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Advanced Organic Chemistry: Part B: Reaction and Synthesis
The two-part, fifth edition of Advanced Organic Chemistry has been substantially revised and reorganized for greater clarity. The material has been updated to reflect advances in the field since the previous edition, especially in computational chemistry. Part B describes the most general and useful synthetic reactions, organized on the basis of reaction type. It can stand-alone; together, with Part Structure and Mechanisms, the two volumes provide a comprehensive foundation for the study in organic chemistry. Companion websites provide digital models for students and exercise solutions for instructors.
1322 pages, Hardcover
First published September 1, 1983
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Displaying 1 - 5 of 5 reviews
May 25, 2023
Introduction
Advanced Organic Chemistry, Part B: Reaction and Synthesis by Francis A. Carey and Richard J. Sundberg is a comprehensive textbook designed for readers who want to move beyond the fundamentals of organic chemistry and develop a sophisticated understanding of synthetic transformations. Published by Springer, the fifth edition appeared in 2007 and contains approximately 1,300 pages of detailed discussions, reaction schemes, references, and problems.
Since the series first appeared in 1977, it has become an established reference for advanced undergraduate and beginning graduate students. Part B focuses on synthetically useful reactions, organising the material by reaction type and illustrating how individual transformations can be applied to the construction of complex molecules. Its extensive engagement with the primary and review literature also makes it a valuable resource for students preparing to undertake independent research.
The defining feature of the book is its combination of breadth and depth. Rather than offering a compact catalogue of reagents and their products, Carey and Sundberg explain the context in which reactions are useful, the factors governing their outcomes, and their place within a broader synthetic strategy. The result is a demanding but rewarding textbook that helps readers progress from learning individual reactions to understanding how those reactions contribute to purposeful molecular design.
Content and Organisation
The fifth edition contains 13 principal chapters, covering carbon–carbon bond formation, functional-group interconversion, additions, reductions, organometallic chemistry, pericyclic reactions, aromatic substitution, oxidation, and multistep synthesis. The organisation is particularly effective because it groups related transformations together, allowing readers to compare methods and identify common synthetic principles. Springer, fifth edition.
1. Enolates and carbon–carbon bond formation
The early chapters explore the generation and alkylation of enolates and other carbon nucleophiles, followed by their reactions with carbonyl compounds.
This material is central to synthetic organic chemistry. Reactions such as aldol additions, Claisen condensations, and Michael additions provide powerful methods for constructing carbon frameworks and introducing new functional groups.
Carey and Sundberg's treatment is valuable because it places these transformations within a broader framework of reactivity and selectivity. Readers are encouraged to consider how reaction conditions, substrate structure, and competing pathways influence the outcome.
The discussions of regioselectivity and kinetic versus thermodynamic control are particularly useful for students who understand the basic mechanisms but need a deeper appreciation of why one product is favoured over another.
2. Functional-group interconversion and substitution
Functional-group interconversion is indispensable in multistep synthesis, where a molecule must be modified repeatedly without disrupting the structural features needed for later reactions.
The book examines substitution chemistry alongside protecting-group strategies and deprotection. These topics demonstrate that successful synthesis depends not only on identifying a reaction that works, but also on ensuring that it is compatible with the rest of the molecule.
The material is particularly relevant to the preparation of complex intermediates, where chemoselectivity and the order of operations can determine whether an entire synthetic sequence succeeds.
3. Electrophilic additions and transformations of multiple bonds
The discussion of electrophilic additions to carbon–carbon multiple bonds explains how alkenes and alkynes can be converted into more functionalised products.
These reactions are important both as individual transformations and as tools for building complexity into a molecule. Understanding their scope and selectivity allows readers to recognise when a multiple bond can serve as a useful starting point for further functionalisation.
The treatment also complements the mechanistic foundations developed in Part A, reinforcing the relationship between reaction conditions, intermediate stability, and product formation.
4. Reduction chemistry
Reduction is another major component of the text. The relevant chapter covers methods for reducing carbon–carbon multiple bonds, carbonyl groups, and other functional groups.
The breadth of coverage helps readers compare different approaches to achieving a desired oxidation state or functional-group change. In practical synthesis, this knowledge is essential because a reducing agent must be selected not simply for its ability to react, but also for its compatibility with other functional groups.
