PDF General Organic Biological Chemistry Third Edition Janice G Smith Ebook Full Chapter
PDF General Organic Biological Chemistry Third Edition Janice G Smith Ebook Full Chapter
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1A
Periodic Table of the Elements
8A
1
18
1 2
1 H 3A 4A 5A 6A 7A He 1
2A
1.008
2 13 14 15 16 17 4.003
3 4 5 6 7 8 9 10
2 Li Be B C N O F Ne 2
6.941 9.012 10.81 12.01 14.01 16.00 19.00 20.18
11 12 13 14 15 16 17 18
3 Na Mg 3B 4B 5B 6B 7B 8B 1B 2B Al Si P S Cl Ar 3
22.99 24.31 3 4 5 6 7 8 9 10 11 12 26.98 28.09 30.97 32.07 35.45 39.95
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
4 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 4
39.10 40.08 44.96 47.88 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.41 69.72 72.64 74.92 78.96 79.90 83.80
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
5 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 5
85.47 87.62 88.91 91.22 92.91 95.94 (98) 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
6 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 6
132.9 137.3 138.9 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (209) (210) (222)
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg Cn – Fl – Lv – – 7
(223) (226) (227) (267) (268) (271) (272) (270) (276) (281) (280) (285) (284) (289) (289) (293) (294) (294)
58 59 60 61 62 63 64 65 66 67 68 69 70 71
6 Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 6
140.1 140.9 144.2 (145) 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0
90 91 92 93 94 95 96 97 98 99 100 101 102 103
7 Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr 7
232.0 231.0 238.0 (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (262)
The Elements
Atomic Atomic
Element Symbol Number Relative Atomic Mass* Element Symbol Number Relative Atomic Mass*
Actinium Ac 89 (227) Mendelevium Md 101 (258)
Aluminum Al 13 26.98 Mercury Hg 80 200.6
Americium Am 95 (243) Molybdenum Mo 42 95.94
Antimony Sb 51 121.8 Neodymium Nd 60 144.2
Argon Ar 18 39.95 Neon Ne 10 20.18
Arsenic As 33 74.92 Neptunium Np 93 (237)
Astatine At 85 (210) Nickel Ni 28 58.69
Barium Ba 56 137.3 Niobium Nb 41 92.91
Berkelium Bk 97 (247) Nitrogen N 7 14.01
Beryllium Be 4 9.012 Nobelium No 102 (259)
Bismuth Bi 83 209.0 Osmium Os 76 190.2
Bohrium Bh 107 (272) Oxygen O 8 16.00
Boron B 5 10.81 Palladium Pd 46 106.4
Bromine Br 35 79.90 Phosphorus P 15 30.97
Cadmium Cd 48 112.4 Platinum Pt 78 195.1
Calcium Ca 20 40.08 Plutonium Pu 94 (244)
Californium Cf 98 (251) Polonium Po 84 (209)
Carbon C 6 12.01 Potassium K 19 39.10
Cerium Ce 58 140.1 Praseodymium Pr 59 140.9
Cesium Cs 55 132.9 Promethium Pm 61 (145)
Chlorine Cl 17 35.45 Protactinium Pa 91 231.0
Chromium Cr 24 52.00 Radium Ra 88 (226)
Cobalt Co 27 58.93 Radon Rn 86 (222)
Copernicium Cn 112 (285) Rhenium Re 75 186.2
Copper Cu 29 63.55 Rhodium Rh 45 102.9
Curium Cm 96 (247) Roentgenium Rg 111 (280)
Darmstadtium Ds 110 (281) Rubidium Rb 37 85.47
Dubnium Db 105 (268) Ruthenium Ru 44 101.1
Dysprosium Dy 66 162.5 Rutherfordium Rf 104 (267)
Einsteinium Es 99 (252) Samarium Sm 62 150.4
Erbium Er 68 167.3 Scandium Sc 21 44.96
Europium Eu 63 152.0 Seaborgium Sg 106 (271)
Fermium Fm 100 (257) Selenium Se 34 78.96
Flerovium Fl 114 (289) Silicon Si 14 28.09
Fluorine F 9 19.00 Silver Ag 47 107.9
Francium Fr 87 (223) Sodium Na 11 22.99
Gadolinium Gd 64 157.3 Strontium Sr 38 87.62
Gallium Ga 31 69.72 Sulfur S 16 32.07
Germanium Ge 32 72.64 Tantalum Ta 73 180.9
Gold Au 79 197.0 Technetium Tc 43 (98)
Hafnium Hf 72 178.5 Tellurium Te 52 127.6
Hassium Hs 108 (270) Terbium Tb 65 158.9
Helium He 2 4.003 Thallium Tl 81 204.4
Holmium Ho 67 164.9 Thorium Th 90 232.0
Hydrogen H 1 1.008 Thulium Tm 69 168.9
Indium In 49 114.8 Tin Sn 50 118.7
Iodine I 53 126.9 Titanium Ti 22 47.88
Iridium Ir 77 192.2 Tungsten W 74 183.8
Iron Fe 26 55.85 Uranium U 92 238.0
