This book is designed for those who have had no more than a brief introduction to organic chemistry and who require a broad understanding of the subject. The book is in two parts. In Part I, reaction mechanism is set in its wider context of the basic principles and concepts that underlie chemical reactions: chemical thermodynamics, structural theory, theories of reaction kinetics, mechanism itself and stereochemistry. In Part II these principles and concepts are applied to the formation of particular types of bonds, groupings, and compounds. The final chapter in Part II describes the planning and detailed execution of the multi-step syntheses of several complex, naturally occurring compounds.
Introduction what is organic chemistry all about?; Structural organic chemistry the shapes of molecules functional groups; Organic nomenclature; Alkanes; Stereoisomerism of organic molecules; Bonding in organic molecules atomic-orbital models; More on nomenclature compounds other than hydrocarbons; Nucleophilic substitution and elimination reactions; Separation and purification identification of organic compounds by spectroscopic techniques; Alkenes and alkynes. Ionic and radical addition reactions; Alkenes and alkynes; Oxidation and reduction reactions; Acidity or alkynes.
Class-tested and thoughtfully designed for student engagement, Principles of Organic Chemistry provides the tools and foundations needed by students in a short course or one-semester class on the subject. This book does not dilute the material or rely on rote memorization. Rather, it focuses on the underlying principles in order to make accessible the science that underpins so much of our day-to-day lives, as well as present further study and practice in medical and scientific fields. This book provides context and structure for learning the fundamental principles of organic chemistry, enabling the reader to proceed from simple to complex examples in a systematic and logical way. Utilizing clear and consistently colored figures, Principles of Organic Chemistry begins by exploring the step-by-step processes (or mechanisms) by which reactions occur to create molecular structures. It then describes some of the many ways these reactions make new compounds, examined by functional groups and corresponding common reaction mechanisms. Throughout, this book includes biochemical and pharmaceutical examples with varying degrees of difficulty, with worked answers and without, as well as advanced topics in later chapters for optional coverage. Incorporates valuable and engaging applications of the content to biological and industrial uses Includes a wealth of useful figures and problems to support reader comprehension and study Provides a high quality chapter on stereochemistry as well as advanced topics such as synthetic polymers and spectroscopy for class customization
Organic Chemistry: Structure, Mechanism, Synthesis, Second Edition, provides basic principles of this fascinating and challenging science, which lies at the interface of physical and biological sciences. Offering accessible language and engaging examples and illustrations, this valuable introduction for the in-depth chemistry course engages students and gives future and new scientists a new approach to understanding, rather than merely memorizing the key concepts underpinning this fundamental area. The book builds in a logical way from chemical bonding to resulting molecular structures, to the corresponding physical, chemical and biological properties of those molecules. The book explores how molecular structure determines reaction mechanisms, from the smallest to the largest molecules—which in turn determine strategies for organic synthesis. The book then describes the synthetic principles which extend to every aspect of synthesis, from drug design to the methods cells employ to synthesize the molecules of which they are made. These relationships form a continuous narrative throughout the book, in which principles logically evolve from one to the next, from the simplest to the most complex examples, with abundant connections between the theory and applications. Featuring in-book solutions and instructor PowerPoint slides, this Second Edition offers an updated and improved option for students in the two-semester course and for scientists who require a high quality introduction or refresher in the subject. - Offers improvements for the two-semester course sequence and valuable updates including two new chapters on lipids and nucleic acids - Features biochemistry and biological examples highlighted throughout the book, making the information relevant and engaging to readers of all backgrounds and interests - Includes a valuable and highly-praised chapter on organometallic chemistry not found in other standard references
The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations.
The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework Organic synthesis is an advanced but important field of organic chemistry, however resources for advanced undergraduates and graduate students moving from introductory organic chemistry courses to organic synthesis research are scarce. Introduction to Strategies for Organic Synthesis is designed to fill this void, teaching practical skills for making logical retrosynthetic disconnections, while reviewing basic organic transformations, reactions, and reactivities. Divided into seven parts that include sections on Retrosynthesis and Protective Groups; Overview of Organic Transformations; Synthesis of Monofunctional Target Molecules; Synthesis of Target Molecules with Two Functional Groups; Synthesis of Aromatic Target Molecules; Synthesis of Compounds Containing Rings; and Predicting and Controlling Stereochemistry, the book covers everything students need to successfully perform retrosynthetic analyses of target molecule synthesis. Starting with a review of functional group transformations, reagents, and reaction mechanisms, the book demonstrates how to plan a synthesis, explaining functional group analysis and strategic disconnections. Incorporating a review of the organic reactions covered, it also demonstrates each reaction from a synthetic chemist's point of view, to provide students with a clearer understanding of how retrosynthetic disconnections are made. Including detailed solutions to over 300 problems, worked-through examples and end-of-chapter comprehension problems, Introduction to Strategies for Organic Synthesis serves as a stepping stone for students with an introductory knowledge of organic chemistry looking to progress to more advanced synthetic concepts and methodologies.
