《有机化学》课程教学资源（参考书籍）The Vocabulary and Concepts of Organic Chemistry, 2nd Ed 2005, Milton Orchin, Roger S. Macomber, Allan R. Pinhas, R. Marshall Wilson

THE VOCABULARY AND CONCEPTS OF ORGANIC CHEMISTRY SECOND EDITION Milton Orchin Roger S.Macomber Allan R.Pinhas R.Marshall Wilson WILEY-INTERSCIENCE A John Wiley Sons,Inc.,Publication

THE VOCABULARY AND CONCEPTS OF ORGANIC CHEMISTRY SECOND EDITION Milton Orchin Roger S. Macomber Allan R. Pinhas R. Marshall Wilson A John Wiley & Sons, Inc., Publication ffirs.qxd 5/20/2005 9:02 AM Page iii

CONTENTS 1 Atomic Orbital Theory 2 Bonds Between Adjacent Atoms:Localized Bonding Molecular Orbital Theory 25 3 Delocalized(Multicenter)Bonding 54 4 Symmetry Operations,Symmetry Elements,and Applications 83 5 Classes of Hydrocarbons 110 6 Functional Groups:Classes of Organic Compounds 139 7 Molecular Structure Isomers,Stereochemistry,and Conformational Analysis 221 8 Synthetic Polymers 291 9 Organometallic Chemistry 343 10 Separation Techniques and Physical Propertie 387 11 Fossil Fuels and Their Chemical Utilization 419 12 Thermodynamics,Acids and Bases,and Kinetics 450 13 Reactive Intermediates (Ions,Radicals,Radical Ions, Electron-Deficient Species,Arynes) 吃 14 Types of Organic Reaction Mechanisms 535 15 Nuclear Magnetic Resonance Spectroscopy 分

CONTENTS 1 Atomic Orbital Theory 1 2 Bonds Between Adjacent Atoms: Localized Bonding, Molecular Orbital Theory 25 3 Delocalized (Multicenter) Bonding 54 4 Symmetry Operations, Symmetry Elements, and Applications 83 5 Classes of Hydrocarbons 110 6 Functional Groups: Classes of Organic Compounds 139 7 Molecular Structure Isomers, Stereochemistry, and Conformational Analysis 221 8 Synthetic Polymers 291 9 Organometallic Chemistry 343 10 Separation Techniques and Physical Properties 387 11 Fossil Fuels and Their Chemical Utilization 419 12 Thermodynamics, Acids and Bases, and Kinetics 450 13 Reactive Intermediates (Ions, Radicals, Radical Ions, Electron-Deficient Species, Arynes) 505 14 Types of Organic Reaction Mechanisms 535 15 Nuclear Magnetic Resonance Spectroscopy 591 v ftoc.qxd 6/11/2005 9:32 AM Page v

vi CONTENTS 16 Vibrational and Rotational Spectroscopy:Infrared,Microwave, and Raman Spectra 657 17 Mass Spectrometry 703 18 Electronic Spectroscopy and Photochemistry 京 Name Index 833 Compound Index 837 General Index 849

vi CONTENTS 16 Vibrational and Rotational Spectroscopy: Infrared, Microwave, and Raman Spectra 657 17 Mass Spectrometry 703 18 Electronic Spectroscopy and Photochemistry 725 Name Index 833 Compound Index 837 General Index 849 ftoc.qxd 6/11/2005 9:32 AM Page vi

PREFACE It has been almost a quarter of a century since the first edition of our book The Chmistry was published.Like the vocabulary of ever Vocabulary ing language old y wew on hes emerge .In dition to ot obvious of these is in the title,which has been expanded to ulary,other im t changes have bee n incorporate Vocabulary and Concepts of Organic Chemistry in recognition of the fact that in addressing the language of a science,we found it frequently necessary to define and explain the concepts that have led to the vocabulary.The second change from the first edition is authorship.Three of the original authors of the first edition have par- ticipated in this new version:the two lost collaborators were sorely missed. Professor Hans Zimmer died on June 13,2001.His co ntribution to the first edition elevated its scholarship .He had grasp of the PolKluable mbulin cti stry and his pro knowledge of f attention to small detail,his organizational expertise,and his patient examination of the limits of definitions,both inclusive and exclusive,were some of the many advan- tages of his co-authorship.We regret that his other interests prevented his participa tion in the present effort.However,these unfortunate losses were more than ompensated by the addition of a new w author.Professor Allan Pinhas,whose knowl nthusia and matchless enery lubricated the ntir process of getting this on to the publishe Having addressed the changes in title and authorship.we need to describe the changes in content.Two major chapters that appeared in the first edition no longer appear here:"Named Organic Reactions"and"Natural Products."Since 1980,sev- eral excellent books on named organic reactions and their mechanisms have appeared,and some of us felt our treatment would be redundant.The second dele- tion.dealing with natural products,we decided would better be treated in an antici- pated second volume to this edition that will address not only this topic,but also the ing interes st in biological molecules.These ons ma de it p ble to in lude othe areas of organic chemistry not covered in our first edit namely the powerful spectroscopic tools so important in structure determination infrared spectroscopy,NMR,and mass spectroscopy,as well as ultraviolet spec- troscopy and photochemistry.In addition to the new material,we have updated mate- rial covered in the first edition with the rearrangement of some chapters,and of course,we have taken advantage of reviews and comments on the earlier edition to revise the discussion where necessary. vii

