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One approach to organic synthesis is retrosynthetic analysis. With this approach a chemist will start with the structure of their target molecule and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials. This “disconnection” approach to synthesis is now a fundamental part of every organic synthesis course.
Organic Synthesis: The Disconnection Approach, 2nd Edition introduces this important technique, to help students to design their own organic syntheses. There are forty chapters: those on the synthesis of given types of molecules alternate with strategy chapters in which the methods just learnt are placed in a wider context. The synthesis chapters cover many ways of making each type of molecule starting with simple aromatic and aliphatic compounds with one functional group and progressing to molecules with many functional groups. The strategy chapters cover questions of selectivity, protection, stereochemistry, and develop more advanced thinking via reagents specifically designed for difficult problems.
Examples are drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavouring compounds, dyestuffs, monomers, and intermediates used in more advanced synthetic work. Reasons for wishing to synthesise each compound are given.
This second edition has been fully revised and updated with a modern look. Recent examples and techniques are included and illustrated additional material has been added to take the student to the level required by the sequel, “Organic Synthesis: Strategy and Control”.
Several chapters contain extensive new material based on courses that the authors give to chemists in the pharmaceutical industry.
Organic Synthesis: The Disconnection Approach, 2nd edition provides a full course in retrosynthetic analysis for chemistry and biochemistry students and a refresher for organic chemists working in industry and academia.
- Sales Rank: #304313 in Books
- Published on: 2008-12-31
- Original language: English
- Number of items: 1
- Dimensions: 9.70" h x .80" w x 7.50" l, 1.65 pounds
- Binding: Paperback
- 344 pages
Review
?The authors have succeeded admirably in the updating of a classic in the pedagogy of organic chemistry.? ( Journal of Medicinal Chemistry , August 2009)
?This book is suitable for advanced undergraduate students, researchers and professional chemists. Both the writing and the diagrams are simple and clear.? ( Reviews, May 2009)
From the Publisher
A workbook providing additional examples, problems, and solutions for use with Warren's Organic Synthesis: The Disconnection Approach. Exercises correspond to chapters in the main text. Problems of special ease or difficulty are labeled for optional use. Workbook includes a formula index of all target molecules contained in the text and workbook.
From the Back Cover
"Organic Synthesis: Strategy and Control" is a sequel to Stuart Warren's bestseller "Organic Synthesis: The Disconnection Approach," The 'Disconnection' book concentrated on the planning behind the synthesis of compounds.
The two themes of this new book are "strategy" and "control: " solving problems either by finding an alternative strategy or by controlling any established strategy to make it work.
The book is divided into five sections that deal with selectivity, carbon-carbon single bonds, carbon-carbon double bonds, stereochemistry and functional group strategy. Interpenetrating this structure, the 36 chapters start with classic methods and progress to modern methods and modern strategic considerations. Heterocyclic chemistry is treated throughout the book with full mechanistic explanations as part of organic chemistry rather than a separate mystery.
A comprehensive, practical account of the key concepts involved in synthesising compounds. Takes a mechanistic approach, which explains reactions and gives guidelines on how reactions might behave in different situations. Focuses on reactions that really work rather than those with limited application. Extensive, up-to-date references in each chapter.
Students and professional chemists familiar with "Organic Synthesis: The Disconnection Approach" will enjoy the leap into a book designed for chemists at the coalface of organic synthesis.
Most helpful customer reviews
16 of 18 people found the following review helpful.
Retrosynthetic Analysis
By Matthew M. Yau
Warren's Organic Synthesis-Disconnection Approach focuses on retrosynthetic analysis in organic synthesis. Some of the central concepts introduced in this strategy book are synthons, target molecule, FGI (functional group interconversion), disconnection, and reagent.
Synthons: an idealized fragment, usually a cation or an anion, resulting from a disconnection. Synthons may or may not be an intermediate in the corresponding reaction.
Disconnection: the reverse operation to a reaction. The imagined cleavage of a bond to "break" the molecule into possible starting materials.
Functional group interconversion: the process of converting one functional group into another by substitution, addition, elimination, oxidation, or reduction, and the reverse operation used in retrosynthetic analysis.
Reagent: Warren introduces a formal and rigid definition of reagent in this book. Reagent is a compound used in practice for a synthon.
Warren's treatise of organic synthesis emphasizes visualizing and choosing not only the most obvious but the most efficient disconnection (retrosynthesis) in synthesizing a target molecule. The book is set up in a fashion such that synthetic strategies and organic reactions are presented in alternating chapters. Strategies aim to enforce tricks and concepts of organic synthesis like stereoselectivity, control of regiochemistry and stereochemistry, control of carbonyl condensation, order of events in synthesis, rearrangements, use of ringed molecules. Reaction chapters present some of the most significant reactions in organic synthesis, with an emphasis of those involve carbon-carbon formation.
