BROWN IVERSON ANSLYN FOOTE Organic Chemistry SEVENTH EDITION CpeIefL OL&SUIG
7th edition Organic Chemistry William H.Brown Beloit College Brent L.Iverson University of Texas,Austin Eric V.Anslyn Christopher S.Foote University of Califomia,Los Angeles Bruce M.Novak University of Texas at Dallas WADWORTH Australia Brazil Japan·Korea Mexico·Singapore Spain-United KingdomUnited State
Organic Chemistry William H. Brown Beloit College Brent L. Iverson University of Texas, Austin Eric V. Anslyn University of Texas, Austin Christopher S. Foote University of California, Los Angeles Chapter 29 was originally contributed by Bruce M. Novak University of Texas at Dallas 7th edition Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it
Dedication This Seventh Edition is dedicated to the memory of our dear friend and colleague,Christopher Foote.Chris's insights,encouragement,and dedication to this project can never be replaced.His kind and nurturing spirit lives on in all who are lucky enough to have known him
Dedication This Seventh Edition is dedicated to the memory of our dear friend and colleague, Christopher Foote. Chris’s insights, encouragement, and dedication to this project can never be replaced. His kind and nurturing spirit lives on in all who are lucky enough to have known him. Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it
ABOUT THE AUTHORS William H.Brown is an Emeritus Professor of Chemistry at Beloit College, where he has twice been named Teacher of the Year.His teaching responsibilities included organic chemistry,advanced organic chemistry,and special topics in phar macology and drug synthesis.He received his Ph.D.from Columbia University under the direction of Gilbert Stork and did postdoctoral work at the California Institute of Technology and the University of Arizona. Brent L.Iverson received his B.S.from Stanford University and his Ph.D. from the Califoria Institute of Technology.He is a University Distinguished Teaching Professor at the University of Texas at Austin as well as a respected researcher.Brent's research spans the interface of organic chemistry and molecular biology.His group has developed several patented technologies,including an effective treatment for anthrax. Eric V.Anslyn received his B.S.from Califomia State University,Northridge,and his Ph.D.from the Califomia Institute of Technology.He is the Nomman Hackerman Professor and a University Distinguished Teaching Professor at the University of Texas at Austin.Eric's research focuses on the physical and bioorganic chemistry of synthetic and natural receptors and catalysts. Christopher S.Foote received his B.S.from Yale University and his Ph.D. from Harvard University.His scholarly credits include Sloan Fellow;Guggenheim Fellow;ACS Baekland Award;ACS Cope Scholar;Southern Califomia Section ACS Tolman Medal;President,American Society for Photobiology;and Senior Editor, Accounts of chemical research.He was a professor of chemistry at ucla
Unless otherwise noted all art on this page © Cengage Learning 2013 William H. Brown is an Emeritus Professor of Chemistry at Beloit College, where he has twice been named Teacher of the Year. His teaching responsibilities included organic chemistry, advanced organic chemistry, and special topics in pharmacology and drug synthesis. He received his Ph.D. from Columbia University under the direction of Gilbert Stork and did postdoctoral work at the California Institute of Technology and the University of Arizona. Brent L. Iverson received his B.S. from Stanford University and his Ph.D. from the California Institute of Technology. He is a University Distinguished Teaching Professor at the University of Texas at Austin as well as a respected researcher. Brent’s research spans the interface of organic chemistry and molecular biology. His group has developed several patented technologies, including an effective treatment for anthrax. Eric V. Anslyn received his B.S. from California State University, Northridge, and his Ph.D. from the California Institute of Technology. He is the Norman Hackerman Professor and a University Distinguished Teaching Professor at the University of Texas at Austin. Eric’s research focuses on the physical and bioorganic chemistry of synthetic and natural receptors and catalysts. Christopher S. Foote received his B.S. from Yale University and his Ph.D. from Harvard University. His scholarly credits include Sloan Fellow; Guggenheim Fellow; ACS Baekland Award; ACS Cope Scholar; Southern California Section ACS Tolman Medal; President, American Society for Photobiology; and Senior Editor, Accounts of Chemical Research. He was a Professor of Chemistry at UCLA. About the Authors Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it
Contents in Brief 1.Covalent Bonding and Shapes of Molecules /1 2 Alkanes and Cycloalkanes /65 3.Stereoisomerism and Chirality /117 4.Acids and Bases/157 5.Alkenes:Bonding,Nomenclature,and Properties /191 Primer I Reaction Mechanisms 213 6.Reactions of Alkenes 221 7.Alkynes /275 8. Haloalkanes,Halogenation,and Radical Reactions /305 9.Nucleophilic Substitution and B-Elimination /341 10.Alcohols/401 11.Ethers,Epoxides,and Sulfides /451 12.Infrared Spectroscopy/491 13. Nuclear Magnetic Resonance Spectroscopy /512 14.Mass Spectrometry /557 15.An Introduction to Organometalic Compounds/579 16.Aldehydes and Ketones /600 17.Carboxvlic Acids 669 Primer Il Carboxylic Acid Derivative Reaction Mechanisms /701 18.Functional Derivatives of Carboxylic Acids /704 19.Enolate Anions and Enamines/763 20.Dienes,Coniugated Systems.and Pericyclic Reactions/831 21.Benzene and the Concept of Aromaticity 873 22. Reactions of Benzene and Its Derivatives/926 23.Amines 967 24. Catalytic Carbon-Carbon Bond Formation /1021 25.Carbohydrates /1058 26.Lipids 1093 27.Amino Acids and Proteins /1120 28.Nucleic Acids /1156 29.Organic Polymer Chemistry /1180 UhesohewitnotedaaftomhisgeeCeg3geleamig2013
Unless otherwise noted all art on this page © Cengage Learning 2013 v 1. Covalent Bonding and Shapes of Molecules / 1 2. Alkanes and Cycloalkanes / 65 3. Stereoisomerism and Chirality / 117 4. Acids and Bases / 157 5. Alkenes: Bonding, Nomenclature, and Properties / 191 Primer I Reaction Mechanisms / 213 6. Reactions of Alkenes / 221 7. Alkynes / 275 8. Haloalkanes, Halogenation, and Radical Reactions / 305 9. Nucleophilic Substitution and b-Elimination / 341 10. Alcohols / 401 11. Ethers, Epoxides, and Sulfides / 451 12. Infrared Spectroscopy / 491 13. Nuclear Magnetic Resonance Spectroscopy / 512 14. Mass Spectrometry / 557 15. An Introduction to Organometallic Compounds / 579 16. Aldehydes and Ketones / 600 17. Carboxylic Acids / 669 Primer II Carboxylic Acid Derivative Reaction Mechanisms / 701 18. Functional Derivatives of Carboxylic Acids / 704 19. Enolate Anions and Enamines / 763 20. Dienes, Conjugated Systems, and Pericyclic Reactions / 831 21. Benzene and the Concept of Aromaticity / 873 22. Reactions of Benzene and Its Derivatives / 926 23. Amines / 967 24. Catalytic Carbon-Carbon Bond Formation / 1021 25. Carbohydrates / 1058 26. Lipids / 1093 27. Amino Acids and Proteins / 1120 28. Nucleic Acids / 1156 29. Organic Polymer Chemistry / 1180 Contents in Brief Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it