Krypton Kr 36 83.80 Vanadium V 23 50.94
Lanthanum La 57 138.9 Xenon Xe 54 131.3
Lawrencium Lr 103 (262) Ytterbium Yb 70 173.0
Lead Pb 82 207.2 Yttrium Y 39 88.91
Lithium Li 3 6.941 Zinc Zn 30 65.41
Livermorium Lv 116 (293) Zirconium Zr 40 91.22
Lutetium Lu 71 175.0 113** (284)
Magnesium Mg 12 24.31 115 (289)
Manganese Mn 25 54.94 117 (294)
Meitnerium Mt 109 (276) 118 (294)
*Values in parentheses represent the mass number of the most stable isotope.
**The names and symbols for elements 113, 115, 117, and 118 have not been chosen.
General, Organic, & Biological
Published by McGraw-Hill Education, 2 Penn Plaza, New York, NY 10121. Copyright © 2016 by McGraw-Hill
Education. All rights reserved. Printed in the United States of America. Previous editions © 2013, 2010. No part
of this publication may be reproduced or distributed in any form or by any means, or stored in a database or re-
trieval system, without the prior written consent of McGraw-Hill Education, including, but not limited to, in any
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Some ancillaries, including electronic and print components, may not be available to customers outside the
United States.
1 2 3 4 5 6 7 8 9 0 DOW/DOW 1 0 9 8 7 6 5
ISBN 978-0-07-351124-5
MHID 0-07-351124-2
All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.
Smith, Janice G
General, organic, & biological chemistry / Janice Gorzynski Smith,
University of Hawaii at Manoa. — Third edition.
pages cm
Includes index.
ISBN 978-0-07-351124-5 (alk. paper)
1. Chemistry—Textbooks. I. Title II. Title: General, organic, and biological chemistry.
QD31.3.S63 2016
540—dc23
2014017720
The Internet addresses listed in the text were accurate at the time of publication. The inclusion of a website does
not indicate an endorsement by the authors or McGraw-Hill Education, and McGraw-Hill Education does not
guarantee the accuracy of the information presented at these sites.
www.mhhe.com
About the Author
Janice Gorzynski Smith was born in Schenectady, New York, and grew up follow-
ing the Yankees, listening to the Beatles, and water skiing on Sacandaga Reservoir. She became
interested in chemistry in high school, and went on to major in chemistry at Cornell University
where she received an A.B. degree summa cum laude. Jan earned a Ph.D. in Organic Chemistry
from Harvard University under the direction of Nobel Laureate E. J. Corey, and she also spent a
year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard. During
her tenure with the Corey group, she completed the total synthesis of the plant growth hormone
gibberellic acid.
Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College where
she was employed for 21 years. During this time she was active in teaching chemistry lecture
and lab courses, conducting a research program in organic synthesis, and serving as department
chair. Her organic chemistry class was named one of Mount Holyoke’s “Don’t-miss courses”
in a survey by Boston magazine. After spending two sabbaticals amidst the natural beauty and
diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently in 2000. Most
recently, she has served as a faculty member at the University of Hawai‘i at Ma–noa, where she
has taught a one-semester organic and biological chemistry course for nursing students, as well
as the two-semester organic chemistry lecture and lab courses. She has also served as the faculty
advisor to the student affiliate chapter of the American Chemical Society. In 2003, she received
the Chancellor’s Citation for Meritorious Teaching.
Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician. She has
four children and three grandchildren. When not teaching, writing, or enjoying her family, Jan
bikes, hikes, snorkels, and scuba dives in sunny Hawai‘i, and time permitting, enjoys travel and
Hawaiian quilting.
