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Advanced Organic Chemistry: Structure and Mechanisms (Part A)

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Title: Advanced Organic Chemistry: Structure and Mechanisms (Part A)
by Francis A. Carey, Richard J. Sundberg
ISBN: 0-306-46243-5
Publisher: Plenum Pr
Pub. Date: June, 2001
Format: Paperback
Volumes: 1
List Price(USD): $49.50
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Average Customer Rating: 4.5 (8 reviews)

Customer Reviews

Rating: 4
Summary: Update of a Classic
Comment: This is an update on a classic text that has been used by many graduate and advanced undergraduate students. The core of the book is still an excellent survey of older literature and of enormous use to students. There are also many excellent problems. Unfortunately, there is not as much new material or references in some sections. I found I had to frequently supplement the text with current readings. The use of modern theory is especially lacking.

Rating: 5
Summary: Course on Physical Organic Chemistry
Comment: 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.

Rating: 5
Summary: Great book, a must have
Comment: 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!!

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