[...]... terrific women who have transformed the ideas and manuscript pages of the last two editions of Organic Chemistry into stunning texts—Tami Hodge (Senior Sponsoring Editor), Donna Nemmers (Senior Developmental Editor), and Jayne Klein (Senior Project Manager) All aspects of this project— from devising the overall plan for the third edition to obtaining valuable reviews to setting a workable production schedule—... who are responsible for the visually pleasing appearance of this edition Thanks are again due to Professor Spencer Knapp and his crew at Rutgers University, who prepared the many new spectra that appear in the third edition, and to freelance Developmental Editor John Murdzek for his meticulous editing and humorous insights on my project Organic Chemistry is complemented with useful supplements prepared... pieces, I have found that many students find organic chemistry an intense but learnable subject Many, in fact, end the year-long course surprised that they have actually enjoyed their organic chemistry experience Organization and Presentation For the most part, the overall order of topics in the text is consistent with the way most instructors currently teach organic chemistry There are, however, some... Isomers—A Summary 181 Physical Properties of Stereoisomers 182 Chemical Properties of Enantiomers 186 Key Concepts 188 Problems 190 6 Understanding Organic Reactions 196 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 6.10 6.11 Writing Equations for Organic Reactions 197 Kinds of Organic Reactions 198 Bond Breaking and Bond Making 200 Bond Dissociation Energy 203 Thermodynamics 206 Enthalpy and Entropy 209 Energy Diagrams... Characteristic NMR Absorptions A-11 Appendix G General Types of Organic Reactions A-13 Appendix H How to Synthesize Particular Functional Groups A-15 Glossary G-1 Credits C-1 Index I-1 smi75625_fm_00i-xxxiv.indd xvii 11/17/09 11:21:40 AM Preface My goal in writing Organic Chemistry was to create a text that showed students the beauty and logic of organic chemistry by giving them a book that they would use... interactions with them, and I hope that the wider chemistry community can benefit from this experience by the way I have presented the material in this text This third edition has evolved based on the helpful feedback of many people who reviewed the second edition, classtested the book, and attended focus groups or symposiums These many individuals have collectively provided constructive improvements to the... Preface xix • Functional groups Chapter 3 uses the functional groups to introduce important properties of organic chemistry Relevant examples—PCBs, vitamins, soap, and the cell membrane—illustrate basic solubility concepts In this way, practical topics that are sometimes found in the last few chapters of an organic chemistry text (and thus often omitted because instructors run out of time) are introduced... Concepts End-of-chapter summaries succinctly summarize the main concepts and themes of the chapter, making them ideal for review prior to working the end-of-chapter problems or taking an exam New to the Third Edition • In response to reviewer feedback, new sections have been added on fragmentation patterns in mass spectrometry (Section 13.3) and peptide sequencing (Section 28.6) In addition, sections on... the chemical reaction • Twenty new NMR spectra have been added in Chapters 14–25 to give students additional practice in this important type of analysis • Over 350 new problems are included in the third edition The majority of these problems are written at the intermediate level—more advanced than the easier drill problems, but not as complex as the challenge problems Beginning with Chapter 11, there... (trade name Truvia), a sweetening agent isolated from a plant source, and many others smi75625_fm_00i-xxxiv.indd xix 11/17/09 11:21:42 AM Tools to Make Learning Organic Chemistry Easier 11-trans 11-cis N opsin hν Illustrations H CH3 + crowding Organic Chemistry is supported by a well-developed illustration program Besides traditional skeletal (line) structures and condensed formulas, there are numerous . AM Organic Chemistry Third Edition Janice Gorzynski Smith University of Hawai’i at Ma - noa TM smi75625_fm_00i-xxxiv.indd ismi75625_fm_00i-xxxiv.indd i 11/17/09 11:21:07 AM11/17/09 11:21:07 AM ORGANIC. Ma - noa TM smi75625_fm_00i-xxxiv.indd ismi75625_fm_00i-xxxiv.indd i 11/17/09 11:21:07 AM11/17/09 11:21:07 AM ORGANIC CHEMISTRY, THIRD EDITION Published by McGraw-Hill, a business unit of The McGraw-Hill Companies, Inc., 1221. Data Smith, Janice G. Organic chemistry / Janice Gorzynski Smith. — 3rd ed. p. cm. Includes index. ISBN 978–0–07–337562–5 — ISBN 0–07–337562–4 (hard copy : alk. paper) 1. Chemistry, Organic Textbooks.