Organic Chemistry: Principles and Mechanisms PDF
Preview Organic Chemistry: Principles and Mechanisms
Organic Chemistry Principles and Mechanisms Joel M. Karty Elon University b W. W. Norton & Company has been independent since its founding in 1923, when William Warder Norton and Mary D. Herter Norton first published lectures delivered at the People’s Institute, the adult education division of New York City’s Cooper Union. The firm soon expanded its program beyond the Institute, publishing books by celebrated academics from America and abroad. By mid-century, the two major pillars of Norton’s publishing program—trade books and college texts—were firmly established. In the 1950s, the Norton family transferred control of the company to its employees, and today—with a staff of four hundred and a comparable number of trade, college, and professional titles published each year—W. W. Norton & Company stands as the largest and oldest publishing house owned wholly by its employees. Copyright © 2014 by W. W. Norton & Company, Inc. All rights reserved. Printed in the United States of America. Editor: Erik Fahlgren Assistant Editor: Renee Cotton Developmental Editor: John Murdzek Manuscript Editor: Julie Henderson Project Editor: Christine D’Antonio Marketing Manager, Chemistry: Stacy Loyal Science Media Editor: Rob Bellinger Associate Media Editor: Jennifer Barnhardt Assistant Media Editor: Paula Iborra Production Manager: Eric Pier-Hocking Photo Editor: Michael Fodera Photo Researcher: Jane Miller Permissions Manager: Megan Jackson Text Design: Lisa Buckley Art Director: Hope Miller Goodell Composition: codeMantra Illustrations: Imagineering Manufacturing: Courier, Kendallville Library of Congress Cataloging-in-Publication Data has been applied for. ISBN 978-0-393-91904-2 W. W. Norton & Company, Inc., 500 Fifth Avenue, New York, NY 10110 www.wwnorton.com W. W. Norton & Company Ltd., Castle House, 75/76 Wells Street, London W1T 3QT 1 2 3 4 5 6 7 8 9 0 To Pnut, Fafa, and Jakers About the Author JOEL KARTY earned his B.S. in chemistry at the University of Puget Sound and his Ph.D. at Stanford University. He joined the faculty of Elon University in 2001, where he currently holds the rank of associate professor. He teaches primarily the organic chemistry sequence and also teaches general chemistry. In the summer, Joel teaches at the Summer Medical and Dental Education Program through the Duke University medical center. His research interests include investigating the roles of resonance and inductive effects in fundamental chemical systems and studying the mechanism of pattern formation in Liesegang reactions. He has written a very successful student supplement, Get Ready for Organic Chemistry, Second Edition (formerly called The Nuts and Bolts of Organic Chemistry). Brief Contents 1 Atomic and Molecular Structure 1 11 Electrophilic Addition to Nonpolar (cid:283) Bonds 1: Nomenclature Addition of a Brønsted Acid 570 1 Introduction: The Basic System for Naming Simple Organic Compounds: 12 Electrophilic Addition to Nonpolar (cid:283) Bonds 2: Alkanes, Cycloalkanes, Haloalkanes, Nitroalkanes, Reactions Involving Cyclic Transition States 610 and Ethers 54 13 Organic Synthesis 1: Beginning Concepts 645 2 Three-Dimensional Geometry, Intermolecular 14 Orbital Interactions 2: Extended (cid:283) Systems, Interactions, and Physical Properties 76 Conjugation, and Aromaticity 676 3 Orbital Interactions 1: Hybridization and 15 Structure Determination 1: Ultraviolet-Visible Two-Center Molecular Orbitals 128 and Infrared Spectroscopies 715 Nomenclature 2 Naming Alkenes, Alkynes, and 16 Structure Determination 2: Nuclear Benzene Derivatives 163 Magnetic Resonance Spectroscopy and Mass 4 Isomerism 1: Conformational and Constitutional Spectrometry 757 Isomers 176 17 Nucleophilic Addition to Polar (cid:283) Bonds 1: 5 Isomerism 2: Chirality, Enantiomers, and Addition of Strong Nucleophiles 815 Diastereomers 224 18 Nucleophilic Addition to Polar (cid:283) Bonds 2: Nomenclature 3 Considerations of Addition of Weak Nucleophiles and Acid and Base Stereochemistry: R and S Configurations Catalysis 861 about Tetrahedral Stereocenters and Z and E 19 Organic Synthesis 2: Intermediate Topics Configurations about Double Bonds 276 of Synthesis Design, and Useful Reduction and 6 The Proton Transfer Reaction: An Introduction Oxidation Reactions 919 to Mechanisms, Thermodynamics, and Charge 20 Nucleophilic Addition–Elimination Reactions 1: Stability 295 The General Mechanism Involving Strong 7 An Overview of the Most Common Elementary Nucleophiles 962 Steps 351 21 Nucleophilic Addition–Elimination Reactions 2: Interchapter 1 Molecular Orbital Theory and Weak Nucleophiles 1006 Chemical Reactions 388 22 Electrophilic Aromatic Substitution 1: Nomenclature 4 Naming Compounds with Substitution on Benzene; Useful Accompanying Common Functional Groups: Alcohols, Amines, Reactions 1065 Ketones, Aldehydes, Carboxylic Acids, Acid Halides, 23 Electrophilic Aromatic Substitution 2: Acid Anhydrides, Nitriles, and Esters 398 Substitution Involving Mono- and Disubstituted 8 An Introduction to Multistep Mechanisms: S 1 Benzene and Other Aromatic Rings 1104 N and E1 Reactions 420 24 The Diels–Alder Reaction and Other Pericyclic 9 Nucleophilic Substitution and Elimination Reactions 1154 Reactions 1: Competition among S 2, S 1, E2, and N N 25 Reactions Involving Free Radicals 1199 E1 Reactions 466 Interchapter 2 Fragmentation Pathways in 10 Nucleophilic Substitution and Elimination Mass Spectrometry 1245 Reactions 2: Reactions That Are Useful for Synthesis 524 26 Polymers 1255 ix
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