Advanced Organic Chemistry: Part A: Structure and Mechanisms [Hardcover]

Francis A. Carey (Author), Richard J. Sundberg (Author)

Book Description

ISBN-10: 0306462427 | ISBN-13: 978-0306462429 | Publication Date: May 2000 | Edition: 4th

Since its original appearance in 1977, this textbook has found wide use as a work providing broad coverage of the structure, reactivity and synthesis of organic compounds. This fourth edition provides updated material but continues the essential elements of the previous edition. The material in Part A is organized on the basis of fundamental structural topics such as stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. The material in Part B is organized on the basis of reaction type with emphasis on reactions of importance in laboratory synthesis. 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 fourth edition updates certain topics that have advanced rapidly since the third edition was published, including computational chemistry, structural manifestations of aromaticity, enantioselective reactions and lanthanide catalysis. The two parts stand alone, although there is considerable cross-referencing. Part A emphasizes quantitative and qualitative description of structural effects on reactivity and mechanism. Part B emphasizes the most general and useful synthetic reactions. The focus is on the core of organic chemistry, but the information provided forms the foundation for future study and research in medicinal and pharmaceutical chemistry, biological chemistry and physical properties of organic compounds.

Editorial Reviews

Review

From a review of an earlier edition:
`The book is a gold mine of information and can be highly recommended to those who wish to increase their understanding of advanced organic chemistry.'
Journal of the American Chemical Society
--This text refers to an alternate Hardcover edition.

From the Back Cover

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. Part A begins with the fundamental concepts of structure and stereochemistry, and the thermodynamic and kinetic aspects of reactivity. Major reaction types covered include nucleophilic substitution, addition reactions, carbanion and carbonyl chemistry, aromatic substitution, pericyclic reactions, radical reactions, and photochemistry.

Among the changes:

• Coverage of the importance of computational chemistry in modern organic chemistry, including applications to many specific reactions.
• Expanded coverage of stereoselectivity and enantioselectivity, including discussion of several examples of enantioselective reagents and catalysts
• Chapter 10, Concerted Pericyclic Reactions, has been reorganized and now begins with cycloaddition reactions.
• The treatment of photochemical reactions has been extensively updated to reflect both experimental and computational studies of the transient intermediates involved in photochemical reactions.
• A companion Web site provides digital models for study of structure, reaction and selectivity. Here students can view and manipulate computational models of reaction paths. These sites also provide exercises based on detailed study of the computational models.
• Several chapters in Part A conclude with Topics – short excursions into specific topics such as more detailed analysis of polar substituent effects, efforts to formulate substituent effects in terms of density functional theory, or the role of carbocations in petroleum refining
• Solutions to the chapter problems are provided to instructors online

Advanced Organic Chemistry Part A provides a close look at the structural concepts and mechanistic patterns that are fundamental to organic chemistry. It relates those mechanistic patterns, including relative reactivity and stereochemistry, to underlying structural factors. Understanding these concepts and relationships will allow students to recognize the cohesive patterns of reactivity in organic chemistry. Part A: Structure and Mechanism and Part B: Reaction and Synthesis - taken together - are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a foundation to comprehend and use the research literature in organic chemistry

--This text refers to an alternate Hardcover edition.

Product Details

• Hardcover: 818 pages
• Publisher: Springer; 4th edition (May 2000)
• Language: English
• ISBN-10: 0306462427
• ISBN-13: 978-0306462429
• Product Dimensions: 10.2 x 7.4 x 2 inches
• Shipping Weight: 4.2 pounds
• Average Customer Review: 3.9 out of 5 stars  See all reviews (19 customer reviews)
• Amazon Best Sellers Rank: #3,787,524 in Books (See Top 100 in Books)

Customer Reviews

Most Helpful Customer Reviews

30 of 32 people found the following review helpful:

5.0 out of 5 stars Course on Physical Organic Chemistry, March 3, 2002

By 

Matthew M. Yau "Voracious reader" (San Francisco, CA) - See all my reviews
(REAL NAME)   

This review is from: Advanced Organic Chemistry: Structure and Mechanisms (Part A) (Advanced Organic Chemistry / Part A: Structure and Mechanisms) (Paperback)

Carey and Sundberg had written the most detailed and briliant account in the subject of organic chemistry. This volume along with Part B (Reactions and Synthesis) contribute to the most updated account in advanced organic chemistry. Part A deals with chemical bonding + structure, basic stereochemical principles, conformational analysis, stereoelectronic effects, and organic reaction mechanisms.

