Introduction to Organic Chemistry, 6th Edition

Author: William H. Brown,Thomas Poon

Publisher: Wiley Global Education

ISBN: 1119233755

Category: Science

Page: 696

View: 5432

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Introduction to Organic Chemistry, 6th Edition provides an introduction to organic chemistry for students who require the fundamentals of organic chemistry as a requirement for their major. It is most suited for a one semester organic chemistry course. In an attempt to highlight the relevance of the material to students, the authors place a strong emphasis on showing the interrelationship between organic chemistry and other areas of science, particularly the biological and health sciences. The text illustrates the use of organic chemistry as a tool in these sciences; it also stresses the organic compounds, both natural and synthetic, that surround us in everyday life: in pharmaceuticals, plastics, fibers, agrochemicals, surface coatings, toiletry preparations and cosmetics, food additives, adhesives, and elastomers.
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Experimental Organic Chemistry: A Miniscale & Microscale Approach

Author: John C. Gilbert,Stephen F. Martin

Publisher: Cengage Learning

ISBN: 1305687876

Category: Science

Page: 960

View: 9172

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Perform chemistry experiments with skill and confidence in your organic chemistry lab course with this easy-to-understand lab manual. EXPERIMENTAL ORGANIC CHEMISTRY: A MINISCALE AND MICROSCALE APPROACH, Sixth Edition first covers equipment, record keeping, and safety in the laboratory, then walks you step by step through the laboratory techniques you'll need to perform all experiments. Individual chapters show you how to use the techniques to synthesize compounds and analyze their properties, complete multi-step syntheses of organic compounds, and solve structures of unknown compounds. New experiments in Chapter 17 and 18 demonstrate the potential of chiral agents in fostering enantioselectivity and of performing solvent-free reactions. A bioorganic experiment in Chapter 24 gives you an opportunity to accomplish a mechanistically interesting and synthetically important coupling of two a-amino acids to produce a dipeptide. Important Notice: Media content referenced within the product description or the product text may not be available in the ebook version.
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SPECTROMETRIC IDENTIFICATION OF ORGANIC COMPOUNDS, 6TH ED

Author: Robert Silverstein & Francis Webster

Publisher: John Wiley & Sons

ISBN: 9788126509720

Category: Chemistry

Page: 496

View: 8103

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Market_Desc: Organic and Analytical in the Forensics, Chemical and Pharmaceutical Industries Special Features: · A how-to, hands-on teaching manual· Considerably expanded NMR coverage--NMR spectra can now be interpreted in exquisite detail· New chapters on correlation NMR spectrometry (2-D NMR) and spectrometry of other important nuclei· Uses a problem-solving approach with extensive reference charts and tables· An extensive set of real-data problems offers a challenge to the practicing chemist About The Book: The book provides a thorough introduction to the three areas of spectrometry most widely used in spectrometric identification: mass spectrometry, infrared spectrometry, and nuclear magnetic resonance spectrometry.
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Fundamentals of General, Organic, and Biological Chemistry,6th Ed, Mc Murry-Castellion-Ballantine-Hoeger-Peterson,2010

