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Organic Chemistry, Second Edition

Thomas N. Sorrell University of North Carolina, Chapel Hill

The Second Edition of Organic Chemistry maintains all the innovative features of the first edition in a sleeker, slimmer, and easier-to-navigate design.  Hailed by J Chem Ed as “the new wave” in organic textbooks, this book’s mechanistic approach constructs organic chemistry from the ground up.

ISBN 978-1-891389-38-2
eSBN 978-1-891389-91-7
Copyright 2006
988 pages, Clothbound


The Second Edition of Organic Chemistry maintains all the innovative features of the first edition in a sleeker, slimmer, and easier-to-navigate design.  Hailed by J Chem Ed as “the new wave” in organic textbooks, this book’s mechanistic approach constructs organic chemistry from the ground up.  By focusing on the points of reactivities in organic, this text allows students to approach more and more complex molecules with enhanced understanding.  Also noteworthy are the biochemical examples for their variety, substance, and depth.  Despite its unique emphasis on reactivity, the book facilitates easy adoption by covering organic compound classes in the traditional order.  Hundreds of worked examples and student exercises combine with clear writing and sound pedagogy to make this text an exceptional choice.  

What’s New in this Edition?

  • a sleeker, slimmer volume

  • improved organization designed for ease of use

  • more examples and solved exercises

  • fewer specialized topics

  • the first chapter on nucleophilic substitution has been expanded and divided into two chapters, allowing alkyl halides and alcohol substitution reactions to be treated separately

  • oxidation reactions of alcohols have been removed from the chapter on elimination reactions,  and a separate chapter on reduction and oxidation reactions has been created (Chapter 11), which  also includes discussions about the reduction and oxidation reactions of alkenes

  • the chemistry of dienes, including the Diels-Alder reaction, have been collected in a chapter separate from the one devoted to the addition reactions of simple alkenes

  • the order of topics in the chapters presenting spectroscopic methods has been reversed, so nuclear magnetic resonance spectroscopy is now covered first 

  • the chapter that introduces synthetic methods has been largely preserved from the first edition, but it is followed directly by the chapter on enantioselective synthesis

  • the discussion of enantioselective reactions has been completely rewritten, and its emphasis has been changed to encourage students to think about designing enantioselective syntheses without having to memorize a lot of details about specific reagents and conditions

  • the topic of aromatic compounds— benzene and its derivatives—has been moved, and the presentations about diazonium compounds and nucleophilic aromatic substitution reactions, have been incorporated into new Chapter 17 

  • the chapter about about aldehydes, ketones, and carbohydrates has been divided into two chapters in the current edition, with the division made according to the reaction mechanisms involved, not according to the functional groups that are undergoing the reactions

  • the chapter on nitrogen-containing compounds  has been parceled in this edition among several chapters in the new edition

  •  in contrast, the discussions of polymer chemistry, which were interspersed throughout the book in the first edition, have been collected to form Chapter 26 in this edition

Link to Solutions Manual

Table of Contents

Chapter 1 The Structures of Organic Molecules

Chapter 2 Bonding in Organic Molecules

Chapter 3 The Conformations of Organic Molecules

Chapter 4 The Stereochemistry of Organic Molecules

Chapter 5 Chemical Reactions and Mechanisms

Chapter 6 Substitution Reactions of Alkyl Halides

Chapter 7 Substitution Reactions of Alcohols and Related Compounds

Chapter 8 Elimination Reactions of Alkyl Halides, Alcohols and Related Compounds

Chapter 9 Addition Reactions of Alkenes and Alkynes

Chapter 10 Addition Reactions of Conjugated Dienes

Chapter 11 Oxidation and Reduction Reactions

Chapter 12 Free Radicals: Substitution and Addition Reactions

Chapter 13 Proton and Carbon Nuclear Magnetic Resonance Spectroscopy

Chapter 14 Determining the Structures of Organic Molecules

Chapter 15 Organometallic Reagents and Chemical Synthesis

Chapter 16 Asymmetric Reactions and Synthesis

Chapter 17 The Chemistry of Benzene and Its Derivativesa

Chapter 18 Nucleophilic Addition Reactions of Aldehydes and Ketones

Chapter 19 Addition-Substitution Reactions of Aldehydes and Ketones; The Chemistry of Carbohydrates

Chapter 20 Addition-Elimination Reactions of Aldehydes and Ketones

Chapter 21 Addition-Elimination Reactions of Carboxylic Acids and Derivatives

Chapter 22 The Acid-Base Chemistry of Carbonyl Compounds

Chapter 23 The Nucleophilic Addition Reactions of Enolate Ions

Chapter 24 Conjugate Addition Reactions of Unsaturated Carbonyl Compounds

Chapter 25 The Chemistry of Polycyclic and Heterocyclic Arenes

Chapter 26 Polymers and Polymerization

Chapter 27 Amino acids, Peptides, and Proteins

Chapter 28 Nucleic acids and Molecular Recognition

View PDF File of Complete Frontmatter


“Sorrell writes well, and has a knack for lucid explanations. He uses excellent examples and well designed exercises to make his points. The sections integrating chapter topics with biochemical examples are the best that I have seen. My students have found his book a pleasure to read.”
-Douglas Dyckes, University of Colorado, Denver

“Student response to the first edition of Sorrell’s Organic Chemistry has been overwhelmingly positive. I expect response to the streamlined second edition to be even better.”
-René Boeré, The University of Lethbridge

“The Second Edition of Sorrell’s Organic Chemistry is working well for our course on organic chemistry with a biological emphasis. It is a great combination of rigor and easy reading.”
-Martin Semmelhack, Princeton University

“Sorrell’s Organic Chemistry is a breath of fresh air. It is a truly distinctive approach to the discipline that emphasizes the mechanistic similarities of processes rather than presenting them in the standard functional group approach.”
-Peter Dibble

“This new edition of Sorrell’s Organic Chemistry is a great contribution to those interested in teaching organic with an eye toward biochemistry. Students very much appreciated the clarity of the writing and pertinent biological examples.”
-Josh Rabinowitz, Princeton University

Thomas N. Sorrell University of North Carolina, Chapel Hill

Thomas Sorrell received a BA in chemistry from New College (Sarasota, FL) 1973 and a PhD in organic chemistry from Stanford University in 1977. He subsequently joined the faculty at University of North Carolina at Chapel Hill, where he has taught and conducted research in organic and bioinorganic chemistry. Sorrell has been named an Alfred P. Sloan Research Fellow, and he has authored two textbooks in addition to dozens of research papers. Sorrell enjoys playing violin with the UNC Symphony Orchestra, and he is an avid watercolor painter. His landscape “White Rim, Green River” was accepted for display in an “Arts for the Parks” exhibition, an acclaimed international art competition aimed at raising awareness for the National Parks in the U.S.

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