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Designed to supplement existing organic textbooks, Hybrid Retrosynthesis presents a relatively simple approach to solving synthesis problems, using a small library of basic reactions along with the computer searching capabilities of Reaxys and SciFinder. This clear, concise guide reviews the essential skills needed for organic synthesis and retrosynthesis, expanding reader knowledge of the foundational principles of these techniques, whilst supporting their use via practical methodologies. Perfect for both graduate and post-graduate students, Hybrid Retrosynthesis provides new applied skills and tools to help during their organic synthesis courses and future careers, whilst simultaneously acting as useful resource for those setting tutorial and group problems, and as a helpful go-to guide for organic chemists involved in either industry or academia. * Ideal revision and hands on learning guide for organic synthesis * Clearly explains the principles and practice of retrosynthesis, which is often not covered in other books * Encourages readers to practice their synthetic knowledge supported by real life examples.
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Addressing a dynamic aspect of organic chemistry, this book describes synthetic strategies and applications for multicomponent reactions including key routes for synthesizing complex molecules. Illustrates the crucial role and the important utility of multicomponent reactions (MCRs) to organic syntheses Compiles novel and efficient synthetic multicomponent procedures to give readers a complete picture of this class of organic reactions Helps readers to design efficient and practical transformations using multicomponent reaction strategies Describes reaction background, applications to synthesize complex molecules and drugs, and reaction mechanisms.
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• PREFACE TO THE SECOND EDITION
• .1. INTRODUCTION.1.1 The Structure and Forms of Water.1.2 Properties of Water.1.3 Solvation.1.4 Hydrophobic Effect.1.5 Salt Effect.1.6 Water Under Extreme Conditions.References.
• 2. ALKANES.2.1 Oxygenation of Alkanes.2.2 Halogenation of Alkanes.2.3 Formation of Carbon-Carbon Bonds.2.4 D/H Exchange of Alkanes in Water.References.
• 3. ALKENES.3.1 Reduction.3.2 Electrophilic Additions.3.3 Radical Reactions of Alkenes.3.4 Carbene Reactions.3.5 Alkene Isomerization.3.6 Transition-Metal Catalyzed C-C Formation Reactions.3.7 Olefin Metathesis.3.8 Reaction of Allylic C-H Bond
• .4. ALKYNES.4.1 Reaction of Terminal Alkynes.4.2 Additions of C C bonds.4.3 Transition-Metal Catalyzed Cycloadditions.4.4 Other Reactions.References.
• 5. ALCOHOLS, PHENOLS, ETHERS, THIOLS, AND THIOETHERS.5.1 Oxidation of Alcohols.5.2 Substitutions/Elimination.5.3 Addition of Alcohols, Phenols, and Thiols to Alkene and Alkyne Bonds.5.4 Addition of Alcohols to C=O Bonds: Esterification and Acetal Formations.5.5 Reaction of Ethers and Cyclic Ethers.5.6 Reaction of Sulfur Compounds
• .6. ORGANIC HALIDES.6.1 General.6.2 Reduction.6.3 Elimination Reactions.6.4 Nucleophilic Substitutions.6.5 Reductive Coupling.6.6 Carbonylation of Organic Halides.6.7 Transition-Metal Catalyzed Coupling Reactions.References.
• 7. AROMATIC COMPOUNDS.7.1 General.7.2 Substitution Reactions.7.3 Oxidation Reactions.7.4 Reductions.References.
• 8. ALDEHDYE AND KETONES.8.1 Reduction.8.2 Oxidation.8.3 Nucleophilic Addition: C-C Bond Formation.8.4 Pinacol Coupling.8.5 Other Reactions (Halogenation and Oxidation of alpha-H).References.
• 9. CARBOXYLIC ACIDS AND DERIVATIVES.9.1 General.9.2 Carboxylic Acids.9.3 Carboxylic Acid Derivatives.References.
• 10. CONJUGATED CARBONYL COMPOUNDS.10.1 Reduction.10.2 Epoxidation, Dihydroxylation, Hydroxyamination.10.3 Conjugate Addition: Heteroatom.10.4 C-C Bond Formation.10.5 Other Reactions.References.