Fundamentals of General, Organic, and Biological Chemistry

Author: Prentice Hall-Pearson Education, Inc

Publisher: Bukupedia

ISBN: N.A

Category: Science

Page: 992

View: 9714

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John McMurry, educated at Harvard and Columbia, has taught approximately 17,000 students in general and organic chemistry over a 30-year period. AProfessor of Chemistry at Cornell University since 1980, Dr. McMurry previously spent 13 years on the faculty at the University of California at Santa Cruz. He has received numerous awards, including the Alfred P. Sloan Fellowship (1969 71), the National Institute of Health Career Development Award (1975 80), the Alexander von Humboldt Senior Scientist Award (1986 87), and the Max Planck Research Award (1991). About the Authors David S. Ballantine received his B.S. in Chemistry in 1977 from the College of William and Mary in Williamsburg, VA, and his Ph.D. in Chemistry in 1983 from the University of Maryland at College Park. After several years as a researcher at the Naval Research Labs in Washington, DC, he joined the faculty in the Department of Chemistry and Biochemistry of Northern Illinois University, where he has been a professor for the past twenty years. He was awarded the Excellence in Undergraduate Teaching Award in 1998 and was recently named the departmental Director of Undergraduate Studies. In addition, he is the faculty advisor to the NIU Chemistry Club, an American Chemical Society Student Affiliate program. Carl A.Hoeger received his B.S. in Chemistry from San Diego State University and his Ph.D. in Organic Chemistry from the University of Wisconsin, Madison in 1983. After a postdoctoral stint at the University of California, Riverside, he joined the Peptide Biology Laboratory at the Salk Institute in 1985 where he ran the NIH Peptide Facility while doing basic research in the development of peptide agonists and antagonists. During this time he also taught general, organic, and biochemistry at San Diego City College, Palomar College, and Miramar College. He joined the teaching faculty at University of Califiornia, San Diego in 1998. Dr. Hoeger has been teaching chemistry to undergraduates for over 20 years, where he continues to explore the use of technology in the classroom. In 2004 he won the Paul and Barbara Saltman Distinguished Teaching Award from UCSD. He is currently the General Chemistry coordinator at UCSD, where he is also responsible for the training and guidance of over 100 teaching assistants in the Chemistry and Biochemistry departments. Virginia E. Peterson received her B.S. in Chemistry in 1967 from the University of Washington in Seattle, and her Ph.D. in Biochemistry in 1980 from the University of Maryland at College Park. Between her undergraduate and graduate years she worked in lipid, diabetes, and heart disease research at Stanford University. Following her Ph.D. she took a position in the Biochemistry Department at the University of Missouri in Columbia and is now an Associate Professor. Currently she is the Director of Undergraduate Advising for the department and teaches both senior capstone classes and biochemistry classes for nonscience majors. Awards include both the college level and the university-wide Excellence in Teaching Award and, in 2006, the University s Outstanding Advisor Award and the State of Missouri Outstanding University Advisor Award. Dr. Peterson believes in public service and in 2003 received the Silver Beaver Award for service from the Boy Scouts of America. This textbook is primarily designed to provide students in the allied health sciences with an appropriate background in chemistry and biochemistry. But it also provides a general context for many of the chemical concepts so that students in other disciplines will gain a better appreciation of the importance of chemistry in everyday life. The coverage in this sixth edition includes sufficient breadth and depth to ensure adequate context and to provide students with opportunities to expand their knowledge. To teach chemistry all the way from What is an atom? to How do we get energy from glucose? is a challenge. Throughout our general chemistry and organic chemistry coverage, the focus is on concepts fundamental to the chemistry of living things and everyday life. In our biochemistry coverage we strive to meet the further challenge of providing a context for the application of those concepts in biological systems. Our goal is to provide enough detail for thorough understanding while avoiding so much detail that students are overwhelmed. Many practical and relevant examples are included to illustrate the concepts and enhance student learning. The material covered is ample for a two-term introduction to general, organic, and biological chemistry. While the general and early organic chapters contain concepts that are fundamental to understanding the material in biochemistry, the later chapters can be covered individually and in an order that can be adjusted to meet the needs of the students and the duration of the course. The writing style is clear and concise and punctuated with practical and familiar examples from students personal experience. Art work, diagrams, and molecular models are used extensively to provide graphical illustration of concepts to enhance student understanding. Since the true test of knowledge is the ability to apply that knowledge appropriately, we include numerous worked examples that incorporate consistent problem-solving strategies. Regardless of their career paths, all students will be citizens in an increasingly technological society. When they recognize the principles of chemistry at work not just in their careers but in their daily lives, they are prepared to make informed decisions on scientific issues based on a firm understanding of the underlying concepts. Organization GENERAL CHEMISTRY: CHAPTERS 1 11 The introduction to elements, atoms, the periodic table, and the quantitative nature of chemistry (Chapters 1 3) is followed by chapters that individually highlight the nature of ionic and molecular compounds (Chapters 4 and 5). The next two chapters discuss chemical reactions and their stoichiometry, energies, rates, and equilibria (Chapters 6 and 7). Topics relevant to the chemistry of life follow: Gases, Liquids, and Solids (Chapter 8); Solutions (Chapter 9); and Acids and Bases (Chapter 10). Nuclear Chemistry (Chapter 11) closes the general chemistry sequence. ORGANIC CHEMISTRY: CHAPTERS 12 17 These chapters concisely focus on what students must know in order to understand biochemistry. The introduction to hydrocarbons (Chapters 12 and 13) includes the basics of nomenclature, which is thereafter kept to a minimum. Discussion of functional groups with single bonds to oxygen, sulfur, or a halogen (Chapter 14) is followed by a short chapter on amines, which are so important to the chemistry of living things and drugs (Chapter 15). After introducing aldehydes and ketones (Chapter 16), the chemistry of carboxylic acids and their derivatives (including amides) is covered (Chapter 17), with a focus on similarities among