Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey & Sundberg.pdf - Organiczna - derbich_45

Advanced Organic

Chemistry

Part A: Structure and Mechanisms

FIFTH

EDITION

Advanced Organic Chemistry

PART A: Structure and Mechanisms

PART B: Reactions and Synthesis

Advanced Organic

Chemistry

FIFTH

EDITION

Part A: Structure and Mechanisms

FRANCIS A. CAREY

and RICHARD J. SUNDBERG

University of Virginia

Charlottesville, Virginia

Francis A. Carey

Richard J. Sundberg

Department of Chemistry

University of Virginia

Charlottesville, VA 22904

Library of Congress Control Number: 2006939782

ISBN-13: 978-0-387-44897-8 (hard cover)

e-ISBN-13: 978-0-387-44899-3

ISBN-13: 978-0-387-68346-1 (soft cover)

Printed on acid-free paper.

permission of the publisher (Springer Science+Business Media, LLC, 233 Spring Street, New York,

NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in

connection with any form of information storage and retrieval, electronic adaptation, computer software, or

by similar or dissimilar methodology now know or hereafter developed is forbidden.

The use in this publication of trade names, trademarks, service marks and similar terms, even if they are

not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject

to proprietary rights.

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springer.com

Preface

This Fifth Edition marks the beginning of the fourth decade that Advanced Organic

Chemistry has been available. As with the previous editions, the goal of this text is to

allow students to build on the foundation of introductory organic chemistry and attain

a level of knowledge and understanding that will permit them to comprehend much

of the material that appears in the contemporary chemical literature. There have been

major developments in organic chemistry in recent years, and these have had a major

influence in shaping this new edition to make it more useful to students, instructors,

and other readers.

The expanding application of computational chemistry is reflected by amplified

discussion of this area, especially density function theory (DFT) calculations in

Chapter 1. Examples of computational studies are included in subsequent chapters

that deal with specific structures, reactions and properties. Chapter 2 discusses the

principles of both configuration and conformation, which were previously treated in

two separate chapters. The current emphasis on enantioselectivity, including devel-

opment of many enantioselective catalysts, prompted the expansion of the section on

stereoselective reactions to include examples of enantioselective reactions. Chapter 3,

which covers the application of thermodynamics and kinetics to organic chemistry,

has been reorganized to place emphasis on structural effects on stability and reactivity.

This chapter lays the groundwork for later chapters by considering stability effects on

carbocations, carbanions, radicals, and carbonyl compounds.

Chapters 4 to 7 review the basic substitution, addition, and elimination mecha-

nisms, as well as the fundamental chemistry of carbonyl compounds, including enols

and enolates. A section on of the control of regiochemistry and stereo- chemistry of

aldol reactions has been added to introduce the basic concepts of this important area. A

more complete treatment, with emphasis on synthetic applications, is given in Chapter

2 of Part B.

Chapter 8 deals with aromaticity and Chapter 9 with aromatic substitution, empha-

sizing electrophilic aromatic substitution. Chapter 10 deals with concerted pericyclic

reactions, with the aromaticity of transition structures as a major theme. This part of

the text should help students solidify their appreciation of aromatic stabilization as a

fundamental concept in the chemistry of conjugated systems. Chapter 10 also considers

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