• 11. NITROGEN COMPOUNDS.11.1 Amines.11.2 Imines.11.3 Diazo Compounds.11.4 Azides.11.5 Nitro Compounds.References.
• 12. PERICYCLIC REACTIONS.12.1 Introduction.12.2 Diels-Alder Reactions.12.3 Sigmatropic Rearrangements.12.4 Photochemical Cycloaddition Reactions.References. INDEX.
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This is an extensive update of the classic reference on organic reactions in water. Published almost a decade ago, the first edition has served as the guide for research in this burgeoning field. Due to the cost, safety, efficiency, and environmental friendliness of water as a solvent, there are many new applications in industry and academic laboratories. More than forty percent of this extensively updated second edition covers new reactions. For ease of reference, it is organized by functional groups.A core reference, "Comprehensive Organic Reactions in Aqueous Media, Second Edition": provides the most comprehensive coverage of aqueous organicreactions available; covers the basic principles and theory and progresses to applications; includes alkanes, alkenes, aromatics, electrophilic substitutions, carbonyls, alpha, beta-unsaturated carbonyls, carbon-nitrogen bonds, organic halides, pericyclic reactions, photochemical reactions, click chemistry, and multi-step syntheses; and, provides examples of applications in industry. This is the premier reference for chemists and chemical engineers in industry or research, as well as for students in advanced-level courses.
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• Introduction to the 2nd Edition. Acyloin Ester Condensation. Aldol Reaction. Alkene Metathesis. Arbuzov Reaction. Arndt--Eistert Synthesis. Baeyer--Villiger Oxidation. Bamford--Stevens Reaction. Barton Reaction. Baylis--Hillman Reaction. Beckmann Rearrangement. Benzidine Rearrangement. Benzilic Acid Rearrangement. Benzoin Condensation. Bergman Cyclization. Birch Reduction. Blanc Reaction. Bucherer Reaction. Cannizzaro Reaction. Chugaev Reaction. Claisen Ester Condensation. Claisen Rearrangement. Clemmensen Reduction. Cope Elimination Reaction. Cope Rearrangement. Corey--Winter Fragmentation. Curtius Reaction. 1,3--Dipolar Cycloaddition. [2Y2 ] Cycloaddition. Darzens Glycidic Ester Condensation. Del-epine Reaction. Diazo Coupling. Diazotization. Diels--Alder Reaction. Di--p--Methane Rearrangement. D otz Reaction. Elbs Reaction. Ene Reaction. Ester Pyrolysis. Favorskii Rearrangement. Finkelstein Reaction. Fischer Indole Synthesis. Friedel--Crafts Acylation. Friedel--Crafts Alkylation. Friedl ander Quinoline Synthesis. Fries Rearrangement. Gabriel Synthesis. Gattermann Synthesis. Glaser Coupling Reaction. Glycol Cleavage. Gomberg--Bachmann Reaction. Grignard Reaction. Haloform Reaction. Hantzsch Pyridine Synthesis. Heck Reaction. Hell--Volhard--Zelinskii Reaction. Hofmann Elimination Reaction. Hofmann Rearrangement. Hunsdiecker Reaction. Hydroboration. Japp--Klingemann Reaction. Knoevenagel Reaction. Knorr Pyrrole Synthesis. Kolbe Electrolytic Synthesis. Kolbe Synthesis of Nitriles. Kolbe--Schmitt Reaction. Leuckart--Wallach Reaction. Lossen Reaction. Malonic Ester Synthesis. Mannich Reaction. McMurry Reaction. Meerwein--Ponndorf--Verley Reduction. Michael Reaction. Mitsunobu Reaction. Nazarov Cyclization. Neber Rearrangement. Nef Reaction. Norrish Type I Reaction. Norrish Type II Reaction. Ozonolysis. Paterno--B uchi Reaction. Pauson--Khand Reaction. Perkin Reaction. Peterson Olefination. Pinacol Rearrangement. Prilezhaev Reaction. Prins Reaction. Ramberg--B acklund Reaction. Reformatsky Reaction. Reimer--Tiemann Reaction. Robinson Annulation. Rosenmund Reduction. Sakurai Reaction. Sandmeyer Reaction. Schiemann Reaction. Schmidt Reaction. Sharpless Epoxidation. Simmons--Smith Reaction. Skraup Quinoline Synthesis. Stevens Rearrangement. Stille Coupling Reaction. Stork Enamine Reaction. Strecker Synthesis. Suzuki Reaction. Swern Oxidation. Tiffeneau--Demjanov Reaction. Vilsmeier Reaction. Vinylcyclopropane Rearrangement. Wagner--Meerwein Rearrangement. Weiss Reaction. Willgerodt Reaction. Williamson Ether Synthesis. Wittig Reaction. Wittig Rearrangement. Wohl--Ziegler Bromination. Wolff Rearrangement. Wolff--Kishner Reduction. Wurtz Reaction. Index.