the derivatives. xv Preface BIOLOGICAL CHEMISTRY: CHAPTERS 18 29 Rather than proceed through the complexities of protein, carbohydrate, lipid, and nucleic acid structure before getting to the roles of these compounds in the body, structure and function are integrated in this text. Protein structure (Chapter 18) is followed by enzyme and coenzyme chemistry (Chapter 19). After that we cover the function of hormones and neurotransmitters, and the action of drugs (Chapter 20). With enzymes introduced, the central pathways and themes of biochemical energy production can be described (Chapter 21). If the time you have available to cover biochemistry is limited, stop with Chapter 21 and your students will have an excellent preparation in the essentials of metabolism. The following chapters cover carbohydrate chemistry (Chapters 22 and 23), then lipid chemistry (Chapters 24 and 25). Next we discuss nucleic acids and protein synthesis (Chapter 26) and genomics (Chapter 27). The last two chapters cover protein and amino acid metabolism (Chapter 28) and provide an overview of the chemistry of body fluids (Chapter 29). Changes to This Edition COVERAGE OF GENERAL CHEMISTRY Once again, there is a major emphasis in this edition on problem-solving strategies. This is reflected in expanded solutions in the Worked Example problems and the addition of more Key Concept Problems that focus on conceptual understanding. The most significant change in the Worked Example problems is the addition of a Ballpark Estimate at the beginning of many problems. The Ballpark Estimate provides an opportunity for students to evaluate the relationships involved in the problem and allows them to use an intuitive approach to arrive at a first approximation of the final answer. The ability to think through a problem before attempting a mathematical solution is a skill that will be particularly useful on exams, or when solving real world problems. Other specific changes to chapters are provided below: Chapter 1 The Scientific Method is introduced in the text and reinforced in Applications presented in the chapter. Chapter 3 Discussion of the critical experiments of Thomson, Millikan, and Rutherford are included in the Application Are Atoms Real to provide historical perspective on the development of our understanding of atomic structure. Electron dot structures are introduced in Chapter 3 to emphasize the importance of the valence shell electronic configurations with respect to chemical behavior of the elements. Chapter 4 Electron dot structures are used to reinforce the role of valence shell electronic configurations in explaining periodic behavior and the formation of ions. Chapter 5 The two methods for drawing Lewis dot structures (the general method and the streamlined method for molecules containing C, N, O, X, and H) are discussed back-to-back to highlight the underlying principle of the octet rule common to both methods. Chapter 6 The concept of limiting reagents is incorporated in Section 6.7 in the discussion of reaction stoichiometry and percent yields. xvi Preface Chapter 7 The discussion of free energy and entropy in Section 7.4 has been revised to help students develop a more intuitive understanding of the role of entropy in spontaneous processes. Section 7.8 includes more discussion of how the equilibrium constant is calculated and what it tells us about the extent of reaction. Chapter 8 Sections 8.3 8.10 include more emphasis on use of the kinetic molecular theory to understand the behavior of gases described by the gas laws. Section 8.15 includes more discussion on the energetics of phase changes to help students understand the difference between heat transfer associated with a temperature change and heat transfer associated with the phase change of a substance. Chapter 9 Discussion of equivalents in Section 9.10 has been revised to emphasize the relationship between ionic charge and equivalents of ionic compounds. Discussion of osmotic pressure (Section 9.12) now includes the osmotic pressure equation and emphasizes the similarity with the ideal gas law. Chapter 10 Both the algebraic and logarithmic forms of K w are presented in Section 10.8 to give students another approach to solving pH problems. The discussion of buffer systems now introduces the Henderson-Hasselbalch equation. This relationship makes it easier to identify the factors that affect the pH of a buffer system and is particularly useful in biochemical applications in later chapters. Discussion of common acid-base reactions has been moved back in the chapter to provide a more logical segue into titrations in Section 10.15. Chapter 11 Treatment of half-life in Section 11.5 now includes a generic equation to allow students to determine the fraction of isotope remaining after an integral or non-integral number of half-lives, which is more consistent with real world applications. The Applications in this chapter have been expanded to include discussion of new technologies such as Boron Neutron-Capture Therapy (BNCT), or to clear up misconceptions about current methods such as MRI. COVERAGE OF ORGANIC CHEMISTRY Amajor emphasis in this edition was placed on making the fundamental reactions organic molecules undergo much clearer to the reader, with particular vision toward those reactions encountered again in biochemical transformations. Also new to this edition is the expanded use and evaluation of line-angle structure for organic molecules, which are so important when discussing biomolecules. Most of the Applications have been updated to reflect current understanding and research. Other specific changes to chapters are provided below: Chapter 12 This chapter has been significantly rewritten to provide the student with a stronger foundation for the organic chemistry chapters that follow. Aclearer description of what a functional group is, as well as a more systematic approach to drawing alkane isomers have been made. Preface xvii The topic of how to draw and interpret line structures for organic molecules has been added, along with worked examples of such. The discussion of conformations has been expanded. Chapter 13 Amore general discussion of cis and trans isomers has been added. The discussion of organic reaction types, particularly rearrangement reactions, have been simplified. Chapter 14 The topic of oxidation in organic molecules has been clarified. Chapter 15 The role of NO in human biology has been updated to reflect current research. Chapter 16 A more detailed discussion of what is meant by toxic or poisonous has been added. Chapter 17 Adiscussion of ibuprofen has been added. COVERAGE OF BIOLOGICAL CHEMISTRY New topics, such as the use of anabolic steroids in sports, have been added to many of these chapters to highlight the relevance of biochemistry in modern society. In this text, nutrition is not treated as a separate subject but is integrated with the discussion of each type of biomolecule. Chapter 18 The discussion of sickle cell anemia has been expanded and the role of an amino acid substitution on hemoglobin structure clarified. The Application Prions Proteins That Cause Disease has been