Advanced Organic Chemistry: Part A: Structure and Mechanisms (Advanced Organic Chemistry / Part A: Structure and Mechanisms)

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 material in Part A is organized on the basis of fundamental structural topics such as structure, stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. Together with Part B: Reaction and Synthesis, 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.

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.


Great book, a must have   August 16, 2001
Carlos Valdez (Castro Valley, CA United States)
5 out of 6 found this review helpful

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!!


Dr. Carey serves up a smash hit!!   March 1, 2008
Guy F. Airey (San Antonio, TX USA)
2 out of 2 found this review helpful

Everyone in the world of organic chemistry knows of Dr. Carey and the great author and chemist he is. Hardly anyone could compare with the way he slides from subject to subject, explaining in detail and ease subjects that can be rather difficult to grasp. However, his method, because of his complete understanding of the subject matter is amazing. Often I wish I had had him for an instructor for at least one course in organic or any other for that matter. It is his ability to break down difficult concepts, and introduce them in logical and orderly fashion as to make that same difficult concept... much more easy to understand. If you are thinking about graduate school, or even want to make better grades in your soph-jr 2 semester organic chem class, use this book. It will help you understand some of the topics your "quick course" book leaves out! I cannot recommend this book high enough. guyairey


Comments on Carey 2007   August 25, 2007
Marilia O. F. Goulart (Maceio, Brazil)
1 out of 1 found this review helpful

I have been using this book since the first edition, in my postgraduation courses and each time, it is better. The 5th edition introduced aspects that we awere longing for, like, for example, new achievements in the area of aromaticity and improvements in the first chapter. The best improvement was attached to problems solving (despite being not so friendly) and 3D figures. A CD should be added to the next edition.


Complete Organic Chemistry   July 1, 2000
Meciya K Selvam (Peoria, IL,USA)
7 out of 10 found this review helpful

This book of two volumes covers the core of Organic Chemistry including stero chemistry, standard reactions, reaction mechanisms in porper depth. if one can have two books for organic chemistry, then this is it. the reader may branch out into the relevant topics in depth like Carpenter( for synthesis), Lowry/Richardson(for steroChem & mechanisms) etc. This is, without a trace of doubt, one of the finest in Organic Chemistry. Two thumbs up !