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The collection of chapters in this first volume of Stereochemistry – Basic to Advances in Organic Chemistry covers a range of topics that reflects both the evolution of the field of stereochemistry and the most exciting advances that presage its future. Thus, it was expressly by design that there be conceptually focused chapters on the basic principles of molecular chirality and asymmetric amplification to perfectly predict the structure of organic molecules. The goal, as in the first edition, is to give equal weight to the fundamental aspects of the study of stereochemistry. The history of organic chemistry goes back to the days of Friedrich Wohler, two centuries ago. The stereochemical underpinnings of organic chemistry were set by Louis Pasteur, and the concept of chirality was advanced by Lord Kelvin, nearly a century later. The first stereochemical notation – that of the asymmetric carbon atom – had to await the Cahn-Ingold-Prelog (CIP) R/S rules – a half-century later; it took yet another quartercentury for the E/Z configurational notation for double bonds to be formulated. Indeed, the development of organic stereochemical language has lagged and continues to lag experimental organic chemistry. In the last quarter-century or so, there have been only two seminal contributions – both by Kurt Mislow and his coworkers – ones that have clarified the basic concepts of stereotopicity and chirotopicity. Since last two decades, scientists are working very hard to establish the unknown organic structure through the correlation of stereochemical aspects and predicting its potency and efficiency based on these parameters. Also, the national universities and central examinations organizations focused more to incorporate the stereochemistry in basics to the complex molecular framework. The past years have witnessed a rapid development of biochemistry and molecular biology. The chemical structures of many complex biopolymers such as proteins and nucleic acids have been elucidated. Moreover, the understanding of the stereochemical details of many important transformations catalyzed by various metal and non-metal reactions reflect the structural complexity of organic, inorganic and biomolecular chemistry. This book provides an insightful analysis of the foundations of molecular chirality, topological chirality, definitions of chirality measures, rules applying during nomenclature, set of rules for predicting the stereochemistry, dynamic stereochemical concepts, and most important, practice with suitable examples for the readers. Nevertheless, students will often wish to pursue individual topics further. This part of the work is an attempt to present the elements of a simple, uniform and comprehensive language of organic stereochemistry. An effort has therefore been made to guide the reader to give a piece of small information that is quite useful to understand the concepts. Furthermore, in a graduate course, students should be encouraged to consult primary sources. Authors are hoping that this book will not only be of interest to specialists but will also provide general information useful to organic chemists, biochemists and molecular biologists for their research and reference work during international publications. Contents - 1. Isomers 2. Various Types of Projection in Stereochemistry 3. Conformation of Acyclic System 4. D & L Nomenclature 5. Absolute Configuration 6. Threo and Erythro Nomenclature 7. Conformational Analysis of Cyclohexane 8. Conformational Analysis of Mono Substituted Cyclohexane 9. Flipping in Cyclohexane 10. Some Basic Terms Used in Stereochemistry 11. Residual Stereoisomers 12. Meso Compounds 13. Plane of Symmetry (σ) Chirality 14. Racemic Modification 15. Racemic Compound or Racemate 16. Racemization 17. Resolution of Racemic Mixture 18. Threo and Erythro Nomenclature 19. Dynamic Stereochemistry 20. Product Stereoselectivity 21. Prochirality/Prostereoisomerism 22. Nomenclature of Prochiral Faces/Groups/Ligands 23. Diastereomers of Acyclic Molecules/Stereoselectivity of Carbonyl Compounds/Cram's Rule and their Newman Projection and Fisher Projection 24. Application of Cram's Rule 25. Felkin-Anh Model or Karabatsos Model 26. Diastereoseletivity in Aldol Condensation Reaction 27. Stereochemical Aspects of Aldol Condensation with Respect to Re and Si Face 28. Stability of Exo and Endo Stereoisomer 29. Conformation of Tetrahydropyran Aromatic Effect 30. Exo Anomeric Effect 31. Conformations of Fused Bicyclic 32. Concept of I-Strain 33. Dihedral Angle 34. Torsional Angle 35. Angle and Pitzer Strain 36. Conformation of Cyclopropane and Cyclobutane 37. Conformation of Substituted Cyclohexanes 38. Freezing of Conformational Inversions in Cyclohexane Chair Form 39. Conformation of Decalines 40. Conformation of Decalones 41. Confirmation of Bridged System 42. Stereoselective Reactions of Acyclic Alkenes 43. Addition of Carbenes to Alkenes 44. Hydrogen Addition-Selectivity 45. Oxidation of Alkenes: Epoxidation and Hydroxylation 46. Chirality and Drug Development 47. R-S Examples for Practice 48. Some Examples of Chiral Drugs 49. Some Questions for Competitive Exam 50. Bibliography