updated to reflect current research. Chapter 19 Incorporated the information about lead poisoning into the discussion of enzyme inhibition. Chapter 20 The discussion of anabolic steroids has been updated. The discussion of drugs and their interaction with the neurotransmitter acetylcholine has been expanded. Chapter 21 The discussion of ATP energy production has been revised. Chapter 22 An explanation of the chair conformation of glucose has been included to enhance understanding of the shape of cyclic sugars. The Application Chirality and Drugs has been updated. The Application Cell Surface Carbohydrates and Blood Type has been revised. xviii Preface Chapter 23 The explanation of substrate level phosphorylation has been expanded for clarity. The emerging medical condition referred to as Metabolic Syndrome has been added to the text discussion of diabetes. The Application Diagnosis and Monitoring of Diabetes has been updated to include metabolic syndrome. Section 23.11 now contains an expanded discussion of gluconeogenesis. The discussion of polysaccharides has been updated. Chapter 24 The description of the cell membrane has been expanded. A discussion of some inhibitors of Cox 1 and Cox 2 enzymes, important in inflammation, has been added. Chapter 25 The discussion of triacylglycerol synthesis has been expanded. The discussion of ketone body formation has been expanded. A thorough explanation of the biosynthesis of fatty acids has been added. Chapter 26 The Application Viruses and AIDS has been updated. Information about the 1918 influenza pandemic was included in the Application Bird Flu : The Next Epidemic? Chapter 27 A discussion of the problems associated with using recombinant DNA for commercial protein manufacture has been added. In Section 27.5, new bioethical issues are pointed out to reflect modern concerns. The discussion of recombinant DNA and polymerase chain reactions has been moved to this chapter from Chapter 26. Focus on Learning WORKED EXAMPLES Most Worked Examples, both quantitative and not quantitative, include an Analysis section that precedes the Solution. The Analysis lays out the approach to solving a problem of the given type. When appropriate, a Ballpark Estimate gives students an overview of the relationships needed to solve the problem, and provides an intuitive approach to arrive at a rough estimate of the answer. The Solution presents the worked-out example using the strategy laid out in the Analysis and, in many cases, includes expanded discussion to enhance student understanding. The use of the two-column format introduced in the fifth edition for quantitative problems has been applied to more Worked Examples throughout the text. Following the Solution there is a Ballpark Check that compares the calculated answer to the Ballpark Estimate, when appropriate, and verifies that the answer makes chemical and physical sense. KEY CONCEPT PROBLEMS are integrated throughout the chapters to focus attention on the use of essential concepts, as do the Understanding Key Concepts problems at the end of each chapter. Understanding Key Concepts problems are designed to test students mastery of the core principles developed in the chapter. Students thus Preface xix have an opportunity to ask Did I get it? before they proceed. Most of these Key Concept Problems use graphics or molecular-level art to illustrate the core principles and will be particularly useful to visual learners. PROBLEMS The problems within the chapters, for which brief answers are given in an appendix, cover every skill and topic to be understood. One or more problems, many of which are new to this edition, follow each Worked Example and others stand alone at the ends of sections. MORE COLOR-KEYED, LABELED EQUATIONS It is entirely too easy to skip looking at a chemical equation while reading. We have extensively used color to call attention to the aspects of chemical equations and structures under discussion, a continuing feature of this book that has been judged very helpful. MOLECULAR MODELS Additional computer-generated molecular models have been introduced, including the use of electrostatic-potential maps for molecular models. KEY WORDS Every key term is boldfaced on its first use, fully defined in the margin adjacent to that use, and listed at the end of the chapter. These are the terms students must understand to get on with the subject at hand. Definitions of all Key Words are collected in the Glossary. END-OF-CHAPTER SUMMARIES Here, the answers to the questions posed at the beginning of the chapter provide a summary of what is covered in that chapter. Where appropriate, the types of chemical reactions in a chapter are also summarized. Focus on Relevancy Chemistry is often considered to be a difficult and tedious subject. But when students make a connection between a concept in class and an application in their daily lives the chemistry comes alive, and they get excited about the subject. The applications in this book strive to capture student interest and emphasize the relevance of the scientific concepts. The use of relevant applications makes the concepts more accessible and increases understanding. Applications are both integrated into the discussions in the text and set off from the text in Application boxes. Each boxed application provides sufficient information for reasonable understanding and, in many cases, extends the concepts discussed in the text in new ways. The boxes end with a cross-reference to end-of-chapter problems that can be assigned by the instructor. Some wellreceived Applications from previous editions that have been retained include Breathing and Oxygen Transport, Buffers in the Body, Prions, Protein Analysis by Electrophoresis, The Biochemistry of Running, and DNA Fingerprinting. New Applications in this edition include Aspirin A Case Study, Temperature- Sensitive Materials, Anemia A Limiting Reagent Problem, GERD: Too Much Acid or Not Enough, and It s a Ribozyme! FOCUS ON MAKING CONNECTIONS AMONG GENERAL, ORGANIC, AND BIOLOGICAL CHEMISTRY This can be a difficult course to teach. Much of what students are interested in lies in the last part of the course, but the material they need to understand the biochemistry is found in the first two-thirds. It is easy to lose sight of the connections among general, organic, and biological chemistry so we use a feature, Concepts to Review, to call attention to these connections. From Chapter 4 on, the Concepts to Review section at the beginning of the chapter lists topics covered in earlier chapters that form the basis for what is discussed in the current chapter. xx Preface We have also retained the successful concept link icons and Looking Ahead notes. Concept link icons are used extensively to indicate places where previously covered material is relevant to the discussion at hand. These links provide for cross-references and also serve to highlight important chemical themes as they are revisited. Looking Ahead notes call attention to connections between just-covered material and discussions in forthcoming chapters. These notes are designed to illustrate to the students why what