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This Second edition contains consise information on 134 carefully chosen named organic reactions - the standard set of undergraduate and graduate synthetic organic chemistry courses. Each reaction is detailed with clearly drawn mechanisms, references from the primary literature, and well-written accounts covering the mechanical aspects of the reactions, and the details of side reactions and substrate limitations. For the 2nd edition the complete text has been revised and updated, and four new reactions have been added: Baylis-Hillmann Reaction, Sonogashira Reaction, Pummerer Reaction, and the Swern Oxidation und Cyclopropanation. An essential text for students preparing for exams in organic chemistry.
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This work helps students identify basic reaction types in organic chemistry and methods for determining mechanisms, including product studies, kinetics and the identification of intermediates.
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• Molecular Structure and Reactivity. General Principles for Writing Organic Mechanisms. Reactions of Nucleophiles and Bases. Reactions Involving Acids and Other Electrophiles. Radicals and Radical Anions. Pericyclic Reactions. Additional Problems.
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Writing Reaction Mechanisms in Organic Chemistry, Second Edition, is an invaluable guide to charting the movements of atoms and electrons in the reactions of organic molecules. Miller and Solomon illustrate that understanding organic reactions is based on applying general principles rather than the rote memorization of unrelated processes, and, in turn, emphasize that writing mechanisms is a practical method of applying knowledge of previously encountered reactions and reaction conditions to new reactions. Students and research chemists alike will find this book useful in providing a method of organizing and synthesizing an oftentimes overwhelming quantity of information into a set of general principles and guidelines for determining and describing organic reaction mechanisms.
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• Partial table of contents: Aldol Reaction. Benzoin Condensation. 1,3-Dipolar Cycloaddition. Diazo Coupling. Friedel-Crafts Alkylation. Grignard Reaction. Haloform Reaction. Malonic Ester Synthesis. Ozonolysis. Perkin Reaction. Sharpless Epoxidation. Vinylcyclopropane Rearrangement. Wittig Reaction. Index.
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From the Acyloin Condensation to the Wurtz Reaction. A compact collection of 134 important named organic reactions from modern organic chemistry with clearly outlined reaction mechanisms and applications of each reaction. Named Organic Reactions provides The perfect revision aid to key organic reactions References for easy information access Further information, including side reactions, yields and variations of the reaction This book is the essential guide to named organic reactions for chemistry students.
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• 1. The Transition State
• 2. Kinetics and Mechanism
• 3. The Effect of Changes in Reactant Structure
• 4. Kinetic and Equilibrium Isotope Effects
• 5. Transition States from External Effects
• 6. Transition State Structures - Anomalies
• 7. Bioorganic Group Transfer Reactions
• 8. Catalysis
• 9. Complexation Catalysis 10.Some Enzyme Systems.
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Provides a comprehensive and detailed discussion of the investigation of organic and bioorganic reaction mechanisms. It addresses questions such as: 'How are bonds between atoms rearranged?', 'What sort of structural changes take place to cause bond fission and formation?' and 'How do catalysts lower the activation energies of reactions?'.