This book is a hands-on guide for the organic chemist. Focusing on the most reliable and useful reactions, the chapter authors provide the information necessary for a chemist to strategically plan a synthesis, as well as repeat the procedures in the laboratory. Consolidates all the key advances/concepts in one book, covering the most important reactions in organic chemistry, including substitutions, additions, eliminations, rearrangements, oxidations, reductions Highlights the most important reactions, addressing basic principles, advantages/disadvantages of the methodology, mechanism, and techniques for achieving laboratory success Features new content on recent advances in CH activation, photoredox and electrochemistry, continuous chemistry, and application of biocatalysis in synthesis Revamps chapters to include new and additional examples of chemistry that have been demonstrated at a practical scale
Organic Synthesis, Fourth Edition, provides a reaction-based approach to this important branch of organic chemistry. Updated and accessible, this eagerly-awaited revision offers a comprehensive foundation for graduate students coming from disparate backgrounds and knowledge levels, to provide them with critical working knowledge of basic reactions, stereochemistry and conformational principles. This reliable resource uniquely incorporates molecular modeling content, problems, and visualizations, and includes reaction examples and homework problems drawn from the latest in the current literature. In the Fourth Edition, the organization of the book has been improved to better serve students and professors and accommodate important updates in the field. The first chapter reviews basic retrosynthesis, conformations and stereochemistry. The next three chapters provide an introduction to and a review of functional group exchange reactions; these are followed by chapters reviewing protecting groups, oxidation and reduction reactions and reagents, hydroboration, selectivity in reactions. A separate chapter discusses strategies of organic synthesis, and he book then delves deeper in teaching the reactions required to actually complete a synthesis. Carbon-carbon bond formation reactions using both nucleophilic carbon reactions are presented, and then electrophilic carbon reactions, followed by pericyclic reactions and radical and carbene reactions. The important organometallic reactions have been consolidated into a single chapter. Finally, the chapter on combinatorial chemistry has been removed from the strategies chapter and placed in a separate chapter, along with valuable and forward-looking content on green organic chemistry, process chemistry and continuous flow chemistry. Throughout the text, Organic Synthesis, Fourth Edition utilizes Spartan-generated molecular models, class tested content, and useful pedagogical features to aid student study and retention, including Chapter Review Questions, and Homework Problems. A full Solutions Manual is also available online for qualified instructors, to support teaching. - Winner, 2018 Textbook Excellence Award (Texty) from the Textbook and Academic Authors Association - Fully revised and updated throughout, and organized into 19 chapters for a more cogent and versatile presentation of concepts - Includes reaction examples taken from literature research reported between 2010-2015 - Features new full-color art and new chapter content on process chemistry and green organic chemistry - Offers valuable study and teaching tools, including Chapter Review Questions and Homework Problems for students; Solutions Manual for qualified course instructors
The view of organic synthesis as "a concentrated expression of predictive ability and creative capacity" was advocated in the early 1950s. A concise and readable account of the role of synthesis in modern science, Organic Synthesis: The Science Behind the Art presents the general ideology of pursuits in the area of organic synthesis, and examines the methodologies that have evolved in the search for solutions to synthetic problems. This unique book details outstanding achievements of modern organic synthesis, not only for their scientific merits, but also for the aesthetic appeal of the target molecules chosen and the intrinsic beauty of the solutions to the problems posed. By judicious selection of data covering the main areas of synthetic explorations, this book serves to illustrate both the evolution of well-known approaches as well as recently emerged trends most likely to determine the future development of organic synthesis. Special attention is given to the consideration of principles of molecular design in promising and challenging areas of current research. Primarily aimed at advanced undergraduate and graduate students, Organic Synthesis: The Science Behind the Art will also be of interest to teachers, researchers and anyone requiring an introduction to the problems of organic synthesis.