they are learning will be useful in what lies ahead. Making It Easier to Teach: Supplements for Instructors MasteringChemistry (www.masteringchemistry.com) MasteringChemistry is the first adaptive-learning online homework system. It provides selected end-of-chapter problems from the text, as well as hundreds of tutorials with automatic grading, immediate answer-specific feedback, and simpler questions on request. Based on extensive research of precise concepts students struggle with, MasteringChemistry uniquely responds to your immediate needs, thereby optimizing your study time. Instructor Resource Manual (0-32-161241-8) Features lecture outlines with presentation suggestions, teaching tips, suggested in-class demonstrations, and topics for classroom discussion. Test Item File (0-32-161514-X) Updated to reflect the revisions in this text and contains questions in a bank of more than 2,000 multiple-choice questions. Transparency Pack (0-32-161513-1) More than 225 full-color transparencies chosen from the text put principles into visual perspective and save you time while you are preparing for your lectures. Instructor Resource Center on CD/DVD (0-32-161242-6) This CD/DVD provides an intergrated collection of resources designed to help you make efficient and effective use of your time. This CD/DVD features most art from the text, including figures and tables in PDF format for high-resolution printing, as well as four pre-built PowerPoint presentations. The first presentation contains the images/ figures/tables embedded within the PowerPoint slides, while the second includes a complete modifiable lecture outline. The final two presentations contain worked in chapter sample exercises and questions to be used with Classroom Response Systems. This CD/DVD also contains movies and animations, as well as the TestGen version of the Test Item File, which allows you to create and tailor exams to your needs. BlackBoard® and WebCT® Practice and assessment materials are available upon request in these course management platforms. Making It Easier to Learn: Supplements for Students Study Guide and Full Solutions Manual (0-32-161238-8) and Study Guide and Selected Solutions Manual (0-32-161239-6), both by Susan McMurry. The selected version provides solutions only to those problems that have a short answer in the Preface xxi text s Selected Answer Appendix (problems numbered in blue in the text). Both versions explain in detail how the answers to the in-text and end-of-chapter problems are obtained. They also contain chapter summaries, study hints, and self-tests for each chapter. For the Laboratory Exploring Chemistry: Laboratory Experiments in General, Organic and Biological Chemistry, 2nd Edition (0-13-047714-1) by Julie R. Peller of Indiana University. Written specifically to accompany Fundamentals of General, Organic and Biological Chemistry, this manual contains 34 fresh and accessible experiments specifically for GOB students. Catalyst: The Prentice Hall Custom Laboratory Program for Chemistry. This program allows you to custom-build a chemistry lab manual that matches your content needs and course organization. You can either write your own labs using the Lab Authoring Kit tool, or select from the hundreds of labs available at www. prenhall.com/catalyst. This program also allows you to add your own course notes, syllabi, or other materials. Acknowledgments From conception to completion, the development of a modern textbook requires both a focused attention on the goals and the coordinated efforts of a diverse team. We have been most fortunate to have had the services of many talented and dedicated individuals whose efforts have contributed greatly to the overall quality of this text. First and foremost, we are grateful to Kent Porter Hamann who, as senior editor of this text through many past revisions, provided exemplary leadership and encouragement to the team in the early stages of this project. Very special appreciation goes to Ray Mullaney, editor in chief of book development, who mentored the new team members and managed to coordinate the many and varied details. Irene Nunes, our developmental editor, worked closely with the authors to ensure accuracy and consistency. We also are grateful for the services of Wendy Perez, project manager; Laurie Varites, assistant editor; Lia Tarabokjia, and Jill Traut and Robert Walters, production project managers. Finally, special thanks also to Susan McMurry and Margaret Trombley, whose efforts on the Solutions Manuals and MasteringChemistry tutorial software, respectively, have added value to the overall package. Finally, many instructors and students who have used the fifth edition have provided valuable insights and feedback and improved the accuracy of the current edition. We gratefully acknowledge the following reviewers for their contributions to the sixth edition: xxii Preface Sheikh Ahmed, West Virgina University Stanley Bajue, CUNY-Medgar Evers College Daniel Bender, Sacramento City College Dianne A. Bennett, Sacramento City College Alfredo Castro, Felician College Gezahegn Chaka, Louisiana State University, Alexandria Michael Columbia, Indiana University- Purdue University, Fort Wayne Rajeev B. Dabke, Columbus State University Danae R. Quirk-Dorr, Minnesota State University, Mankato Pamela S. Doyle, Essex County College Marie E. Dunstan, York College of Pennsylvania Karen L. Ericson, Indiana University-Purdue University, Fort Wayne Charles P. Gibson, University of Wisconsin, Oshkosh Clifford Gottlieb, Shasta College Mildred V. Hall, Clark State Community College Meg Hausman, University of Southern Maine Ronald Hirko, South Dakota State University L. Jaye Hopkins, Spokane Community College Margaret Isbell, Sacramento City College James T. Johnson, Sinclair Community College Margaret G. Kimble, Indiana University- Purdue University Fort Wayne Preface xxiii Grace Lasker, Lake Washington Technical College Ashley Mahoney, Bethel University Matthew G. Marmorino, Indiana University, South Bend Diann Marten, South Central College, Mankato Barbara D. Mowery, York College of Pennsylvania Tracey Arnold Murray, Capital University Andrew M. Napper, Shawnee State University Lisa Nichols, Butte Community College Glenn S. Nomura, Georgia Perimeter College Douglas E. Raynie, South Dakota State University Paul D. Root, Henry Ford Community College Victor V. Ryzhov, Northern Illinois University Karen Sanchez, Florida Community College, Jacksonville-South Mir Shamsuddin, Loyola University, Chicago Jeanne A. Stuckey, University of Michigan John Sullivan, Highland Community College Deborah E. Swain, North Carolina Central University Susan T. Thomas, University of Texas, San Antonio Yakov Woldman, Valdosta State University The authors are committed to maintaining the highest quality and accuracy and look forward to comments from students and instructors regarding any aspect of this text and supporting materials. Questions or comments should be directed to the lead co-author. David S. Ballantine [email protected]
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Techniques and Experiments for Organic Chemistry