One of the book's strengths is its attention to the broader chemical context of these transformations rather than treating each reagent as an isolated fact to memorise.
5. Cycloadditions, rearrangements, and thermal eliminations
The treatment of concerted cycloadditions, unimolecular rearrangements, and thermal eliminations extends the reader's understanding beyond conventional substitution and addition chemistry.
These reactions can provide efficient routes to rings, reorganised carbon skeletons, and structurally complex products. Their inclusion demonstrates the diversity of strategies available to the synthetic chemist and encourages readers to consider alternative pathways when planning a transformation.
This section is particularly useful for students who want to understand the conceptual foundations of advanced synthesis rather than simply accumulate a list of named reactions.
6. Organometallic and transition-metal chemistry
The chapters on organometallic compounds and transition-metal reactions are among the most important parts of the book for readers interested in modern synthetic methodology.
Organometallic reagents provide versatile methods for forming carbon–carbon bonds and functionalising organic molecules. Transition-metal chemistry expands these possibilities through catalytic processes and bond-forming reactions that can be difficult to achieve efficiently by other means.
The discussion provides a foundation for understanding the broader significance of metal-mediated transformations in complex synthesis.
However, the fifth edition was published in 2007. Although its core principles remain valuable, readers working with contemporary catalytic methods should supplement the book with recent reviews and research papers.
7. Carbon–carbon bond formation using boron, silicon, and tin
The book's coverage of reactions involving compounds of boron, silicon, and tin broadens the range of synthetic tools available to the reader.
These elements can play important roles in controlling reactivity and enabling selective bond formation. The associated transformations also illustrate how the properties of different organometallic and main-group compounds can be exploited to achieve specific synthetic objectives.
This is a particularly useful feature for postgraduate students, who need to recognise not only familiar textbook reactions but also the broader families of methods used in research.
8. Carbocations, carbenes, radicals, and aromatic substitution
The chapters on reactive intermediates and aromatic substitution provide further breadth. They explore reaction families that rely on distinct modes of reactivity, including ionic and radical pathways.
This organisation helps readers compare reactions that may produce similar structural changes through different mechanisms. It also reinforces the importance of understanding substrate effects, reaction conditions, and competing transformations when choosing a synthetic route.
The aromatic substitution chapter provides a systematic treatment of an important class of transformations, while the discussion of reactive intermediates connects synthetic applications with the mechanistic principles that underpin them.
9. Oxidation and multistep synthesis
The final chapters address oxidation chemistry and multistep synthesis, bringing together many of the principles developed earlier.
Oxidation methods allow chemists to adjust functional groups and oxidation states in preparation for subsequent transformations. The multistep synthesis chapter is especially important because it shifts attention from individual reactions to the planning and execution of an entire sequence.
This is where the book's practical value becomes clearest. Real synthetic problems rarely involve a single transformation. They require decisions about reaction order, functional-group compatibility, selectivity, and the efficient construction of a target structure.
By placing individual reactions within the larger context of synthesis, Carey and Sundberg help readers develop a more strategic approach to organic chemistry.
Strengths
Comprehensive coverage
The book's greatest strength is its extensive coverage of synthetically useful organic reactions. It provides a substantial reference for students who need to understand the scope and limitations of different reaction classes.
Its breadth is especially valuable during postgraduate research, when a chemist may need to investigate an unfamiliar transformation or compare several possible routes to the same intermediate.
Strong emphasis on synthetic reasoning
The text encourages readers to think beyond memorising reagents. By organising chemistry around reaction types and discussing transformations in context, it helps students recognise recurring patterns and understand how individual reactions contribute to larger synthetic objectives.
This is an important step towards independent research, where selecting and adapting a reaction is often more demanding than recalling its textbook mechanism.
Extensive references to the literature
The references to primary and review literature are a major advantage. They provide a pathway from textbook explanations to the original experimental studies and broader reviews on which the subject is built.
For postgraduate students, this feature is particularly valuable because it supports the transition from textbook learning to critical engagement with scientific publications.
