PART ONE: An Introduction to the Study of Organic Chemistry 1. Remembering General Chemistry: Electronic Structure and Bonding 2. Acids and Bases: Central to Understanding Organic Chemistry TUTORIAL: Acids and Bases 3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure   PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization TUTORIAL: Using Molecular Models 4. Isomers: The Arrangement of Atoms in Space TUTORIAL: Interconverting Structural Representations 5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics TUTORIAL: Drawing Curved Arrows 6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions 7. The Reactions of Alkynes • An Introduction to Multistep Synthesis 8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene TUTORIAL: Drawing Resonance Contributors   PART THREE: Substitution and Elimination Reactions 9. Substitution and Elimination Reactions of Alkyl Halides 10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds 11. Organometallic Compounds 12. Radicals TUTORIAL: Drawing Curved Arrows in Radical Systems   PART FOUR: Identification of Organic Compounds 13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy 14. NMR Spectroscopy   PART FIVE: Carbonyl Compounds 15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives 16. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives 17. Reactions at the α-Carbon TUTORIAL: Synthesis and Retrosynthetic Analysis   PART SIX: Aromatic Compounds 18. Reactions of Benzene And Substituted Benzenes 19. More About Amines • Reactions of Heterocyclic Compounds   PART SEVEN: Bioorganic Compounds 20. The Organic Chemistry Of Carbohydrates 21. Amino Acids, Peptides, and Proteins 22. Catalysis in Organic Reactions and in Enzymatic Reactions 23. The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins 24. The Organic Chemistry of the Metabolic Pathways 25.  The Organic Chemistry of Lipids 26. The Chemistry of the Nucleic Acids   PART EIGHT: Special Topics in Organic Chemistry 27. Synthetic Polymers 28. Pericyclic Reactions   Appendix I pKa Values Appendix II Kinetics Appendix III Summary of Methods Used to Synthesize a Particular Functional Group Appendix IV Summary of Methods Employed to Form Carbon-Carbon Bonds Appendix V  Spectroscopy Tables Appendix VI Physical Properties of Organic Compounds Appendix VII Answers to Selected Problems      

About the Book   A modern, streamlined organization emphasizes unifying principles of reactivity, offering an economy of presentation and discouraging memorization The text consistently highlights the fundamental reason for all chemical reactions – electrophiles combine with nucleophiles — in order to keep students focused on the key ideas. Students are introduced to synthetic and retrosynthetic chemistry early on, allowing them to grasp multistep synthesis from the beginning. The textbook bridges the gap between organic chemistry and biochemistry Because bioorganic chemistry is the bridge between organic chemistry and biochemistry, the text emphasizes thatthe organic reactions that chemists carry out in the laboratory are similar to those performed by nature inside a cell. These connections are especially important to biological science majors. In Chapters 1-20, the bioorganic material is presented as “interest boxes” and within the last sections of the chapters so that this material is available to the student without requiring the instructor to introduce bioorganic topics into the course. Chapters 21—26 focus on the organic chemistry of living systems. These chapters have the unique distinction of containing more chemistry than is typically found in the corresponding parts of a biochemistry text. Chapter 21   Amino Acids, Peptides, And Proteins Chapter 22   Catalysis In Organic Reactions And In Enzymatic Chapter 23   The Organic Mechanisms Of The Coenzymes, Compounds Derived From Vitamins Chapter 24   The Organic Chemistry Of The Metabolic Pathways Chapter 25   The Organic Chemistry Of Lipids Chapter 26   The Chemistry Of The Nucleic Acids   UPDATED! Revised, accuracy-checked text provides increased exam relevancy To better prepare students for the MCAT exam, MCAT learning outcomes and MCAT-style questions have been added to the Student’s Study Guide and Solutions Manual, as well as MasteringChemistry. Contributing author Richard Morrison, University of Georgia, has reviewed and honed the problem solving presentations, end of chapter problems, and the solutions manual.   NEW! Improved visuals and organization engage students with difficult subject matter, organizes the chapter content and improves ease of use: NEW! Expanded annotations reinforce the revised art program and help keep students focused on the most important material.  NEW! Numerous subheads are part of a redesigned text that enhances ease of use and gives the text a modern look and feel. Subheads help students locate important topics, show how that content develops within the section, and break the presentation into “bite-sized” portions that are easier to comprehend and connect.   Strengthened emphasis on the strategies needed to solve problems and master the content Passages explaining important problem-solving strategies — content the student must learn — are clearly labeled with a LEARN THE STRATEGY label. Follow-up problems that require students to apply the just learned strategy are labeled with a USE THE STRATEGY label. These labels, which are implemented throughout the entire text, allow students to easily find important content and practice its use.     