Author: Addison Ault

Publisher: University Science Books

ISBN: 9780935702767

Category: Science

Page: 664

View: 6127

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This student text explains how to perform operations, as well as providing recipes for the preparation of a variety of organic compounds. There are sections on procedures, techniques, safety, glassware, clean up, collection and disposal of waste, and the laboratory notebook.
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Quinica Organica, 6th Ed, Carey, 2006

Organic Chemistry

Author: McGraw-Hill

Publisher: Bukupedia

ISBN: N.A

Category: Science

Page: 1422

View: 611

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¿POR QUÉ ES DISTINTO ESTE LIBRO? El mensaje central de la química es que las propiedades de una sustancia se deben a su estructura. Lo que es menos obvio, pero muy importante, es el corolario. Alguien con instrucción química puede observar la estructura de una sustancia e indicar muchas de sus propiedades. La química orgánica siempre ha sido, y continúa siendo, la rama de la química que mejor relaciona la estructura con las propiedades. Nuestro objetivo ha sido subrayar la relación entre estructura y propiedades, usando las herramientas mejor adaptadas para hacer esa conexión. Organización por grupo funcional Una herramienta es la organización. El demostrado método por grupos dirige la atención hacia las unidades estructurales dentro de una molécula que se identifican más estrechamente con sus propiedades. El texto se organiza de acuerdo con grupos funcionales, pero subraya los mecanismos, y anima a los estudiantes a que aprecien las semejanzas en los mecanismos entre distintos grupos funcionales. Visualización de la química orgánica Otra herramienta se relaciona con la presentación. Decidimos hacer resaltar el modelado molecular en la tercera edición. Los modelos moleculares y los programas informáticos que elaboran sus propios modelos no sólo hacen más accesible la química orgánica para los alumnos que son “de aprendizaje visual”, sino que enriquecen también la experiencia educativa de todos. AUDIENCIA Desde la primera hasta esta sexta edición, Química Orgánica se ha diseñado para satisfacer las necesidades de un curso de Química Orgánica de dos semestres, para el “tronco común” de licenciatura. Desde el principio, y en cada nueva edición, nos hemos basado en algunas nociones fundamentales. Entre ellas están temas importantes acerca de los alumnos a quienes va dirigida. ¿Es adecuado el tema para ellos con respecto a sus intereses, aspiraciones y experiencia? Tiene igual importancia la necesidad de presentar un panorama exacto del estado actual de la química orgánica. ¿Cómo sabemos que sabemos? ¿Qué hace importante conocer de química orgánica? ¿Dónde estamos ahora? ¿Hacia dónde nos dirigimos? CONSEJOS EXPERTOS NOS AYUDAN A SATISFACER SUS NECESIDADES Hoy, desarrollar un texto implica la participación de una gran cantidad de personas, ya que a los profesores de todo el país se les invita constantemente a compartir sus conocimientos y experiencia con nosotros, a través de repasos y de grupos de enfoque. Toda la retroalimentación que hemos recibido ha conformado esta edición, y el resultado es un capítulo nuevo, la reorganización del contenido existente, y un examen más PREFACIO para formar un puente de hidrógeno entre las dos moléculas. δ+ Un protón del OH de una molécula de etanol δ- interacciona con el oxígeno de un segundo etanol Este protón del OH está disponible para formar un puente de hidrógeno con el oxígeno de una cuarta molécula de etanol. Este oxígeno está disponible para formar un puente de hidrógeno con el protón del OH de una tercera molécula de etanol. detallado de las áreas clave. Este texto ha estado evolucionando como resultado de la retroalimentación de profesores de química orgánica en las aulas. Nos han dicho una y otra vez que un contenido actual y acertado, una redacción clara con explicaciones concisas, ilustraciones de alta calidad y materiales dinámicos de presentación, son los factores más importantes, según ellos, en la evaluación de los textos. Hemos dejado que esos criterios guíen nuestra revisión del texto y nuestro desarrollo de recursos auxiliares. ¿QUÉ HAY DE NUEVO? Particularidades de la sexta edición Temas y organización Hay cambios clave que van desde ampliar el contenido existente hasta agregar nuevos temas y un nuevo capítulo. • ¡NUEVO! El capítulo 29, Polímeros sintéticos elabora lo presentado en los capítulos anteriores acerca de los polímeros, para satisfacer las necesidades de aquellos alumnos que requieren más que una introducción a la química de los polímeros. Una de las cosas que me gustan del texto del Dr. Carey es que se esfuerza por incorporar la química de los polímeros dentro del texto. Veo que este capítulo tiene un buen enfoque y una ampliación de esos componentes... Me sentiría bien al usar este capítulo tanto como uno sobre polímeros, pero también como una oportunidad de repasar la química de todo el curso. —Paul T. Buonora. Universidad del Estado de California, Long Beach • ¡NUEVO! Se ha modificado y ampliado la notación de flechas curvas, y se ha convertido en una sección por mérito propio en el capítulo 1. • ¡NUEVO! Debido a la gran aceptación del tratamiento más amplio de las reacciones ácidobase en el capítulo 1 de la quinta edición, este material y su carácter “orgánico” reciben todavía más atención en esta edición. • ¡NUEVO! La sección 5.17, “Efectos isotópicos y el mecanismo E2”, es nueva en esta edición. • ¡NUEVO! Continuando el material de introducción en los capítulos 1 a 5, el capítulo 6 ahora incluye una sección titulada “Termodinámica de los equilibrios de adición-eliminación”, que describe la interacción de entalpía, entropía y energía libre de Gibbs en algunas reacciones orgánicas fundamentales. • ¡NUEVO! El capítulo 14: Compuestos organometálicos, se ha ampliado para contener secciones separadas sobre hidrogenación catalítica homogénea y metátesis de olefinas. • ¡NUEVO! El capítulo 18, Enoles y enolatos, se ha reorganizado para aprovechar el énfasis sobre la química de ácidos-bases en los capítulos anteriores. La nueva organización presenta las reacciones de los enolatos antes de las de los enoles, y refleja mejor su importancia en síntesis orgánicas. • ¡NUEVO! Una sección nueva, “m- y p-bencino” se agregó al capítulo 23, para complementar el material que existía sobre el o-bencino. Esta nueva sección tiene ejemplos de la ciclización de Bergman. • También el repaso de los enlaces, de la química general, se ha ampliado en el capítulo 1. • Se ha integrado con más detalle en el texto el valor económico y la aplicación cotidiana de la química orgánica. Pedagogía • ¡NUEVO! Se ha agregado una lista de tablas y mecanismos a los preliminares (páginas xxii-xxvi) como referencia rápida de esos importantes auxiliares de aprendizaje en cada capítulo. • ¡NUEVO! Cada capítulo comienza con una presentación, en dos páginas, de las “atracciones venideras”, donde se presenta una lista de los títulos de la sección y de los mecanismos de reacción, junto con sus números de página correspondientes. • ¡NUEVO! Se dio un formato único a los mecanismos de reacción para hacerlos más visibles. 