Dedicated to my family
iii
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Brief Contents
19 Lipids 638
20 Carbohydrates 678
21 Amino Acids, Proteins, and Enzymes 715
22 Nucleic Acids and Protein Synthesis 760
23 Metabolism and Energy Production 797
24 Carbohydrate, Lipid, and Protein Metabolism 824
v
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Contents
Preface xxii
P.A.V.E. the Way to Student Learning xxvi
Acknowledgments xxxii
List of How To’s xxxiii
List of Applications xxxiv
vii
viii Contents
2.3 Isotopes 43
2.3A Isotopes, Atomic Number, and Mass Number 43
2.3B Atomic Weight 46
2.3C FOCUS ON HEALTH & MEDICINE: Isotopes in Medicine 47
2.4 The Periodic Table 47
2.4A Basic Features of the Periodic Table 48
2.4B Characteristics of Groups 1A, 2A, 7A, and 8A 49
2.4C The Unusual Nature of Carbon 51
2.5 Electronic Structure 52
2.6 Electronic Configurations 55
2.6A First-Row Elements (Period 1) 55
2.6B Second-Row Elements (Period 2) 56
2.6C Electronic Configurations of Other Elements Using the
Periodic Table 58
2.7 Valence Electrons 60
2.7A Relating Valence Electrons to Group Number 60
2.7B Electron-Dot Symbols 62
2.8 Periodic Trends 63
2.8A Atomic Size 63
2.8B Ionization Energy 64
Chapter Highlights 66
Key Terms 66
Key Concepts 66
Problems 67
Challenge Problems 71
3 Ionic Compounds 72
3.1 Introduction to Bonding 73
3.2 Ions 75
3.2A Cations and Anions 75
3.2B Relating Group Number to Ionic Charge for Main Group Elements 78
3.2C Metals with Variable Charge 80
3.2D FOCUS ON THE HUMAN BODY: Important Ions in the Body 81
3.3 Ionic Compounds 83
3.3A Formulas for Ionic Compounds 84
3.3B FOCUS ON HEALTH & MEDICINE: Ionic Compounds
in Consumer Products 86
3.4 Naming Ionic Compounds 87
3.4A Naming Cations 87
3.4B Naming Anions 87
3.4C Naming Ionic Compounds with Cations from Main Group Metals 88
3.4D Naming Ionic Compounds Containing Metals
with Variable Charge 89
3.4E Writing a Formula from the Name of an Ionic Compound 90
3.5 Physical Properties of Ionic Compounds 90
3.6 Polyatomic Ions 92
3.6A Writing Formulas for Ionic Compounds with Polyatomic Ions 92
3.6B Naming Ionic Compounds with Polyatomic Ions 94
3.6C FOCUS ON HEALTH & MEDICINE: Useful Ionic Compounds 94
3.6D FOCUS ON HEALTH & MEDICINE: Treating Osteoporosis 95
Chapter Highlights 95
Key Terms 95
Key Concepts 95
Problems 96
Challenge Problems 100
Contents ix
8 Solutions 262
8.1 Mixtures 263
8.1A Solutions 263
8.1B Colloids and Suspensions 264
8.2 Electrolytes and Nonelectrolytes 265
8.2A Classification 265
8.2B Equivalents 266
8.3 Solubility—General Features 268
8.3A Basic Principles 268
8.3B Ionic Compounds—Additional Principles 271
8.4 Solubility—Effects of Temperature and Pressure 272
8.4A Temperature Effects 272
8.4B Pressure Effects 272
8.5 Concentration Units—Percent Concentration 273
8.5A Weight/Volume Percent 273
8.5B Volume/Volume Percent 275
8.5C Using a Percent Concentration as a Conversion Factor 275
8.5D Parts Per Million 277
8.6 Concentration Units—Molarity 278
8.7 Dilution 281
8.8 Colligative Properties 283
8.8A Boiling Point Elevation 283
8.8B Freezing Point Depression 285
8.9 Osmosis and Dialysis 286
8.9A Osmotic Pressure 286
8.9B FOCUS ON THE HUMAN BODY: Osmosis and Biological Membranes 287
8.9C FOCUS ON HEALTH & MEDICINE: Dialysis 288
xii Contents
12 Alkanes 407
12.1 Introduction 408
12.2 Simple Alkanes 409
12.2A Acyclic Alkanes Having Fewer Than Five Carbons 409
12.2B Acyclic Alkanes Having Five or More Carbons 411
12.2C Classifying Carbon Atoms 412