NEW and UPDATED! New and restructured features give students additional conceptual and skill building support UPDATED! Tutorial spreads and Design a Synthesis sections explicitly highlight essential skills. NEW! Marginal notes highlighting relative reactivity and the Organizing What We Know feature now align with each other to better relate skill building to conceptual understanding. Newly highlighted Problem-Solving Strategies guide students on how to approach various problems and help to develop critical thinking skills. See more at: http://www.pearsonhighered.com/educator/product/Organic-Chemistry-Plus-MasteringChemistry-with-eText-Access-Card-Package/9780321803078.page#sthash.8kPWNcIB.dpuf Seven special Design A Synthesis sections introduce and help students through the iterative process of solving complex problems. End of chapter Problems review key topics and reinforce essential skills. End of chapter Reaction Summaries ensure students fully grasp how each reaction occurs. NEW and UPDATED! Applications boxes connect the discussion to Medical, Environmental, Biological, Pharmaceutical, Nutritional, Chemical, Industrial, Historical, and General applications, and help students relate the material to real life and potential future careers. Bruice provides more of this kind of material than any other competing text on the market.   Redesigned! Organizing What We Know about the Reactions of Organic Compounds Table This informative and powerful table summarizes Bruice’s approach to teaching organic chemistry by categorizing all organic reactions into four groups having similar chemical behavior. Group I: electrophilic addition reactions Group II: nucleophilic substitution reactions and elimination reactions Group III: nucleophilic ddition reactions and nucleophilic addition—elimination reactions Group IV: electrophilic (and nucleophilic) aromatic substitution reactions The table builds as students gain knowledge about groups of organic compounds as they work through the text. The easy to interpret table emphasizes the key characteristics common to the group of organic compounds covered in preceding chapters.   Content Updates and Revisions to the Table of Contents streamline and improve clarity in the presentation. Using the E,Z system to name alkenes was moved to Chapter 4, so it appears immediately after using cis, trans to distinguish alkene stereoisomers. Catalytic hydrogenation and relative stabilities of alkenes was moved from Chapter 6 to Chapter 5 (thermodynamics), so it can be used to illustrate how H° values can be used to determine relative stabilities. As a result, all the reactions in Chapter 6 have well-defined mechanisms where the first step in each of them is addition of the electrophile to the sp2 carbon bonded to the most hydrogens. NEW! The two chapters in the previous edition on Substitution and Elimination reactions of alkenes have been combined into one chapter (Chapter 9). The recent compelling evidence showing that alkyl halides do not undergo SN1 solvolysis reactions has allowed this material to be greatly simplified, so now it fits nicely into one chapter. The structure of benzene is covered in Chapter 8 (the chapter on resonance) because it is the ideal compound to use to explain the concept of delocalized electrons. A discussion on aromaticity is also found in this chapter, so a short introduction to electrophilic aromatic substitution reactions is now included. This allows students to see how aromaticity causes benzene to undergo electrophilic substitution rather than electrophilic addition–the reactions they have just finished studying. NEW! Electronic effects are discussed in Chapter 8 and used to teach students how substituents affect the pKa values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene. Electronic effects can help students understand the directing effects of substituents on benzene rings. With the Eighth Edition, electronic effects are discussed in Chapter 8 in order to teach students how substituents affect the pKa values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene. NEW! Chapter on Lipids. The lipid material previously in the chapter on carboxylic acids and their derivatives (fatty acids, waxes, phospholipids, etc.) has been moved into a new chapter to help students see that the outcome of all reactions in the chapter could be determined simply by understanding how a tetrahedral intermediate partitions. The discussion of terpenes from the metabolism chapter has also been moved into this chapter, along with some new material. The IR spectra have been updated throughout the text and the solutions manual while additional spectroscopy problems have been added to the solutions manual. Bruice’s Study Guide and Solutions Manual now offers a diverse group of 60 spectroscopy problems.   