Organic Mechanisms: Reactions, Stereochemistry and Synthesis / Edition 1

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Overview

This English edition of a best-selling and award-winning German textbook Reaction Mechanisms: Organic Reactions · Stereochemistry · Modern Synthetic Methods is aimed at those who desire to learn organic chemistry through an approach that is facile to understand and easily committed to memory. Michael Harmata, Norman Rabjohn Distinguished Professor of Organic Chemistry (University of Missouri) surveyed the accuracy of the translation, made certain contributions, and above all adapted its rationalizations to those prevalent in the organic chemistry community in the English-speaking world.

Throughout the book fundamental and advanced reaction mechanisms are presented with meticulous precision. The systematic use of red "electron-pushing arrows" allows students to follow each transformation elementary step by elementary step. Mechanisms are not only presented in the traditional contexts of rate laws and substituent effects but, whenever possible, are illustrated using practical, useful and state-of-the-art reactions. The abundance of stereoselective reactions included in the treatise makes the reader familiar with key concepts of stereochemistry.

The fundamental topics of the book address the needs of upper-level undergraduate students, while its advanced sections are intended for graduate-level audiences. Accordingly, this book is an essential learning tool for students and a unique addition to the reference desk of practicing organic chemists, who as life-long learners desire to keep abreast of both fundamental and applied aspects of our science. In addition, it will well serve ambitious students in chemistry-related fields such as biochemistry, medicinal chemistry and pharmaceutical chemistry.

From the reviews:

"Professor Bruckner has further refined his already masterful synthetic organic chemistry classic; the additions are seamless and the text retains the magnificent clarity, rigour and precision which were the hallmark of previous editions. The strength of the book stems from Professor Bruckner’s ability to provide lucid explanations based on a deep understanding of physical organic chemistry and to limit discussion to very carefully selected reaction classes illuminated by exquisitely pertinent examples, often from the recent literature. The panoply of organic synthesis is analysed and dissected according to fundamental structural, orbital, kinetic and thermodynamic principles with an effortless coherence that yields great insight and never over-simplifies. The perfect source text for advanced Undergraduate and Masters/PhD students who want to understand, in depth, the art of synthesis ."
Alan C. Spivey, Imperial College London

"Bruckner’s ‘Organic Mechanisms’ accurately reflects the way practicing organic chemists think and speak about organic reactions. The figures are beautifully drawn and show the way organic chemists graphically depict reactions. It uses a combination of basic valence bond pictures with more sophisticated molecular orbital treatments. It handles mechanisms both from the "electron pushing perspective" and from a kinetic and energetic view. The book will be very useful to new US graduate students and will help bring them to the level of sophistication needed to be serious researchers in organic chemistry."
Charles P. Casey, University of Wisconsin-Madison

"This is an excellent advanced organic chemistry textbook that provides a key resource for students and teachers alike."
Mark Rizzacasa, University of Melbourne, Australia.

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Editorial Reviews

From the Publisher
From the reviews:

"The new edition of the textbook of R. Bruckner is accurate, all important modern mechanistic and synthetic concepts of organic chemistry are presented in a very didactic fashion, a superb book to put in the hands of all who would want to learn synthetic organic chemistry or refresh their knowledge."
Paul Knochel, Ludwig-Maximilians-University Munich

"Over its three editions, Professor Bruckner has significantly fine-tuned his outstanding textbook titled ‘Organic Mechanisms’, now available in English. This text is aimed squarely at students that have completed a typical one-year introductory course in organic chemistry and now wish to continue refining their understanding of the subject. At this level, the text is appropriately focused on providing the reader with an enhanced fundamental understanding of an ambitious range of organic reactions. Along with reminding the reader about fundamental principles necessary to understand the topic, Bruckner’s updated edition also provides a solid physical organic perspective on a wide range of processes. The text is not meant to be an exhaustive survey of reactions, but more of a sound introduction to the underlying principles that control reactivity in variety of transformations that chemistry students should be familiar with. The book, therefore, is particularly well suited for “intermediate” and “advanced” classes in organic chemistry, usually found in upper class electives and introductory graduate classes. The book will also serve as a valuable starting point for the more experienced chemist wishing to brush-up on organic transformations that they might be less familiar with.”
Marc L. Snapper, Boston College