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• Pericyclic Reactions. Nucleophilic Additions and Substitutions. Metal
• Mediated Reactions. Transition--Metal--Catalyzed Reactions. Oxidations and Reductions. Industrial Applications. Index.
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From cost and safety to synthetic efficiency and environmental friendliness, water has many potential advantages as a solvent for organic reactions. This book examines different aspects of organic reactions in water, enabling readers to gain an essential understanding of current thinking on a range of reaction types and techniques. Beginning with basic theory and progressing to synthetic applications, Organic Reactions in Aqueous Media is an ideal platform for both advanced-level study and practical research. It covers these key areas: Fundamental properties of water Pericyclic reactions-including Diels-Alder reactions Nucleophilic additions and substitutions Metal mediated reactions Transition metal catalyzed reactions Oxidations and reductions Industrial applications.
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• 1. Chemical structure
• 2. Ionic species
• 3. Why reactions happen
• 4. Reactive carbon species
• 5. The effect of heteroatoms
• 6. Types of reaction
• 7. Techniques for investigating mechanisms
• 8. How to suggest mechanisms
• 9. Case histories
• Glossary
• Answers to problems
• Index.
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An understanding of organic reaction mechanisms is an essential part of any undergraduate chemistry course. This book describes the principles that govern chemical reactivity, and shows how these principles can be used to make predictions about the mechanisms and outcomes of chemical reactions. Molecular orbital theory is used to provide up-to-date explanations of chemical reactivity, in an entirely non-mathematical approach suited to organic chemists. A valuable section explains the use of curly arrows, vital for describing reaction mechanisms. A whole chapter is devoted to exploring the thought processes involved in predicting the mechanisms of unfamiliar reactions. Each chapter is followed by a summary of the important points and a selection of problems to help the reader make sure that the material in that chapter has been assimilated. The book concludes with a comprehensive glossary of technical terms. This text will be of valuable for first- and second-year chemistry undergraduates studying organic chemistry.
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• Carbonyl Group: Additions and Addition-Elimination Reactions
• The Carbonyl Group: Enolization - Michael Addition
• The Carbonyl Group, Aldol Condensation
• Some Solutions to the Problem of Selectivity
• Protection and Regeneration, Examples of the Alcohol and Carbonyl Group, Inversion of Polarity
• Activation
• Building of Rings
• Functional Adaptation: Substitutions
• Functional Adaptation: Reductions
• Functional Adaptation: Oxidations
• Addition-Elimination Reactions
• Functionalizations: Conversion of Carbonyl Compounds into Olefins by the Wittig Reaction
• Rearrangements
• Synthons: Donor Synthons
• Synthons: Acceptor Synthons
• Retrosynthetic Analysis.
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• Partial table of contents: Carbonyl Group: Additions and Addition-Elimination Reactions. Carbonyl Group: Enolization--Michael Addition. Carbonyl Group: Aldol Condensation. Some Solutions to the Problem of Selectivity (Chemo-, Regio-, Stereo-). Protection and Regeneration: Cases of the Alcohol and Carbonyl Group, Inversion of Polarity. Protection and Regeneration: Examples of the Alcohol and Carbonyl Group, Inversion of Polarity. Activation. Building of Rings. Functionalizations: Reductions. Functionalizations: Wittig Conversion of Carbonyl Compounds to Olefins. Synthons: Donor Synthons. Retrosynthetic Analysis. Index.
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This text provides a first introduction to the fascinating world of organic chemistry. Each chapter deals with both the practical and theoretical aspects of organic synthesis. A rigorous treatment of the underlying principles of all major classes of reactions are given, followed by a discussion of the applications, history, development and discovery of these pathways. Students are made aware of the impact organic synthesis has on everyday life, and of the elementary logic and simplicity of organic chemistry.