For many organic students, a basic picture of chemical bonding and structure is more than adequate. The mathematical complications in physical chemistry have haunted many organic students including myself. Carey and Sundberg discuss concepts in chemical bonding and structure most relevant to organic chemistry and organic compounds in very plain language. This volume covers valence bond, molecular orbital theory (MO), Huckel molecular orbital theory, interaction between sigma and pi systems, hyperconjugation. The book also frontier orbital theory (HOMO, LUMO, PMO) in the context of perturbation theory.

The coverage on stereochemistry is succinct but detailed. It introduces ideas of enantiomeric and diastereomeric relationships. It also emphasizes on the significance and consequence of prochiral relationships and stereochemistry of dynamic processes. Conformational analysis is discussed mostly in the context of 3-membered to 7-membered ring systems. The book also provides thorough discussion on kinetic vs. thermodynamic control in mechanisms. Some of the less-easy-to-grasp concepts are discussed in details such as the Hammond's Postulate, Curtin-Hammett Principles and isotope effects. The book also contains a section on inorganic catalysis, Lewis acid catalysis and solvent effects. It further reinforces the theory and concept studied in introductory courses.

The rest of the book focuses on some of the most significant organic reactions: their substrates, reaction mechanism, choice of solvents, intermediates, and possible stereochemical outcomes. Part A mostly deal with all the above except for stereochemical outcomes. This book covers nucleophilic substitution (Sn1, Sn2, Sn1b), polar addition and elimination reaction, carbocation and cabanion chemistry, and finally an introduction of reactions of carbonyl compounds without emphasizing on the stereochemical outcomes. The book provides an abundance of reaction examples organized in schemes. It makes studying very effective and helpful. The coverage on factors affecting nucleophilic reactions (leaving group ability, steric strain, substitutent effect, solvent, neighboring group participation) is excellent, so much better than most titles currently available.

The book concludes with sections on aromaticity, aromatic substitution, concerted reactions, and free-radical reaction. The section on aromatic substitution covers structure-reactivity relationships and specific reactions such as nitration, halogenation, Friedel-Crafts, diazonium coupling and addition-elimination. The section on cncerted reactions are basic meant to give a taste of these reactions. A more detailed account of these reactions will be found in Part B. Overall Carey and Sundberg is not an easy book to read. It assumes a basic knowledge of an introductory organic chemistry course. Advanced undergraduates and graduate students will welcome this new edition and the depth of materials covered.

7 of 7 people found the following review helpful:

4.0 out of 5 stars should be in every chemistry grad students private library, April 22, 2000

By 

Neil Brown (Manhattan, Kansas, USA) - See all my reviews

This review is from: Advanced Organic Chemistry : Structure and Mechanisms (Part A) (Paperback)

An extremely useful text for courses involving organic chemistry at graduate level and an excellent reference text, it is much better than many other similar texts on the market. Probably most useful for the study of physical organic chemistry and studying for cumulative exams in the graduate chemistry program. This is probably the only such text you would need for mechanism determination problems. This text also has many example problems to work through which chemistry students would find the most useful.

9 of 10 people found the following review helpful:

5.0 out of 5 stars Great book, a must have, August 16, 2001

By 

Carlos Valdez (Castro Valley, CA United States) - See all my reviews

This review is from: Advanced Organic Chemistry : Structure and Mechanisms (Part A) (Paperback)

This book is outstanding in explaining the kinetic/mechanistic aspect of reactions and the study of mechanisms in organic as well as in inorganic chemistry (catalysis). It starts out with a nice introduction of the relevant concepts (i.e. MO theory, PMO theory and Quantum Mechanics-not rigourously) specially designed for organic chemists and students who do not have/need a very intricate mathematical background, with the overall achievement of making it a really easy book to read and understand. Definitely, this book and Part B of it are a must have for any chemist!!