An excellent companion to Part A
Part B complements Advanced Organic Chemistry, Part A: Structure and Mechanisms. Part A concentrates on the theoretical foundations of chemical reactivity, while Part B focuses on the reactions used to transform molecules.
Together, the volumes provide a broad framework for advanced organic chemistry. Readers can use Part A to deepen their understanding of why a reaction proceeds through a particular pathway and Part B to explore how the transformation can be applied in synthesis.
Neither volume makes the other redundant; their strengths lie in their different but complementary purposes.
Weaknesses and Limitations
Significant demands on the reader
This is not a beginner's textbook. The book assumes that readers have completed an introductory organic chemistry course and are familiar with basic reaction mechanisms, functional groups, and stereochemical concepts.
Its detailed treatment can be challenging for students who have not yet developed a secure foundation. Readers seeking concise explanations or rapid examination revision may find it unnecessarily dense.
Length and accessibility
At approximately 1,300 pages, the fifth edition is an extensive reference work rather than a book that most students will read continuously from beginning to end.
Its organisation makes selective reading practical, but locating the most relevant information can still require time and familiarity with the subject. Students may benefit from pairing it with a more concise synthesis textbook or course notes.
Advanced Organic Chemistry, Part B: Reaction and Synthesis by Francis A. Carey and Richard J. Sundberg is a comprehensive textbook designed for readers who want to move beyond the fundamentals of organic chemistry and develop a sophisticated understanding of synthetic transformations. Published by Springer, the fifth edition appeared in 2007 and contains approximately 1,300 pages of detailed discussions, reaction schemes, references, and problems.
Since the series first appeared in 1977, it has become an established reference for advanced undergraduate and beginning graduate students. Part B focuses on synthetically useful reactions, organising the material by reaction type and illustrating how individual transformations can be applied to the construction of complex molecules. Its extensive engagement with the primary and review literature also makes it a valuable resource for students preparing to undertake independent research.
The defining feature of the book is its combination of breadth and depth. Rather than offering a compact catalogue of reagents and their products, Carey and Sundberg explain the context in which reactions are useful, the factors governing their outcomes, and their place within a broader synthetic strategy. The result is a demanding but rewarding textbook that helps readers progress from learning individual reactions to understanding how those reactions contribute to purposeful molecular design.
Content and Organisation
The fifth edition contains 13 principal chapters, covering carbon–carbon bond formation, functional-group interconversion, additions, reductions, organometallic chemistry, pericyclic reactions, aromatic substitution, oxidation, and multistep synthesis. The organisation is particularly effective because it groups related transformations together, allowing readers to compare methods and identify common synthetic principles. Springer, fifth edition.
1. Enolates and carbon–carbon bond formation
The early chapters explore the generation and alkylation of enolates and other carbon nucleophiles, followed by their reactions with carbonyl compounds.
This material is central to synthetic organic chemistry. Reactions such as aldol additions, Claisen condensations, and Michael additions provide powerful methods for constructing carbon frameworks and introducing new functional groups.
Carey and Sundberg's treatment is valuable because it places these transformations within a broader framework of reactivity and selectivity. Readers are encouraged to consider how reaction conditions, substrate structure, and competing pathways influence the outcome.
The discussions of regioselectivity and kinetic versus thermodynamic control are particularly useful for students who understand the basic mechanisms but need a deeper appreciation of why one product is favoured over another.
2. Functional-group interconversion and substitution
Functional-group interconversion is indispensable in multistep synthesis, where a molecule must be modified repeatedly without disrupting the structural features needed for later reactions.
The book examines substitution chemistry alongside protecting-group strategies and deprotection. These topics demonstrate that successful synthesis depends not only on identifying a reaction that works, but also on ensuring that it is compatible with the rest of the molecule.
The material is particularly relevant to the preparation of complex intermediates, where chemoselectivity and the order of operations can determine whether an entire synthetic sequence succeeds.
3. Electrophilic additions and transformations of multiple bonds
The discussion of electrophilic additions to carbon–carbon multiple bonds explains how alkenes and alkynes can be converted into more functionalised products.
These reactions are important both as individual transformations and as tools for building complexity into a molecule. Understanding their scope and selectivity allows readers to recognise when a multiple bond can serve as a useful starting point for further functionalisation.