12.2D Bond Rotation and Skeletal Structures for Acyclic Alkanes 413
12.3 An Introduction to Nomenclature 414
12.3A The IUPAC System of Nomenclature 414
12.3B FOCUS ON HEALTH & MEDICINE: Naming New Drugs 415
12.4 Alkane Nomenclature 415
12.4A Naming Substituents 416
12.4B Naming an Acyclic Alkane 417
xiv Contents
19 Lipids 638
19.1 Introduction to Lipids 639
19.2 Fatty Acids 641
19.3 Waxes 644
19.4 Triacylglycerols—Fats and Oils 646
19.4A General Features 646
19.4B FOCUS ON HEALTH & MEDICINE: Fats and Oils in the Diet 649
19.5 Hydrolysis of Triacylglycerols 650
19.5A FOCUS ON THE HUMAN BODY: Metabolism of Triacylglycerols 651
19.5B Soap Synthesis 653
19.6 Phospholipids 654
19.6A Phosphoacylglycerols 654
19.6B Sphingomyelins 656
19.7 Cell Membranes 658
19.7A Structure of the Cell Membrane 658
19.7B Transport Across a Cell Membrane 660
19.8 FOCUS ON HEALTH & MEDICINE: Cholesterol, the Most Prominent Steroid 661
19.9 Steroid Hormones 664
19.10 FOCUS ON HEALTH & MEDICINE: Fat-Soluble Vitamins 666
19.11 FOCUS ON HEALTH & MEDICINE: Prostaglandins and Leukotrienes 668
19.11A Prostaglandins 668
19.11B Asthma and Leukotrienes 669
Chapter Highlights 670
Key Terms 670
Key Reactions 670
Key Concepts 671
Problems 672
Challenge Problems 677
20 Carbohydrates 678
20.1 Introduction 679
20.2 Monosaccharides 680
20.2A Fischer Projection Formulas 682
20.2B Monosaccharides with More Than One Chirality Center 683
20.2C Common Monosaccharides 685
20.3 The Cyclic Forms of Monosaccharides 686
20.3A The Cyclic Forms of D-Glucose 687
20.3B Haworth Projections 689
20.3C The Cyclic Forms of Fructose, a Ketohexose 691
20.4 Reduction and Oxidation of Monosaccharides 691
20.4A Reduction of the Aldehyde Carbonyl Group 692
20.4B Oxidation of the Aldehyde Carbonyl Group 693
20.4C FOCUS ON HEALTH & MEDICINE: Monitoring Glucose Levels 695
20.5 Disaccharides 695
20.5A FOCUS ON HEALTH & MEDICINE: Lactose Intolerance 698
20.5B FOCUS ON HEALTH & MEDICINE: Sucrose and Artificial Sweeteners 699
20.6 Polysaccharides 700
20.6A Cellulose 701
20.6B Starch 702
20.6C Glycogen 703
20.7 FOCUS ON THE HUMAN BODY: Useful Carbohydrate Derivatives 704
20.7A Glycosaminoglycans 704
20.7B Chitin 704
20.8 FOCUS ON THE HUMAN BODY: Blood Type 706
Contents xix
Appendixes
A Useful Mathematical Concepts A-1
B Answers to Selected In-Chapter and End-of-Chapter Problems B-1
Glossary G-1
Credits C-1
Index I-1
Preface
M y goal in writing this text was to relate the fundamental concepts of general, organic, and
biological chemistry to the world around us, and in this way illustrate how chemistry
explains many aspects of everyday life. I have followed two guiding principles:
• use relevant and interesting applications for all basic chemical concepts
• present the material in a student-friendly fashion using bulleted lists, extensive illustrations,
and step-by-step problem solving
This text is different—by design. Since today’s students rely more heavily on visual imagery
to learn than ever before, this text uses less prose and more diagrams and figures to reinforce
the major themes of chemistry. A key feature is the use of molecular art to illustrate and explain
common phenomena we encounter every day. Each topic is broken down into small chunks of
information that are more manageable and easily learned. Students are given enough detail to
understand basic concepts, such as how soap cleans away dirt and why trans fats are undesirable
in the diet, without being overwhelmed.
