Advanced Organic Chemistry: Part A: Structure and Mechanisms

by Francis A. Carey and Richard J. Sundberg

Book Overview

The purpose of this edition, like that of the earlier ones, is to provide the basis for a deeper understanding of the structures of organic compounds and the mechanisms of organic reactions. The level is aimed at advanced undergraduates and beginning graduate students. Our goals are to solidify the student's understanding of basic concepts provided by an introduction to organic chemistry and to present more information and detail, including quantitative...

• Format: Paperback
• Language: English
• ISBN: 0306434474
• ISBN13: 9780306434471
• Release Date: January 1990
• Publisher: Springer
• Length: 832 Pages
• Weight: 3.80 lbs.
• Dimensions: 1.8" x 7.1" x 10.0"

Customer Reviews

Comments on Carey 2007

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.

Course on Organic Synthesis

Carey and Sundberg had written the most detailed and briliant account in the subject of organic chemistry. This volume along with Part A (Structure and Mechanisms) contribute to the most updated account in advanced organic chemistry. Part B deals with organic reactions with emphasis on stereochemical consequences. Discussion focuses on the most important reactions and methods in modern organic synthesis.Alkylation of nucleophilic carbon intermediates discuss regioselectivity and stereoselectivity in enolate formation. The coverage on enolate alkylation is excellent that emphasizes on the model that predicts the stereochemistry of alkylation. The discussion also introduces Ireland model and Zimmerman-Traxler model. Reaction of carbon nucleophiles with carbonyl groups focuses on some of the most significant reactions: Mannich reaction, mixed aldol reaction, Wittig reaction and the Horner-Wadsworth-Emmon reaction. The discussion again focuses on control of regiochemistry and stereochemistry of the condensation via the use of chair transition states.The best sections in this Part B volume of the book is the complete detailed discussion on reduction and oxidation, Reduction reagents and methods introduced include hydrogenation, hydride donors, stereoselective hydride reduction, various dissolving metal reductions. Oxidation chapter summerizes all important methods like transition-metal oxidant, Collins reagents, epoxidation, peroxidic reagents, ozonolysis, and selective oxidation of certain functional groups. The revised Part B edition also includes full discussion on reactions involving transition metals and organoboron, organosilicon, and organotin compounds. This includes some of the most updated and current research topics. Other topics covered include reaction of reactive intermediates like carbocations, carbenes, and radicals. Finally, a chapter is devoted to the cycloadditions, unimolecular rearrangements, and thermal eliminations. The last chapter deals with planning multi-step organic synthesis with an emphasis on retrosynthetic analysis. This book has made organic synthesis approachable and easier to comprehend.

Course on Physical Organic Chemistry

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 re

Magnificient in its own essence

I found this book extremely easy to read and makes a great addition to the library owned by an organic chemist. Certainly, this book deserves much attention and I believe that it describes many concepts in a simpler manner when comparison to Jerry March's book is called upon. The book is well-written and is exactly what undergraduate students interested in organic chemistry need to read if they want to expand their knowledge of the field without getting into a complex text right away. Definitively, I recommend this book in the shelf of any practicing and non-practicing chemist.

Complete Organic Chemistry

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 !