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Marc Loudon, Jim Parise Organic Chemistry .pdf
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Author: Marc Loudon and Jim Parise
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Organic Chemistry
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Organic Chemistry
sixth edition
Marc Loudon
PUrdUe University
Jim Parise
University of notre dame
NEW YORK
W. H. Freeman and Company
One New York Plaza,
Suite 4500,
New York, NY 10004
www.macmillanhighered.com
Publisher: Ben Roberts; Production Editor: Julianna Scott Fein; Manuscript Editor: John Murdzek;
Creative Director: Emiko-Rose Paul; Text and Cover Designer: Jeanne Schreiber; Cover Art: Quade Paul;
Illustrators: Marc Loudon and Quade Paul; Photo Researcher: Sharon Donahue; Proofreader: Kate St.Clair.
The text was set in 10/12 Times LT Std by TECHarts of Colorado and printed on #40 Liberty Dull by Transcontinental Printing.
About the cover: The Aldol Condensation
The reaction on the cover is a stylized representation of the aldol condensation, one of the most important reactions in organic chemistry and a very important reaction in biology. The cover reaction is shown in the text as
Eq. 22.45 on p. 1122. Research on improvements to the aldol condensation has continued to the present time.
Discovery of the aldol condensation was announced independently in 1872 by Charles-Adolphe Wurtz, a widely
recognized French chemist, and by Alexandr Borodin, holder of a professorial chair at the Medical-Surgical
Academy in St. Petersburg. Borodin was not only a chemist and a surgeon, but was also an accomplished
amateur musician and composer whose compositions are widely played to this day. Borodin was an advocate
of women’s rights, and he also championed medical education for women. (For more on Borodin, see p. 1122.)
The cover reaction symbolizes the continuity of organic chemistry from its medical origins to the important
position it holds today as both a basic chemical discipline and a foundation of modern biology.
Copyright © 2016 by W. H. Freeman and Company, Reproduction or translation of any part of this work beyond
that permitted by Section 107 or 108 of the 1976 United States Copyright Act without permission of the copyright
owner is unlawful. Requests for permission or further information should be addressed to the Permissions
Department at W. H. Freeman and Company.
Library of Congress Cataloging-in-Publication Data
Loudon, G. Marc.
Organic chemistry / Marc Loudon, Purdue University, Jim Parise, University of Notre Dame. -- Sixth edition.
pages cm
Includes bibliographical references and index.
ISBN 978-1-936221-34-9
1. Chemistry, Organic--Textbooks. I. Parise, Jim, 1978- II. Title.
QD251.3.L68 2016
547--dc23
015014647
Manufactured in Canada
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To Tarra and Shala . . .
Wives of the sons have become daughters of the father.
and to Julian . . .
His effervescence foretells a prized vintage.
—ML
To Kat, and my family.
—JP
Brief Contents
vi
1
Chemical Bonding and Chemical Structure
2
Alkanes
3
Acids and Bases. The Curved-Arrow Notation
4
Introduction to Alkenes. Structure and Reactivity
5
Addition Reactions of Alkenes
6
Principles of Stereochemistry 229
7
Cyclic Compounds. Stereochemistry of Reactions 272
8
Noncovalent Intermolecular Interactions 324
9
The Chemistry of Alkyl Halides
1
45
87
125
181
382
10
The Chemistry of Alcohols and Thiols 452
11
The Chemistry of Ethers, Epoxides, Glycols, and Sulfides 511
12
Introduction to Spectroscopy.
Infrared Spectroscopy and Mass Spectrometry
13
Nuclear Magnetic Resonance Spectroscopy 611
569
14
The Chemistry of Alkynes 681
15
Dienes, Resonance, and Aromaticity
16
The Chemistry of Benzene and Its Derivatives
17
Allylic and Benzylic Reactivity
18
The Chemistry of Aryl Halides, Vinylic Halides, and Phenols.
Transition-Metal Catalysis 879
19
The Chemistry of Aldehydes and Ketones.
Carbonyl-Addition Reactions 946
20
The Chemistry of Carboxylic Acids
21
The Chemistry of Carboxylic Acid Derivatives 1044
22
The Chemistry of Enolate Ions, Enols, and
a,b-Unsaturated Carbonyl Compounds 1103
23
The Chemistry of Amines
24
Carbohydrates
25
The Chemistry of Thioesters, Phosphate Esters,
and Phosphate Anhydrides 1283
26
The Chemistry of the Aromatic Heterocycles and Nucleic
Acids 1327
27
Amino Acids, Peptides, and Proteins 1373
28
Pericyclic Reactions 1449
712
789
836
1004
1183
1232
vii
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General, Organic & Biological Chemistry, 1st Edition
Janice Gorzynski Smith, UNIV OF HAWAII MANOA|2010|918 pages|PDF|72 Mb.
This new GOB textbook is written with the same student-focused, direct writing style that has been so successful in the Smith:Organic Chemistry text. Smith writes with a bulleted approach that delivers need-to-know information in a succinct style fortoday’s students. Armed with an excellent illustration program full of macro-to-micro art, as well as many applications to
biological, medical, consumer, and environmental topics, this book is a powerhouse of learning for students.
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