404 CAPÍTULO DIEZ Conjugación en alcadienos y sistemas alílicos MECANISMO 10.1 Hidrólisis de un halogenuro alílico (3-Cloro-3-metil-1-buteno) Reacción total: (CH3)2CCHoeCH2 H2O –±£ (CH3)2CCHoeCH2 (CH3)2CoeCHCH2OH Paso 1: El halogenuro de alquilo se ioniza para formar un carbocatión. Este paso es determinante de la velocidad: Paso 2: El carbocatión (mostrado en su forma de resonancia más estable) reacciona con agua. El agua actúa como un nucleófilo y puede atacar ya sea al carbono terciario o al carbono primario. W Cl W OH 3-Cloro-3-metil-1-buteno Agua 2-Metil-3-buten-2-ol 3-Metil-2-buten-1-ol 3-Cloro-3-metil-1-buteno Ion cloruro Catión 1,1-dimetilalilo Agua Catión 1,1-dimetilalilo Ion 1,1-dimetilaliloxonio Contribuyente principal Contribuyente menor Cl –±£ Cl lento La carga positiva en el catión 1,1-dimetilalilo es compartida entre dos carbonos alílicos. ¢–£ O H H –±£ O rápido O –±£ rápido H H H H C A P Í T U L O 10.15 ANÁLISIS DE ORBITALES MOLECULARES [1] DE LA REACCIÓN DE DIELS-ALDER . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 423 10.16 RESUMEN . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 425 PROBLEMAS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 427 Mecanismos 10.1 Hidrólisis de un halogenuro alílico. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 404 10.2 Cloración alílica del propeno . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 407 10.3 Adición de cloruro de hidrógeno al 1,3-ciclopentadieno . . . . . . . . . . . . . . . . . . . . . 415 10.4 Interacciones orbitales en la reacción de Diels-Alder . . . . . . . . . . . . . . . . . . . . . . . 424 399 Conjugación en alcadienos y sistemas alílicos 398 Esbozo del capítulo 10.1 EL GRUPO ALILO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400 10.2 CARBOCATIONES ALÍLICOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400 10.3 REACCIONES SN1 DE HALOGENUROS ALÍLICOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 402 10.4 RADICALES LIBRES ALÍLICOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 405 10.5 HALOGENACIÓN ALÍLICA . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 406 10.6 CLASES DE DIENOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 408 10.7 ESTABILIDADES RELATIVAS DE LOS DIENOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 409 10.8 ENLACES EN DIENOS CONJUGADOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 410 10.9 ENLACES EN ALENOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 412 10.10 PREPARACIÓN DE DIENOS. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 413 10.11 ADICIÓN DE HALOGENUROS DE HIDRÓGENO A DIENOS CONJUGADOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 414 10.12 ADICIÓN DE HALÓGENOS A DIENOS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 417 ■ Polímeros de dienos . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 418 10.13 LA REACCIÓN DE DIELS-ALDER. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 418 10.14 LOS ORBITALES MOLECULARES [1] DEL ETILENO Y DEL 1,3-BUTADIENO. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 422 No todas las propiedades de los alquenos se revelan enfocándose en forma exclusiva en el comportamiento del grupo funcional del enlace doble. Un enlace doble puede afectar las propiedades de una segunda unidad funcional a la que está unido en forma directa. Por ejemplo, puede ser un sustituyente en un carbono con carga positiva, en un carbocatión alílico, o en un carbono que lleva un electrón no apareado, en un radical libre alílico, o puede ser un sustituyente en un segundo enlace doble, en un dieno conjugado. Conjugar es un verbo latino que significa “unir o poner yugo”, y los carbocationes alílicos, los radicales libres alílicos y los dienos conjugados son todos ejemplos de sistemas conjugados. En este capítulo se verá cómo la conjugación permite que dos unidades funcionales dentro de una molécula exhiban una clase de reactividad que es cualitativamente diferente de la de cualquier unidad sola. C C C Carbocatión alílico C C C Radical libre alílico C C C C Dieno conjugado xxviii PREFACIO PREFACIO xxix • ¡NUEVO! Se han agregado problemas a varios ensayos en el texto, para dar mayor importancia a estos elementos esenciales. • ¡NUEVO! Se han agregado problemas al final del capítulo. • ¡NUEVO! Tabla 1.5: Un método sistemático para escribir estructuras de Lewis, y la tabla 1.6: Introducción a las reglas de resonancia, se modificaron respecto a las tablas de la quinta edición, que tuvieron buena aceptación, para hacer que fueran todavía más útiles a los alumnos al avanzar de la química general a la orgánica. • Las tablas de resumen permiten al alumno un fácil acceso a un gran acopio de información, en un formato fácil de usar, y al mismo tiempo repasar información de capítulos anteriores. • Los resúmenes de final del capítulo resaltan y consolidan todos los conceptos y reacciones importantes dentro de un capítulo. Solución de problemas • Se da importancia a estrategias y destrezas de solución de problemas en todo el libro. Se refuerza la comprensión, en forma continua, con problemas que aparecen dentro de las secciones acerca de los temas. Para muchos problemas se presentan soluciones de muestra, incluyendo algunos ejemplos de soluciones manuscritas por el autor. Me gusta mucho este método, que muestra la resolución de un problema a mano y sobre papel . . . los ejemplos refuerzan la lógica y describen el método de resolver problemas que yo trato de inculcar en mis alumnos . . . Creo que es bueno que los alumnos vean cómo deberían organizar en un papel la información presentada y los conceptos que conocen para resolver los problemas. —John Barbaro, Universidad de Florida, Gainesville Aplicaciones en biología • Además de cuatro capítulos que describen las biomoléculas (capítulos 25 a 28) con regularidad en todo el texto, y en los ensayos, aparecen aplicaciones en biología. • El capítulo 28: Nucleósidos, nucleótidos y ácidos nucleicos hace