WHAT’S NEW?

Features of the Sixth Edition

• NEW! Chapter 29: Synthetic Polymers builds on the coverage of polymers in earlier chapters to serve the needs of those students who require more than an introduction to polymer chemistry.
  “One of the things I like about Dr. Carey’s text is that he makes an effort to incorporate polymer chemistry into the larger body of the text. I see this chapter as a nice focusing and expansion of those components. . . . I would be comfortable in using this chapter as both a chapter of polymers, but also as an opportunity to overview chemistries from across the course.”
  —Paul T. Buonora,
  California State University Long Beach
• NEW! Curved-arrow notation has been revised and expanded to become a section of its own in Chapter 1.
• NEW! In view of the broad acceptance of the expanded treatment of acid–base reactions in Chapter 1 of the fifth edition, this material and its already “organic” character receive even greater emphasis in this edition.
• NEW! Section 5.17 “Isotope Effects and the E2Mechanism” is new to this edition.
• NEW! Building on introductory material in Chapters 1–5, Chapter 6 now includes a section entitled “Thermodynamics of Addition–Elimination Equilibria,” which describes the interplay of enthalpy, entropy, and Gibbs free energy in some fundamental organic reactions.
• NEW! Chapter 14: Organometallic Compounds has been expanded to include separate sections on homogeneous catalytic hydrogenation and olefin metathesis.
• NEW! Chapter 18: Enols and Enolates has been reorganized to take advantage of the increased emphasis on acid–base chemistry in earlier chapters. The new organization places enolate reactions before those of enols and better reflects their synthetic importance.
• NEW! A new section “m- and p-Benzyne” has been added to Chapter 23 to complement the existing material on o-benzyne. This new section includes examples of the Bergman cyclization.
• The review of bonding from general chemistry has also been expanded in Chapter 1.
• The economic value and everyday application of organic chemistry has been integrated more thoroughly into the text.

Pedagogy

• NEW! A list of tables and mechanisms has been added to the front matter (pages xix–xxii) as a quick reference to these important learning tools in each chapter.
• NEW! Each chapter opens with a two-page spread of “coming attractions” that lists section headings and reaction mechanisms along with their corresponding page numbers.
• NEW! Reaction mechanisms are uniquely formatted to be more visible.
• NEW! Problems have been added to various boxed essays in the text to give this essential element more importance.
• NEW end-of-chapter problems have been added.
• NEW! Each chapter ends with a stand-alone collection of molecular modeling problems designed to instruct the student in applications of the Spartan software.
• NEW! Table 1.5: A Systematic Approach to Writing Lewis Structures and Table 1.6: Introduction to the Rules of Resonance are revised from well-received tables of the fifth edition to make them even more useful to students as they progress from general chemistry to organic.
• Summary tables allow the student easy access to a wealth of information in an easy-to-use format while reviewing information from previous chapters.
• End-of-Chapter Summaries highlight and consolidate all of the important concepts and reactions within a chapter.

Problem-Solving

• Problem-solving strategies and skills are emphasized throughout. Understanding is continually reinforced by problems that appear within topic sections. For many problems, sample solutions are given, including some examples of handwritten solutions from the author.
  “I really like this approach, showing the working out of a problem by hand on paper . . .examples reinforce logical, outlining approach to problem solving that I try to encourage my students to use. . . . I think it is good for students to see how they should be organizing the information given and the concepts that they know on paper to solve problems.”
  —John Barbaro,
  University of Florida, Gainesville

Biological Applications

• In addition to four chapters that deal with biomolecules (Chapters 25–28), biological applications appear regularly throughout the text and in boxed essays.
• Chapter 28: Nucleosides, Nucleotides, and Nucleic Acids testifies to the explosive growth of the molecular basis of genetics.
• Numerous boxed essays throughout the text highlight biological applications of organic chemistry.

Art Program

• NEW! Hand-drawn pieces (rendered by the author) have been added to the sample solutions in the in-text problems throughout to assist students in developing drawings for their own work.
• The artwork in the sixth edition has also been revised to make the use of color more consistent and to give the text a more modern look.
• Molecular models make organic chemistry more accessible and enrich the education experience for all.
• Molecular models are integrated into the content, revealing key features more clearly than words or structural formulas alone.
• Nodal properties of orbitals are included to show this important aspect of bonding theory.

Media

• NEW! Mechanism Animations for the instructor. Created by David Collard (Georgia Institute of Technology), this set of animations illustrates nine basic mechanisms: SN 1: Unimolecular Nucleophilic Substitution; SN 2: Bimolecular Nucleophilic Substitution; E1: Unimolecular -Eliminations; E2: Bimolecular -Eliminations; Electrophilic Addition to Alkenes; Electrophilic Aromatic Substitution; Diels–Alder Reaction; Nucleophilic Acyl Substitution; and Radical Halogenation. Each animation includes an Introduction and Overview to describe the mechanism and outline the experimental observations for the student. The animation then visualizes the mechanism for the student. Navigation tools allow the student to “step through” each reaction so that students may proceed at their own speed. They may also pause, rewind, or fast-forward to further review crucial steps. Each animation ends with a Summary and Extension to generalize the mechanism and reactions and relate them to other reactions. The animations can be viewed individually by students or presented full-screen size in the classroom as an interactive part of the lecture presentation.
• NEW! ChemCoach. ChemCoach Synthesis is an online interactive program enabling a student to practice solving synthesis problems using the most efficient logical approach, termed retrosynthetic analysis. A problem is presented that the student then solves in a step-by-step process. Because more than one correct solution to an organic chemistry problem is often possible, the ChemCoach program will accommodate and track all variations of a given solution. Scores are then graded and recorded to an online gradebook for the instructor.
• NEW! The Classroom Performance System’s (CPS) eInstruction brings interactivity into the classroom or lecture hall. It is a wireless response system that gives the instructor and students immediate feedback from the entire class. The wireless response pads are essentially remotes that are easy to use and engage students. CPS allows instructors to motivate student preparation, interactivity, and active learning. Instructors receive immediate feedback to gauge which concepts students understand. Questions covering the content of the Organic Chemistry text and formatted in the CPS eInstruction software are available on the Organic Chemistry Online Learning Center.
• The Learning By Modeling CD developed by Wavefunction, Inc., in connection with the fourth edition of this text accompanies the sixth as well. We were careful to incorporate Spartan so it would be a true amplifier of the textbook—from the author creating the Spartan images used in the text to directing the student to an icon in the text that identifies opportunities to build models of their own or to examine and access more than 1000 molecules in a database designed specifically for this text.