisoners: of whom syr Richard
Harbert was the tallest gentilman both of his person and handes that
euer I read or heard of. At which time also, Robin of Ridsdale,[1115] a
rebell of the earle of Warwicke’s raysing, tooke the earle Riuers, king
Edwarde’s wiue’s father, and his sonne Iohn, at his manour of
Grafton, and carried them to Northampton, and there without cause
or proces beheaded them. Which spites to requite, king Edward
caused the lord Stafford of Sowthwike, one of Warwicke’s chiefe
frendes, to be taken at Brent march, and headed at Bridgewater.
This caused the earle shortly to raise his power, to encounter the
king which came against him with an army, beside Warwicke at
Wolney, where hee wan the field, tooke the king prisoner, and kept
him a while in Yorkeshire in Middleham castle: whence (as some
say) hee released him againe, but other thinke hee corrupted hys
keepers and so escaped. Then through the lords the matter was
taken vppe betweene them, and they brought to talke togeather, but
because they could not agree, the earle araised a new army,
whereof he made captayn the lord Welles’ sonne, which broile king
Edward minding to appease by pollicy, fouly distained his honour,
committing periury: for hee sent for the lord Welles and his brother
sir Thomas Dymocke, vnder safe conduite promising them vpon his
fayth to keepe them harmelesse. But after, because the lord Welles’
sonne would not dissolue his army, beheaded them both and went
with his power into Lincolnshire and there fought with sir Robert
Welles, and slewe ten thousand of his souldiers (yet ran they away
so fast, that casting of their clothes for the more speede, caused it to
bee called Lose coate fielde) and tooke sir Robert and other, and put
them to death in the same place. This misfortune forced the earle of
Warwicke to saile into Fraunce where hee was entertained of the
king a while, and at last with such poore helpe as hee procured there
of duke Rainer and other, hee came into England againe, and
encreased such a power in king Henrie’s name, that as the lord
Typtofte sayd in his tragedy, king Edward vnable to abide him, was
faine to flie ouer the washes in Lincolnshire to get a ship to saile out
of his kingdome to his brother in lawe the duke of Burgoine. So was
king Henry restored againe to his[1116] kingdome. All these despites
and troubles the earle wrought against king Edward. But Henry was
so infortunate that ere halfe a yeare was expired, king Edward came
backe againe, and enprisoned him and gaue the earle a fielde,
wherein hee slewe both him and his brother. I haue recounted thus
much before hand for the better opening of the story, which, if it
should haue beene spoken in his tragedy, would rather haue made a
volume then a pamphlete. For I entend onely to say in the tragedy,
what I haue noted in the earle of Warwicke’s person, wishing that
these other noble men, whome I haue by the way touched, should
not bee forgotten. And therefore imagine that you see this earle lying
with his brother in Paule’s church[1117] in his coate armoure, with
such a face and countinaunce as he beareth in portraiture ouer the
dore in Paule’s, at the going down to Iesus chappell from the south
end of the quier stayres, and saying as followeth.”]

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(eBook PDF) Organic and Biological

Chemistry 7th Edition

Answers to Selected Exercises A-1

3-14 Structural Characteristics of Ethers 112 5-11 Preparation of Esters 176

Part II b io lo g ic a l C hemistry 8 Lipids 303

9-B Denaturation and Human Hair 387 Chemical connections

13-9 Hormonal Control of Carbohydrate Metabolism 575 15 Protein Metabolism 612

New Features Added to the Seventh Edition

Important Continuing Features in the Seventh Edition

organic chemistry, and understanding organic chemistry in turn depends on knowing

a Arrangement b Backbone c Backbone atomic d Top view of an a

Chemistry at a Glance Visual summaries called Chemistry at a Glance pull together

jj Changing a Fischer Projection Formula to a Haworth Projection Formula

Reviewers of the 7th edition:

Reviewers of the 6th edition:

Reviewers of the 5th edition:

1-1 Organic and Inorganic Compounds

1-2 Bonding Characteristics of the Carbon Atom

Section 1-2 Quick Quiz

1-3 Hydrocarbons and Hydrocarbon Derivatives

Figure 1-2 A summary of

Hydrocarbons and their

Compounds containing Compounds containing carbon,

Hydrocarbons in which Hydrocarbons containing one or

Two categories of saturated hydrocarbons exist, those with acyclic carbon

1-4 Alkanes: Acyclic Saturated Hydrocarbons

An alkane is a saturated hydrocarbon in which the carbon atom arrangement is acy-

Methane Ethane Propane

Section 1-4 Quick Quiz

The Occurrence of Methane

Bacteria that live in termites and in the digestive tracts

large cow (via belching and flatulence) can reach 20 ­liters

His cursed sonne ensued his cruell path,

For whan king Henry,[974] of that name the fifte,

Thus whan the linage of the Mortimers

Yet at the last, in Henrye’s dayes the sixt,

O Lord, what hap had I through mariage,

Through helpe of whome and fortune’s louely looke,

And maugre him, so choyse, lo, was my chaunce,

This spitefull duke, his seely king[993] and queene,

Before this last were other battayles three,

This boy and I, in Ireland did vs saue,

This done I came[1001] to England all in haste,

But sith the king had raigned now so long,[1006]

Whereof shee warnd preparde a mighty powre,

And so was slaine at first: and while my childe

Wherefore see, Baldwine, that thou set it forth,

Far[1020] better it were to lose a piece of right,

Wherefore warne princes not to wade[1024] in war

Open confession axeth open pennaunce,

As for my selfe my faultes be out so playne,

I am the same that[1043] slue duke Richard’s childe,

I meane by rancour the parentall[1047] wreke

Because my father lord Iohn Clyfford, dyed,

This made mee with my bloudy[1054] dagger wound

This finde I true, for as I lay in stale,

Was this a chaunce? no sure, God’s iust awarde,

Wherefore, good Baldwine, warne the[1070] bloudy sort,

The glorious man is not so loth to lurke,

Or might report vprightly vse her tong,

This doth appeare (I dare say) by my story,

Unfruitfull Fabian followed the face

But seing causes are the chiefest thinges

large cow (via belching and flatulence) can reach 20 liters