Art of Writing Reasonable Organic Reaction Mechanisms

ISBN-10: 0387954686

ISBN-13: 9780387954684

Edition: 2nd 2003 (Revised)

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Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. The treatment emphasizes unifying principles, showing how common mechanisms link seemingly disparate reactions. Each chapter discusses common mechanistic pathways and suggests practical tips for drawing them. Worked problems are included in the discussion of each mechanism, and "common error alerts" are scattered throughout the text to warn readers about pitfalls and misconceptions that bedevil students. Each chapter is capped by a large problem set. The author has drawn on his own research and the current literature to ensure that appropriate attention is given to topics across the range of modern organic chemistry. The text is unique in its inclusion of a chapter on reactions mediated or catalyzed by transition metals, an area in which mechanistic understanding is now essential. Relatively new topics such as olefin metathesis and cycloaromatization are covered without giving short shrift to more traditional areas such as carbonyl chemistry. The text assumes a basic knowledge of organic chemistry. It can be used either in a formal course or by students working on their own, and will be particularly useful for graduate students studying for qualifying examinations. It will also be useful to students and researchers in biochemistry, pharmacology, and inorganic chemistry.   "This is an excellent and well-presented work.... The author ... has succeeded well in treating the central ideas of reactivity and selectivity in an integrated whole. The clear style of writing, the well chosen examples, and the ... concise summaries of the main points provided at the end of each chapter should enable the reader to easily consolidate what has been learned.... The book is indeed a little work of art." -- Jens Hartung, Angewandte Chemie International Edition   "I have taught a one-credit course with this book for three years, and, uniformly, the students have rated this book highly for its clarity and for the scope of the problems. ... This book does an excellent job at its stated goal: 'to teach students to come up with reasonable mechanisms for reactions they have never seen before.'" -- Amy Howell, Synthesis   "I have just finished my first year of graduate studies in organic chemistry at Duke University. I just wanted to let you know how much your book got me through the past year of course work.... When it came to mechanisms, I found the clarity and thoroughness I needed only in your book. It was impressive how you were able to present so much information in a clear and comprehensive manner yet keep the book so manageable in size. In addition to the text, I also was able to benefit from the problems.... Great practice!! The on-line answers are much better than looking up answers by reference.... I am reading it again this summer in preparation for my preliminary exam next spring." -- David Gooden
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Book details

List price: $64.95
Edition: 2nd
Copyright year: 2003
Publisher: Springer
Publication date: 7/31/2007
Binding: Hardcover
Pages: 360
Size: 6.50" wide x 9.50" long x 0.75" tall
Weight: 1.672
Language: English

Preface to the Student
Preface to the Instructor
The Basics
Structure and Stability of Organic Compounds
Conventions of Drawing Structures; Grossman's Rule
Lewis Structures; Resonance Structures
Molecular Shape; Hybridization
Bronsted Acidity and Basicity
pK[subscript a] Values
Kinetics and Thermodynamics
Getting Started in Drawing a Mechanism
Classes of Overall Transformations
Classes of Mechanisms
Polar Mechanisms
Free-Radical Mechanisms
Pericyclic Mechanisms
Transition-Metal-Catalyzed and -Mediated Mechanisms
Polar Reactions under Basic Conditions
Substitution and Elimination at C(sp[superscript 3])-X [sigma] Bonds, Part I
Substitution by the S[subscript N]2 Mechanism
[beta]-Elimination by the E2 and Elcb Mechanisms
Predicting Substitution vs. Elimination
Addition of Nucleophiles to Electrophilic [pi] Bonds
Addition to Carbonyl Compounds
Conjugate Addition; The Michael Reaction
Substitution at C(sp[superscript 2])-X [sigma] Bonds
Substitution at Carbonyl C
Substitution at Alkenyl and Aryl C
Metal Insertion; Halogen-Metal Exchange
Substitution and Elimination at C(sp[superscript 3])-X [sigma] Bonds, Part II
Substitution by the S[subscript RN]1 Mechanism
Substitution by the Elimination-Addition Mechanism
Substitution by the One-Electron Transfer Mechanism
Metal Insertion; Halogen-Metal Exchange
[alpha]-Elimination; Generation and Reactions of Carbenes
Base-Promoted Rearrangements
Migration from C to C
Migration from C to O or N
Migration from B to C or O
Two Multistep Reactions
The Swern Oxidation
The Mitsunobu Reaction
Polar Reactions Under Acidic Conditions
Carbocation Stability
Carbocation Generation; The Role of Protonation
Typical Reactions of Carbocations; Rearrangements
Substitution and [beta]-Elimination Reactions at C(sp[superscript 3])-X
Substitution by the S[subscript N]1 and S[subscript N]2 Mechanisms
[beta]-Elimination by the E1 Mechanism
Predicting Substitution vs. Elimination
Electrophilic Addition to Nucleophilic C=C [pi] Bonds
Substitution at Nucleophilic C=C [pi] Bonds
Electrophilic Aromatic Substitution
Aromatic Substitution of Anilines via Diazonium Salts
Electrophilic Aliphatic Substitution
Nucleophilic Addition to and Substitution at Electrophilic [pi] Bonds
Heteroatom Nucleophiles
Carbon Nucleophiles
Pericyclic Reactions
Classes of Pericyclic Reactions
Polyene MOs
Electrocyclic Reactions
Typical Reactions
Typical Reactions
Sigmatropic Rearrangements
Typical Reactions
Ene Reactions
Free-Radical Reactions
Free Radicals
Generation from Closed-Shell Species
Typical Reactions
Chain vs. Nonchain Mechanisms
Chain Free-Radical Reactions
Substitution Reactions
Addition and Fragmentation Reactions
Nonchain Free-Radical Reactions
Photochemical Reactions
Reductions and Oxidations with Metals
Miscellaneous Radical Reactions
1,2-Anionic Rearrangements; Lone-Pair Inversion
Triplet Carbenes and Nitrenes
Transition-Metal-Mediated and -Catalyzed Reactions
Introduction to the Chemistry of Transition Metals
Conventions of Drawing Structures
Counting Electrons
Typical Reactions
Stoichiometric vs. Catalytic Mechanisms
Addition Reactions
Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh)
Hydroformylation (Co, Rh)
Hydrozirconation (Zr)
Alkene Polymerization (Ti, Zr, Sc, and others)
Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti)
Dihydroxylation and Aminohydroxylation of Alkenes (Os)
Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd)
Conjugate Addition Reactions (Cu)
Reductive Coupling Reactions (Ti, Zr)
Pauson-Khand Reaction (Co)
Dotz Reaction (Cr)
Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh)
Substitution Reactions
Hydrogenolysis (Pd)
Carbonylation of Alkyl Halides (Pd, Rh)
Heck Reaction (Pd)
Coupling Reactions Between Nucleophiles and C(sp[superscript 2])-X: Kumada, Stille, Suzuki, Negishi, Buchwald-Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu)
Allylic Substitution (Pd)
Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation
Tebbe Reaction (Ti)
Propargyl Substitution in Co-Alkyne Complexes
Rearrangement Reactions
Alkene Isomerization (Rh)
Olefin and Alkyne Metathesis (Ru, W, Mo, Ti)
Elimination Reactions
Oxidation of Alcohols (Cr, Ru)
Decarbonylation of Aldehydes (Rh)
Mixed-Mechanism Problems
A Final Word
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