patente el crecimiento explosivo de la base molecular de la genética. • Numerosos ensayos en todo el texto resaltan las aplicaciones de la química orgánica en la biología. Una desventaja mucho más seria de usar fármacos quirales como mezclas racémicas es ilustrada por la talidomida, empleada como sedante y fármaco contra las náuseas en Europa durante el periodo de 1959-1962. Las propiedades de la (R)-talidomida son las deseadas. Sin embargo, la (S)-talidomida tiene un espectro muy diferente de actividad biológica; además, se demostró que fue la causa, en más de 2 000 cua do se p epa e u á aco ue o, d se a su s tes s de modo que se obtenga sólo el enantiómero deseado. Un incentivo para desarrollar versiones enantioméricamente puras de los fármacos existentes consiste en que los nuevos métodos de producción que se requieren pueden hacerlos elegibles para quedar protegidos por patentes diferentes de las de los fármacos originales. Por tanto, la posición de monopolio temporal que las leyes de patentes ven como esencial para fomentar la innovación puede extenderse al transformar un fármaco quiral exitoso, pero racémico, en una versión enantioméricamente pura. PROBLEMA 7.11 Tanto el naproxeno (antiinflamatorio) como el captopril (usado para el tratamiento de la hipertensión arterial) son fármacos sintéticos que se preparan y se venden como enantiómeros puros. Todos los centros de quiralidad (uno en el naproxeno y dos en el captopril) tienen la configuración S. Construya los modelos moleculares de ambos. Naproxeno CH3 CHCO2H CH3O Captopril N CO2H CCHCH2SH O CH3 Ibuprofeno 6.23 RESUMEN Los alquenos son hidrocarburos insaturados y reaccionan con sustancias que se adicionan al enlace doble. Sección 6.1 Vea la tabla 6.6. Sección 6.2 La hidrogenación de alquenos es exotérmica. Los calores de hidrogenación pueden medirse y usarse para evaluar la estabilidad de varios tipos de enlaces dobles. La información es paralela a la obtenida de los calores de combustión. 6.23 Resumen 277 TABLA 6.6 Reacciones de adición de los alquenos Reacción (sección) y comentarios Ecuación general y ejemplo específico R2C CR2 RCH CR2 HX CR2 X RCH2 H2 R2CHCHR2 Hidrogenación catalítica (secciones 6.1-6.3) Los alquenos reaccionan con hidrógeno en presencia de un catalizador de platino, paladio, rodio o níquel para formar el correspondiente alcano. Adición de halogenuros de hidrógeno (secciones 6.4-6.7) Un protón y un halógeno se adicionan al enlace doble de un alqueno para producir un halogenuro de alquilo. La adición procede de acuerdo con la regla de Alqueno Alcano Hidrógeno Pt, Pd, Rh o Ni cis-Ciclododeceno Ciclododecano (100%) H2 Pt Alqueno Halogenuro de hidrógeno Halogenuro de alquilo Debido a que los dihalogenuros vecinales se preparan por adición de cloro o bromo a alquenos (sección 6.15), los alquenos, en especial los alquenos terminales, pueden servir como materias primas para la preparación de alquinos, como se muestra en el siguiente ejemplo: Br2 3-Metil-1-butino (52%) (CH3)2CHC CH 1,2-Dibromo-3-metilbutano (CH3)2CHCHCH2Br Br 3-Metil-1-buteno (CH3)2CHCH CH2 1. NaNH2, NH3 2. H2O 380 CAPÍTULO NUEVE Alquinos PROBLEMA 9.7 Dé las estructuras de tres dibromuros isoméricos que se podrían usar como materiales iniciales para la preparación de 3,3-dimetil-1-butino. 3,3-Dimetil-1-butino Eliminar H y Br de carbonos adyacentes dos veces y y PROBLEMA 9.8 Muestre, escribiendo una serie de ecuaciones apropiadas, cómo podría preparar propino a partir de cada uno de los siguientes compuestos como materias primas. Puede usar cualquier reactivo orgánico o inorgánico necesario. a) 2-Propanol d) 1,1-Dicloroetano b) 1-Propanol e) Alcohol etílico c) Bromuro de isopropilo SOLUCIÓN MUESTRA a) Debido a que se sabe que se puede convertir el propeno en propino por la secuencia de reacciones todo lo que resta para completar la descripción de la síntesis es mostrar la preparación de propeno a partir de 2-propanol. La deshidratación catalizada por ácido es adecuada. (CH3)2CHOH 2-Propanol CH3CHoeCH2 Propeno H2SO4 calor CH3CHoeCH2 Propeno CH3CHCH2Br W Br 1,2-Dibromopropano CH3CPCH Propino Br2 1. NaNH2, NH3 2. H2O Programa de ilustraciones • ¡NUEVO! Se han agregado ilustraciones (realizadas a mano por el autor) a las soluciones de ejemplo en los problemas dentro del texto, para ayudar a los alumnos a hacer esquemas de sus trabajos. • Los modelos moleculares hacen más accesible la química orgánica, y enriquecen la experiencia educativa de todos. • Se integran modelos moleculares en el contenido para mostrar las propiedades clave con más claridad que sólo con palabras o fórmulas estructurales. • Se incluyeron propiedades nodales de los orbitales, para mostrar este importante aspecto de la teoría de los enlaces. Centro de
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Fundamentals of Organic Chemistry

Author: John McMurry,Eric Simanek

Publisher: Thomson

ISBN: 9780495125907

Category: Chemistry, Organic

Page: 640

View: 9605

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Written for the short course–where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Sixth Edition, continues to provide an effective, clear, and readable introduction to the beauty and logic of organic chemistry. McMurry presents only those subjects needed for a brief course while maintaining the important pedagogical tools commonly found in larger books. With clear explanations, thought-provoking examples, and an innovative vertical format for explaining reaction mechanisms, FUNDAMENTALS takes a modern approach: primary organization is by functional group, beginning with the simple (alkanes) and progressing to the more complex. Within the primary organization, there is also an emphasis on explaining the fundamental mechanistic similarities of reactions. Through this approach, memorization is minimized and understanding is maximized.The sixth edition brings in new content that applies organic chemistry to students, for example all of the chapter openers have been changed and incorporate a model and photograph of an application of organic chemistry such as Taxol from the pacific yew tree. The book introduces a running application in the Interlude boxes and in the problems relating agricultural chemicals intended to unify the subject further for students. All of the problems have been reorganized by topic to make easier to assign and review. New problem categories have been added. The new problem categories are "In the Field with Agrochemicals" and "In the Medicine Cabinet" to reinforce the focus on applications.
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