Also available as a Pearson eText or packaged with Mastering Chemistry   Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience that can be adopted on its own as the main course material. It lets students highlight, take notes, and review key vocabulary all in one place, even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. Educators can easily share their own notes with students so they see the connection between their eText and what they learn in class — motivating them to keep reading, and keep learning. Learn more about Pearson eText. MasteringChemistry is the leading online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics™. Students can further master concepts after class through traditional and adaptive homework assignments that provide hints and answer-specific feedback. The Mastering gradebook records scores for all automatically graded assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions.   Mastering brings learning full circle by continuously adapting to each student and making learning more personal than ever–before, during, and after class.   Before Class NEW!  Organic Chemistry Dynamic Study Modules focus on general chemistry remediation, acid-base chemistry, functional groups, nomenclature, and key mechanisms. The modules help students study effectively on their own by continuously assessing their activity and performance in real time. Here's how it works: students answer a set of questions and indicate their confidence level for each answer. The questions repeat until students answer them all correctly and confidently. Once completed, the module explains the key concept. Dynamic Study Modules are available as graded assignments for prior to class, and are accessible on smartphones, tablets, and computers. NEW! Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience available within Mastering. It lets students easily highlight, take notes, and review key vocabulary all in one place — even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. During Class NEW! Learning Catalytics™ generates class discussion, guides your lecture, and promotes peer-to-peer learning with real-time analytics. MasteringChemistry with eText now provides Learning Catalytics–an interactive student response tool that uses students’ smartphones, tablets, or laptops to engage them in more sophisticated tasks and thinking. Instructors can: Pose a variety of open-ended questions that help students develop critical thinking skills around structure and reactivity in organic chemistry with 10 new Learning Catalytics questions for each chapter of Organic Chemistry, Eighth Edition. Monitor responses to find out where students are struggling Use real-time data to adjust the instructional strategy and engage students during class Manage student interactions by automatically grouping students for discussion, teamwork, and peer-to-peer learning   After Class NEW! MasteringChemistry's Organic Chemistry Drawing Tool is a customized version of Java Free MarvinSketch that accommodates the diversity of structures and reaction mechanisms inherent to learning organic chemistry while providing students with a wrong answer specific feedback. This educational version of MarvinSketch has been customized in response to input from hundreds of undergraduate students. The drawing tool includes comprehensive MasteringChemistry tutorials, specific to drawing with MarvinSketch, that equip students to start quickly drawing organic structures and mechanisms to complete homework. The tutorials cover how to accurately draw reaction mechanisms, how to modify answers, and how to use the palette. All mechanism-based problems provide feedback specific to each step of the reaction, and new visual cues help clarify exact placement of arrows, enable selection of the electron, and highlight which bonds have been formed or broken. Assignable, textbook specific skill building tutorials guide students through the toughest topics in organic chemistry including: Acids and Bases (after chapter 2) Using Molecular Models (after Chapter 3) Interconverting Structural Representations (after Chapter 4) Drawing Curved Arrows (after Chapter 5) Drawing Resonance Contributors (after chapter 8) Drawing Curved Arrows in Radical Systems (after Chapter 13) Synthesis and Retrosynthetic Analysis (after Chapter 17) Rate Changes and Kinetics (Appendix II) NEW! Six NMR/IR Spectroscopy simulations (a partnership with ACD labs) allow professors and students access to limitless spectral analysis with guided activities that can be used in the lab, in the classroom, or after class to study and explore spectra virtually. Activities authored by Mike Huggins, University of West Florida, prompt students to utilize the spectral simulator and walk them through different analyses and possible conclusions. 120 Organic Chemistry-specific tutorials built around the most challenging topics in Organic Chemistry provide wrong answer specific feedback and Socratic and declarative hints so students learn where they are going wrong. 1500 automatically graded questions can be assigned as homework or practice. These questions are specific to the Eighth Edition and the majority requires drawing structures and reactions. Enhanced end-of-chapter problems now includewrong-answer specific feedback on all mechanism problems so students have the opportunity to practice and test their understanding of organic reactivity outside of class with the help and ease of an updated drawing tool and detailed feedback on their work.  