The treatment also complements the mechanistic foundations developed in Part A, reinforcing the relationship between reaction conditions, intermediate stability, and product formation.
4. Reduction chemistry
Reduction is another major component of the text. The relevant chapter covers methods for reducing carbon–carbon multiple bonds, carbonyl groups, and other functional groups.
The breadth of coverage helps readers compare different approaches to achieving a desired oxidation state or functional-group change. In practical synthesis, this knowledge is essential because a reducing agent must be selected not simply for its ability to react, but also for its compatibility with other functional groups.
One of the book's strengths is its attention to the broader chemical context of these transformations rather than treating each reagent as an isolated fact to memorise.
5. Cycloadditions, rearrangements, and thermal eliminations
The treatment of concerted cycloadditions, unimolecular rearrangements, and thermal eliminations extends the reader's understanding beyond conventional substitution and addition chemistry.
These reactions can provide efficient routes to rings, reorganised carbon skeletons, and structurally complex products. Their inclusion demonstrates the diversity of strategies available to the synthetic chemist and encourages readers to consider alternative pathways when planning a transformation.
This section is particularly useful for students who want to understand the conceptual foundations of advanced synthesis rather than simply accumulate a list of named reactions.
6. Organometallic and transition-metal chemistry
The chapters on organometallic compounds and transition-metal reactions are among the most important parts of the book for readers interested in modern synthetic methodology.
Organometallic reagents provide versatile methods for forming carbon–carbon bonds and functionalising organic molecules. Transition-metal chemistry expands these possibilities through catalytic processes and bond-forming reactions that can be difficult to achieve efficiently by other means.
The discussion provides a foundation for understanding the broader significance of metal-mediated transformations in complex synthesis.
However, the fifth edition was published in 2007. Although its core principles remain valuable, readers working with contemporary catalytic methods should supplement the book with recent reviews and research papers.
7. Carbon–carbon bond formation using boron, silicon, and tin
The book's coverage of reactions involving compounds of boron, silicon, and tin broadens the range of synthetic tools available to the reader.
These elements can play important roles in controlling reactivity and enabling selective bond formation. The associated transformations also illustrate how the properties of different organometallic and main-group compounds can be exploited to achieve specific synthetic objectives.
This is a particularly useful feature for postgraduate students, who need to recognise not only familiar textbook reactions but also the broader families of methods used in research.
8. Carbocations, carbenes, radicals, and aromatic substitution
The chapters on reactive intermediates and aromatic substitution provide further breadth. They explore reaction families that rely on distinct modes of reactivity, including ionic and radical pathways.
This organisation helps readers compare reactions that may produce similar structural changes through different mechanisms. It also reinforces the importance of understanding substrate effects, reaction conditions, and competing transformations when choosing a synthetic route.
The aromatic substitution chapter provides a systematic treatment of an important class of transformations, while the discussion of reactive intermediates connects synthetic applications with the mechanistic principles that underpin them.
9. Oxidation and multistep synthesis
The final chapters address oxidation chemistry and multistep synthesis, bringing together many of the principles developed earlier.
Oxidation methods allow chemists to adjust functional groups and oxidation states in preparation for subsequent transformations. The multistep synthesis chapter is especially important because it shifts attention from individual reactions to the planning and execution of an entire sequence.
This is where the book's practical value becomes clearest. Real synthetic problems rarely involve a single transformation. They require decisions about reaction order, functional-group compatibility, selectivity, and the efficient construction of a target structure.
By placing individual reactions within the larger context of synthesis, Carey and Sundberg help readers develop a more strategic approach to organic chemistry.
Strengths
Comprehensive coverage
The book's greatest strength is its extensive coverage of synthetically useful organic reactions. It provides a substantial reference for students who need to understand the scope and limitations of different reaction classes.
Its breadth is especially valuable during postgraduate research, when a chemist may need to investigate an unfamiliar transformation or compare several possible routes to the same intermediate.
Strong emphasis on synthetic reasoning
The text encourages readers to think beyond memorising reagents. By organising chemistry around reaction types and discussing transformations in context, it helps students recognise recurring patterns and understand how individual reactions contribute to larger synthetic objectives.
This is an important step towards independent research, where selecting and adapting a reaction is often more demanding than recalling its textbook mechanism.