Topics of Warren's Organic Synthesis:
Synthesis Strategies
-The Disconnection Approach
-The Order of Events
-Chemoselectivity
-Reversal of Polarity, Cyclization Reactions
-Protecting Groups
-Choosing a Disconnection (General Strategy)
-Stereoselectivity
-Regioselectivity
-Use of Acetylenes
-Introduction of Carbonyl Condensations
-Control in Carbonyl Condensations
-Use of Aliphatic Nitro Compounds in Synthesis
-Radical Reactions in Synthesis
-Reconnections
-Introduction to Ring Synthesis, Saturated Heterocycles
-Rearrangements in Synthesis
-Use of Ketenes in Synthesis
-Pericyclic Rearrangements in Synthesis
-Special Methods for 5-Membered Rings
Reaction Methods
-One Group C-X Disconnections
-Two Group C-X Disconnections
-Amine Synthesis
-One Group C-C Disconnections: Alcohols
-One Group C-C Disconnections: Carbonyl Compounds
-Alkene Synthesis
-Two Group Disconnections: Diels-Alder Reactions
-Two Group Disconnections: 1,3-Difunctionalized Compounds and alpha,beta-unsaturated Carbonyl Compounds
-Two Group Disconnections: 1,5-Difunctionalized Compounds, Michael Addition, Robinson Annulation
-Two Group Disconnections: 1,2-Difunctionalized Compounds
-Two Group Disconnections: 1,4-Difunctionalized Compounds
-Two Group Disconnections: 1,6-Difunctionalized Compounds
-Three-Membered Rings
-Four-Membered Rings: Photochemistry in Synthesis
-Five-Membered Rings
-Six-Membered Rings
-Aromatic Heterocycles
The book teaches retrosynthetic analysis in organic synthesis. The ability to recognize an obvious and/or obscure disconnection facilitates organic synthesis tremendously. The methods and strategies presented in Warren gives advanced undergraduate students, graduate students and practicing chemists an overview of the most significant retrosynthetic pathways. Exceptional work.
7 of 7 people found the following review helpful.
Excellent, definitive
By Chris Joslin
An amazing and incisive description of retrosynthetic techniques, written at the advanced undergraduate level.
My criticisms would be:
(1) Rather too terse at some points; a few more words would make it flow more smoothly;
(2) As the book progresses, there are increasing references to "Strategy and Control", and more annoyingly, the workbook; the text is not entirely self contained, and I should not have to purchase the workbook for simple clarification;
(3) The index is really poor. This is the book's principal failing, and makes hunting around for cross references much harder than it should be.
Nevertheless, this is a wonderful work on an exciting and important area of organic chemistry, and I heartily recommend it.
5 of 5 people found the following review helpful.
An excellent primer for any organic synthesis course.
By M. Sanderon
Warrens book "Organic Synthesis: The Disconnection Approach" serves as an excellent bridge between the elementary education received at the undergraduate level and the more complex problems faced by synthetic practitioners. Strictly speaking, the book does not stray much beyond the complement of reactions that are learned at the undergraduate level, so much of the chemistry should be familiar to anyone having taken a two semester course. The strength of this rather short book lies in its ability to identify synthetic challenges by analyzing the retrosynthetic disconnections that create them.
Chapters alternate between the identification of a retrosynthetic disconnection and a discussion of a synthetic strategy. The book is valuable in that it distinguishes seemingly related compounds, such as 1,3-dicarbonyl compounds and 1,4-dicarbonyl compounds, and exposes the need for different synthetic strategies in each case - normal synthon polarity in the first case and inverse, or "umpolung", polarity in the second. Identifying relationships between functional groups in a molecule is presented as a means to determining possible strategies for its synthesis. Other important topics that are addressed include synthetic planning (order of events), stereochemistry, ring formation, reconnection, heterocycles, radical species, and many others.
Overall, students should expect to gain competency in the retrosynthetic analysis of molecules of moderate complexity. The book overlooks many modern day methods, but prepares students well for a graduate level synthesis course that would include such methods and gives students a better appreciation for the problems these new methods address. In my opinion, it is one of the best introductions available. In combination with the recently published sequel "Organic Synthesis: Strategy and Control", which addresses many modern day strategies, an excellent foundation has been laid for the education of up-and-coming synthetic chemists.
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