Organic chemistry

Description

A new style of textbook, aimed principally at the European (and British in particular) student. It is needed because almost all current organic chemistry texts are written to a fixed American pattern. This text is different from these in a number of important ways: The approach is based on explanation rather than fact. The functional group approach (alkane, alkene, alkyne) has served American State College readers well but increasingly students and instructors are attracted more to an approach based on mechanism and reaction type. This approach aims at understanding rather than factual knowledge and, though slower at the start, eventually gives the student power to understand compounds and reactions never previously encountered. This is a big advantage in a science already too large for individuals to learn and which is annually expanding at an ever greater rate. The basics of the subject are explained carefully and thoroughly. How to draw molecules realistically and how to draw mechanisms to reveal the fundamental chemistry are both emphasised. Important points are revisited when they become relevant in later chapters. Examples are very important too. New examples are given each time a concept resurfaces, and examples from everyday life and medicinal chemistry are frequently used. The authors want the readers to be excited by the universality of organic chemistry rather than be overwhelmed by facts. The design of the book has features to help comprehension. Structures are drawn in red, and black is used on them for emphasis. Other colours are used flexibly to draw attention to atoms, molecules, orbitals, arrows or whatever the authors want to emphasise rather than being used in a rigid systematic way. There are four types of "box" used to separate material from the main text, ranging from extra important summaries to diversions which can be omitted at first reading. The early chemistry chapters feature carbonyl group reactions because addition to carbonyl groups is probably the easiest reaction to understand. Thereafter the chemistry develops in a logical sequence but chapters on spectroscopy, stereochemistry etc are interspersed among those dealing with chemical reactions. From time to time review chapters summarise what has been described in a particular area. A personal and honest approach is adopted. The authors write clearly and directly to the reader, sharing their enthusiasms, understandings and doubts. If they believe an explanation is imperfect or controversial, they say so. They show that organic chemistry is developing rapidly, and that new ideas continually emerge to replace the old. The authors know from experience what conceptual difficulties often overwhelm students at an early stage in their studies and they devote more space to these points, give more examples, and revisit them when they can be applied. The aim is to help the readers master these points for themselves rather than just learn them off by heart. 1. What is organic chemistry?......Page 1 2. Organic structures......Page 18 3. Determining organic structures......Page 46 4. Structure of molecules......Page 79 5. Organic reactions......Page 110 6. Nucleophilic addition to the carbonyl group......Page 131 7. Delocalization and conjugation......Page 147 8. Acidity, basicity, and pKa......Page 177 9. Using organometallic reagents to make C-C bonds......Page 205 10. Conjugate addition......Page 223 11. Proton nuclear magnetic resonance......Page 239 12. Nucleophilic substitution at the carbonyl (C=O) group......Page 274 13. Equilibria, rates, and mechanisms: summary of mechanistic principles......Page 299 14. Nucleophilic substitution at C=O with loss of carbonyl oxygen......Page 330 15. Review of spectroscopic methods......Page 352 16. Stereochemistry......Page 372 17. Nucleophilic substitution at saturated carbon......Page 397 18. Conformational analysis......Page 436 19. Elimination reactions......Page 465 20. Electrophilic addition to alkenes......Page 490 21. Formation and reactions of enols and enolates......Page 509 22. Electrophilic aromatic substitution......Page 532 23. Electrophilic alkenes......Page 565 24. Chemoselectivity: selective reactions and protection......Page 598 25. Synthesis in action......Page 625 26. Alkylation of enolates......Page 645 27. Reactions of enolates with aldehydes and ketones: the aldol reaction......Page 671 28. Acylation at carbon......Page 705 29. Conjugate addition of enolates......Page 731 30. Retrosynthetic analysis......Page 752 31. Controlling the geometry of double bonds......Page 784 32. Determination of stereochemistry by spectroscopic methods......Page 804 34. Diastereoselectivity......Page 831 37. Rearrangements......Page 855 38. Fragmentation......Page 889 39. Radical reactions......Page 906 40. Synthesis and reactions of carbenes......Page 940 41. Determining reaction mechanisms......Page 965 42. Saturated heterocycles and stereoelectronics......Page 1006 43. Aromatic heterocycles 1: structures and reactions......Page 1031 44. Aromatic heterocycles 2: synthesis......Page 1068 45. Asymmetric synthesis......Page 1103 46. Organo-main-group chemistry I: sulfur......Page 1131 47. Organo-main-group chemistry II: boron, silicon, and tin......Page 1160 48. Organometallic chemistry......Page 1194 49. The chemistry of life......Page 1227 50. Mechanisms in biological chemistry......Page 1263 51. Natural products......Page 1295 52. Polymerization......Page 1332 53. Organic chemistry today......Page 1361 Index......Page 1371