This textbook is written for students who have an interest in nursing, nutrition, environmen-
tal science, food science, and a wide variety of other health-related professions. The content of
this book is designed for an introductory chemistry course with no chemistry prerequisite, and is
suitable for either a two-semester sequence or a one-semester course. I have found that by intro-
ducing one new concept at a time, keeping the basic themes in focus, and breaking down complex
problems into small pieces, many students in these chemistry courses acquire a new appreciation
of both the human body and the larger world around them.
xxii
Preface xxiii
dd 214
• Macro-to-Micro Illustrations Because today’s 12/08/14 12:42 PM
Sodium metal and chlorine gas are both elements. Sodium chloride is an ionic compound
composed of sodium ions and chloride ions.
How To Name an Ionic Compound That Contains a Metal with Variable Charge
• Problem Solving Sample Problems lead students Example: Give the name for CuCl2.
Step [1] Determine the charge on the cation.
through the thought process tied to success- • Since there are two Cl− anions, each of which has a −1 charge, the copper cation must have a +2 charge to make the overall
ful problem solving by employing Analysis and charge zero.
CuCl2 2 Cl− anions The total negative charge is −2.
Solution parts. Sample Problems are categorized
Cu must have a +2 charge to balance the −2 charge of the anions.
sequentially by topic to match chapter organiza- Cu2+
tion, and are often paired with practice problems to Step [2] Name the cation and anion.
allow students to apply what they have just learned. • Name the cation using its element name followed by a Roman numeral to indicate its charge. In the common system, use the
suffix -ous or -ic to indicate charge.
Students can immediately verify their answers to • Name the anion by changing the ending of the element name to the suffix -ide.
Cu2+ copper(II) or cupric
the follow-up problems in the appendix at the end Cl– chloride
of the book. Step [3] Write the name of the cation first, then the anion.
• Answer: Copper(II) chloride or cupric chloride
• How To’s Key processes are taught to students in a straightforward and easy-to-understand manner by
using examples and multiple, detailed steps to solving problems.
• Applications Common applications of chemistry to everyday life are found in margin-placed Health
Notes, Consumer Notes, and Environmental Notes, as well as sections entitled “Focus on Health &
Medicine,” “Focus on the Environment,” and “Focus on the Human Body.”
General
• Problem sets. More problems with molecular art and 3-D models have been added to the
text and the ends of the chapters.
• Design and layout. An effort has been made with the revised third edition design and layout
to move all photos, graphics, and tables closer to related material in the text.
• Photos. Roughly one-half of the chapter-opening photos have been replaced with photos
emphasizing relevant material within the chapter. More marginal photos of applications have
also been added.
• Art. The colors of subatomic particles in all nuclear art were revised for clarity and consis-
tency (Chapters 2, 3, and 10).
• To divide two numbers in scientific notation, divide the coefficients and subtract the
exponents in the powers of 10.
Divide coefficients.
6.0 × 102
Subtract exponents. = 3.0 × 10−18
Practice chemistry through stepped-out practice
(6.0 ÷ 2.0) 2.0 × 1020 (2 − 20)
For a number written in scientific
notation as y × 10x, y is the coefficient
problems and end-of-chapter problems categorized
and x is the exponent in the power of 10 Sample Problems 5.9 and 5.10 illustrate how to interconvert moles and molecules. In both prob-
(Section 1.6). lems we follow the stepwise procedure for problem solving using conversion factors outlined in
Section 1.7B.
sequentially by topic to match chapter organization.
SAMPLE PROBLEM 5.9
How To boxes offer step-by-step strategies for difficult
Converting moles to number of molecules: How many molecules are contained in 5.0 mol of
carbon dioxide (CO2)?
concepts.
Analysis and Solution
[1] Identify the original quantity and the desired quantity.
[2] Write out the conversion factors. How To Use Boyle’s Law to Calculate a New Gas Volume or Pressure
or so that
• Choose the conversion factor that places the unwanted unit, mol, in the denominator
Example: If a 4.0-L container of helium gas has a pressure of 10.0 atm, what pressure does the gas exert if the volume is increased
the units cancel. to 6.0 L?
Step [1] Identify the known quantities and the desired quantity.
1 mol 6.02 × 1023 molecules
or • To solve an equation using Boyle’s law, we must know three quantities and solve for one quantity. In this case P1, V1, and V2 are
6.02 × 1023 molecules 1 mol known and the final pressure, P2, must be determined.