About the Book   The textbook bridges the gap between organic chemistry and biochemistry Because bioorganic chemistry is the bridge between organic chemistry and biochemistry, the text emphasizes thatthe organic reactions that chemists carry out in the laboratory are similar to those performed by nature inside a cell. These connections are especially important to biological science majors. In Chapters 1-20, the bioorganic material is presented as “interest boxes” and within the last sections of the chapters so that this material is available to the student without requiring the instructor to introduce bioorganic topics into the course. Chapters 21—26 focus on the organic chemistry of living systems. These chapters have the unique distinction of containing more chemistry than is typically found in the corresponding parts of a biochemistry text. Chapter 21   Amino Acids, Peptides, And Proteins Chapter 22   Catalysis In Organic Reactions And In Enzymatic Chapter 23   The Organic Mechanisms Of The Coenzymes, Compounds Derived From Vitamins Chapter 24   The Organic Chemistry Of The Metabolic Pathways Chapter 25   The Organic Chemistry Of Lipids Chapter 26   The Chemistry Of The Nucleic Acids   UPDATED! Revised, accuracy-checked text provides increased exam relevancy To better prepare students for the MCAT exam, MCAT learning outcomes and MCAT-style questions have been added to the Student’s Study Guide and Solutions Manual, as well as MasteringChemistry. Contributing author Richard Morrison, University of Georgia, has reviewed and honed the problem solving presentations, end of chapter problems, and the solutions manual.   NEW! Improved visuals and organization engage students with difficult subject matter, organizes the chapter content and improves ease of use: Expanded annotations reinforce the revised art program and help keep students focused on the most important material. Numerous subheads are part of a redesigned text that enhances ease of use and gives the text a modern look and feel. Subheads help students locate important topics, show how that content develops within the section, and break the presentation into “bite-sized” portions that are easier to comprehend and connect.   Strengthened emphasis on the strategies needed to solve problems and master the content Passages explaining important problem-solving strategies — content the student must learn — are clearly labeled with a LEARN THE STRATEGY label. Follow-up problems that require students to apply the just learned strategy are labeled with a USE THE STRATEGY label. These labels, which are implemented throughout the entire text, allow students to easily find important content and practice its use.     NEW and UPDATED! New and restructured features give students additional conceptual and skill building support UPDATED! Tutorial spreads and Design a Synthesis sections explicitly highlight essential skills. NEW! Marginal notes highlighting relative reactivity and the Organizing What We Know feature now align with each other to better relate skill building to conceptual understanding. Newly highlighted Problem-Solving Strategies guide students on how to approach various problems and help to develop critical thinking skills. See more at: http://www.pearsonhighered.com/educator/product/Organic-Chemistry-Plus-MasteringChemistry-with-eText-Access-Card-Package/9780321803078.page#sthash.8kPWNcIB.dpuf Seven special Design A Synthesis sections introduce and help students through the iterative process of solving complex problems. End of chapter Problems review key topics and reinforce essential skills. End of chapter Reaction Summaries ensure students fully grasp how each reaction occurs. NEW and UPDATED! Applications boxes connect the discussion to Medical, Environmental, Biological, Pharmaceutical, Nutritional, Chemical, Industrial, Historical, and General applications, and help students relate the material to real life and potential future careers. Bruice provides more of this kind of material than any other competing text on the market.   Redesigned! Organizing What We Know about the Reactions of Organic Compounds Table This informative and powerful table summarizes Bruice’s approach to teaching organic chemistry by categorizing all organic reactions into four groups having similar chemical behavior. Group I: electrophilic addition reactions Group II: nucleophilic substitution reactions and elimination reactions Group III: nucleophilic ddition reactions and nucleophilic addition—elimination reactions Group IV: electrophilic (and nucleophilic) aromatic substitution reactions The table builds as students gain knowledge about groups of organic compounds as they work through the text. The easy to interpret table emphasizes the key characteristics common to the group of organic compounds covered in preceding chapters.   Content Updates and Revisions to the Table of Contents streamline and improve clarity in the presentation. Using the E,Z system to name alkenes was moved to Chapter 4, so it appears immediately after using cis, trans to distinguish alkene stereoisomers. Catalytic hydrogenation and relative stabilities of alkenes was moved from Chapter 6 to Chapter 5 (thermodynamics), so it can be used to illustrate how H° values can be used to determine relative stabilities. As a result, all the reactions in Chapter 6 have well-defined mechanisms where the first step in each of them is addition of the electrophile to the sp2 carbon bonded to the most hydrogens. NEW! The two chapters in the previous edition on Substitution and Elimination reactions of alkenes have been combined into one chapter (Chapter 9). The recent compelling evidence showing that alkyl halides do not undergo SN1 solvolysis reactions has allowed this material to be greatly simplified, so now it fits nicely into one chapter. The structure of benzene is covered in Chapter 8 (the chapter on resonance) because it is the ideal compound to use to explain the concept of delocalized electrons. A discussion on aromaticity is also found in this chapter, so a short introduction to electrophilic aromatic substitution reactions is now included. This allows students to see how aromaticity causes benzene to undergo electrophilic substitution rather than electrophilic addition–the reactions they have