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Written by one of the worlds leading researchers and teachers in organic chemistry, this book focuses on the living core of chemistry, organic synthesis. A rational treatment allows an economical presentation of both the theory and the actual procedures for synthetic pathways. Organic Reactions: Simplicity and Logic the students and lecturers ideal companion, provides:a superb overview of organic reactionsa rigorous introduction to the underlying theoretical conceptsinsight into the logic and simplicity underpinning organic synthesisbiographies of, and mini-essays devoted to, great scientists who have shaped chemistry and biochemistryexamples of industrial organic chemistryan easy-to-read, well-written, highly illustrated textan essential learning tool for chemistry, biochemistry and polymer science coursesOrganic Reactions: Simplicity and Logic presents a lucid introduction to organic synthesis which will appeal to students and lecturers in organic, medicinal, pharmaceutical and industrial chemistry as well as biochemistry, polymer and materials science.
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• Foreword. Preface.
• 1. Basics. Substitution:
• 2. Nucleophilic Substitution.
• 3. Electrophilic Substitution.
• 4. Radical Substitution. Addition:
• 5. Electrophilic addition.
• 6. Radical addition.
• 7. Nucleophilic addition. Elimination:
• 8. Nucleophilic (base-induced) elimination.
• 9. Electrophilic (acid-induced) elimination.
• 10. Radical elimination. Index.
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A simpler, less sophisticated treatment than the Guidebook, providing a basic understanding of the mechanism of organic reactions.
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• General principles for writing organic mechansims
• reactions of nucleophiles and bases
• reactions involving acids and other electrophiles
• radicals and radical anions
• pericyclic reactions
• a mixed bag - additional problems.
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Designed for advanced undergraduate and first-year graduate students, Audrey Miller's "Writing Reaction Mechanisms in Organic Chemistry" may assist students who need to strengthen their ability to write mechanisms. Mechanisms are valuable not only as a means of understanding specific reactions, but as a means of classifying the huge number of known reactions of the nearly infinite number of potential organic compounds. They also serve as an organized means to apply known conditions of known compounds to the prediction of reactions to produce potential (unknown) compounds. Furthermore, mechanisms provide a means of applying knowledge of the chemical stabilities of known compounds to prediction of the stability of potential (yet to be synthesized) compounds. Therefore, a working knowledge of organic mechanisms is essential to carying out an organized program aimed at the synthesis of new compounds with target chemical and/or physical properties. This book may help them with competency exams and qualifying exams. Each chapter is organized so that a reaction type is defined, examples are given and related problems are presented. Examples include references to the literature, pointers as to how to derive mechanistic evidence from the literature, and ways to evaluate mechanisms presented. At the end of each chapter, answers to the problems are given, including the reasoning applied and explanation of why alternative answers (also given) are considered less appropriate.
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During the last two decades the photochemistry of organic molecules has grown into an important and pervasive branch of organic chemistry. In "Modern Molecular Photochemistry", the author brings students up to date with the advances in this field - the development of the theory of photoreactions, the utilization of photoreactions in synthetic sequences, and the advancement of powerful laser techniques to study the mechanisms of photoreactions.
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• Solubility, Intermolecular Forces, and Thermodynamics
• Activities of Solutes, Selection of Standard State and Henry's Law Constants
• Specific Interactions in Solubility Phenomena
• Influence of Complexation, Especially Hydrogen Bonding, on Solubility in Organic Solvents: Prediction of Association Constants
• Structure of Solvents and Effects of Self-Association on Solubility
• Group Contributions in Prediction
• Solubility in and Partitioning into Water
• Ion Pairs and Solubility Behavior
• Phase-Solubility Analysis and Complexation in Aqueous Solution
• Dissolution Rates of Solids
• Afterword
• References
• Author Index
• Subject Index.
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This book explains the various factors, particularly the chemical nature of the molecules, which influence and control the solubility of an organic compound in a particular solvent, especially organic solvents, mixed organic solvents, water and aqueous solutions. The book also explains how to predict the solubility of an organic compound in the solvents mentioned above. Furthermore, the book similarly treats the partition (distribution) coefficient of an organic compound between two relatively immiscible solvents. Thus solubility behaviour comprises both solubility and partitioning between two solvents. This book provides an understanding of concepts of solubility behaviour and practical means for predicting solubilities, partition coefficients and dissolution rates.
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