P1 = 10.0 atm
Choose this conversion factor to cancel mol.
V1 = 4.0 L V2 = 6.0 L P2 = ?
known quantities desired quantity
[3] Set up and solve the problem.
• Multiply the original quantity by the conversion factor to obtain the desired quantity. Step [2] Write the equation and rearrange it to isolate the desired quantity on one side.
• Rearrange the equation for Boyle’s law so that the unknown quantity, P2, is present alone on one side.
Convert to a number between 1 and 10.
6.02 × 1023 molecules P1V1 = P2V2 Solve for P2 by dividing both sides by V2.
5.0 mol × = 30. × 1023 molecules
1 mol
P1V1
Moles cancel. = 3.0 × 1024 molecules of CO2 = P2
V2
Answer Step [3] Solve the problem.
• Substitute the known quantities into the equation and solve for P2. Identical units must be used for two similar quantities (liters
• Multiplication first gives an answer that is not written in scientific notation since the in this case) so that the units cancel.
coefficient (30.) is greater than 10. Moving the decimal point one place to the left and d
P1V1 (10.0 atm)(4.0 L)
increasing the exponent by one gives the answer written in the proper form. P2 = = = 6.7 atm
V2 6.0 L
PROBLEM 5.18 Liters cancel. Answer
How many carbon atoms are contained in each of the following number of moles: (a) 2.00 mol; • In this example, the volume increased so the pressure decreased.
(b) 6.00 mol; (c) 0.500 mol; (d) 25.0 mol?
are very well written and solved with the P1V1 = P2V2 Solve for V2 by dividing both sides by P2.
P1V1
appropriate level of detail. They illustrate P2
= V2
Section 1.1), are isolated directly from a natural source, most widely used drugs are synthe-
sized in the laboratory. All common pain relievers—aspirin, acetaminophen, and ibuprofen—
are synthetic. The same is true for the bronchodilator albuterol (trade names Proventil or
Apply chemistry through “Focus on Health & Medicine,” Ventolin), the antidepressant fluoxetine (trade name Prozac), and the cholesterol-lowering
medication atorvastatin (trade name Lipitor), whose three-dimensional structures are shown
“Focus on the Human Body,” and “Focus on the in Figure 5.8.
Once it has been determined that a drug is safe and effective, a pharmaceutical company must be
Environment” sections woven throughout the text. Chemistry able to prepare large quantities of the material cost-efficiently. This means that cheap and readily
applications are also woven into marginal notes that cover available starting materials must be used. It also means that the reactions used to synthesize a
drug must proceed in high yield. Rarely is a drug prepared in a single step, and typically, five or
topics on consumer, health, and environmental issues. more steps may be required in a synthesis.
• To determine the overall percent yield in a synthesis that has more than one step, multiply
the percent yield for each step.
For example, if a synthesis has five steps and each step has a 90.% yield (0.90 written as a
decimal), the overall yield is
0.90 × 0.90 × 0.90 × 0.90 × 0.90 = 0.59 = 59%
xxvi
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Louis XV, of France, 140
Louis, Saint, Psalter of, described, 128–131;
death of, 129
Lounsbury, Professor, of Yale, 84
Lowell, James Russell, 178
Luther, Martin, 215, 224
University Press, the old, Cambridge, Mass., 5, 38, 41, 42, 46, 47, 49, 51, 102
Upsala, Sweden, 119
Urbino, the Duke of, 12
Wages, in 1891, 58
Walker, Emery, designs the Doves type, 18, 19;
engraves plates for Humanistic Petrarch, 28;
at the Doves Press, 263;
referred to, 71
Walpole, Horace, 163
Warner, Sir George, 140
Widener, Joseph E., library of, 196
Wiggin, Rev. James Henry, 52
Wiggin, Kate Douglas, 177
Wilhelm, Kaiser, 103, 104
William of Orange, founds the University of Leyden, 239
William the Conqueror, 158
Wilson, Francis, 38
Wilson, John, 5, 6, 38, 40, 42, 46, 52, 53, 55
Windsor Castle, 140
Wood, Gen. Leonard, 82
Wood cuts, 106
Wordsworth, William, quoted, 20
World War, the, 103
Worsley, Sir Robert, 136
Writing, see Hand lettering
Written book, the printed book had to compete against, 199