vii PREFACE It has been almost a quarter of a century since the first edition of our book The Vocabulary of Organic Chemistry was published. Like the vocabulary of every liv￾ing language, old words remain, but new ones emerge. In addition to the new vocab￾ulary, other important changes have been incorporated into this second edition. One of the most obvious of these is in the title, which has been expanded to The Vocabulary and Concepts of Organic Chemistry in recognition of the fact that in addressing the language of a science, we found it frequently necessary to define and explain the concepts that have led to the vocabulary. The second change from the first edition is authorship. Three of the original authors of the first edition have par￾ticipated in this new version; the two lost collaborators were sorely missed. Professor Hans Zimmer died on June 13, 2001. His contribution to the first edition elevated its scholarship. He had an enormous grasp of the literature of organic chem￾istry and his profound knowledge of foreign languages improved our literary grasp. Professor Fred Kaplan also made invaluable contributions to our first edition. His attention to small detail, his organizational expertise, and his patient examination of the limits of definitions, both inclusive and exclusive, were some of the many advan￾tages of his co-authorship. We regret that his other interests prevented his participa￾tion in the present effort. However, these unfortunate losses were more than compensated by the addition of a new author, Professor Allan Pinhas, whose knowl￾edge, enthusiasm, and matchless energy lubricated the entire process of getting this edition to the publisher. Having addressed the changes in title and authorship, we need to describe the changes in content. Two major chapters that appeared in the first edition no longer appear here: “Named Organic Reactions” and “Natural Products.” Since 1980, sev￾eral excellent books on named organic reactions and their mechanisms have appeared, and some of us felt our treatment would be redundant. The second dele￾tion, dealing with natural products, we decided would better be treated in an antici￾pated second volume to this edition that will address not only this topic, but also the entire new emerging interest in biological molecules. These deletions made it possi￾ble to include other areas of organic chemistry not covered in our first edition, namely the powerful spectroscopic tools so important in structure determination, infrared spectroscopy, NMR, and mass spectroscopy, as well as ultraviolet spec￾troscopy and photochemistry. In addition to the new material, we have updated mate￾rial covered in the first edition with the rearrangement of some chapters, and of course, we have taken advantage of reviews and comments on the earlier edition to revise the discussion where necessary. fpref.qxd 6/11/2005 9:31 AM Page vii

viii PREFACE The final important ques tion.we turn to the objective of the book.which is to identify the fundamental vocabulary and concepts of organic chemistry and present concise,accurate descrip- tions of them with examples when appropriate.It is not intended to be a dictionary but is organized into a sequence of chapters that reflect the way the subject is taught Related terms appear in close proximity to each other,and hence,fine distinct ons me understandable.Students and instructors may concentration ject matter into the essential a pects of the various topics overed.Inaddit we hope the book ill appeal toand prove useful to.many others in thech community who either in the recent past,or even remote past,were familiar with the topics defined,but whose precise knowledge of them has faded with time. In the course of writing this book,we drew generously from published books and articles,and we are grateful to the many authors who unknowingly contributed their expertise.We have also taken advantage of the special knowledge of some of our colleagues in the Department of Chemistry and we acknowledge them in appropri ate chapters MILTON ORCHIN ROGER S.MACOMBER ALLAN R.PINHAS R.MARSHALL WILSON

viii PREFACE The final item that warrants examination is perhaps one that should take prece￾dence over others. Who should find this book useful? To answer this important ques￾tion, we turn to the objective of the book, which is to identify the fundamental vocabulary and concepts of organic chemistry and present concise, accurate descrip￾tions of them with examples when appropriate. It is not intended to be a dictionary, but is organized into a sequence of chapters that reflect the way the subject is taught. Related terms appear in close proximity to each other, and hence, fine distinctions become understandable. Students and instructors may appreciate the concentration of subject matter into the essential aspects of the various topics covered. In addition, we hope the book will appeal to, and prove useful to, many others in the chemical community who either in the recent past, or even remote past, were familiar with the topics defined, but whose precise knowledge of them has faded with time. In the course of writing this book, we drew generously from published books and articles, and we are grateful to the many authors who unknowingly contributed their expertise. We have also taken advantage of the special knowledge of some of our colleagues in the Department of Chemistry and we acknowledge them in appropri￾ate chapters. MILTON ORCHIN ROGER S. MACOMBER ALLAN R. PINHAS R. MARSHALL WILSON fpref.qxd 6/11/2005 9:31 AM Page viii