Extensive references to the literature
The references to primary and review literature are a major advantage. They provide a pathway from textbook explanations to the original experimental studies and broader reviews on which the subject is built.
For postgraduate students, this feature is particularly valuable because it supports the transition from textbook learning to critical engagement with scientific publications.
An excellent companion to Part A
Part B complements Advanced Organic Chemistry, Part A: Structure and Mechanisms. Part A concentrates on the theoretical foundations of chemical reactivity, while Part B focuses on the reactions used to transform molecules.
Together, the volumes provide a broad framework for advanced organic chemistry. Readers can use Part A to deepen their understanding of why a reaction proceeds through a particular pathway and Part B to explore how the transformation can be applied in synthesis.
Neither volume makes the other redundant; their strengths lie in their different but complementary purposes.
Weaknesses and Limitations
Significant demands on the reader
This is not a beginner's textbook. The book assumes that readers have completed an introductory organic chemistry course and are familiar with basic reaction mechanisms, functional groups, and stereochemical concepts.
Its detailed treatment can be challenging for students who have not yet developed a secure foundation. Readers seeking concise explanations or rapid examination revision may find it unnecessarily dense.
Length and accessibility
At approximately 1,300 pages, the fifth edition is an extensive reference work rather than a book that most students will read continuously from beginning to end.
Its organisation makes selective reading practical, but locating the most relevant information can still require time and familiarity with the subject. Students may benefit from pairing it with a more concise synthesis textbook or course notes.
November 6, 2018
It is very comprehensive and has thousands of examples, many of whose mechanisms my friends and I worked out on our own so that we'd gain confidence in the process. Also, we followed the procedure given in this book for the synthesis of Z-Jasmone, Juvabione etc
But essentially, this is advanced and we mainly used it as a reference book.
But essentially, this is advanced and we mainly used it as a reference book.
June 27, 2026
Ok this book is insane! It really pulls you in, but I couldn't recommend it as a supplement to a normal sessional school course, because it is really a bit of a Pandora's box and you may just spend the entirety of your night understanding a theoretical Diels-Alder product for a select reaction under the specific reagents and conditions formerly established..it's a huge book of niche case examples and a generic lay of the land for graduate organic chemistry, but I think the sheer volume of case examples could be overwhelming. That said if you happen to have the time on your hands and an interest of the craft, or want to delve into one specific class of reactions for the purposes of experimental work, I couldn't recommend it enough!
May 5, 2014
*Parts A and B may stand alone; together, they provide a comprehensive foundation for the study in organic chemistry...
*Updated material reflecting scientific advances since 2001’s Fourth Edition, especially in computational chemistry...
*Companion Websites provide digital models for students and exercise solutions for instructors...
Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed.
The two-part fifth edition has been substantially revised and reorganized for greater clarity. Among the changes: Updated material reflecting advances in the field since 2001’s Fourth Edition, especially in computational chemistry; A companion Web site provides digital models for study of structure, reaction and selectivity; Solutions to the exercises provided to instructors online.
The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. Part B describes the most general and useful synthetic reactions, organized on the basis of reaction type. Together with Part A: Structure and Mechanisms, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.
*Updated material reflecting scientific advances since 2001’s Fourth Edition, especially in computational chemistry...
*Companion Websites provide digital models for students and exercise solutions for instructors...
Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed.
The two-part fifth edition has been substantially revised and reorganized for greater clarity. Among the changes: Updated material reflecting advances in the field since 2001’s Fourth Edition, especially in computational chemistry; A companion Web site provides digital models for study of structure, reaction and selectivity; Solutions to the exercises provided to instructors online.
The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. Part B describes the most general and useful synthetic reactions, organized on the basis of reaction type. Together with Part A: Structure and Mechanisms, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.
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April 28, 2009I Farid.I am from Azerbaijan ! How are You? I am very glad with you from acquaintance.I am working at the Baku State University as researcher in organic chemistry laboratory. I searched your last book on internet. I have not access to get this book! But I am very interested with this book. Could you please send me your book (or electron version) with your personal signature in first page of this book. It would be great honour for me!
Best regards !!!
Best regards !!!
Displaying 1 - 5 of 5 reviews