just finished studying. NEW! Electronic effects are discussed in Chapter 8 and used to teach students how substituents affect the pKa values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene. Electronic effects can help students understand the directing effects of substituents on benzene rings. With the Eighth Edition, electronic effects are discussed in Chapter 8 in order to teach students how substituents affect the pKa values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene. NEW! Chapter on Lipids. The lipid material previously in the chapter on carboxylic acids and their derivatives (fatty acids, waxes, phospholipids, etc.) has been moved into a new chapter to help students see that the outcome of all reactions in the chapter could be determined simply by understanding how a tetrahedral intermediate partitions. The discussion of terpenes from the metabolism chapter has also been moved into this chapter, along with some new material. The IR spectra have been updated throughout the text and the solutions manual while additional spectroscopy problems have been added to the solutions manual. Bruice’s Study Guide and Solutions Manual now offers a diverse group of 60 spectroscopy problems. Also available as a Pearson eText or packaged with Mastering Chemistry   Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience that can be adopted on its own as the main course material. It lets students highlight, take notes, and review key vocabulary all in one place, even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. Educators can easily share their own notes with students so they see the connection between their eText and what they learn in class — motivating them to keep reading, and keep learning. Learn more about Pearson eText. MasteringChemistry is the leading online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics™. Students can further master concepts after class through traditional and adaptive homework assignments that provide hints and answer-specific feedback. The Mastering gradebook records scores for all automatically graded assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions. Mastering brings learning full circle by continuously adapting to each student and making learning more personal than ever–before, during, and after class.   Before Class Organic Chemistry Dynamic Study Modules focus on general chemistry remediation, acid-base chemistry, functional groups, nomenclature, and key mechanisms. The modules help students study effectively on their own by continuously assessing their activity and performance in real time. Here's how it works: students answer a set of questions and indicate their confidence level for each answer. The questions repeat until students answer them all correctly and confidently. Once completed, the module explains the key concept. Dynamic Study Modules are available as graded assignments for prior to class, and are accessible on smartphones, tablets, and computers. During Class Learning Catalytics™ generates class discussion, guides your lecture, and promotes peer-to-peer learning with real-time analytics. MasteringChemistry with eText now provides Learning Catalytics–an interactive student response tool that uses students’ smartphones, tablets, or laptops to engage them in more sophisticated tasks and thinking. Instructors can: Pose a variety of open-ended questions that help students develop critical thinking skills around structure and reactivity in organic chemistry with 10 new Learning Catalytics questions for each chapter of Organic Chemistry, Eighth Edition. Monitor responses to find out where students are struggling Use real-time data to adjust the instructional strategy and engage students during class Manage student interactions by automatically grouping students for discussion, teamwork, and peer-to-peer learning Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience available within Mastering. It lets students easily highlight, take notes, and review key vocabulary all in one place – even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. After Class MasteringChemistry's Organic Chemistry Drawing Tool is a customized version of Java Free MarvinSketch that accommodates the diversity of structures and reaction mechanisms inherent to learning organic chemistry while providing students with a wrong answer specific feedback. This educational version of MarvinSketch has been customized in response to input from hundreds of undergraduate students. The drawing tool includes comprehensive MasteringChemistry tutorials, specific to drawing with MarvinSketch, that equip students to start quickly drawing organic structures and mechanisms to complete homework. The tutorials cover how to accurately draw reaction mechanisms, how to modify answers, and how to use the palette. All mechanism-based problems provide feedback specific to each step of the reaction, and new visual cues help clarify exact placement of arrows, enable selection of the electron, and highlight which bonds have been formed or broken. Assignable, textbook specific skill building tutorials guide students through the toughest topics in organic chemistry including: Acids and Bases (after chapter 2) Using Molecular Models (after Chapter 3) Interconverting Structural Representations (after Chapter 4) Drawing Curved Arrows (after Chapter 5) Drawing Resonance Contributors (after chapter 8) Drawing Curved Arrows in Radical Systems (after Chapter 13) Synthesis and Retrosynthetic Analysis (after Chapter 17) Rate Changes and Kinetics (Appendix II) Six NMR/IR Spectroscopy simulations (a partnership with ACD labs) allow professors and students access to limitless spectral analysis with guided activities that can be used in the lab, in the classroom, or after class to study and explore spectra virtually. Activities authored by Mike Huggins, University of West Florida, prompt students to utilize the spectral simulator and walk them through different analyses and possible conclusions.   Enhanced end-of-chapter problems now includewrong-answer specific feedback on all mechanism problems so students have the opportunity to practice and test their understanding of organic reactivity outside of class with the help and ease of an updated drawing tool and detailed feedback on their work.