This updated version of Professor Brückner’s ‘Organic Mechanisms’ provides a thorough overview of modern organic synthesis that is both comprehensive and accessible to chemists with all levels of experience. Detailed reaction mechanisms are illustrated with clear schemes that effectively convey the electronic and structural principles influencing reactivity and selectivity for the most common transformations used in organic synthesis. The pragmatic division of the material into introductory and more advanced sections enables the text to be used both as a teaching resource for both undergraduate chemistry students and researchers from allied disciplines and as a valuable text for experienced researchers. The book prompts the reader to readily grasp important concepts, while providing ample scope for extension and development of more advanced students of organic chemistry. ‘Organic Mechanisms’ is also a valuable resource for those involved in the application and practice of organic synthesis on a professional level. The range of topics discussed provides an up-to-date compendium of current methods, of relevance to both academia and industry, with the references at the end of each chapter providing a useful starting point for more detailed further reading. Overall, the new English edition of ‘Organic Mechanisms’ is an excellent single reference for those wishing to learn or better understand the complex practice of modern synthetic organic chemistry. It is long overdue and I look forward to having a copy readily available for my students.
Margaret Brimble, The University of Auckland

Having held in high regard the 1st English edition of Bruckner's textbook Organic Reaction Mechanisms I have been waiting for years for an updated version to appear. This long-expected textbook is now available. It has been completely revised and considerably expanded and is a meticulously composed treatise at the interface between synthetic organic chemistry and mechanistic analysis. Every student of advanced organic chemistry will benefit from this book."
Koichi Narasaka, Nayang Technical University, Singapore.

“This English edition of the German textbook by Bruckner … is an excellent resource for advanced academic students. … The presentation is impressive, and clear illustrations appear throughout the book. … This makes the work a very interesting read and offers abundant opportunities for students to create new problem sets. … For graduate students and instructors, this work offers a wealth of information. The end-of-chapter references are comprehensive and thorough. Summing Up: Highly recommended. Graduate students, researchers/faculty, and professionals.” (S. Rajaraman, Choice, Vol. 48 (3), November, 2010)

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Product Details

  • ISBN-13: 9783642036507
  • Publisher: Springer Berlin Heidelberg
  • Publication date: 3/23/2010
  • Edition description: 2010
  • Edition number: 1
  • Pages: 856
  • Product dimensions: 7.90 (w) x 9.80 (h) x 1.60 (d)

Meet the Author

Professor Dr. Reinhard Brückner arbeitet seit 1998 am Institut für Organische Chemie und Biochemie der Universität Freiburg. Seine Forschungsgebiete sind Naturstoffsynthese und die Entwicklung neuer Methoden im Bereich der Stereoselektiven Synthese. Zuvor war er Professor für Organische Chemie an den Universitäten Würzburg und Göttingen bzw. Gastprofessor an der University of Wisconsin in Madison (USA), der Universidade de Santiago de Compostela (Spanien), der Indiana University Bloomington (USA) und der Tokyo University (Center of Excellence Program).

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Table of Contents

1 Radical Substitution Reactions at the Saturated C Atom

2 Nucleophilic Substitution Reactions at the Saturated C Atom

3 Electrophilic Additions to the C-C Double Bond

4 ß-Eliminations

5 Substitution Reactions on Aromatic Compounds

6 Nucleophilic Substitution Reactions at the Carboxyl Carbon

7 Carboxylic Compound, Nitriles and Their Mutual Transformation

8 Carbonic Acid Derivatives and Heterocumulenes and their Mutual Transformation

9 Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Subsequent Reactions - Condensaations of Heteroatom Nucleophiles with Carbonyl Compounds

10 Addition of Hydride Donors and Organometallic Compounds to Carbonyl Compounds

11 Conversion of Phosphorus- or Sulfur-Stabilized C Nucleophiles with Carbonyl Compounds: Addition-induced Condensations

12 The Chemistry of Enoles and Enamines

13 Chemistry of the Alkaline Earth Metal Enolates

14 Rearrangements

15 Thermal Cycloadditions

16 Transition Metal-Mediated Alkenylations, Arylations, and Alkynylations

17 Oxidations and Reductions

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